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Patent 2232334 Summary

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(12) Patent Application: (11) CA 2232334
(54) English Title: FLAVOUR EXTRACT
(54) French Title: EXTRAIT AROMATIQUE
Status: Dead
Bibliographic Data
(51) International Patent Classification (IPC):
  • A23L 27/20 (2016.01)
  • A23L 27/10 (2016.01)
  • A23L 27/21 (2016.01)
(72) Inventors :
  • CERNY, CHRISTOPH (Switzerland)
  • HEYLAND, SVEN (Switzerland)
(73) Owners :
  • SOCIETE DES PRODUITS NESTLE S.A. (Switzerland)
(71) Applicants :
  • SOCIETE DES PRODUITS NESTLE S.A. (Switzerland)
(74) Agent: BORDEN LADNER GERVAIS LLP
(74) Associate agent:
(45) Issued:
(22) Filed Date: 1998-04-23
(41) Open to Public Inspection: 1998-11-15
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
97201469.0 European Patent Office (EPO) 1997-05-15

Abstracts

English Abstract



Process for the extraction of flavours in which a mixture
is prepared containing, at least, a source of sulphur, a
reducing sugar, a phosphate compound and water, this
mixture is heated, this mixture is subjected to a CO2
counter-current liquid extraction and a separation is then
performed on the CO2 loaded with flavours, so as to obtain
a liquid flavour extract.


French Abstract

Méthode pour l'extraction d'arômes, dans laquelle on prépare un mélange renfermant au moins une source de soufre, un sucre réducteur, un phosphate et de l'eau; le mélange est chauffé et soumis à une extraction à CO2 liquide à contre-courant; on procède ensuite à une séparation sur le CO2 chargé d'arômes, de façon à obtenir un extrait aromatique liquide.

Claims

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


16
Claims

1. Process for the extraction of flavours in which:
- a mixture is prepared containing, at least, a source of
sulphur, a reducing sugar, a phosphate compound and water,
- this mixture is heated at 50-180°C for 30 min to 5 h,
- this mixture is subjected to a CO2 counter-current liquid
extraction at 70-350 bar,
- a separation is then performed on the CO2 loaded with
flavours, so as to obtain a liquid flavour extract.

2. Process according to claim 1, in which a mixture is
prepared containing, at least, 1-30% of a source of
sulphur, 1-30% of a reducing sugar, 1-15% of a phosphate
compound and 25-55% water.

3. Process according to claim 1, in which the mixture
contains glutathione, cysteine, thiamine and/or an
inorganic sulphur as the source of sulphur.

4. Process according to claim 1, in which 5-20 kg of CO2/kg
of mixture are used to perform the counter-current
extraction.

5. Process according to claim 1, in which the CO2 counter-current
liquid extraction is performed on the mixture at
20-31°C.

6. Process according to claim 1, in which a CO2 counter-current
liquid extraction is performed on the mixture at a
temperature greater than 31°C and less than 100°C.

7. Process according to claim 1, in which the liquid
flavour extract is dried so as to obtain a powdered flavour
extract.

17

8. Flavour extract obtained by implementing the process
according to one of claims 1 to 7.

9. Use of a flavour extract according to claim 8 for the
preparation of a food composition.

Description

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


CA 02232334 1998-04-23

Flavour extract

The present invention relates to a process for the
extraction of flavours, and to the use of these flavours
for making food compositions.

The extraction of flavours in the presence of polar
solvents is known.

The extraction of meat or fish flavours using water as a
polar solvent is particularly known. The flavour extract
isolated by means of this type of extraction contains
flavours but also non-volatile compounds which are
important to the taste.
Thus, US 3957745 describes a process for the preparation of
a mixture of flavours in which a source of sulphur, i.e.
inorganic sulphur and/or an amino acid, reacts with an
alpha-hydroxycarbonyl, a beta-epoxycarbonyl or an alpha-
epoxycarbonyl in the presence of at least one polarsolvent, at a temperature of 65-200~C and a pressure of 1 to
100 atm, so as to produce flavours and the flavours are
then separated from the residue, particularly by
filtration. These flavours are particularly used to modify
the flavour note or the taste of a food product.

