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Patent 1237938 Summary

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(12) Patent: (11) CA 1237938
(21) Application Number: 467546
(54) English Title: FLAVOR ENHANCING SEASONINGS AND FOODS HAVING ENHANCED FLAVOR
(54) French Title: ASSAISONNEMENTS AUGMENTANT LA SAPIDITE ET ALIMENTS ASSAISONNES DE LA SORTE
Status: Expired
Bibliographic Data
(52) Canadian Patent Classification (CPC):
  • 99/139.09
(51) International Patent Classification (IPC):
  • A23L 27/21 (2016.01)
(72) Inventors :
  • KIMIZUKA, AKIMITSU (Japan)
  • UEDA, YOUICHI (Japan)
  • SAKAGUCHI, MAKOTO (Japan)
  • MORI, NORIKAZU (Japan)
  • MIYAJIMA, RYUICHI (Japan)
(73) Owners :
  • AJINOMOTO CO., INC. (Japan)
(71) Applicants :
(74) Agent: NORTON ROSE FULBRIGHT CANADA LLP/S.E.N.C.R.L., S.R.L.
(74) Associate agent:
(45) Issued: 1988-06-14
(22) Filed Date: 1984-11-09
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data: None

Abstracts

English Abstract



ABSTRACT OF THE DISCLOSURE

The invention relates to seasoning and foods
comprising
i) a taste intensifying substance, and
ii) a flavor enhancing substance which is at
least one member selected from the group consisting of
glutathione, a salt of glutathione, oxidized
glutathione, a salt of oxidized glutathione sulfonic
acid, cycloallin, a salt of cycloallin, lenitinic acid,
a salt of lentinic acid, des-glutamyl lentinic acid, a
salt of des-glutamyl lentinic acid, methionine methyl
sulfonium, a salt of methionine methyl sulfonium, a
compound of the formulae

Image (I) Image (2)

wherein R is hydrogen, a saturated or unsaturated aliphatic hydro-
carbon group of from 1 to 3 carbon atoms or a carboxyalkyl group
wherein said alkyl is from 1 to 6 carbon atoms, R' is OH, or a
carboxymethylamino group and R" is H or a .gamma.-glutamyl group,
a salt of compound (1) and a salt of compound (2).


Claims

Note: Claims are shown in the official language in which they were submitted.


The embodiments of the invention in which an exclusive
property or privilege is claimed are defined as follows:

1. A composition comprising:
i) a taste intensifying substance, and
ii) a flavor enhancing substance comprising at
least one member selected from the group consisting of
glutathione, salts of glutathione, oxidized glutathione,
salts of oxidized glutathione, glutathione sulfonic acid,
salts of glutathione sulfonic acid, cycloallin, salts of
cycloallin, lenitinic acid, salts of lentinic acid, des-
glutamyl lentinic acid, salts of des-glutamyl lentinic
acid, methionine methyl sulfonium, salts of methionine methyl
sulfonium, compounds of the formula:


Image
(I)
Image
(2)

or salts thereof wherein R is hydrogen, a saturated or unsaturated
aliphatic hydrocarbon group of from 1 to 3 carbon atoms or a
carboxyalkyl group wherein the alkyl moiety has from 1 to 6
carbon atoms,
R' is OH, a carboxymethyl amino group or a salt of
a carboxymethyl amino group, and
R" is H, a .gamma.-glutamyl group or a salt of a .gamma.-glutamyl

group.

92

2. A composition according to claim 1, wherein salt
flavor enhancing substance comprises at least one non-toxic,
organoleptically acceptable salt of said compound of formula
(1) or (2).

3. A composition according to claim 1, wherein said
taste intensifying substance comprises glutamic acid, a salt
of glutamic acid or a mixture thereof.

4. A composition according to claim 3, wherein said
taste intensifying substance comprises a non-toxic, organo-
leptically acceptable salt of glutamic acid.

5. A composition according to claim 1, 2 or 3,
wherein said flavor enhancing substance is present in an
amount in the range of 0.1 to 1000% by weight based on the
weight of said taste intensifying substance.

6. A composition according to claim 4, wherein said
flavor enhancing substance is present in an amount in the
range of 0.1 to 1000% by weight based on the weight of said
taste intensifying substance.

7. A composition of claim 1, 2 or 3, wherein said taste
intensifying substance is present in an amount sufficient to
obtain an adequate taste intensifying strength.



8. A composition of claim 4, wherein said taste
intensifying substance is present in an amount sufficient to
obtain an adequate taste intensifying strength.

9. A composition according to claim 1, 2 or 3, wherein
said flavor enhancing substance is present in an amount in
the range of 0.1 to 1000% by weight based on the weight of
said taste intensifying substance, and said taste intensifying
substance is present in an amount sufficient to obtain an
adequate taste intensifying strength.

10. A composition according to claim 4, wherein said
flavor enhancing substance is present in an amount in the
range of 0.1 to 1000% by weight based on the weight of said
taste intensifying substance, and said taste intensifying sub-
stance is present in an amount sufficient to obtain an adequate
taste intensifying strength.

11. A composition according to claim 1, wherein said
taste intensifying substance comprises a nucleic acid or a
salt of a nucleic acid.

12. A composition according to claim 11, wherein said
taste intensifying substance comprises a non-toxic, organo-
leptically acceptable salt of a nucleic acid.

94


13. A composition according to claim 11, wherein said
taste intensifying substance comprises 5'-inosinate, a salt
of 5'-inosinate, 5'-guanylate, a salt of 5'-guanylate or a
mixture thereof.

14. A composition according to claim 11, wherein said
taste intensifying substance comprises a non-toxic, organo-
leptically acceptable salt of 5'-inosinate or 5'-guanylate or
a mixture thereof.

15. A composition according to claim 11, 12 or 13,
wherein said flavor enhancing substance is used in an amount
in weight ratio of 1 : 99 to 99 ; 1 relative to said taste
intensifying substance.

16. A composition according to claim 14, wherein said
flavor enhancing substance is used in an amount in weight
ratio of 1 : 99 to 99 : 1 relative to said taste intensifying
substance.

17. A composition according to claim 1, wherein said
taste intensifying substance comprises glutamic acid or a
salt of glutamic acid, said taste intensifying substance
further comprising at least one member selected from the group
consisting of 5'-inosinate, a salt of 5'-inosinate, 5'-
guanylate and a salt of 5'-guanylate;



wherein the taste intensifying strength of said
substance is determined as follows;
i) for 5'-inosinate or a salt thereof:
y = u 1218 uv
ii) for 5'-guanylate or a salt thereof:
y = u 2800 uv;
wherein
y is the taste intensifying strength,
u is the glutamic acid or glutamic acid salt con-
centration expressed as a weight %,
v is the 5'-inosinate or 5'-inosinate salt con-
centration expressed as a weight %, or
v is the 5'-guanylate or 5'-guanylate salt con-
centration expressed as a weight %; and
y is in the range of 0.1 to 30 weight %.

18. A composition according to claim 17, wherein said
taste intensifying substance comprises a non-toxic, organo-
leptically acceptable salt of glutamic acid and said further
taste intensifying substance comprises a non-toxic, organo-
leptically acceptable salt of said group.

19. A food composition comprising a food component
and a flavor enhancing amount of a composition as defined in
claim 1.

96

20. A food composition according to claim 19, wherein
said food component comprises a pork sausage, tomato juice,
Japanese sake, consomme soup, noodle soup, corn cream soup, soy
sauce, soybean taste soup, Worcester sauce, seaweed boiled
down in soy sauce, sea urchin egg paste, beef extract,
shrimp extract, onion extract, curry, garlic extract or rice.

97

Description

Note: Descriptions are shown in the official language in which they were submitted.


- 6 US
~L~3~1




TITLE OF THE INVENTION
-

FLAVOR ENHANCING SEASONINGS AND
FOODS AGO ENHANCED FLAVOR

BACKGROUND OF THE INVENTION.
Field of the Invention:
.
This invention relates to seasoning and food
having enhanced flavor by the addition of sulfur-
containing compound.

n of the Prior Art:
The taste intensity imparting function of
representative "Umami" substances, namely, sodium
L-glutamate (MUG), sodium insinuate (IMP) and sodium
5'~guanylate (GYP) is widely known. A wide variety of
seasonings obtained from MUG, IMP and GYP can be
appropriately combined with protein hydrolysate~ (HOP,
ZAP), yeast extract (YE), amino acids etc. In their
various application, these substances have been
increasingly used for the purpose ox enhancing
organoleptic characteristics of foods such as the
"Umami" (MUG like ticket flavor etc.
Although ~Umami" substance enjoy popularity and
wide application, there has still been a demand for

--2-- `



extending their function; to further develop their
flavor characteristics More specifically, there ha
till been a demand to further develop the thickness,
amplitude, continuity etc. of Umami~ substance This
it a property which is different from their taste which
tithe effect achieved by a combination of saltlnes~,
sweetness, acid taste etc. a it done to further
enhance a taste.
Hence, throughout this text the term tasty is used
to de crime the basic saltiness, sweetness and acidity
properties of the "Umami" substance described above.
The term flavor it lied to describe the thickness,
amplitude and continuity properties of "Umami"
subcutaneous. The terms asset and flavor do not describe
the aye properties. Rather they describe different
properties which can be complementary.

SUMMARY OF THE INVENTION
Accordingly, one object of this invention is to
provide a novel enhanced flavor seasoning so food
having enhanced flavor.
The prevent inventor have discovered that
(1) glutathione (GUSH) and oxidized glutathione SAG --
hereinafter called generically as 'IGSHn -,
I glutathione sulfonic acid (GSO3~, (3) cycloallin --
hereinafter called KIWI -, (4) lentinic acid,

I
--3--



des-glutamyl lentinic acid and the salts thereof --
hereinafter called generically as "LA" -,
(5) methionine methyl sulfonium (MUMS), and (6) compound
of the following general formula (1) or (2):

o




R-S- CH2-CHCOR' R-S-CH2CHCOR'
NOR" (I)
NHCOCH2-CH2CHCOOH
NH2 (2)
wherein R is hydrogen, a saturated or unsaturated aliphatic
hydrocarbon group of 1-3 carbon atoms or a carboxyalkyl
group wherein the alkyd group is from Of to I
R' it OH or a carboxymethylamino group, and
I" is H or a y-glutamyl group,
have flavor intensifying properties.
As the result of further detailed investigations
on taste and flavor intensity, it has been discovered
that they compounds manifest strong flavor enhancement
in the presence of MUG, a nucleic acid type taste
intensifying substance or a mixture thereof.

DETAILED DESCRIPTION OF TOE PREFERRED EMBODIMENTS
Glutathione tGSH)I oxidized glutathione ~GSSG),
glutathione sulfonic acid (GSO3H), cycloallin (CA),
lentinic acid and des-glutamyl lentinic acid (both
hereinafter generically referred to a LA) and
methionine methyl sulfonium MUMS have been confirmed
to be widely present in foods, natural products etc.


. . .

