EP1051085A1 - Verfahren zur herstellung von aromastoffen und deren anwendung in lebensmitteln - Google Patents

Verfahren zur herstellung von aromastoffen und deren anwendung in lebensmitteln

Info

Publication number
EP1051085A1
EP1051085A1 EP98957065A EP98957065A EP1051085A1 EP 1051085 A1 EP1051085 A1 EP 1051085A1 EP 98957065 A EP98957065 A EP 98957065A EP 98957065 A EP98957065 A EP 98957065A EP 1051085 A1 EP1051085 A1 EP 1051085A1
Authority
EP
European Patent Office
Prior art keywords
process according
flavour
sulfur
flavouring
yeast
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98957065A
Other languages
English (en)
French (fr)
Inventor
Rachid Bel Rhlid
Imre Blank
Christophe Cerny
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe des Produits Nestle SA
Nestle SA
Original Assignee
Societe des Produits Nestle SA
Nestle SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Societe des Produits Nestle SA, Nestle SA filed Critical Societe des Produits Nestle SA
Priority to EP98957065A priority Critical patent/EP1051085A1/de
Publication of EP1051085A1 publication Critical patent/EP1051085A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/40—Feeding-stuffs specially adapted for particular animals for carnivorous animals, e.g. cats or dogs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2056—Heterocyclic compounds having at least two different hetero atoms, at least one being a nitrogen atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/24—Synthetic spices, flavouring agents or condiments prepared by fermentation
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/14—Nitrogen or oxygen as hetero atom and at least one other diverse hetero ring atom in the same ring