It is further known to use CO2 to extract spices and herbs
or to isolate flavours of oil, fats, fruits or coffee, for
example.
Thus, US 3477856 describes a process for the isolation of
volatile flavours from fruit juices or essences in which a
liquid CO2 extraction is performed on a fruit juice or
essence, the phase containing the flavours is separated
from the residual fruit juice or essence phase and the CO2
contained in this phase is then evaporated so as to isolate
a liquid extract containing volatile fruit flavours.

CA 02232334 1998-04-23


Further, US 4328255 describes a process for the extraction
of a coffee oil containing flavours in a stable form, in
which a supercritical CO2 extraction is performed on
roasted coffee at no less than 80 atm and at a temperature
greater than 31.3~C.

The object of the present invention is to propose a simple
and rapid process enabling volatile flavours to be
extracted. In addition, the process according to the
present invention has the advantage of enabling very
concentrated flavours to be obtained.

To this end, in the process for the extraction of flavours
according to the present invention, a mixture is prepared
containing, at least, a source of sulphur, a reducing
sugar, a phosphate compound and water, this mixture is
heated at 50-180~C for 30 min to 5 h, this mixture is
subjected to a CO2 counter-current liquid extraction at
70-350 bar and a separation is then performed on the CO2
loaded with flavours, so as to obtain a liquid flavour
extract.

Hereafter in the description, the expression "phosphate
compound" will be used to refer to phosphate, biphosphate
or a polyphosphate.

In addition, hereafter in the description, the expression
"extraction yield" will be used to refer to the ratio of
the quantity of flavour extract obtained according to the
present invention to the quantity of starting mixture.

Surprisingly, it has been found that the process according
to the present invention allows volatile flavours to be
extracted simply and rapidly.


CA 02232334 1998-04-23



For this purpose, then, a mixture is prepared containing,
at least, a source of sulphur, a reducing sugar, a
phosphate compound and water. A mixture may be prepared
containing, at least, 1-30~ of a source of sulphur, 1-30%
of a reducing sugar, 1-15% of a phosphate compound and
25-55% of water, for example.

A mixture may be prepared containing glutathione, cysteine,
thiamine and/or inorganic sulphur, for example, as the
source of sulphur.

A mixture may be prepared containing glucose and/or xylose,
for example, as the reducing sugar.

A mixture may be prepared containing a phosphate compound,
particularly in such a way as to maintain the pH of the
mixture at a value of between 4.5-7.5 inclusive. Phosphate,
biphosphate or a polyphosphate is therefore used as the
phosphate compound. An ammonium phosphate is preferably
used.

This mixture is thus heated at 50-180~C for 30 min to 5 h so
as to carry out a Maillard reaction, i.e. so as to make the
reducing function of the sugar react with the amine
function of the source of sulphur or of another compound
contained in the mixture. If the source of sulphur does not
have an amine function, ammonium phosphate may be used as
the phosphate compound, for example, so as to carry out the
Maillard reaction. The phosphate compound contained in the
mixture acts as a catalyst during this reaction, in
addition to its buffer capacity. In this way the flavours
of the mixture are developed. This step may be performed
with agitation, particularly in a double casing reactor
such as that marketed by Schmizo A.G., Luzerner Strasse 27,
CH-4665 Zofingen, so as to obtain a homogeneous reaction,
for example.

CA 02232334 1998-04-23



A CO2 counter-current liquid extraction is then performed
on this mixture at 70-350 bar. This counter-current
extraction may be performed in an extractor, particularly
in a column extractor in which the mixture is fed in
through the top of the column and the CO2 is fed in through
the bottom of the column, for example.