--4--



Part of compounds (1) and (2) shown above were
known as precursor substance for specific taste
components in food in which these are present. Other
parts of compounds (1) and (2) are presumed to be
present in the metabolism route in foods, but no
reference has been made to their relation to flavor
intensity. Further, it is impossible to guess what
flavor intensifying function these compounds manifest
in the presence of the Umami components.
It has now been discovered that GUSH, GSSG, GSO3~,
CA, LA, MUMS and compounds of the general formulae (1)
and (2) shown below

O
R-S- SHEA -SHAKER ' R-S-CH2 SHAKER '
NOR" (I)
NHCOCH2 -Chihuahuas SCHICK
NH2 ( 2 )


wherein R is hydrogen, a saturated or unsaturated aliphatic
hydrocarbon group of 1 to 3 carbon atoms or a
carboxyalkyl group wherein the alkyd group is from C
to C6,
R' is OH or a carboxymethylamino group, and
R" is or a y-glutamyl group
manifest strong flavor enhancement in the presence of
MUG, a nucleic acid type taste intensifying substance
or a mixture thereof. As the result of a detailed

I.


--5--



study on various combination and formulations of
glutamic acid, glutamic acid alto or nucleic acid type
taste intensifying substances with scan, "GSHn,
"GS03~", Nolan or MUMS it ha been discovered that
these 3ulfur-containing compound are widely effective
in the enhancement ox flavor. Their discovery thus
provides the possibility for novel flavor enhancing
seasoning and foods by incorporating together "Umami"
components and the ~ulfur-containing compounds. The
prevent invention relates to such combinations.
GUSH ha been studied forts physiological
activity, pharmacological efficacy etc. It has been
used as eye a liver disease treatirlg agent, an
antipyretic etc. Various application of GUSH to foods
are Allah known Some of these applications are given
below. (1) GUSH ha been added to dough product of
go flour etc. as thy occlude amino acid type,
reducing agent like Sistine etc. ( Sex Japanese Patent
Publication Nos. 19863/1974. 16418/1975, 1773/1976,
9019/1976, 33981/1976, 9893/1981, Japanese Patent
Application Laid-open No. 11967/1972, 30855~1972,
98052/1973, 122762/1979, 23853/1981 etc.) ,
(2) Similarly, GO has been added to sour milk and baby
foods a a storage stabilizer for vitamin C. (See
Japanese Patent. Publication Nos. 7143/1975 and
21606/1370.) (3) GO has been added to wish pate

--6--



products such a boiled fish taste as a decomposition
inhibitor for nucleic acid type taste intensifying
substance. (See Japanese Patent Publication No.
8694/1968.) (4) GUSH has been added as an agent to
relieve the yeast odor of yeast extract. see Japanese
Patent Publication No. 6232/1969. ) (5) GO has been
used for the purpose of preventing the discoloration of
canned fruit (See Japanese Patent Publication No.
206~5~1965.) (6) It has been used to intensify the
flavor of foods, especially canned meat by being
combined with sugar, amino acids etc. by reaction.
see Japanese Patent Publication Nos. 22194/1967,
35149tl974, aye etc.) (7) It has been used to
intensify cheese flavor. (See Japanese Patent
Publication No. aye and the like.)
In these examples of applications of GUSH to foods,
GUSH is used as a physical property modifier
as in above (1). In I (6) and (7)
etc. above, there are no comments regarding the taste
intensity of GUSH. Furthermore, the amounts of GUSH
added are only extremely small amounts. For example,
only 0.01 I 0~05~ GUSH is added in the cave of dough
products, 0.001 to 0.02~ in the case of baby foods.
Even in the case of taste intensification in meats or
cheese (a in (6) or (7) above), a similarly extremely
small amount is added Therefore, it it clear from the

331
--7--



above examples that there ha been no finding in the
prior art of GUSH actually having a flavor intensifying
function. Moreover, it is entirely impossible Jo Know
or predict what flavor intensifying function, if any,
GUSH would manifest in the presence of other taste
component.
GSO38 is known a a component in enokidake. It
presence has also been confirmed in a part of other
mushrooms. The significance of it presence or its
lo role in food have not yet been described There it no
reference in the prior art concerning the taste
intensity of GSO3H. Further it it entirely impossible
to know or predict what flavor intensifying functions,
it any, GSO3H manifests in the presence of the "Umami"
component.
Lentinic acid is contained in ~hiitake and it
known as a precursor to the odor of Shattuck. When
Shattuck tissue is damaged or dried Shattuck it
reconstituted with water, it undergoes various chemical

and/or biochemical reactions; e.g., enzymatic action by
y-glutamyl transfers, C-S lease etc. Resultingly
lenthionine which is an odorous principle of Shattuck
it f orbed.
In non of the aboYe-de~cribed research was there
any mention suggesting the flavor intensity of lentinic

-a-

acid. Further, it it entirely impossible to know or
predict what flavor intensifying function, if any,
lentinic acid manifests in the presence of the "Umami"
components.
MUMS is Allah known as vitamin I. It has been
intensively investigated for its pharmacological
efficacy and has been used as e.g. an anti ulcer
agent. Various applications of MUMS in foods are also
known. Some of these applications are given below.

(1) MUMS has been used also for the purpose of
intensifying and modifying the taste of food by adding
it as a so-called taste precursor substance to the food
and subsequently converting it into a taste substance
by heating. (See Japanese Patent Application Laid-open
No. 92663/1979 etc.) I MUMS has been used for the
purpose of enhancing the nutritional value of soybean
paste, bean milk etc. (See Japanese Patent Publication
Nos. 19827/1968 and 13979/1974.) (3) It is used as an
antioxidant for oils and fats. (See Japanese Patent
Publication No. 1125/1975.) (4) And it is used for the
purpose of preventing the decomposition of vitamin
By. In this use it is incorporated in compositions to
which sulfurous acid has been added to serve as a
deterioration inhibitor, e.g., medicines, foods etc.
(See Japanese Patent Publication No. 6153/1963.)

- 9 -

There has been no disclosure relating to the
flavor intensity of MUMS in any of these application.
Further, it it entirely impossible to guess or predict
what flavor intensifying function, if any, MUMS
manifests in the presence of the nUmami" components.
Cycloallin is also crown as amino acid. It it a
sulfur-containing component in onion and garlic. There
are only few studio of it characteristics. It is
known that cycloallin is formed by reaction of 5 -

propenylcysteinsulfoxide which is contained in 3% by
wt. as a dry matter in onion. In none of the research
relating to cycloallin, described above, are there any
remarks of the flavor intensity of cycloallin.
Further, it is entirely impossible to know or predict
what flavor intensifying junctions, if any, cycloallin
manifest in the presence of the "Umami" components.
In accordance with the punt invention, a
characteristic flavor intensity enhancing effect can be
obtained by using 'IGSH", GSO3H, "Can, "LA" and/or MUMS
in combination with conventionally known "Umami"
compounds such as MUG, IMP, GYP etc. The prevent
invention further provide that these combinations are
made in accordance with specified ratios. This
invention relates to the intensification of the
impression ox taste (flavor enhancement and to further

--10--

impart flavor. flavor here is the continuity,
' amplitude, thickness, etc. of the original taste
"Umami~, bitterness, sweetness, acid taste, saltiness
etc. while the original taste remain unchanged
The mixing ratio of the "Umami" component to thes,ulfur-containing component selected from the group
consisting ox lush GS03~, "con, ALA" and.MMS may be
determined as follows. The amount of the sulfur-
containing compound or compounds added is within the
range of 0.1 to 1000% by weight based on the weight of
the present "Mom" component. The "Umami" component
it calculated as the weight of IS required to manifest
the same "Umami" strength. All comparisons are made
.. .
to the "Umami'l strength ox MUG- When a nucleic acid type
taste intensifying substance such as IMP, GYP etch ;
is.used..a:lone, the mixing ratio of ~ulfur-containing
compound or compounds is 1 : 99 to I :.1.
For example, in the cave where the "Umami" component
comprises only MUG, the ~ulfur-containing compound or

compounds are present at a concentration of 0.001 to 10
time that of MSG. In the other cave, i.e. where MUG
and IMP or GYM are also present a the nUmami"
component, the "Umami" strength (y value) may be
determined according to the following equation:
IMP: y = u + 1218 us
GYP: y = u 28,00 us

~7~3~


wherein u = MUG concentration 1%), and v = IMP or GYP
concentration
While the conversion equation to obtain each y
value can vary depending on the kinds and number of the
tastiness components etc., the conversion equation
e~kabli~hed by organoleptic comparison with a
- simple aqueous solution of MUG may be appropriately
used. For instance, the y value where IMP and GYP are
used in combination at a ratio ox 50:50 is as follow:


y = u + 2010 us


wherein u = MUG concentration I and v = IMP/GMP
mixture concentration t%).
In this invention a characteristic flavor
enhancing effect can also be obtained by using the
compounds of the general formulae (1) and (2) (shown
below) either singly or as a mixture.




R-S-CH2-CHCOOR' (1) R-S-CHCOOR' (2)
NOR NHCOCH2CH2CHCOOEI
NH2

wherein R it a saturated or unsaturated aliphatic
hydrocarbon group of 1 to 3 carbon atom, or a

carboxyalkyl group wherein the alkyd group is from C
to C6,

-12-



I' is H or a carboxymethylamino group, and
R" is or a y-glutamyl group.
The compounds of general formulae (1) and (2) are
used in an amount falling in a specified ratio to the
"Umami" components such a MUG, IMP, GYP etc. The
effect in this case it to intensify the impression of
the taste and further impart flavor, to further develop
the continuity, amplitude, thickness etc. The flavor
thus obtained is characterized by that the original
taste -- nUmami" bitterness, Whitney g, acid taste,
~altine3~ etc. -- remain unchanged.
The mixing ratio of the "Umami" component to these
compounds may be determined as follows. The amount of
compound (1) or (2) or combination thereof added is
0~1 to 1000% by weight bayed on the weight of the also
prevent "Umami" component. The weight of the Allah
present "Umami" component it calculated as the weight
of, e.g. MUG, required to manifest the tame "Umami"
strength. When a nucleic acid type taste intensifying
substance ugh as IMP, GYP etc. are used alone, the
mixing ratio of these to compounds if) or I or
combination thereof is in the range of l:99 to 99:1.
In other words, in the case where the "Umami n component
comprises only MUG, compound if) or (2) or combination
thereof are prevent in an amount of 0.001 to 10 times
the concentration ox MUG In the other cave, i.e.,


..


i ,

-13-



where MUG and IMP or GYP are present as the "Umami"
components, the "Umami n strength (y value) may be
determined according to the fang equations:
IMP: y = u + 1218 us
GMP y = u + 2800 us
wherein u = MUG concentration (%), and v = IMP or GYP
concentration (%).
While the conversion equation to obtain each y
- value can very depending on the kinds and number of the
"Umami" components etc., y values established by
organoleptic comparison against a simple aqueous
solution of MUG may be appropriately used. For
instance, the y value where IMP and GYP are used in
combination at a ratio of 50:50 is as follows:
y - u 2010 us
wherein u - MUG concentration I and v - IMP/GMP
mixture concentration
The compounds of formulae (1) and (2) can also be
used in combination with any of the other sulfur-
containing compound: "GUSH", GS03H, "CA", "LA" and
MUMS
Other features ox the invention will become
apparent in the course of the following descriptions of
exemplary embodiment which are given for illustration

I
-14-



of the invention and are not intended to be limiting
thereof.


