Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
lOS~ 5
This invention relates to ~lavor compo~itions and mora par-
ticularly to flavor compositions containing certain dialkyl; ~J ~
diacyl succinate3. . ::
Ik i~ well known that synthetic flavor enhancere such a~ ;
Maltol, Ethyl MaltolJ and 4-hydroxy-2,5-dime~hyl-3(2H~-furanone are ~
useful a~ flavor enhancers. ~owever, ~uch flavor enhancers are very~ :
expen~ive and increase the cost of products in which they are used~
In accordance with this invention, dialkyl-a,~-diacyl ~ucci-
nate~ are added to 1avor component~ to impart significantly en~
hanced ~lavors to a wide variety of flavor componente. For example,
butterscotch flavors are materially improved in smoothness. Straw-
berry flavor~ are given a striking freshness. Banana ~lavor~ are
rounded out to give the ~lavor of a ripe banana. When added to
smoking tobacco or ~ynthetic tobacco, the re~ulting p:eoduct i8 in-
~rea~ed in sweetnsss, the ta~te of the smoke is ~o~tened and the
flow o~ saliva i8 increa~ed, which le~sens dryxle~s of the mouth
'
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during smoking. W~en addad to cough syrup~ contai~ing ~heophyl-
line, tha flavor enhancers of this invention cover up the bittar
tasto. ~he~e flavor enhancer~ can also be used to replace part
of the sugar content of a wide variety of sweetened beverage~ and
food~, producing excellant flavor at lower cost.
The dialkyl~ diacyl succinates employad in tha ~lavor com-
po~ition~ o~ thi~ ~nv~ntion have ~he ~ormula~
O O
Rl ~~ O--R2
R2 ~ ~,~ Rl
Il 11 .
O 0,
in which Rl i~ a straig~t or ~ranched chain al~yl having les~
~ or cyclhe~<yl
L ~ than 6 carbon atom ~ and ~2 is a ~traight or branched chain alkyl
having le88 than 7 carbon atoms, cyclopentyl or cyclohexyl.
Example~ of Rl are methyl, ethyl, propyl, i~opropyl, butyl,
ieobutyl, am~l or isoamyl.
Bxamplee o R2 are methyl, ethylJ propyl, iaop~py.l, bukylO
~o~ut~l, amyl, isoam~lJ hexyl or ieohexyl.
Rl and ~2 may be the ~ame or differer~t.
When R2 ie ethyl or methyl, the ~uccinate is prepared by the
method de~ribed by ~., S. ~ewman and ~. S. Cella~ ~L ~38,
3482 ~1973). When R2 is other than ethyl or methyl, and Rl i5
other than methyl, the procedure is the same except that the
appropriate ~-ketoesters are used instead of the acetoacetic esters.
The flavor compcsitions of this i~vention comprise at least
0.0025% by weight of a dialkyl~ diacyl succinate. The total
amou~t o dialkyl-a,~ diacyl succinate or succinates may vary
.
~ 2 --
-
8~
within wid~ ranges such as 0.0001% to 30% by weight. More advan-
tageously the range may be between 0.001% and 20% by weight of the
flavor composition and preferably between 0.0025% and 5% by weight
of the flavor composition~
Examples of flavor components of the flavor compositions of
this invention are flavor mixtures per se such as pineapple, but~
terscotch, banana, and strawberry; foodstu~fs such as meats, pro-
~ein ~ources, fruitsJ cereals and other comestible~; beverages such
as soft drinks, wines, alcoholic drinks, carbonated beverages;
smoking tobacco; liquid medicaments such as cough syrups; and sugar
ubstitutes in a wide range of edible or drinkable products.
A more comprehensivs understanding o~ this invention is
obtained from the ~ollowing examples. Examples I and II show com-
positions produced with two levels o~ concentration o~ the dialkyl-
aJ~-diacyl succinate employed.