Definitions

  • the present invention relates to a process for the preparation of flavouring compositions, more particularly the biogeneration of mixtures comprising sulfur-containing compounds and having roasty, meaty-like or sausage-like notes, and which are usable in foodstuffs, especially for intensifying the meaty flavour thereof.
  • Sulfur-containing compounds are important known flavour constituents in many foods, such as meat.
  • heterocyclic compounds such as thiazoles and furans , as well as their derivatives play a key role in roasted flavours.
  • S-containing compounds are known as constituents of meat flavours and having a meaty and roasty flavour character and a very low sensory threshold value, such as 2-methyl-3-furanthiol (MFT) (see for example U.S. pat. 4,139,649). Also 2-methyl-thiazolidine (MT) has been used in combination with other odorants to enhance meat-like flavours, as reported for example in U.S. pat. 3,881,025.
  • MFT 2-methyl-3-furanthiol
  • MT 2-methyl-thiazolidine
  • the purpose of this invention is to provide a new and natural route for obtaining food grade complex mixtures containing heterocyclic compounds, especially furan and thiazol derivatives, as well as other sulfur- containing compounds .
  • the object of the present invention is thus a process for the preparation of a flavouring composition containing 2-acetyl-2-thiazoline (2-AT) and precursors thereof, as well as additional flavour ingredients, such as alkylated thiazolidines, 2-methyl-3-f ranthiol (MFT) and mercaptopentanone, which comprises the bioconversion of a sulfur-containing compound and an organic acid or a derivative thereof in the presence of a yeast.
  • a flavouring composition containing 2-acetyl-2-thiazoline (2-AT) and precursors thereof, as well as additional flavour ingredients, such as alkylated thiazolidines, 2-methyl-3-f ranthiol (MFT) and mercaptopentanone, which comprises the bioconversion of a sulfur-containing compound and an organic acid or a derivative thereof in the presence of a yeast.
  • composition obtained can be used directly as the liquid reaction mixture, or can be submitted to a separation step, so as to recover the supernatant from said reaction mixture.
  • the process can be carried out under aerobic or anaerobic conditions.
  • the supernatant separated from the reaction mixture for example by centrifugation, is usable as a flavouring composition either directly in liquid form or in powder from obtained by mild dehydration methods .
  • the starting sulfur-containing compound can be selected from the group comprising the compounds having the following formula (I) :
  • - X is H, HC1, HBr or -CO- (CH 2 ) 2 -CH(NH 2 )-COOH
  • n 1 or 2 , as well as peptides including said compounds of formula
  • cysteamine and cysteine or the salts and derivatives thereof, as well as glutathione .
  • organic acids those being of food grade such as the hydroxy- or keto-propionic acids, as well as their derivates, esters and salts thereof, can be used, for example lactic or pyruvic acids, or esters thereof such as ethyl-lactate or ethyl-pyruvate.
  • the preferred yeast used for the bioconversion is baker's yeast, for example in the form of a powder, an extract or a cream solution, but other kinds of microorganisms can also be used, such as for example Candida versatilis, Debaromyces hansenii, Saccharomyces bayanus, etc.
  • the yeast is fresh, up to about 8 days, advantageously up to about 4 days, and kept in the refrigerator .
  • the respective quantities of the two starting products they can be such as the molar ratio between the sulfur-containing compounds and the organic acid is about 1:1 or up to about 1:2.
  • the concentration of these substrates in the reactional medium can be of 1 to 100 mMol, preferably from 10 to 30 mMol .
  • the yeast cream solution is used as from 20 to 60 ml per mMol of substrate, but this range can be adjusted according to the yeast and the substrates concerned.
  • the incubation with yeast can be carried out in presence of a sugar, such as tetroses, pentoses, hexoses, preferably glucose.
  • a sugar such as tetroses, pentoses, hexoses, preferably glucose.
  • the incubation with the microorganisms can be carried out under aerobic or anaerobic conditions, preferably aerobic during 2 to 72 hr, preferably 4 to 48 hr, and at a pH of 7.0 to 11.0, preferably 8.0 to 10.0.
  • the temperature of the reaction can be of 20 to 50°C, preferably about 30°C, and it can be carried out under medium to high agitation conditions .
  • the reaction medium can be water or a buffer solution, such as phosphate or carbonate-bicarbonate .
  • flavouring composition thus obtained by the process according to the invention surprisingly revealed a flavour described after sensory evaluation as roasty, meaty, sausage-like, dried sausage-like and somewhat amine-like.
  • the reaction mixture can be used directly as such in liquid form, especially in petfood for aromatising this kind of products.
  • reaction mixture is advantageously submitted after bioconversion to a separation step, preferably by centrifugation, so as to recover the supernatant from the mycelium.
  • the supernatant can be either maintained as it is in liquid form or dehydrated into a powder under mild conditions, e.g. by spray or freeze drying, this without modifying the aroma thereof.
  • This composition can be thus advantageously used in foodstuffs in order to intensify the meaty flavour thereof, more particularly in soups, sauces, sausages, meat based dishes and snacks, and other culinary products, as well as in processed meat flavours and petfood.
  • flavouring composition can also be combined with other known flavouring agents and/or food additives, possibly in presence of a support such as maltodextrine or cyclodextrine, and thermally processed to increase various types of meaty notes .