Experimental Example l
(Evaluation in Swim to A use Solution S stems)
P_. q _ _ Y

. Using as a control a mixed aqueous solution of
0.05 gel of MUG and 0.05 gel of IMP value = 3.09),
sample solutions were prepared by adding 0.001 to 0.5
gel of GO to the mixed aqueous solution. These
sample solutions were organoleptically evaluated by
paired comparison texts against the control using an
organoleptic panel of 20 member (N = 20). The results
are given in Tub l.


Table l
M = 20

Formulation Taste Intensifying Effect
Strength of
MUG IMP GUSH Strength of Flavor
gel gel do "Umami" _ Enhancement
Control 0.05 0.05 -- +
simply A n Al 0 . 001 i .
n 0 . 01 + I+
C O . 05 + ~+~
D ++++
E n Al o ., 3 it ++++++

F n o . 5 I



.,

- l s -

The following notation it used throughout the
examples: (~) = enhancement of property being
investigated, (+~) = pronounced enhancement, etc.,
(~) = no noticeable enhancement, (-) = mitigation of
property being investigated.)


... . .
As shown in Table 1, with less than 0.1% of GUSH
added, bayed on the y value (MUG calculated amount),
the strength of flavor is comparable to that of the
control. But by the addition of 0.1% or more of GO
the flavor alone it remarkably increased without
changing the strength of ~Umami" and other basic
tastes. If the absolute concentration of GUSH exceeds
1.0%, specific thickness in taste is manifested and the
total taste balance is lost. Therefore, the amount of
GUSH added should suitably be in the range of 0.1 to
1000% by weight, preferably 0.1 to 50% by weight, based
on the weight of the also present tastiness
component. Where the amount of tastiness component
used is calculated as the weight of MUG having the same
"Umami" strength. (See equations above Further, GO
manifest the most preferred effect in the presence of
an appropriate amount of the above "Umaci n component,
that is, when the above y value it 0.1 to 30 as the
concentration at the time of eating.

no
-16-



On the other hand, in the cave where the nucleic
acid type taste intensifying substance such as IMP, GYP
etc. it used alone, if GUSH is added at a ratio of less
than 1/99 to the nucleic acid type taste intensifying
substance, the flavor enhancing effect it not
adequate. Further when GUSH is present in an amount of
250%/wt. or more based on the amount of nucleic acid
type taste intensifying substance, GUSH manifests the
most preferred effect. Whereas if GUSH exceeds a ratio
ox 99/1, a specific thicken in taste is brought about
and the total taste balance is lost.

AL
tEvaluatlon in reef Extract Stems
According to the analytical value of bee
extract, the effect of the addition of GUSH to a
formulation of major components was evaluated by paired
comparison test against a control. The results are
given in Table 3, from which it has been confirmed that
in the synthetic beef extract a well, GUSH imparts a
higher natural taste by manifesting a strong flavor
enhancement.




Jo


table 2
Formulation of Major
Components of Beef Extract

Formulation

MUG 3 %
IMP 3
Nail 11
K2HP04 10
RH2P04 25
dummy lactate 20
Histidine hydrochloride 20
Ala nine 4
Lawson hydrochloride 4
100



Table 3
.
Major . Strength of
Component GUSH Flavor
. gel ~/dl_Enhancement
.
Control 2 0

Sample A n . 0. 01 I+
B n 0.1 to
C n 0~2

.
GUSH in this invention Jay be obtained by any
production process, such as an extraction process, a
synthesis process etc. Further, it it also possible to
replace the whole or part of the required GUSH by a
substance containing GO


~7~13~
-18-



Exeerime to 3
.




(Evaluation in Shrimp Extract Systems)
According to the analytical values of the extract
components I shrimp which it a natural delicious food,
the major components were formulated and organolepti-
gaily evaluated similarly a in Experiment Example 2.
These texts confirm, as shown in Table 5, that GUSH
imparted-a higher natural taste by manifesting a strong
flavor enhancement as it did in beef extract toots.


Table 4
formulation of Major Components)

MUG 3~9 %
IMP 3~9
Nikko 12~6

~2HP4 13.0
~H2P04 5~3
Sodium lactate 15.3
Ala nine 15.4
Gleason 15.3

Arginine 15.3
100 . O



Table 5

major Strength of
Component GUSH Flavor Strength of
gel ancient Natural Fuel
Control 1.3 0 + +
Sample A " 0.006~+ ++++
B 0.06 Ho I+
C n 0 .12 Hut

--19

Experimental Example 4
(Evaluation on simple Awoke Sly stem ?
)




A mixed aqueous solution Go I 05 gel of MUG and
0.05 gel of IMP (y value = 3.09) was used as a
control. Sample solutions were prepared by adding
0.002 to 1.0 gel of GSO3~ to the mixed aqueous
solution, and these were organoleptically-evaluated by
paired comparison text against the control using an
organoleptic panel of 20 members (N = 20). The results
are given in Table 6.
Table 6
N = 20

m~latlo~ Taste Intensifying Effect
Strength of
MUG IMP GO Strength of Flavor
do Ed "Umam.i n Enhancement

Control 0.05 0.05
Sample A N 11 0 . 002 i +
B " " 0.02 + +
C n n 0,05 i t
D n n 0.1 + ++
E n I O, 15 i Jo
E' n Al 0.5 t- t++

F Al n I 0 i to
Go 0.1 Cot it



A shown in Table 6, with lies than 0.1% of GS0
added, based on the y value (MUG calculated amount
the strength of flavor enhancement it comparable to


I I
I



that of the control. By the addition ox 0.1% or more,
the flavor enhancement alone is remarkably increased
without changing the strength of "Umami" component. If
the absolute concentration of GS03H exceeds 1.0%,
specific thickness in taste is manifested and the total
taste balance it lout. Therefore, the amount of GS0
added should suitably be in the range of ,0,1 to 1000%
by weight, preferably 0.1 to 50% by weight, based on
the weight of co-present "Umami" component. The amount
of "Umami~ component used it calculated as the weight
ox MUG having the same "Umamin strength. (Sex
equations.) Further, GS03H manifests the Yost
preferred effect in the presence of an appropriate
amount of the above "Umami~ component, that it, when
the above y value is 0.1 to 30 as the concentration at
the time of eating.
On the other hand, if the nucleic acid type taste
inter flying substance is used alone and GS03~ is added
Nat a ratio of less than 1/99 relative to the nucleic
0 . acid type taste intensifying substance, the flavor
enhancing effect is not adequate, Whereat if this
ratio exceeds 99/1, a specific thickness intuit is
brought about and the total taste balance it 105t.


I
-21-



Experimental Example 5
(Evaluation in Simple Aqueous Solution Systems)


A mixed aqueous solution of 0.05 g/dl.of MUG and
0.05 gel of IMP (y value = 3.09) was used a a
control. Sample solutions were prepared by adding
0.002 to 1.0 gel of lentinic acid or des-glutamyl
lentinic acid (LA) to the mixed aqueous solution. These
sample solutions were organoleptically evaluated by
paired comparison against the control using an

organoleptic panel of 20 member ON = 20). the results
are given in Table 7.


Table 7

Formulation Taste Intenstifyin~ Effect
Strength of
MUG IMP "LA" Strength Flavor
. gel gel ox "Umami" Enhancement

Control 0.05 0.05 -- + +
Sample A n Al 0 . 002 -I +
B " " 0.02 -I +
2 0 C 0 r 0 5 +

D " " 0.1 + -I+
E " " 0.5 + +++

F " " 1.0 -~+~
G Jo 0.1 0.1 - .

~2~3~
-22-



As shown in Table 7, with amounts of added
lentinic acid or des-glutamyl lentinic acid lest than
0.1% bayed on the y value (MUG calculated amount), the
strength of flavor enhancement it comparable to that of
the control. But by the addition of 0~1% or more of
lentinic acid an deq-glutamyl lentinic acid, the flavor
enhancement alone is remarkably increased without
changing the strength of "Umami". If the absolute
concentration of lentinic acid or des-glutamyl lentinic
acid exceeds 1.0%, specific thickness in taste is
manifested and the total taste balance is lost.
Therefore, the amount of "LA" added should suitably be
in the range of 0.1 to 1000% by weight, preferably 0.1
to 50% by weight, based on the weight of co-pre~ent
tastiness component calculated as the weight of MUG
having the tame "Umami" strength. Further, "LA"
manifests the most preferred effect in the presence of
an appropriate amount of the above "Umami" component.
That is, when the above y value is 0.1 to 30 as the
concentration at the time of eating.
On the other hand, in the case where a nucleic
acid type taste intensifying substance such a IMP, GYP
etc. is used alone, if "LA" is added at a ratio of less
than 1~99 to the nucleic acid type taste intensifying
substance the flavor enhancing effect it not

-23



adequate. Whereat if this ratio exceeds 99/1, a
specific thickness in taste it brought about and the
total taste balance it 105t~


Experilnental Example 6
(Evaluation in Simple Aqueous Solution Systems)


A mixed aqueous solution of 0~05 gel of MUG and
0.05 gJdl of IMP (y value = 3.09) way used a a
control. Sample solutions were prepared (1) by adding
Oily to 1.0 gel of MUMS to the mixed aqueous solution,
and (2) by mixing aqueous solutions of 0.1 gel ox IMP
and 0.1 gel of MUMS. These sample solutions were
organoleptically evaluated by paired comparison test
against the control using an organoleptic panel of 20
members (N = 20). The results are given in Table 8.


Table 8 .
N = 20

Formulation Taste _Intenstlfying Effect
Strength of
MUG IMP MUMS Strength Flavor
gel do of '1Umam.i" Enhancement

Control . 050 . 05 -- +
Sample A " " O . 00 2 + +

O . 01 + +
C n n 0.05 i ++
Do It 0.1 + ++++
E n lo o . 5 -I +++++
F n n 1.0 i lo
Ho 0.1 0.1 +++~

I
-24-



As shown in Table 8, when the amount of added MUMS
it lest than 0.1% based on the y value (MUG calculated
amount), the strength of flavor enhancement and the
characteristic sweetness are comparable to that of the
control. But by the addition of 0.1% or more the
flavor enhancement and the characteristic sweetness are
remarkably increased without changing the strength of
"Umami" and the characteristic sweetness. If the
concentration of MUMS exceeds 1.0~, a character tic

lo aroma or specific thickness in taste is manifested and
the total taste balance is lost. Therefore, the amount
of MUMS added should suitably be in the range of 0.1 to
1000~ by weight, preferably 0.1 to 50% by weight, based
on the weight of also prevent "Umami" component. The
amount ox "Umami" component used it calculated a the
weight of MUG having the same "Umami" strength (See
equations.) Further, MUMS manifests the most preferred
effect in the presence of an appropriate amount of the
above "Umami" component. That it, when the above y

value it 0~1 to 30 a the concentration at the time of
eating.
On the other hand, when a nucleic acid type taste
intensifying substance such as IMP, GYP etc. is used
alone, if MUMS is added at a ratio of less than 1/99 Jo
the nucleic acid type taste intensifying substance, thy
flavor enhancement as well a the character~tlc

~L~23~793~3
-25-



sweetness enhancing effect is not adequate. Whereas if
the ratio exceed 99/1, a characteristic sweetness or
specific thickness in taste is brought about and the
total taste balance it lout.