The flavour note of the flavour extract may particularly be
varied according to the temperature at which the CO2
counter-current liquid extraction at 70-350 bar is
performed on the mixture.

Thus, in a first preferred embodiment of the present
process, the CO2 counter-current liquid extraction may be
performed on the mixture at 20-31~C so as to reinforce the
sulphurous flavour note of the flavour extract, for
example. The counter-current liquid extraction is thus
carried out in the presence of liquid CO2.

In a second preferred embodiment of the process, the CO2
counter-current liquid extraction may be performed on the
mixture at a temperature greater than 31~C and less than
100~C, for example. The counter-current liquid extraction is
thus carried out in the presence of super-critical CO2.
5-20 kg of CO2/kg of mixture may be used to perform the
counter-current liquid extraction, for example. The
extraction yield may be increased by increasing the
quantity of CO2/kg of mixture, for example.
An extraction residue on the one hand and, on the other
hand, the CO2 loaded with flavours, which leaves at the top
of the extractor column and which is then passed into the
separator, are then recovered.


CA 02232334 1998-04-23


A separation is then performed on the CO2 loaded with
flavours so as to obtain a liquid flavour extract. This
separation may be performed in a separator in which the
temperature of the medium is lowered to ambient temperature
and the pressure of the medium is lowered to a value of
less than 40 bar so as to reduce the solubility of the
flavours in the CO2 and to enable a liquid flavour extract
to be isolated, for example.

The liquid flavour extract thus obtained may be dried on a
support, such as maltodextrin or a starch, so as to obtain
the flavour extract in the form of a powder, for example.

The SFF 5860 extraction unit, marketed by Separex Chimie
Fine, 5, rue Jean Monod-BP 9, F-54520 Champigneulles, may
particularly be used for the extraction step and the
separation step.

The CO2 may be recompressed and reintroduced into the
extractor for another extraction, for example.

In addition, the extraction residue, which still contains
about 20~ original flavours, as well as reaction products
such as the phosphate compound and the colouring compounds
which are not volatile, may be recovered, for example. This
extraction residue may particularly be mixed with salt, soy
sauce and/or yeast extract. This mixture may then be dried
with a drying support, such as maltodextrin, so as to
obtain a flavouring powder, for example.
The present invention also provides the flavour extract
obtained according to the process and its use for the
preparation of a food composition. Indeed, the flavour
extract made in this way, in liquid or dried form, may
advantageously be used for the preparation of a food
composition, for example. It may particularly be used for

CA 02232334 1998-04-23



the preparation of cooked dishes, sauces or stocks so as to
modify their flavour note, for example.

The process for the extraction of flavours and the flavour
extracts according to the present invention are described
in more detail by means of the analytical tests below. The
percentages are given by weight, unless otherwise
specified.

Test 1: Extraction yield as a function of the quantity of
CO2, the temperature and the pressure during the counter-
current liquid extraction step

5 samples of flavour extract are prepared, obtained by
implementing the process according to the present
invention. The conditions of the counter-current liquid
extraction step are varied (the quantity of CO2, the
temperature and the pressure) for the preparation of these
5 samples, and their extraction yield is then compared.
For this purpose, a mixture is prepared containing 8.37
cysteine, 8.37~ thiamine, 1.90~ xylose, 20.29~ glucose,
10.38~ diammonium phosphate, 2.15~ onion extract, 1.32
sodium hydroxide and 47.36~ water.
This mixture is heated at 100~C for 4 h so as to carry out
the Maillard reaction between the reducing function of the
xylose and the glucose and the amine function of the
thiamine, the cysteine and the diammonium phosphate and
thus to develop the flavours of the mixture.

A CO2 counter-current liquid extraction is then performed
in a column extractor in which the mixture is fed in
through the top of the column and the CO2 is fed in through
the bottom of the column.
For the different tests performed, the temperature and
pressure conditions and the quantity of CO2 used during

CA 02232334 l998-04-23


this CO2 counter-current liquid extraction are indicated in
Table I below.