  • the preferred conditions of the optional heat treatment are the following : 80-120°C, 30 to 120 min, and the pH is comprised between 6 and 10, preferably between 6 and 7.
  • flavouring composition as obtained by the process according to the present invention i.e. by biogeneration without heating
  • the main odorant compounds present in Composition A obtained by the process according to the invention have been identified, and the flavour of said composition has been evaluated, more particularly on diethyl-ether extracts.
  • 15ml of the supernatant of Composition A was saturated with NaCl and extracted with purified diethyl-ether, using a liquid-liquid extractor (rotary perforator).
  • the organic phase was dried over anhydrous sodium sulfate and concentrated to about 1ml by micro-distillation .
  • odor-active volatile compounds were detected in the aroma extract of Composition A by gaz chromatography-olfactometry (GC-O), using "Carlo Erba” gas chromatographs equipped with automatic cold on-column injector, flame ionization detector and sniffing port, and by gas chromatography-mass spectrometry (CG-MS) using a "Finnigan MAT-8430" apparatus.
  • GC-O gaz chromatography-olfactometry
  • CG-MS gas chromatography-mass spectrometry
  • odorants having an aroma intensity higher than 1 are listed in Table 1, e.g. 2-AT, MT, 2-ethyl-3 , 5-dimethylpyrazine and N-acetyl- cystramine, which were identified by GC-0 and GC-MS, their sensory and chromatrophic properties being identical to those of the reference compounds.
  • MFT and 3-mercapto-2- pentanone were identified on the basis of retention index on three differently polar capillaries (FFAP, SE-54, 0V- 1701) and their odour characteristics, which were found to be identical with those of the corresponding reference compounds .
  • the aroma of Composition A was evaluated by sniffing the headspace of the freshly prepared samples and of diethyl-ether extracts thereof.
  • the assessors generally 10) were asked to describe the aroma quality and intensity using sniffing strips.
  • composition A results in a flavour described as roasty, meaty, amine-like (fishy), dried sausage and sausage-like of high intensity, which indicated that the roasty aroma of 2-AT was at least partly "covered” by other odorants having meaty, sulfury and amine-like notes.
  • Table 1 Main odorants detected by GC/Olfactometry (CG/0) and GC/MS in the aroma extract of Composition A.
  • Composition A 1100ml of the liquid preparation Composition A were freeze-dried on plates using a "Lyolab F" apparatus (LSD Secfroid) . The liquid was freezed at -40°C and lyophilised in vacuum at 2 mbar . The temperature of the plates was held at 10°C. About 115g of a homogeneous powder was obtained, i.e. Composition AF . For taste-testing, 0 , 8g of Composition AF and 0,5g table salt were dissolved in 250ml of hot water. The aroma and flavour of the product was described as pleasant sausage-like of high intensity.
  • 35g maltodextrine (Glucide ⁇ S> 01) were dissolved in 500g of the liquid preparation Composition A.
  • the resulting solution was spray-dried on a "B ⁇ chi Mini Spray Dryer" at 115°C (inlet temperature).
  • the powder obtained, as Com- positon AS was homogeneous.
  • 3.4g of Composition AS and 2g table salt were dissolved in 1 It of hot water and compared with the liquid Composition A (20 g/1). A pronounced and pleasant sausage-like flavour was perceived in both samples .
  • composition A can be dried without changing the aroma character (sausage-like).
  • the resulting powders, Composition AF and AS, are thus suitable for aromatising food products.
  • Example 4 Sausage note (fermented meat note)
  • a culinary base mass was prepared by adding molten beef fat (6.00 g) to a mixture comprising the following ingredients :
  • a bouillon (reference sample) was prepared by adding 250ml of boiling water to 3.40g of the culinary base mass and 0.1 Og table salt. The resulting product showed a bouillon flavour, however no pronounced meat character.
  • Example 5 Meat flavour (beef-type note)
  • a culinary base mass was prepared by adding molten beef fat (6.00 g) to a mixture comprising the following ingredients :
  • Yeast extract powder 2.25 g
  • the mixture was homogenised and sieved, thus yielding a culinary base mass.
  • a bouillon (reference sample) was prepared by adding 250 ml of boiling water to 5.00 g of the culinary base mass and 0.10 g table salt. The resulting product showed a good basic bouillon character with a weak beef note.
  • Example 6 Meat flavour (chicken-type note)
  • Chicken fat (5.00 g) was molten together with 0.30 g turmeric, added to 37.80 g table salt and again homogenized. The mixture above was added and again homogenized and sieved.
  • a culinary base mass was prepared by adding 1.30 g fat powder to the mixture.
  • a bouillon (reference sample) was prepared by adding 250 ml of boiling water to 4.75 g of the culinary base mass and 0.10 g table salt. The resulting product showed a good basic bouillon character with a chicken note.
  • Example 7 Process flavour (meaty/roasty note)
  • composition obtained by the process according to the invention can advantageously be used to provide or intensify meaty flavours of foodstuffs, such as soups, sauces, sausages, meat based dishes, snacks, processed flavours or petfood, etc.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biotechnology (AREA)
  • Nutrition Science (AREA)
  • Animal Husbandry (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Birds (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Fodder In General (AREA)
  • Meat, Egg Or Seafood Products (AREA)
  • Seasonings (AREA)
EP98957065A 1997-12-23 1998-12-14 Verfahren zur herstellung von aromastoffen und deren anwendung in lebensmitteln Withdrawn EP1051085A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP98957065A EP1051085A1 (de) 1997-12-23 1998-12-14 Verfahren zur herstellung von aromastoffen und deren anwendung in lebensmitteln