Experimental Example ?
( Evaluation in Onion Extract Systems )


According to the analytical values of the onion
extract, the effect of the addition of MUMS to the
formulation of major components was evaluated by a
paired comparison test against a control case. The
results are given in Table 10, from which it has been
found that MUMS imparts clear vegetable characteristic
Sutton and strong flavor enhancement and gives a
natural feel.


Table 9
(Formulation of Major
Components in Onion Extract)
Formulation (%)

Glucose 25
Sucrose 15
Maltose 25
Amino Acids * 10

No Citrate 15
pa Palate 10
100

* Amino acids: a mixture of MUG, arginine, Lawson,
isoleucine, ~eucine, a~partic acid, Gleason,
phenylalanine and praline.

~37~
-26-

Table 10
Kirk- Flavor
major touristic Enhance- ayatollah
Component MUMS _ Sweetness mint Feel
Control 2 gel -- * +
Sample A " 0.01 gel I I+ +
Sample B " 0.1 Jo Jo
Sample C 0.2 ++ +~++
(cay. 0.04 gel as an MUG concentration)

Experimental Example 8
revaluation in Simple Aqueous Solution Systems)

A mixed aqueous solution of 0.05 gel of MUG and
0.05 gel of IMP (y value = 3.09) was used as a
control. Sample solutions were prepared by (1) adding
0.002 to 1.0 gel of cycloallin to the mixed aqueous
solution and (2) by adding 0.1 gel of cycloallin to an
aqueous solution of 0.1 gel of IMP. These sample
solutions were organoleptically evaluated by paired
comparison tests against the control using an
organoleptic panel of 20 members (N - 20). The results
are given in Table 11.

-27-

Table 11
N = 20
Formulation Taste Intent if in Effect
_ Y 9
Cycle- Strength of
MUG IMP Allen Strength Flavor
do - of ~Umami" Enhancement
Control 0.05 0.05 -- +
Simple A n n 0 002 + +
B " " O o 0 2 + +
C " " 0.05 + -1
D " " 0.1 + I+
E 'I " 0 . 5 + ~+~
F " " 1. 0 + *+ I-
G -- 0.1 0.1 + +

As shown in Table 11, when the amount ox added
cycloallin it less than 0~1% based on the y value (MUG
calculated amount), the strength of flavor enhancement
is comparable to that of the control. But by the
addition of 0~1% or more, the flavor enhancement alone
is remarkably increased without changing the strength
of "Umami". If the absolute concentration of
- cycloallin exceeds 2.0~, specific thickness in taste is
manifested and the total taste balance it 109t.
Therefore, the amount of chin added should suitably be
in the range of 0.1 to 1000% by weight, preferably 0.1
to 50~ by weight, based on the weight of co-presant
"Umami" component calculated as the weight of MUG




.. . .

I
-28-



having the same "Uma~i" strength. Further cycloallin
- manifests the most preferred effect in the presence of
an appropriate amount of the above ~Umamin component.
That is, when the above y value it 0.1 to 30 as the
concentration at the time of eating.
On the other hand, when a nucleic acid type taste
intensifying substance is used alone, if cycloallin is
added at a ratio of less than 1/99 to the nucleic acid
type taste intensifying substance, the flavor enhancing
effect is not adequate. Whereat if the ratio exceeds
99/1, specific thickness in taste is brought about and
the total taste balance is lost.
Gel or GS03H in this invention may be that
produced by any process, e.g., a fermentation process,
an enzymatic process, a chemical synthetic process or
mixtures thereof, etc. Further, it is also possible to
replace the whole or part of the amount of the required
GUSH by a substance containing GUSH at a relatively high
concentration such as yeast extract, garlic extract,
beef extract, chicken extract etc. The same may be
done with GS03H where a substance containing GS03~ at a
relatively high concentration, such as enokidake
extract, is used.
Lentinic acid in this invention may be obtained
from Shattuck as it well known in the art, e.g. by

~L~23~

-29-



extraction with alcohol, extraction with hot water,
etc. Further, it is Allah possible to replace the whole
or part of lentinic acid by an intermediate obtained by
such extraction .
Cycloallin in this invention may be obtained from
onion or garlic as is well known in the art, erg. by
extraction with alcohol, extraction with hot water,
etc. Further, it is alto possible to replace ha whole
or par of cycloallin by an intermediate, end product,
or a chemical or enzymatic-reaction product of the
extract containing the precursor.
Similarly, as regards the glutamic acid, nucleic
acid type taste intensifying substances and other
"Umami" component, the whole or part of said "Umami"
components may be replaced by such "Umami" components
as contained in foods and seasoning per so to which
the sul~ur-containing compound or compounds are to be
added.
The "Umami" components used in combination with
the ~ulfur-containing compounds in this invention
include, in addition to MUG, IMP and GYP, any component
having a "Umami" imparting effect. For example,
potassium glutamate, calcium glutamate, potassium 5'-
insinuate, calcium insinuate, potassium 5'
guanylate, calcium 5'-guanylate etch and any food or

~7~3~
-30-



seasoning which contain at least one tastiness
component a one of its constituent. For example,
ZAP, UP yeast extract, meat extract, fish extract,
vegetable extract etc. may be used.
The flavor enhancement seasoning of this
invention may be prepared by any process. For example,
the seasoning may be prepared by merely dry blending
MUG IMP, GYP etc. with these compounds by poulticing
them together with an appropriate excipient~, etc.
Similarly, with regards to the production of food
having enhanced flavor in accordance with this
invention, the actual manner for the production it not
limited a long as the "Umami" compounds and the
sulfur-containing compound or compounds are co-present
in the final product at the above-described mixing
ratio.
In addition, it it needless to Jay that the use in
combination of various seasonings, for example, salty
taste agents such as table salt, potassium chloride
etc., sweetening agents such as sugar etc., acid taste
agents such as organic acids etc., flavors, spices,
physical property modifiers etc. is possible unwell it
departs from the object of thus invention.
The seasoning or food of this invention manifest
a strong Titans enhancement as is the case when

I
-31-



seasoned with e.g. MUG, IMP, GYP eta, The quality of
these seasonings is refreshing but, differing from the
seasoning effect characterized by such strong single
taste as simple taste. This quality exerts a specific
effect permitting the enhancement of only the flavor
without changing the ~Umami" strength and the original
taste such as saltiness, sweetness and the like. The
seasoning or food of the present invention are
characterized by the impartation ox a complex natural
taste. Therefore the seasonings of the present
invention provide a novel flavor enhancement seasoning
having a high natural taste in the compound seasoning
field.
This invention it more particularly described by
the following example.


Example 1
Formulation of Flavor Enhancement Seasoning A
MUG 80 parts by weight
GUSH 20 "



Formulation of Flavor Enhancement Seasoning B
MUG 75 parts by weight
IMP 5 "
GUSH 20 n

~L~3~3~
-32-

Formulation of Flavor Enhancement Seasoning C
MUG 50 parts by weight
GYP 10 n
GO O n

Formulation of Flavor Enhancement Seasoning D
...
MSG80 part by weigh
IMP 3
3 n
GUSH 14 n

Formulation of Flavor Enhancement Seasoning Do
IMP 30 parts by weight
GYP 30 n
GUSH 40 "

Flavor Enhancement Seasoning A to Do were
prepared by mixing the respective compounds according
to the above formulation Using a each control a
product to which GO had not been added, aqueous
solutions of 0.4 gel of the respective samples were
prepared, and organoleptically evaluated by. a paired
comparison text using a 20 member panel of judge. The
results are given in table 12.

~23~3~ii5
-33-



Tubule
N = 29
A B C D DO

Strength of
n Um~.mi n Jo to +~+

Strength of
Flavor
Enhancement ~+-~ ++++-~ ~++++~ +~+~+ ++~++



Example 2


Table 13
Formulations of Flavor
Enhancement Seasonings E - H
(part by weight)
E F G H

HOP . 60 60 60 60
MUG 26 26 26 26
IN
GYP
Noah Succinate 2 2 2 2
Nail 10 10 10 10
GUSH It 8.3 16D733.3



Flavor enhancement Seasonings E to H were prepared
by mixing the respective components according to the
above formulations. Using a each control a product to
which GUSH had not been added, organoleptic evaluation
way conducted by a paired comparison test similarly as
in example 1. The results are given in Table 14.


EYE
-34-

Table 14
N = 10
Control . E F G H
Concentration 0.6 0.61 0.650.7 0.8
(Simple Sown)
gel
Strength of i i +
"Umami"
Strength of _ ++ +++ -~+~+~ I++++
Flavor Enhancement

Example
Formulation of Flavor Enhancement Seasoning I

MUG 1.5 part by weight
Potassium L-glutamate1.5 "
Nail 8 n
Clue 3 "
K2HP04 10 1-
KH2P04 I "
Sodium lactate 20 n
L-Histidine hydrochloride 20 "
DL-Alanine 4 n
Lawson hydrochloride 4 "
GO 5 n

I
-35-



Flavor Enhancement Swooning I was prepared by
-~~ mixing the respective components according to the above
formulation. A sample was then prepared by adding the
earning I to beef con~ome soup prepared in a
conventional manner at a concentration of 1 gel
Using as a control beef consomme 50Up to which GUSH had
not been added, the beef consomme 30Up was
organoleptically evaluated by a paired comparison test
-using a 20 member panel of judges. The results riven
in Table 15, show that the product of thy invention
enhanced the flavor such as thickness, amplitude,
. .
continuity etc. of the beef consomme soup. The beef
consomme 30Up containing seasoning I way significantly
more flavored as compared with the control.


Table 15
N = 20

Present
Control Invention

Strength of Odor & Flavor 9 . 11
Strength of "UmamiN 6 14**
Strength of Flavor
Enhancement 2 18***
Total Preference 2 18***



*** Significantly different at a risk factor of 0.1
I* Significantly different at a risk factor of I


~23~3~
-36-

Example

Table 16
Formulation of Flavor
Enhancement Seasoning J - M
I to

J R Control 1 L M Control 2
Yea~t100 100 100 100 100 100
Extract
MUG 5 1.5 1~5
IMP - - 1,5 1.5 1.5
GO 1 I - 1 I

Flavor Enhancement Seasonings J to M were prepared
according to the formulations of Table 16. They were
when organoleptically evaluated using 0.1~ aqueous
~olutlons of the respective samples by a paired
comparison test method. The results are given in Table
17~

Table 17
N = 10
Paired Comparison Paired Comparison

J K L. M
Strength of
Flavor
Enhancement -I Jo +!~+ ~++~




.
. .

~3~3~
-37-



A shown in Table 17, it ha been confirmed that
in yeast extract, GUSH had an especially strong effect
to impart flavor enhancement in the presence of
appropriate amounts of MUG and IMP.