The CO2 loaded with flavours, which leaves at the top of
the extraction column, is then recovered and subjected to a
separation in a separator so as to remove the CO2 and to
isolate the liquid flavour extract. For this purpose, the
solubility of the flavours in the CO2 is reduced by
lowering the temperature in the extractor to a temperature
less than or equal to 20~C and lowering the pressure to a
pressure of less than 40 bar.

The removed CO2 is recompressed and reintroduced into the
extractor for another extraction.

The flavour extract is dried using maltodextrin as the
drying support.

For each test performed, the extraction yield is calculated
by calculating the ~6 of flavour extract isolated in
relation to the quantity of starting mixture used.

The results of the different tests performed are shown in
Table I below.

Table I

extraction yield
(~)
tests pressure (bar) temperature (~C) a b c
1 100 75 2.75 4.907.25
2 70 20 1.15 2.052.70
3 140 40 1.90 3.905.40
4 280 77 5.15 8.6511.90
280 20 1.55 2.653.75

CA 02232334 1998-04-23


key: (a) 5 kg CO2/kg of mixture
(b) 10 kg CO2/kg of mixture
(c) 15 kg CO2/kg of mixture

The results of these tests highlight the fact that the
extraction yield of the flavours is better when a greater
quantity of CO2 is used. Indeed, for the 5 tests carried
out, an increase in the extraction yield is observed
depending on whether 5, 10 or 15 kg CO2/kg of mixture was
used during the counter-current liquid extraction on the
mixture.
In addition, the results of these tests highlight the fact
that the extraction yield of the flavours is also better
when the counter-current liquid extraction is performed on
the mixture at elevated temperature. Indeed, tests 1, 3 and
4 give better yield results. For these tests, a counter-
current liquid extraction was performed on the mixture with
super-critical CO2.
The results of these tests also show that the flavour
extraction yield is better when a CO2 counter-current
liquid extraction is performed on the mixture under high
pressure.
Finally, the fact that the density of the CO2 has no
influence on the extraction yield of the flavours is
highlighted.

Thus the extraction yield of the flavours is better when
the CO2 counter-current liquid extraction is performed on
the mixture at elevated temperature, under high pressure
and in the presence of a significant quantity of CO2.

Test 2: Sensory evaluation of the flavour extract

A sensory evaluation is carried out on samples containing a
flavour extract obtained by implementing the process
according to the present invention.

CA 02232334 1998-04-23



~or this purpose, 5 flavour extracts are prepared in
accordance with the process of the present invention.
During the preparation of these 5 extracts, a counter-
current liquid extraction is performed on the mixture, as
described in test 1, in the presence of 15 kg of C02 and
under different temperature and pressure conditions. The
temperature and pressure conditions for the preparation of
these 5 extracts are shown in Table II below.

5 samples are then made by mixing 0.2 g/l of each extract
made in this way per litre of hot water, also containing
2 g/l salt and 1 g/l MSG.

At the same time, a reference sample is made by adding
4 g/l of the mixture, as described in test 1, per litre of
hot water, also containing 2 g/l salt and 1 g/l monosodium
glutamate.

These 5 samples, together with the reference sample, are
then tasted by 5 taste testers so as to describe and
compare their flavour note.

The sensory evaluation of these 5 samples and that of the
reference sample are shown in Table II below.


CA 02232334 1998-04-23


Table II

sample extraction conditions flavour note
pressure (bar) temperature (~C)
reference meat, bitter,
sulphur taste
1 100 75 meat
2 70 20 meat, sulphur
taste
3 140 40 meat
4 280 77 meat
280 20 meat, sulphur
taste

The sensory evaluation enables the fact that the 5 samples
made in this way have a good meat flavour to be
highlighted.
In addition, this evaluation highlights the fact that, when
the counter-current liquid extraction is carried out at low
temperature, i.e. with the aid of liquid CO2, a flavour
extract having a sulphurous flavour note is isolated.