EXAMPLE I
PINEAPPLE FLAVOR COMPOSITIONS
Parts by Parts by
~ wei~ht_
Allyl cyclohexane propionate 1.4 1.4
Geranyl propionate 0.5 0,5
Allyl caproate 13.0 13.0
Ethyl iso valerate 1.0 1.0
Ethyl butyrate 1.0 1.0
Vanillin 0O5 0~5
Oil orange 1~0 1.0
Maltol 2.0 2.0
Diethyl-a,~diacetyl succinats 20.0 2.5
Ethyl alcohol 95% 46.0 46.0
Propylene glycol 13.6 3
100 . O 100 . O
~ 3
" " ~ ' '
~5~
EX~MPLE II
STRAWBERRY FLAVOR COMPOSITIO~JS
Parts by Parts by
Methoxy phenyl butanone 1.0 1.0
Ethyl butyrate 6.0 6.0
Ethyl iso valerate 2.0 2.0
Benzyl butyrate 1.5 1.5
Benzyl iso valerate 0,5 0.5
cis-3-Hexenol 3O0 3.0
Iso7~utyric acid 1,5 1.5
Diacetyl 0.2 0.2
Butyl phenyl acetate 0,4 0,4
Acetaldehyde S0% in ethanol 0.2 0.2
Benzyl dipropyl ketone 0.2 0.2
2-~eptanone 0.1 0.1
Ethyl methyl phenyl glycidate 2.4 2.4
Diethyl-a,~-diacetyl succinate 30.0 5.0
Propylene gly~ol 51.0 51.0
Benzyl alcohol - 25 00
100 . O100 . O
.
. .
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EXAMPLE III
.
BUT~ERSCOTCH FL~OR COMPOSITIO~
Parts by
~Teiqht
:-.
Diethyl-a,~-diacetyl succinate 1.0
Butyl butyrolactate 4,0
~iacatyl 0.2
Ethyl oleate 2.0
Ethyl myristate 0,5
Vanillin 1.5
Acetoin 0.3
Phenyl ethanol . 0.2
Butyric acid 0.1
Ethyl oxyhydrate 0.1
Ethyl maltol 3.0
~Decalactone 0,3
~-~onalactone 0.1
Tincture foenugreek 0,4
~ethyl cyclopenten-ol-one 0.1
Benzyl alcohol 26.0
Propylene glycol
100 . O
' '
; ' '
_ 5 _ :
i
. .
~5~8~5 ~::
EX~MPLE IV
~AN~N~ FLAVOR COMPOSITION
Parts by
~~ .
Iso amyl acetate 12.0
Iso amyl butyrate 10.0
Benzyl butyrate 3,0
I~o amyl iso valerate 2.0
Ethyl butyrate 3.0
Butyric acid 1.5
Oil lemon 2.5
Vanillin 2.0
Ethyl maltol 0,5
~ Undecalactone 0,4
4-~p-Hydroxyphenyl~-2-butanone 0.1
Diethyl~ diacetyl succinate . 10.0 ~ .
Propylene glyco~ 53 o ~.
100.0
~.
'. ~ `
, , - ' ~.
~ .
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~l)S~ 5
EX~MPLE V
PINEAPPLE FLAVOR
Parts by Weight
VA VB VC VD
Allyl Cyclohexane Propionate1.4 l. 4 1~ 4 1 r 4 -
Geranyl Propionate O.5 0.5 0.5 0,5
Allyl Caproats 13.0 13.0 13.0 13.0
Ethyl Iso Valerate 1.0 1.0 1.0 1.0 ~ :
Ethyl Butyrate 1.0 1.0 lo0 1~0
Vanillin 0.5 0,5 0.5 0.5
Oil Orange 1.0 loO 1~0 1~0
Maltol 2.0 2 J O - -
Diethyl~ Diacetyl Succinate20.0 2.5 20.0 2.5
Ethyl Alcohol 95% 46.0 46.0 46~0 46~0
Propylene Glycol 13.6 31.1 15.6 33.1 :~
100 . () 100 . O 100 . O100 . O
Formulas U~ and VB contain Maltol in addition to diethyl-a,~-
diacetyl succinate, while Formulas VC and VD contain only diethyl-
~ diace~yl succinate as a complete replacement for Maltol. q~e
pineapple 1avor achieved by the use of Formula VC is comparabla
.i not superior to the flavor o Formula ~, while the flavor
achi.eved by the use of Formula VD is comparable if not superior to
the flavor of VB. The replacsment proportion of Maltol by diethyl- :
a,~-diacetyl succinate is approximately one part by weight to one
part by weight of the Maltol.
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EXAMPLE VI
WINE FL~VOR COMPOSITION
~ he wine flavor composition is produced by initially a~ding
0~08 parts by weight of diethyl-a,~-diacetyl succinate to 99.92
parts by weight of natural wine flavor. Four liquid ounces of
the wine concentrate are added to one gallon o~ wine.
A wine 1avor composition may also be produced by preparing
a 1% by weight ethanol solution of diethyl-~ diacetyl succinate
and then adding O.32 fluid ounces of the solution to 1 gallon of
wine. This is equivalent to 25 parts per million.