... .
30 Parts by weight of Flavor Enhancement
Seasonings F and H and the control of Example 2 were
added respectively to a seasoning liquor (pi 4.2, 1
gel comprising 0.5 part by weight of citric acid, 0.6
part by weight of manic acid, 0.6 part by weight of
fumaric acid, 0.15 part by weight of succinic acid, 0.5
party by weight sodium polyphosphate, 2.0 parts by
weight of sorbitol and 0.4 part by weight of potassium
sorb ate.
500 g portions of preliminarily pickled radish
were pickled in 300 ml portions of the respective
seasoning liquors obtained above to prepare 3 kinds of
radishes pickled in a jar. These were then
organoleptically evaluated by a paired comparison
text. The results are shown in Table 18. The radishes
to which Flavor Enhancement Seasonings F and H had been
added were superior to the control radishes in both
flavor and preference.

37~3~
-38-



Table 18
N = 20

Control F Added H Added
Section Section Section

Strength of Odor
Flavor i
Strength of "Umami" +

Strength of
Flavor Enhancement +~+ I++
Preference +~+~ +

Example 6

Curry was prepared yin a conventional manner using
the recipe shown below and organoleptically evaluated
for strength ox flavor enhancement and total
preference. The results shown in Table 19 demonstrate
that the curry to which flavor enhancing Seasoning M
had been added had stronger flavor and was
significantly favored as compared with the control.

Recite for Queerly
.




Lard 8 Parts by weight
Low gluten flour 6
Curry powder 1.5
Table ail 1 7 "

Lecithin 0,04 n
Onion powder 0.3 "
Sugar 1.5 "
Flavor Enhancing
Seasoning in
example 4 0.5 "

or Control 2 in
Example 4) (0.5 )

~3~3~
-39-



Table 19
N = 20

Control 2 M Added
Added Section Section

Strength of Flavor
Enhancement 4 16**
Total Preference 5 15*


** Significantly different at a risk factor of 1%
* Significantly different at a risk factor of 5


lo Example 7
Pork sausages were prepared by using 650 parts by
weight of pork, 50 parts by weight of lard, 50 parts by
weight a corn starch, 5 parts by weight aft spices, 25
parts by weight of a salting agent, 220 part by weight
of cold water and 5 parts of each ox flavor enhancement
Seasonings N, P, 0. Pork sausages without seasoning
were used as controls. The seasoning containing pork
sausages and the control pork sausage were prepared by
emulsification according to the formulation shown in

Table 20. The pork sausages were prepared in a
conventional manner, and organoleptically tested to
find as shown in Table 21 that the pork sausage to

which flavor enhancement Seasoning N, P and 0 had been
added were significantly flavored as compared with that
to which the control had been added.

-40

Table 20
Formulation of
youthfulness Seasoning N, P & 0

Part By Weight
Control N P 0
Pork extract 20 20 2020 .
,. . .
Pork fat 20 20 20 20
MUG 10 10 10 .10
IMP 3
~Ajieki'~ produced
by Ajinomoto Kiwi 30 30 30
Sugar ester 2 2 2 2
Reducing dextrin 15 15 15 15
GUSH - 2 10 20

Tale 21
N = 10
Control
Added N Added 0 Added P Added
Section Section Section Section
_ _ .
mutt taste + + ++ ~-~+
Strength of Flavor
Enhancement i + I++ +++~

Preference ++ ++++ +++



* trade Mark

Jo

-41-



E ample 8


Tut confirmed that tomato juice, Japanese sake,
commercial con30mme soup, soy sauce, soybean taste
soup, Worcester sauce and seaweed boiled down in soy
sauce, either in which natural MUG and/or nucleic acid

. .
type taste intensifying substance had been already
present or to which they were added at the time of
production can be enhanced through imparting flavor
enhancement by adding varied amount of GUSH to each.
lo It was found that flavor enhancement was manifested in
a variety of foods by adding an amount of GO falling
. within the ranges shown in Table 22, tush.


Table 22
Effective GUSH Addition Range
Tomato juice 0.02 - 0.4 %
Japan sake 0 . 001 - 0 .1
Consomme soup 0.05 - 0,4
Soy sauce 0.05 - 0.4
Soybean pate soup 0.02 - 0.2
- Worcester sauce 0.05 - 0.4

Seaweed boiled down in
yo-yo sauce 0.1 0.6

I
-42-




Example 9


table I
Flavor Enhancement Seasoning
A' B' C' D' E'

MUG 80 75 50 80
IMP _ 5
GYP - - 10 3 30
GS03H 20 20 .40 14 40


Flavor Enhancement Seasonings Al to En were
prepared by mixing the respective components according
to the formulations outlined in Table 23. Using a a
control in each instance a composition to which G~03~
had not been added, aqueous solutions ox 0~4 gel of
the respective samples were prepared, and
organoleptically evaluated by a paired comparison
test. The results are given in Table 24.


Table 24
A' B' C' Do En

Strength of
n Umami" + Jo ++~ +++


Strength ox
Flavor Enhancement Jo +~+ I+ ++~

--43--



table 25
Formulations of Flavor

Sparta by weight)
FOG' Hi I' J' K'
...
HOP 60 60 6Q 60 - -
HAP -- -- -- -- 60 60
MUG 26 26 26 26 26 26
IMP
GYP
Noah Succinate 2 2 2 2 2 2
Nail 10 10 10 10 10 10
G503H 1.78.316.7 33.3 1.733.3

Flavor Enhancement Seasoning Alto K' were
. prepared by the mixing respective components according
to the above formulations. Using as each control a
composition to which GS03H had not been added,
organoleptic evaluation was conducted by a paired
comparison test. The results are given in Table 26.

Table 26
Control F' G' H' I' J' K
Concentra-
lion gel 0060~610.55 0.7 0.80.61 0.8
Strength ox
"Umami" i + + i + + +
Strength ox
Flavor
Enhancement I: + +++ ++~ I++

~37~
-44-

.

Consomme out were prepared according to thy
following formulations and organoleptically evaluated
for the strength of flavor enhancement and total
preference. The evaluation shows that the con30mme
soup to which Flavor Enhancement Seasoning I' had been
added had a stronger flavor and way significantly
favored a compared with the control.


Recipe for Consomme Soup


Consomme soup stock
(10 y of shaving of
dried bonito) 1000 ml
Soy Sauce 3 ml
Table salt 6.5 g

Flavor Enhancement
5ea~oning of Example 10
(or Control Section in
Example 10) 0.6 g



Table 2?

Flavor Enhancement
Control Added Seasoning H'
Section Added Section

Strength of
Flavor Enhancement 4 16 **

Preference of
Flavor Enhancement 5 5 *


** Significantly different at a risk factor of 1
* Significantly different at a risk factor of 5

I
-45-



Example 12


Noodle soup wag prepared using soy sauce, sweet
sake, sugar, MUG, nucleic acid type earning
hydrolyzed vegetable protein and dried bonito extract
according to the flavor recipe shown below. Organ-
septic evaluations of the strength of the flavor and
the taste of the noodle soup were conducted using a
portion of the soup to which GS03H had not been added
as a control. The evaluation was done by a paired
comparison text, to find as shown in Table 28 that the
portion of soup to which GS03H had been added had a
strong flavor and also was significantly favored for
total taste


Recipe for Noodle Soup
(for use when eating)
Soy sauce 250 g
"Sake" (Japanese rice wine) 50
Sugar 50
"Ajinomoto" 5
IN 0 2
Hydrolyzed vegetable protein 5
Dried bonito extract
t40g of flake of dried bonito we
extracted with 700g of hot water) 700
GS03H 2



* trade mark


it
...~,..,.,~

I
I

Table 28
Control Adagios Added
_ Section Section
S length of
Flavor
Enhancement 4 16**
Preference 4 16*~

_ zoom 13

Table 29
Flavor Enhancing Seasoning
Awn C" D" E
MUG 80 75 50 80
IMP - S - 3 30
GYP - - 10 3 30
Lentinic acid 20 I 40 14 40

Flavor Enhancing Seasoning A" to E" were prepared
by mixing the respective component according to the
above formulations. Using as a control in each
instance a portion to which lentinic acid had not been
added, aqueous solution of 0.4 gel of the respective
samples were prepared and organoleptically evil Ed by
a paired comparison test. The results are given in
Table 30.

I
-47-



Table 30

A By Sun D'' E

Strength of
n Umami n + Jo + t++ I++

Strength of
Flavor
Enhancement +++ -I+++ I++ I++
. . .

Example 14


Table 31
formulations of Flavor
Enhancing Seasonings OK
(parts by weight)
_ G" H" It J R"_

UP 60 60 . 60 60 - -
HAP - - - 60 60
MUG 26 26 26 26 26 26
IMP
GYP
Noah Succinate 2 2 2 2 2 2
I Nail 10 10 10 10 10 10
Lentinic Acid 1.7 8.3 16.7 33.3 1.7 33.3




Flavor Enhancing Seasonings F" to R" were prepared
by mixing the respective components according to the
above formulations. Using as a control in each case a
formulation to which ~entinic acid had not been added
organoleptic evaluation was conducted by a paired
comparison test similarly as in Example 13. The
results are given in Table 32.


~37~
-48~

Table 32
Control_ F" Gun Ho In Jo Kin
Concentra-
lion gel 0.6 0.61 0.65 0.7 0.8 0.610.8
Strength of
" Umami n i + + i i i: i
Strength of
Flavor
Enhancement + + I+ +~+ . I++ + +++

Example

Consomme soups were prepared according to the
formulations given in Table 33 and organoleptically
. evaluated for strength of flavor and total prefer-
once. The evaluations given in Table 34 show that the
. cOn90mme 90Up to which Flavor Enhancing Seasoning H"
had been added had stronger flavor and was signify-
gently favored as compared with the control

Table 33
Recipe for Consomme Soup
Consomme soup stock
(10 g of flake of
dried bonito) 1000 ml
Soy Sauce 3 ml
Table salt 6.5 g
Flavor Enhancing Seasoning
of Example 14 (or Control
Section in Example 14 0.6 g

I
-49-



Table 34

= 20

Flavor Enhancing
Control Added Seasoning on
Section Added Section

Strength of
Flavor Enhancement 4 16 **

Preference 5 15 *

** Significantly different at a risk fac~br of 1%.
* Significantly different at a risk factor of 5



Example 16
.




Rumba Tsukudani (tangle boiled down in soy sauce)
was prepared using tangle, soy sauce, sugar, MUG,
nucleic acid type seasoning, UP and starch syrup
according to the following recipe given in Table 35.
Organoleptic evaluations on the strength of flavor
enhancement and the preference were conducted using a
Rumba Tsukudani to which lentinic acid had not been

-
added a a control. The evaluation were done by a

paired comparison test, to find as shown in Table 35,
that the lentinic acid added section had strong flavor
enhancement and also was significantly favored for the
preference.