Test 3: Evaluation of the extraction yield with the aid of
flavour indicators

A sample of flavour extract, obtained by implementing the
process according to the present invention, is prepared. To
make this sample, a CO2 counter-current liquid extraction
is performed on the starting mixture at a pressure of 280
bar, a temperature of 77~C and in the presence of 15 kg of
CO2-

The extraction yield is evaluated with the aid of flavour
indicators. For this purpose, the concentration of 3
flavour indicators is measured in the starting mixture and
in the flavour extract: 2,5-dimethyl-4-hydroxy-3(2H)-
furanone, acetic acid and sulphurol, having similar

CA 02232334 1998-04-23


chemical properties and a similar polarity to those of the
other relevant flavour compounds contained in the flavour
extract.

The concentration of acetic acid is determined
enzymatically using the 148261 enzymatic kit marketed by
Boehringer Mannheim, CP 6343, Industrie Strasse 7, CH-
Rotkreuz.

The concentration of sulphurol, which is a degradation
product of thiamine, is determined by gas phase
chromatography.

Finally the concentration of 2,5-dimethyl-4-hydroxy-3(2H)-
furanone is determined by marking with an isotope, ~131 by
the method described by Sen et al. (Sen et al., Lebensm
Wiss Technol 24: 364-369, 1991).

The concentration values of the 3 flavour indicators in the
starting mixture and in the flavour extract, as well as the
extraction yields of these 3 flavour indicators, are shown
in Table III below.

Table III

flavour concentration in concentration in extraction
indicator starting mixture flavour extract yield (%)
(mg/kg) (mg/kg)
a 76 308 48
b 470 2800 71
c 12400 7300 70
key: (a) 2,5-dimethyl-4-hydroxy-3(2H)-furanone
(b) acetic acid
(c) sulphurol


CA 02232334 1998-04-23



The results shown in Table III highlight the fact that the
flavour indicators were, in fact, extracted when the
extraction process according to the present invention was
implemented. In addition, the fact is highlighted that even
the highly polar flavours, which are very difficult to
extract by distillation, are extracted during the
extraction according to the present invention. Indeed, 2,5-
dimethyl-4-hydroxy-3(2H)-furanone, which is a highly polar
flavour, has also been extracted. An extraction yield value
of 48~ is obtained for this flavour indicator. It is
therfore assumed that this flavour was probably partially
decomposed during the extraction process according to the
present invention.

The following examples are given as an illustration of an
industrial use, in the foodstuffs sector, of the flavour
extracts according to the present invention. In the
examples below, the percentages are given by weight unless
otherwise indicated.
Example 1

A beef stock is prepared using a flavour extract obtained
by implementing the process according to the present
invention.

For this purpose, a mixture is prepared containing 8.37
cysteine, 8.37~ thiamine, 1.90% xylose, 20.29~ glucose,
10.38~ diammonium phosphate, 2.15~ onion extract, 1.32
sodium hydroxide and 47.36~ water.

This mixture is heated to 100~C for 4h so as to carry out
the Maillard reaction between the reducing function of the
xylose and the glucose, and the amine function of the
thiamine, the cysteine and the diammonium phosphate and to
develop the flavours of the mixture in this way.

CA 02232334 1998-04-23



A CO2 counter-current liquid extraction is then performed
in an extractor, in which the mixture is fed in through the
top of the extraction column and the CO2 is fed in through
the bottom of the extraction column. This extraction is
performed in the presence of 15 kg of CO2 at a temperature
of 77~C and a pressure of 280 bar.

The CO2 loaded with flavours, which leaves at the top of
the extraction column, is then recovered and subjected to
separation in a separator so as to remove the CO2 and
isolate the liquid flavour extract. For this purpose the
solubility of the flavours in the CO2 is reduced by
lowering the temperature to a temperature less than or
equal to 20~C and the pressure to a pressure of less than 40
bar in the extractor.

