WO2012072630A1 - Procédé de production de saveurs - Google Patents

Procédé de production de saveurs Download PDF

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Publication number
WO2012072630A1
WO2012072630A1 PCT/EP2011/071286 EP2011071286W WO2012072630A1 WO 2012072630 A1 WO2012072630 A1 WO 2012072630A1 EP 2011071286 W EP2011071286 W EP 2011071286W WO 2012072630 A1 WO2012072630 A1 WO 2012072630A1
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WO
WIPO (PCT)
Prior art keywords
product
products
amino acid
process according
admixture
Prior art date
Application number
PCT/EP2011/071286
Other languages
English (en)
Inventor
David C. Bom
Gary Kleman
Yuangang Zhang
Original Assignee
Givaudan 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 Givaudan Sa filed Critical Givaudan Sa
Publication of WO2012072630A1 publication Critical patent/WO2012072630A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
    • A23F5/465—Flavouring with flavours other than natural coffee flavour or coffee oil
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/24—Extraction of coffee; Coffee extracts; Making instant coffee
    • A23F5/243—Liquid, semi-liquid or non-dried semi-solid coffee extract preparations; Coffee gels; Liquid coffee in solid capsules
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
    • A23L27/215—Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning

Definitions

  • This disclosure refers to a process for the preparation of flavor compositions with unique flavor profiles obtained by carrying out a reaction of 3,4,5-trihydroxypentan-2- one with amino acids.
  • compositions having unique natural flavoring properties are suitable for use in a variety of products. It has now been found that flavor compositions possessing unique flavor profiles can be obtained by carrying out a heat-induced reaction of 3 ,4,5-trihydroxypentan-2-one with an amino acid source in a liquid phase. The flavor compositions obtained by this process were found to have remarkable flavor characteristics and are particularly useful for imparting pleasant flavor notes to foodstuffs and beverages.
  • a liquid selected from the group consisting of water, oil and alcohol (e.g. methanol or ethanol), or a mixture thereof and an amino acid source;
  • the flavoring composition thus prepared may then optionally be cooled down to room temperature and then either be used as crude product or optionally further processed, e.g. by phase separation, or extraction, e.g. using solvents commonly used in the flavor industry, e.g. 1 ,2,3-triacetoxypropane (more generally known as triacetin) ortriethyl citrate.
  • solvents commonly used in the flavor industry e.g. 1 ,2,3-triacetoxypropane (more generally known as triacetin) ortriethyl citrate.
  • the products may be spray dried or encapsulated using techniques known to the skilled person.
  • Suitable oils are of any kind which are acceptable in the food industry, such as vegetable oils, e.g. sunflower oil, corn oil, soybean oil, palm oil, a medium chain triglyceride (MCT oil) oil, or mixtures thereof.
  • vegetable oils e.g. sunflower oil, corn oil, soybean oil, palm oil, a medium chain triglyceride (MCT oil) oil, or mixtures thereof.
  • MCT oil medium chain triglyceride
  • 3,4,5-Trihydroxypentan-2-one which exists naturally in an equilibrium with its cyclic form, comprises two chiral centers and as such may exist as two diastereomers (la known as 1 -deoxy-D-xylulose (DXX); lb known as 1 -deoxy-D-ribulose) as depicted below, each of which may exist as enantiomer pairs.
  • DXX is commercially available (Carbosynth Limited, or Echelon Biosciences Inc.). It can be produced chemically following the general procedure as described, e.g. by Meyer O., J.F.Hoeffler, C.Grosdemange-Billiard, and M. Rohmer (Tetrahedron 2004 60:12153- 12162). Optionally DXX may be produced according to the following procedure, as depicted in Scheme 1 below, by treating the aldehyde 1 with the ylide 2 in
  • Optically pure DXX could be obtained by treatment of intermediate 3 with catalytic osmium tetroxide, 4-methylmorpholine-/V-oxide NMO and AD-mix ⁇ (e.g. offered by Sigma-Aldrich), followed by hydrogenolysis leading to 1-deoxy-D-xylulose with an ee of 98%, as depicted in Scheme 2.
  • catalytic osmium tetroxide, 4-methylmorpholine-/V-oxide NMO and AD-mix ⁇ e.g. offered by Sigma-Aldrich
  • methanol as solvent
  • ethyl acetate thus eliminating the problem of solvolysis of 6.
  • high pressure (60 psi 4.137 bar) of hydrogen along with Pearlman's catalyst (Pd(OH)2) led to a more efficient hydrogenolysis relative to the reported Pd/C.
  • DXX 1-deoxy-D-xylulose
  • DXXX 1-deoxy-D-xylulose
  • Non-phosphorylated DXX has been found, for example, in the broth of a Streptomyces species (Rohmer, . 2007. Pure Applied Chemistry. 79(4):739-751). It has also been made enzymatically with the enzyme 1-deoxyxylulose synthase. Both the phosphorylated and non-phosphorylated form may be produced depending upon the starting material (if the glyceraldehyde is phosphorylated) (Brammer and Meyers. 2009. Organic Letters. 1 1(20):4748-4751 ).