-50- ~237~

Table _
Recipe for Rumba TsuXudani

Tangle (after reconstitution in water) 1500 g
Soy sauce 1100 ml
Sugar 450 q
n Ajinomoto~ 60 g
n WE I 2 g
"Animate"* 30 g
Starch syrup 400 g
Lentinic acid g

Table 36
Lentinic Acid
Control Section Added Section
_
Strength of
Flavor Enhancement 4 16 **
Preference 4 16 **

Example .17.

Flavor Flavor Flavor Flavor Flavor
EnhancingF.nhancingEnhancing Enhancing Enhancing
SeasoningSea~oning Seasoning Seasoning Seasoning
A"' B"' C"' D"' DO"'
put by wit) opts by wit) opts by wit) (puts. by wit) (puts. by wit)
MUG 80 75 50 80
IMP - 5 - 3 30
GYP -- 10 2 30
MUMS 20 20 40 14 40
at 100 100 100 100 100

* trade mark

7~3~
-51



Flavor Enhancing Seasoning A n- to DO"' were
prepared by mixing the respective component outlined
in the above formulation Using as a control a
product to which MUMS had not been added, aqueous
solution of 0.4 gel of the respective ampule and
solutions incorporating 0.1% by weight of the same
respective samples in commercial tomato juice were
prepared. Their organoleptic evaluation way conducted
using a paired comparison test.
The results are given in Table 37 and Table 38.


table 37
Evaluation of Simple Aqueous Solutions
N = 20
A"' B"' C"' D"'

Strength of
~Umami n + ++ ++++

Strength of
Characteristic
Sweetness + + +++ I ++

Strength of
Flavor
Enhancement +++ ++++++ +~+++++ ++++++ ++~++

-52- I


, .

.
to Jo
a E
. I
,1 I Jo to

I
O
O
1- Go Jo o
O U Jo e an o
EGO Jo _ * Jo O J-
I Jo up CO a u a O
3 TV J
Tony
HO O I,
I to
'JO C , , a O ED
. pa * o Lo
c u * * a h E on
O U us I coy I- O
pa ¢ 3 v
1 I
U U
C
O
O E
Jo
if O
I _ Jo h
1i3 O - or. m *
Jo

Ed
v




o ,: c a
oh us
I En Al s E c
U h MY
JO C O
so s a En
S 3 Jo




.

~7~3~
--53--


I, 0 1~1 ID N O N O t`
= it N
O I) J

_ us o o o o I
_
Z: JO
.
Us
_ O us O O Lo
_

I I W --I JO --I
_ It I N Al I
It
Us
_ I O I
O _
a
a) I I o o -I I o
C _ ¦ I I N

O O
I _ , , I

I O I I I I
I Do

o I I ED
_ I I Jo .
I Us

O I I JO I Jo O
= I I
En I

o I I I o I
_

I_
aye
I . a
I ' V
Q
En Clod. V I h I U)
X 5 Z
ZOO:

54- I

+
o +

o I ++
I) Z +, + +

Z
+

+ +
... .



Al - I +, + .
oily --1 . +

++ +
":1 +' +

-I ++

e ¦ ++
ill I to t' +

- I +

.
L:
s a In. E
or U
C V o
D I C
Us V U31~

I
-55-



Flavor Enhancement Seasoning E no to o n- were
prepared according to the formulation given in
Table 390 (The tastiness strength, y value way
adjusted to 3.8). Using each aqueous solution, organ-
septic evaluations were conducted similarly to Example
17 by a paired comparison test using a control to which
MUMS had not been added.
The results are given in Table 40.



Example lo
.
Formulations consisting of lo parts by weight of

"Ajie~i" (produced by Ajinomoto Co. Inc.), Owl part by
weight of sodium ~uccinate, OHS part by weight of 50%
lactic acid, 0.5 part by weight a table salt and l
part by weight of sugar were dissolved in 100 ml of
water respectively, and 0.5 part by wright of Flavor
enhancing Seasoning G and 0 obtained in Example 2 were
prepared. Controls were similarly prepared omitting
the Flavor Enhancing Seasonings.
500 g of green asparagus was added to 500 ml of
each of the seasoned solutions obtained by adding
Flavor Enhancing Seasoning G and its control respect
lively. After boiling in a conventional manner, the
green asparagus were subjected to organoleptic
evaluation by a paired comparison test. Further, an

-56-



equal amount of corn was added to 500 ml of each of the
end solutions obtained by similarly adding Flavor
Enhancing Seasoning 0 and its control respectively.
After boiling in the conventional manner, these sample
solutions were subjected to organoleptic evaluation by
a paired comparison text. The result are a given in
Table 41, in which the Flavor Enhanced product those
product to which Flavor Enhancing Seasoning G and o
were added) were superior to the respective entirely in
the impartation of flavor, characteristic sweetness an
in preference.


Table 41
N = 20

Rosen Asparagus Sweet Corn
Control G Added Control 0 Added
Section Section Section Section

Strength of
Tattiness 12 18 11 9

Strength of
Characteristic
Sutton 5 15 * 4 16 **

Strength of
flavor
Enhancement 4 16 ** 3 17 **
Preference 4 16 ** 4 16 **


* Significantly different at a risk factor of 5~0
*I Significantly different at a risk factor ox

~2~7~3~
57-



Example 20
-




Corn cream 30up way prepared according to the
formulation outlined below. Then 80 g of this
formulation was fixed with 500 ml of cold water and,
after boiling, organoleptically evaluated for the
strength of flavor, vegetable-like taste and preference
by a paired comparison test against a control
formulation which had no added MUMS. These evaluations
reveal that, as shown in Table 42, the formulation with
added MUMS had a stronger flavor and way significantly
favored for vegetable-like tastiness and total taste.


Formulation for Corn Cream Soup
.
Edible oil 27 Parts by weight
Flour 18
Dried onion flake 1.2
Skimmed milk 12 n
Corn powder 15
Table Walt 10
Onion powder 4
20 MUG 1 n
IMP 0~5
White pepper 0.5 n
MUMS 1~0 n

-58-



Table 42
N = 20

Control MUMS Added
Section Section

Strength of
Flavor En Han event 4 16 *

~egetable-like
Tastiness 4 16 *
Preference 4 16 *


* Significantly different at a risk factor of 5%.



Example 21


A sea-urchin egg "Norm paste way prepared
according to the formulation outlined below this
paste was organoleptically evaluated for strength of
flavor, characteristic sweetness and total preference
by a pair comparison test method. This evaluation,
shown in Table 43 demonstrates that the formulations .
having added MUMS flavor and was significantly favored
as Compared with the control (MUMS not added.


I

Formulation for Sea Urchin Egg Paste

Raw material
sea urchin egg 5 Part by weight
Powdered egg 1 n
Alcohol 0~8
MUG 0.4 "
Gleason 0,4
Methionine 0.1
Courtney U.S.
Water 22.3 "
MUMS 0.3 "

Table 43
N = 20
Control MUMS Added
Section Section
Strength of
Sweetness 6 14
Strength of
Flavor Enhancement 3 17 **
Preference . 5 15 **

* Significantly different at a risk factor ox 5%.
** Significantly different at a risk factor of I

~237~3~
-60-



Example 22


A seaweed composition for rice to be eaten with
hot green tea ~Uchazuke~ was prepared according to the
formulation shown below. 8 g of the prepared
composition way placed on top of boiled rice and hot
green tea was poured to prepare rice and seaweed doused
in hot green tsar The composition wag then
organoleptically evaluated or strength of flavor and
total preference by a pair comparison test method using
a control to which no MUMS had been added. These
evaluations as shown in Table 44, the MUMS added section
had stronger flavor and was significantly savored.


Formulation for Seaweed Composition
For Rice with jot Green Tea


Tangle powder 0.5 Parts by weight
Powdered tea 2.0 n
Sugar 3.0
Table salt 53,0 n
"Ajinomoto" 10.0 n

Gleason 3 0 "
Shredded seaweed 5.0 n
- Rice cake pellets 5.0

MUMS 0.5 n

38
-61-

Table 44
N = 20
Control MUMS Added
Section Section _
Strength of
Flavor Enhancement 4 16 **
Preference 5 15 *
. . .


Table 45
lo Flavor Enhancing Seasoning
A I to C n D n n E
.
SO 80 75 50 ~80 --
IMP 5
GYP 10 3 30
Cycloalliin 20 20 40 14 40

The respective components outlined above were
mixed Jo prepare Flavor Enhancing Seasonings An" to
E"". A product to which cycloalliin had not been added
was used as a control in each cave. Aqueous solutions
containing 0.4 gel of the respective sample were
prepared, and organoleptical evaluation was conducted
by a pair comparison test method. The results are
given in Table 46.

~237~
I

Table 46
An no con Dun Elan
Strength of
n Umami n t+ ++~
Strength of
Flavor
Enhancement++ Jo I+ +++ +++
. . .


Table 47
Formulations of Flavor
Enhancing Seasonings F"" - K ""
(parts by weight)
F"" Go no lo n I no K""
HOP 60 60 60 60
HAP - -- -- -- 60 60
MUG 26 26 26 26 26 26
IMP
GYP
Noah Succinate 2 2 2 2 2 2
Nail 10 10 10 10 10 10
Cycloalliin1.7 3.7 16.7 33.3 1.733.3

The respective components outlined above were
mixed to prepare Flavor Enhancing Seasoning F"" to
I n . Using, as each control a product from which the
cycloalliin had been omitted, organoleptic evaluations



, . .


,

-63-



were conducted similarly as outlined in Example 23 by a
pair comparison test method. The result are given in
Table 48. -,


treble 48
Control Fun Gun Len n In Al Jell n K" I'
__ .
Concentra-
lion gel 0.6 0~61 0.65 0.7 0.8 0.61 0 8

Strength
of "Umami n -t + + t + +

Strength
of Flavor
Enhancement + Jo ~+~ +++ + I++


Example 25


Consomme soups were prepared according to
formulation outlined below. These were organ-
leptically evaluated or the strength of flavor and
total pruriency, to find that the consomme 80Up to
which Flavor Enhancing Seasoning H"" had been added had
stronger flavor and way significantly favored a
compared with the control
. . .
_

Consomme soup stock
(10 g of avowing .
of dried bonito) 1000 ml

Soy Sauce 3 ml

table salt 6.5 g

Flavor Enhancing
Swooning of Example Z4
(or Control Section
in Example 24) 0~6 g

~37~3~
I



Table 49

Flavor Enhancing
Control Added Seasoning H"
Section Added Section

Strength of
Flavor 4 16 **

Preference
of Flavor 5 15


** Significantly different at a risk factor of 1%.
* Significantly different at a risk factor of 5%.



Example 26


Chinese noodle 90Up way prepared using the
formulation outlined below The 90Up was then
organoleptically evaluated for thy strength of flavor
and total preference by a pair comparison test
method. This evaluation shows that the Chinese noodle
90Up to which Flavor Enhancing seasoning H"" had been
added had stronger flavor and was significantly favored
as compared with the control.