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP97122714 1997-12-23
EP97122714A EP0951840A1 (de) 1997-12-23 1997-12-23 Verfahren zur Herstellung von Aromastoffen und deren Anwendung in Lebensmitteln
PCT/IB1998/002004 WO1999033359A1 (en) 1997-12-23 1998-12-14 Process for the preparation of flavouring compositions and use of these compositions in foodstuffs
EP98957065A EP1051085A1 (de) 1997-12-23 1998-12-14 Verfahren zur herstellung von aromastoffen und deren anwendung in lebensmitteln

Publications (1)

Publication Number Publication Date
EP1051085A1 true EP1051085A1 (de) 2000-11-15

Family

ID=8227862

Family Applications (2)

Application Number Title Priority Date Filing Date
EP97122714A Withdrawn EP0951840A1 (de) 1997-12-23 1997-12-23 Verfahren zur Herstellung von Aromastoffen und deren Anwendung in Lebensmitteln
EP98957065A Withdrawn EP1051085A1 (de) 1997-12-23 1998-12-14 Verfahren zur herstellung von aromastoffen und deren anwendung in lebensmitteln

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP97122714A Withdrawn EP0951840A1 (de) 1997-12-23 1997-12-23 Verfahren zur Herstellung von Aromastoffen und deren Anwendung in Lebensmitteln

Country Status (5)

Country Link
EP (2) EP0951840A1 (de)
JP (1) JP2001526911A (de)
AU (1) AU1348399A (de)
CA (1) CA2314904A1 (de)
WO (1) WO1999033359A1 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999056566A1 (fr) * 1998-05-07 1999-11-11 Ajinomoto Co., Inc. Procede relatif a la production de soupes et de sauces en poudre instantanees
WO2001077359A2 (en) * 2000-04-06 2001-10-18 Societe Des Produits Nestle S.A. Preparation of thiols and derivatives by bio-conversion
EP2067408A1 (de) 2007-11-28 2009-06-10 Exquim S.A. Zusammensetzungen zur Erhöhung des Appetits von Ferkeln
JP4783421B2 (ja) * 2008-12-25 2011-09-28 長谷川香料株式会社 ゴマ様香味増強剤
CN102987081B (zh) * 2011-09-15 2014-11-19 上海美农生物科技股份有限公司 一种具有诱食功能的饲料香味剂及其制备方法
EP2995202A1 (de) 2014-07-23 2016-03-16 Interquim, S.A. Tierfutterzusatz
JP6484005B2 (ja) * 2014-11-11 2019-03-13 アサヒビール株式会社 ビール様飲料用風味改善剤
JP2018042497A (ja) * 2016-09-14 2018-03-22 キッコーマン株式会社 加熱肉様の香りが増強された醤油様調味料の製造方法
CN109907293B (zh) * 2019-03-08 2023-04-18 千禾味业食品股份有限公司 一种提高酱油2m3f含量的方法及其用途
JP7471887B2 (ja) * 2020-03-25 2024-04-22 日清食品ホールディングス株式会社 風味増強剤及び風味増強方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3678064A (en) * 1970-01-07 1972-07-18 Lever Brothers Ltd Certain 2-acyl-2-thiazolines
US5039543A (en) * 1990-11-16 1991-08-13 Nestec S.A. Preparation of flavors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9933359A1 *

Also Published As

Publication number Publication date
CA2314904A1 (en) 1999-07-08
WO1999033359A1 (en) 1999-07-08
JP2001526911A (ja) 2001-12-25
AU1348399A (en) 1999-07-19
EP0951840A1 (de) 1999-10-27

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