The extraction and the separation are performed in an SFF
5860 extraction unit, marketed by Separex Chimie Fine,
F-54250 Champigneulles.
The CO2 which has been removed is recompressed and
reintroduced into the extractor for another extraction.

The flavour extract is dried, using maltodextrin as the
drying support.

At the same time a composition is prepared containing 373 g
maltodextrin, 190 g salt, 100 g yeast extract, 90 g
dextrose, 80 g starch, 65 g beef fat, 36 g sugar, 5 g
caramel colour, 2.5 g onions, 2 g citric acid, 1 g pepper,
0.5 g garlic, 0.5 g thyme and 0.5 g marjoram.

0.8 g of the flavour extract, 1.2 g salt and 19 g of this
composition are then added to 1 l of hot water.


CA 02232334 l998-04-23


14
A reference is also made by mixing 19 g of the composition
and 1.2 g salt into 1 l of hot water.

The flavour note of the beef stock prepared with the
flavour extract obtained by implementing the process
according to the present invention is then compared with
that of the reference stock.

The stock made with the flavour extract has a very
pronounced beef flavour whereas the reference stock has a
very weak meat flavour.

Example 2

A chicken stock is prepared using a flavour extract
obtained by implementing the process according to the
present invention.

For this purpose, a flavour extract is prepared as
described in Example 1.

At the same time, a composition is prepared containing
378 g maltodextrin, 190 g salt, 100 g yeast extract, 91 g
dextrose, 80 g starch, 65 g chicken fat, 36 g sugar, 0.5 g
caramel colour, 2.5 g turmeric, 2 g citric acid, 1 g
pepper, 0.5 g garlic, 0.5 g rosemary and 0.5 g ginger.

0.8 g of the flavour extract, 19 g of this composition and
1.2 g salt are then added to 1 l of hot water.
A reference stock is also prepared from 1 l of hot water
into which 19 g of the composition and 1.2 g salt are
mlxed .

The flavour note of the chicken stock prepared with the
flavour extract obtained by implementing the process

CA 02232334 l998-04-23



according to the present invention is then compared with
that of the reference stock.

The stock made with the flavour extract has a very
pronounced chicken flavour whereas the reference stock has
a flavour bearing little resemblance to that of chicken.

Representative Drawing

Sorry, the representative drawing for patent document number 2232334 was not found.

Administrative Status

For a clearer understanding of the status of the application/patent presented on this page, the site Disclaimer , as well as the definitions for Patent , Administrative Status , Maintenance Fee  and Payment History  should be consulted.

Administrative Status

Title Date
Forecasted Issue Date Unavailable
(22) Filed 1998-04-23
(41) Open to Public Inspection 1998-11-15
Dead Application 2004-04-23

Abandonment History

Abandonment Date Reason Reinstatement Date
2003-04-23 FAILURE TO PAY APPLICATION MAINTENANCE FEE
2003-04-23 FAILURE TO REQUEST EXAMINATION

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Registration of a document - section 124 $100.00 1998-04-23
Application Fee $300.00 1998-04-23
Maintenance Fee - Application - New Act 2 2000-04-24 $100.00 2000-03-15
Maintenance Fee - Application - New Act 3 2001-04-23 $100.00 2001-03-15
Maintenance Fee - Application - New Act 4 2002-04-23 $100.00 2002-03-18
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
SOCIETE DES PRODUITS NESTLE S.A.
Past Owners on Record
CERNY, CHRISTOPH
HEYLAND, SVEN
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Cover Page 1998-11-25 1 26
Abstract 1998-04-23 1 11
Description 1998-04-23 15 521
Claims 1998-04-23 2 38
Assignment 1998-07-14 3 74
Correspondence 1998-06-03 1 29
Assignment 1998-04-23 2 115