I
~65-

Formulation of Chinese Noodle Soup
Soy assay Parts by weight
Table salt 16 n
Lard 24 n
Sesame Oil 2 n
Animate
. . .
YE
Vegetable extract 8 n
Flavor Enhancing Sea owning
in Example 24 (or Control
Section 7 in Example 24) 7 n

Table 50
- 20
.. . .
Flavor Enhancing
Control Seasoning H"
Section Added Section
Strength ox
Flavor 4 16 **
Total
Preference 5 15 *

*I Significantly different at a risk factor of 1%.
* Significantly different at a risk factor of 5%.

I
-66-



Experimental Example 9
(Evaluation in Simple Aqueous Solution System)


Using as a control a mixed aqueous solution of
0.05 gel of MUG and 0.05 gel of IMP (y value - 3.09),
sample solution were prepared by adding 0.002 to 0.5
gel of Allen to portions of the mixed ago
- solution. These sample solutions were then organ-
leptically evaluated by paired comparison test against
the control using an organoleptic panel of 20 member
(N - 20). The results are given in Table 5.1.


Table 51

Formulation Tut Intensifying Effect
. Strength of
MUG IMP Allen Strength of Flavor
gel gel ~l_dl "Umami" Enhancement
Control 0.05 0.05
Sample AA n n 0 . 00 2
BY n n 0 . 02 +

CC n 0.05 i ++
2 0 DUD " .1

HE O. 3 i ~+~+
OF n I owe + to ++

GO --JO o l Ox Jo

~3~3~
-67-



As shown in Table 50, with the amount of added
Allen less than 0.1% based on the y value (MUG
calculated amount), the strength of flavor is
comparable to that of the control. But by the addition
of 0.1% or more, the flavor alone is remarkably
increased without changing the strength ofnUmamin. If
the absolute concentration of Allen exceeds 1.0%, a
specific thickness in taste is manifested and the total
taste balance is lout. wherefore, the amount of Allen

added should suitably be in the range of 0.1 to 1000%
by weight, preferably 0.1 to 500% by weight, based on
the weight of co-present component calculated a the
weight of MUG having the same "Umami" strength.
Further, Allen manifests the Yost preferred effect in
the presence of an appropriate amount of the above
"Umami"component, that is, when the above y value is
0~1 to 30 as the concentration at the time of eating.
When a nucleic acid type taste intensifying
substance it used alone, it Allen it added at a ratio

of less than 1/99 to the nucleic acid type taste
intensifying substance, the flavor enhancing effect it
not adequate. Whereas if this ratio exceeds 99/1,
specific thickness in taste is brought about and the
total taste balance is lost.

~3~3~
--68--



Excremental Example 10
( Evaluation in Garlic Extract Stems )


The of fact of the addition of Allen to a
formulation of major component of garlic extract was
evaluated by paired comparison text against a control
which contained no Allen. The result are given in
Table 53, from which it has been confirmed that Allen
impurity a higher natural taste by the manifestation of
wrong flavor with synthetic garlic extract.


Table 52
Formulation of major
Components of Garlic Extract
Formulation

Asp 3~6 %
Gnu 3 3
Lye 6.1.
Art 42.3
Other amino acid * 18.7
Nail 19.7
Clue 6.7
Citric acid 0.1
Succinic acid 0.1
100

* Son, Vet and Pro

-69-



Table 53

Major
Component Allen Strength ox strength of
_ gel gel F1~YOrNatural Taste

Control 1.0 0 i -

Sample AA 0.03 +
EBB n 0.1 ++ t
CC n O . 3 Jo Jo

Allen in this invention may be that obtained by

any production process, such a an extraction process,
a synthesis process etc. Further, it is alto possible
to replace the whole or part of the required Allen by
a substance containing Allen at a relatively high
concentration, or example,. garlic extract, onion
extract or other Allen extract.

Experimental Example 11

(Compari30n of asset Intensifying
Power of Representative Compound ?
Using as a control a mixed aqueous solution of

0.05 gel of MUG and 0.05 gel of IMP (y value = 3.09),
sample solutions were prepared by adding 0.1 gel of
the respective sample compounds shown in Table 52 to
the mixed solution These sample solution were
evaluated by a paired comparison text by an

organoleptic panel consisting of 20 member (N = 20).
The results are shown in Table 54.

~237~3~
-70

Table 54
(N = 20)
n~mami~ Flavor
(1) Control + +
I S-Methylcysteinesulfoxide +++
(3) S-Ethylcysteinesulfoxide + ++
I S-Propylcysteinesulfoxide i ++
(5) S-Propenylcysteinesulfoxide . Jo
(6) y-Glutamylcysteine + +
(7) ~-Gluta~yl-S-methylcysteine i +
(8) y-Gluta~yl-S-ethylcysteine i +
(9) y-Glutamyl-S-propylcysteine + +
(10) y-Glutamyl-S-propenylcysteine +
(11) y-Glutamyl-S-allylcysteine i ++
(12) y-Glutamyl-S-methylcysteinesulfoxide i ++
(13) y-Glutamyl-S-ethylcy~teinesul~oxide ++
(14) y-Glutamyl-S-propylcysteinesulfoxide ++~
(15) y-Glutamyl-S-propenylcysteinesulfoxide Jo
(16) y-Glutamyl-S-allylcysteinesulfoxide + Jo
(17) S-(2-Carhoxypropyl)glutathiorle ++
(18) S- Car boxy -methylethyl)glutathione ++

Experimental Example 12

Using the same mixed aqueous solution ox MUG and
IMP as that used in Experimental Example 11 a a
control, samples were prepared by adding thereto 0.001



I"' ' ' ; .

71_

to lo gel of the sample compounds outlined in
Table 54. Aqueous solutions of 0.1 gel of IMP and 0.1
gel of the respective sample compounds outlined in
Table 54 were alto prepared a someplace All of these
were evaluated by a pair comparison test method against
a control by an organoleptic panel consisting of 20
member (N = 20~. Some of the royalty are given in
Table 55 (the cave ofy-glutamyl-S-
allylcysteinesulfoxide).


lo Table 55

Formulation _ _ Taste Intensifying Effect
Compound
No. 16 in
Experimental
MUG . Example if Strength of Strength of
gel do gamin Flavor
.
Control 0.05 0.05 - i i

Sample M n 0~002 *

lob n n 0. 01 +

2 0 CC n n 0 . 05 i I+

DUD n n 0.10 +

HE " " 0~50 +

OF n n 1.00

0~1 0.10 - ,

~37~3~
-72-



As shown in Table 55, with an added amount of lets
Han 0.1% based on the y value (MUG calculated amount),
the strength of flavor it unchanged. However, with the
addition of 0.1% or more, the flavor is remarkably
increased. In this case, if the absolute concentration
of this compound (compound No. 16 of Experimental
Example 11) exceeds 1.0%, specific thickness in taste
it manifested and the total taste balance it lout.
Therefore, the amount of this compound added should
suitably be in the range of 0.1 to 1000~ by weight,
preferably 0.1 to 50~ by weight, bayed on the co-
present "Umami" component calculated a the weight of
MUG having the same "Mom" strength. Further, the
compound manifests the most preferred effect in the
presence of an appropriate amount of the above "Umami n
component, that it, when the above y value it
0.1 to 30 a the concentration at the time ox eating.
The above fact likewise applies to the other compounds
of the general formulae (1) and (2).
Jon the other hand, in the cave where the nucleic
acid type taste inter ifyiny substance it used alone,
if compound (1) or (2) is added in an amount of Lowe
Han 1/99 at the ratio to the nucleic acid type taste
intensifying substance, the flavor enhancing effect it
snot adequate. Whereat if this ratio exceeds 99/1, a

-73-



specific thickness in taste is brought about and the
total taste balance is lost. This also applies to the
other compound of the general formulae (1) and (2).


I, ' .
revaluation in Garlic Extract Systems)

Each compound set forth in Table 54 was added to a
formulation comprising major component of garlic
extract (set forth in Table 55). The composition were
evaluated by a paired comparison test using a control
which contained no addition of compounds of Table 540
The results are given in Table 57 from which it has
been confirmed that also in the formulated garlic
extract, these compounds impart a higher natural
flavor.

~L23~8
--74--

able 56
Formulation of Ma joy Component
in Garlic Extract

Formulation
Asp - 3 . 6 %
Gnu 3 . 3
.. .
Lye 6.1
Art 42 . 3
Other amino acid* 18 7
Nail 19.4
Clue . 6.7
Citric acid - - Owl
Succinic acid Owe

* Son, Vet, Pro

I
-75--

Table 5?
Concentra- Concentra-
lion of lion of
Formulated Compound Strength of Sterno
Extract Added Flavor of Natural
Compound Added (g/dl1 _ Enhancement flavor
(1) Control 1.0 0
(2) S~Methylcysteine-
~ulfoxi~e n 0.1 ++
I S-E~hylcy~teine-
sulfoxide n 0 1
I S-Propylcysteine-
sulfoxide n 0.1 I+ +
(5) y ~utamyl-
Sistine " 0.1
(6) y-Glutamyl-
S~a~lylcy~teine " 0.1 I+
(7) y-Glutamyl-
S-methylcysteine " 0.1
(8) y-Glu~a~yl-
S-Me~hylcy~teine " 0.1 + t
(g) ~-Glutamyl-
5-propylcysteine 0.1 i
I y-Glutamyl-
S-proFenyl-
cysteinesulfoxide n 0.1 Jo
(11) y-Glutamyl-
S-allylcysteine- .
sulfoxid~ " 0.03 +
~12) y~Glutamyl-
S-allylcysteine
guIfoxide n 0,.1 to
(13) y-&lutamyl-
S-allylcysteine-
sulfoxide 'I 0.3 lot I+

3~1


The compound of the general formulae (1) and (2)
may be used singly or as a mixture of two or more.
They can Allah be wholly or partially replaced by
3ub~tance~ which contain considerably high
concentration of these compounds, such as garlic
extract (preferably, extract from which the odor
component have been removed by deodorizing process
e.g. the processed described in Japanese Patent
Application No. 82169/1983), onion extract etch
Similar, the "Umami" component such a glutamic acid,
nucleic acid type Titans substances etc. can also be
wholly or partially replaced by nUmami n component
contained in the Good or seasoning per ye to which
these compounds are to be added
Examples of the "Umami" component which may be
used in this invention include, in addition to MUG,
IMP, GYP etch, any component having a "Umami" imparting
effect. Some of these are: potassium glutamate,
calcium glutamate, potassium insinuate, calcium 5'-
insinuate, potassium 5'-guanylate, calcium 5'-guanylate
etc. and any food or ~ea!qonin~ which contains said
"Umami" component a one of it constituting
components; for example, protein hydrolysate~ (HAP,
UP), yeast extract, meat extract, vegetable extract
etc.

I
-77-



The Flavor Enhancing seasonings of this invention
may be prepared by any process, for example, by merely
dry blending MUG, IMP, GYP etc. with these compounds by
poulticing them using an appropriate excipient, etc.
Similarly, for the production of food having enhanced
flavor according to thy invention, the actual manner
for the production of the food it not limited as along
as the "Umami~ component and these compounds are co-
present in the final product at the above-de cried
mixing ratio
In addition, it is needless to say that the use in
combination of seasonings, for example, salty taste
agents such as table salt, potassium chloride etc., - -
sweetening agents such as sugar etch, acid taste agents
such as organic acids etc., flavors, spices, quality
modifiers etc. may be possible unless it departs from
the object of this invention.
This invention is more particularly described by
the following examples.