EXAMPLE VII ~ ;
_BACCO FLAVOR CO~POSITION
A 1% ethanol solution of diethyl~a,~diacetyl succinate is
sprayed on smoking tobacco at the rate of 4 ounces of solution
per 100 pounds of tobacco. After the alcohol is allowed to evapo-
rate, a tobacco flavor composition results.
To produce a flavored tobacco which also contains synthetic
tobacco, the procedure for the production of tobacco flavor com~
position heretofore described in this Example is repeated except
that instead of employing smoking tobacco only, synthetic tobacco
such as csllulose fibers, for example~ the cellulose fibers sold
by the Celanese chemical Company under the trademark "CYTREL" or
the cellulose fibers sold by Imperial Chemical Corporation under
the trademark "PO~YSTREP"~ is blended with the flavored tobacco
in a ratio o~ approximately 1 to 1 by weight.
In a ~hird procedure, a 1% ethanol solution of die~hyl-a,~-
~ 8
..
~s~s
diacetyl succinate is sprayed on synthetic tobacco, such ascellulose fibers, at the rate of 4 ounces of solution to 100
pounds of synthe~ic tobacco. After the alcohol i6 allowed to
evaporate, a tobacco flavor synthetic composition results.
~ ny one of the above tobacco flavor compositions may be
used in cigarettes, producing a striking improvement in flavor~
For the treatment of tobacco, it is desirable that the fla-
vor enhancer be in solubilized form, such as in an ekhanol solu
tion, as in the example of diethyl-a,~-diacetyl succinate.
EXAMPLE YIII
CARBON~TED SOFT DRINKS
A fruit flavor carbonated drink is produced by dissolving
one ounce by weight o one of the flavor compositions such as
described in Examples I or II in one gallon of sugar syrup.
one ounce of the resulting mixture is added to about five ounces
of carbonated water to produce six ounces of carbonated beverage.
The flavor composition containing 2.5% by weight of diethyl ~
diacetyl succinate results in a level of 32 parts per million of
the diethyl-a,~ diacetyl succinate flavor enhancer in the total
carbonated drink produced.
In Examples I through IX~ dimethyl-a,~-diacetyl succinate
may be utilized as the flavor enhancer in the same amounts indi-
cated ~or dieth~ diacetyl succinate used in those Examples.
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EXAMPLE IX
BUTTERSCOTCH FLA~OR COMPOSITION
Two butterscotch compositions each containing a different fla-
vor enhancer in accordance with the teaching o~ tha invention were
prepared. For comparison, another composition containing the ~ame
ingredien~s but without either of the flavor enhancers used in A
and B was also prepared as a control. The formulas of the compo-
si~ion-~ are as ollow~:
Parts by Part~ by Parts by
Weight Weight Weight
~Control) ~A~ _
Butyl Butyrolactate 4.0 4O0 4.0
Diacetyl 0.2 0.2 0.2
Ethyl oleate 2.0 2.0 2.0
Ethyl Myristate 0.5 0,5 0.5
Vanillin 1.5 1.5 1.5
Acetyl Methyl Carbinol 0.3 0.3 0.3
Phenyl Ethyl A}cohol 0.2 0.2 0.2
Butyric Acid 0.1 0.1 0.1
~thyl Propionate 0.1 0.1 0.1
Ethyl Maltol 3.0 3.0 3.0 :
~-Decalactone 0.3 0.3 0.3
~-Nonalactone 0.1 0.1 0.1
Methyl Para-Tertiary Butyl
Phenylacetate (in 1% alcohol) 0O1 0.1 0.1 ~.
Tinctuxe Foenugreek 0.4 0.4 0,4
cyclotene 0~1 0.1 0.1
Benzyl Alcohol 27.1 27.1 27.1 :
Propylene Glycol 60.0 57~0 57.0
Diethyl-a,~-Dipropionyl Succinate - - 3.0
Dicy~lohexyl-a,~-Dlacetyl Succinate - 3.0 _
100.0 1~0,.0 100.0
-- 10 --
. _ _ . .. ~ _ _ __ _ _ ___ .. , , . ., .. , ___ _ _ _.. . . .... . ., . .. __ _ _ ~ ~
~.~ . ', . .
, , .
Each of the butterscokch compositions containing the flavor
enhancers (~) and (B) had an immeasurably supexior flavor over
the control. The butterscotch compositions (~) and (B) had a
batter butterscotch caramel flavor and an increased sweetness
and mouth feel. Tha butter no es were al~o anhancedO
~,
.