I
-78-

Example 27

Table 58
Flavor Enhancing Sea~oninq
AA BY CC DUD HE
MUG 80 75 50 80
IMP . 5 3 30
GYP 10 3 30
S-Methylcysteine~
~ulfoxide 20 20 40 14 40

Of the compound ox the general formulae (1) and
(2), the exemplary case of S-methylcysteinesulfoxide is
jet forth in table 58. According to this formulation,
the respective components were mixed to prepare Flavor
Enhancing Seasonings AA to HE. A each control, a
product to which S-methylcysteine~ulfoxide had not been
added was used. aqueous solutions containing 0~4 gel
of the respective sample compounds (outlined in
Table 57) and solutions obtained by adding 0.1~ by
weight ox the sample compounds to commercial consomme
soup were prepared. An organoleptic evaluation was
conducted by a paired comparison test. The results are
given in Table 59 and Table 60.

~37~
-79-

Table 59
_ BY CC DUD HE_
Strength of
n Umami n + I+ ~++~ Jo
Strength of
Flavor I+ +++ ++~ +++ I

...
Table 60
Evaluation when Added to -
Commercial _ consomme S up
= 20
AA BY CC DUD HE
Strength of
"Umami n 12 16 ** 18 *** 17 ** 15 * -
Strength of
Flavor 13 15 * 17 ** 13 16 **
Taste 14 18 *** 18 *** 18 *** 18 ***

Each numeral in the table indicates the number of persons
who have found it preferable or strong.
* Significantly different at a risk factor of 5%.
** Significantly different at a risk factor of 1%.
*** Significantly different at a risk factor of 0.5%.

~3~3~
~80

eye

Table 61
Flavor Enhancing Seasoning
(part by weight)
_ GO HUH II JO OR_ _ _
UP 60 60 60 60 - --
ZAP 60 60
MUG 26 26 26 26 26 26
IMP
GYP
Noah Succinate 2 2 2 2 2
Nail 10 10 10 10 10 10
Sample Compound * 1.7 8.3 16.733.3 1.7 33.3

* Mixture of equal amounts ox S-methylcysteine~ulfoxide,
S-propenylcysteine~ulfoxide, S-propylcysteine3ulfoxide and
y-glutamyl~9-allylcyc~teine~ulfoxide.

According to the above formulation, the respective
components were mixed lo prepare Flavor Enhancing
Seasoning OF to OK. Using as each control a product
I to which the sample compound had not been added,
organoleptic evaluation was conducted as outlined in
Example 27 by a paired comparison text. The results
are given in Table 62.

~23~3~3
~81-



Table 62
Control OF GO HUH II JO OR

Concentration
gel oily 0~65 0~7 0~80~61 0~8

Strength of
numami" t t

Strength of
Flavor + .,~ +



Example 29


Chinese noodle soup was prepared using the
formulation shown below, and organoleptically evaluated
for strength of flavor and total preference by a paired
comparison test. These evaluations show that the
Chinese noodle soup to which Flavor Enhancing Seasoning
HUH had been added had stronger flavor and was signify-
gently favored as compared with the control.


Formulation of Chinese Noodle Sour
Soy Swiss Part by weight
Table salt 16

I Lard 24

Sesame oil 2
nay irate n

YE
Vegetable extract

Flavor Enhancing Seasoning
in Example 28 (or Control
Section in Example 28 ) 7

I

Table 63
N = 20
Flavor Enhancing
Control Seasoning ;
Section Added Section
Strength of
Flavor 4 16 *I
Total
Preference 5 15 *

** Significantly different at a risk factor ox 1%.
* Significantly different at a risk factor of 5%.

Example 30

. Table 64
- LO NUN 00 PUP
MUG 80 75 50 80
IMP -- 5 -- 3 30
GYP -- -- lo 3 30
Allen 20 20 40 14 40

The respective component outlined in the above
formulations were mixed to prepare Flavor Enhancing
Seasoning LO to PP. A each control, a product to
which Allen had not been added way used. Aqueous
sultan containing 0.4 gJdl of the respective
formulations and 901ution9 obtained budding 0.1~ by
.

-83



weight of the above formulations to commercial consomme
soup were prepared. Organoleptical evaluations were
conducted by a paired comparison test. Thy royalty are
given in Table 65 and Table 66.


Table 65
,..... . LO MM NUN OX PUP

- Strength of
Titans ++~+ +~+ +

Strength of
Flavor I+ *++~ ~+~++ ~++~ +~+~



Table. 66
Evaluation When Added to
commercial Consomme Soup
- N = 20

eschew numeral indicate the number of porn
out ox 20 who have wound it preferable or triune).
LO MM NUN 00 PUP

Strength ox
numami~ 12 16 ** 18 *** 17 *I 15 **

Strength of
Flavor 13 15 * 17 ** 13 16 **
Taste 14 18 *** 18 *** 18 *** 18 ***


Comment Aftertaste aftertaste
Strong, Strong,
Flavor Flavor
Strong Strong &
Preferred Preferred


* Significantly different at a risk factor of 5%.
. ** Significantly different at a risk factor of 1%.
**I Significantly different at a risk factor of 0.5~.

I



Example 31
Table 67
.
(parts by weigh)
QQ RR SO TO US TV
HOP 60 60 60 60 - -
HAP Ç0 60
MUG 25 26 26 26 26 26

IMP 1 1 1-
GYP
Noah Succinate 2 2 2 2 2 2
Nail . 10 10 10 10 10 10
Allen . .1.7 8.7 16.7 33.3 1.7 33.3



The respective components outlined in the above
formulations were mixed to prepare Flavor Enhancing
Seasoning QQ to TV. Using, as each control, a product
from which the Allen had been omitted, organoleptic
evaluation was conducted as outlined in Example 30 by a

paired comparison Tut The royalty are given in
Table 68.

I
-85-



Table 68


Control QQ RR SO TO W W

Concentra-
lion (g/dl)0.6 0.61 0.65 0.7 0.8 0.61 0.8

Strength of
Umami i i + i + +

Strength of
Flavor * Jo -Ho oh Ho +



Example 32


using the following recipe, spaghetti teat sauce
was prepared and strength of flavor and total
preference were organoleptically evaluated by paired
comparison text. These evaluations, as shown in Table
68, demonstrate that meat sauce to which Flavor
enhancing Seasoning SO had been added had stronger
flavor and way significantly favored as compared with
the control.




.

I
-36-

Recipe for Meat Sauce
zinced beef and pork 15.7
Onion 39.2
Carrot 4.7
Corn salad oil 7~8
Flour 7.8
. . .
Tomato ketchup 15.7
Tomato puree 4.7
Worcester shire sauce 3.8
Flavor Enhancing seasoning of
Example 31 or Control Section
in Example 31) . 0.6

Table 59
N = 20
Flavor Enhancing
Control Added Seasoning SO
action Added Section
Strength of
Flavor 4 16 **
Total
Preference 5 15 **

** Significantly different at a risk factor of 1%.
* Significantly different at a risk factor of 5%.

7~3~
-87-



Example 33


Barbecue sauce was prepared from refined spook,
soybean oil, Joy sauce, soybean pate (Moe),
granulated sugar, MY starch, synthesized rice wine
(sake) and guard gum according to the recipe outlined
below., The strength of flavor and taste were
organoleptically evaluated by a paired comparison test
using a sample to which Allen had not been added as a
control As shown in Table 70 the Allen added section
had strong flavor and was significantly favored for the
total taste.


Recipe for Barbecue Sauce
Spices 12.5 Part by weight
Refined soybean oil I n
Soy sauce 34
Soybean paste (Moe) 9
Granulated sugar 8 n
MUG
Starch 1 "

Synthesized rice wine
( sake ) 9
Guard gum 0.1 n
Allen 0.5

I 8
-88-



Tubule

ControlAlliin Added
Sect~onSection _

Strength of
Flavor 4 16 **

Total Taste 4 16 **

...
Example 34


hamburgers were prepared a outlined in Table 70
using 30 parts of pork, 15 parts of chicken, 5 parts of

beef, 4 parts of bread crumb, parts of APRON
(produced by ~jinomoto Co.), 4 parts of "SHlN-ESUSAN"
starch (produced by Ajinomoto Co.), 17 parts of onion
and S parts of each of Flavor Enhancing Seasonings WOW,
XX and YE. Controls were prepared according to the
same formulations but without the Flavor Enhancing
Seasonings. These hamburgers were organoleptically
evaluated to find as shown in Table 72 that the
hamburgers to which Flavor Enhancing Seasonings WOW, XX
and YE had been added respectively had stronger flavor

and were significantly favored as compared with that to
which the control had been added.




* trade mark

.

-89-

Table 71
Formulations of Flavor
Enhancing Sweeney W, X and Y
WOW XX Ye
Table salt 8 8 8
Soy sauce 40 40 40
Sugar . 8 8
(Ajinomoto Coy) 8 8 8
wine 10 10 10
MUG 10 10 10
White pepper 6 6 6
Nutmeg 4 4 4
Ginger 6 6 6
Allen 2 10 20

Table 72
Control
Added WOW Added XX Added YE Added
Section Section Section Section
Strength ox
Flavor + +~++
Preference +~+

Example 35

Mix Vegetable Extracts WOW', XX' and YE' prepared
in a conventional manner using the formulations of
Table 73. These were evaluated in Chinese noodle soup

D

~2~7~33~
--so--

to find as shown in Table 74 that the Chinese noodle
90Up to which the mix vegetable extracts had been added
respectively had stronger flavor and each way
significantly favored a compared with control which
contained no mix vegetable extract.


Table 73
Formulation of Mix vegetable
Extract WOW', XX' and YE'
Control We' XX' YE'
__
Onion 60 60 60 60

Garlic 30 30 30 ' 30

Leek 5 S 5

Carrot 5 5 5 5

Allen -- 5 10 15



Recipe for Chinese Noodle S us

Soy sauce 40 Parts by weight

Table Walt 16 "


Lard 24 "

Sesame oil 2 n

WE 1 n

nAjinomoto" 6 n

n Animate" 2 n

YE

Aforesaid Mix
Vegetable Extract 8 . "

~37~3~


--91--

Table 74
Control WOW' XX' YE' _
strength of
Flavor ++ ++++
Preference + ++ ++++ ++++

It will be understood that when the taste enhancing
substance and the flavor enhancing substance are salts, such
salts should be appropriate for their intended function. For
example, they should be non-toxic, at least in the amounts
employed and they should be organoleptically acceptable.

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date 1988-06-14
(22) Filed 1984-11-09
(45) Issued 1988-06-14
Expired 2005-06-14

Abandonment History

There is no abandonment history.

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $0.00 1984-11-09
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
AJINOMOTO CO., INC.
Past Owners on Record
None
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Drawings 1993-08-07 1 14
Claims 1993-08-07 6 146
Abstract 1993-08-07 1 24
Cover Page 1993-08-07 1 18
Description 1993-08-07 91 2,303