  • amino acid source free amino acids, such as alanine, phenylalanine, glutamic acid, lysine, valine, proline, leucine, ornilhine, tyrosine, glycine and citrulllne, and salts thereof (e.g.
  • lysine hydrochloride or a mixture thereof, as well as peptides or hydrolyzed proteins, which may be selected from acidic or enzymatic hydrolyzates of materials rich in vegetable or animal proteins, such as oil seed cakes, soybeans, sugar extraction residues, cereal germs and the extracts or autolyzates of mocroorganisms rich in proteins, such as brewer's or baker's yeast, hydrolyzed dairy proteins such as enzyme modified cheeses or certain bacteria grown on hydrocarbon based substrates.
  • Yeast extracts are commonly available from DSM Food Specialties, Bio-springer and Kerry Bio-science.
  • the molar ratio between 3,4,5-trihydroxypentan-2-one and the amino acid source may be preferably between about 3 :1 to about 1 :10, the ratio being calculated on the estimated free amino acid present. However, even much higher amounts of amino acid equivalents may be added.
  • organic solvents such as triacetin (1 ,2,3- triacetoxypropane) ortriethylcitrate
  • carbohydrates in particular monosaccharides and oligosaccharides (e.g. di- and tri-saccharides) or mixtures thereof.
  • the carbohydrates may be added in its pure form or in form of fruit juices or other food sources containing them.
  • the pH range of the mixture may be adjusted with acid or base solutions, e.g. sodium hydroxide solution, sodium bicarbonate, sodium citrate, or sodium phosphate, to about 2 - 10, e.g., about pH 3 - 8. Controlling the pH during the reaction may maintain conditions to favor certain desired aroma chemicals.
  • Particular treatment temperatures are about 100 - 140° C (e.g. up to 130° C) and the reaction mixture may be maintained at these temperatures for about 30 minutes to 48 hours, e.g., 1 to 16 hours.
  • higher temperatures might be suitable, in particular when a continuous reactor is used for the process instead of a batch reactor.
  • the appropriate time and temperature conditions may easily be evaluated by a person skilled in the art.
  • the flavoring composition obtainable through the process as hereinabove described may be used alone or in combination with a base material.
  • the "base material” includes all known flavor ingredients that will modify, enhance or create flavor to a food product or beverage to be flavored.
  • the flavor composition may contain other ingredients useful as excipients such as carriers, diluents or bulking agents or the like, the purpose of which is to aid in the processing of a flavor composition or a product containing same, or otherwise impart a desirable property on the composition or product.
  • ingredients may include carbohydrates and carbohydrate polymers, e.g. polysaccharides, cyclodextrines, starches, starch hydrolysates, modified starches, modified celluloses, gums such as gum arabic, ghatti gum, traganth, karaya, carrageenan, guar, locust bean, alginates, pectin, inulin, or xanthan.
  • an aroma product comprising flavor compositions, obtainable through the process comprising
  • a liquid selected from the group consisting of water, oil and alcohol (e.g. methanol or ethanol), or a mixture thereof and an amino acid source;
  • composition comprising
  • a liquid selected from the group consisting of water, oil, alcohol (e.g. methanol or ethanol), and mixtures thereof, and an amino acid source;
  • step b) admixing the mixture of step a) to a consumable product
  • the thus obtained consumable product may then either be consumed in its heated form or cooled down either to room temperature or may be frozen.
  • the flavor composition obtained through the process as hereinabove described may be used to impart unique aroma to consumable products.
  • consumable product is meant any product, whether natural or manufactured, intended for oral intake, either for ingestion, or for oral use only followed by spitting out. In general, this includes any foodstuff, beverage, confectionery, medicinal or cosmetic oral care composition, pharmaceutical and the like.
  • Typical non-limiting examples of consumable products include: Animal protein from any desired animal source, for example, beef, pork, poultry, lamb, kangaroo, shell fish, crustaceans, fish, and combinations thereof;
  • Vegetable protein from any vegetable source for example, lupin protein, wheat protein, soy protein, and combinations thereof;
  • Fruit-derived products for example, those derived from tomatoes, apples, avocado, pears, peaches, cherries, apricots, plums, grapes, oranges, grapefruit, lemons, limes, cranberries, raspberries, blueberries, watermelon, cantelope, muskmelon, honeydew melon, strawberries, banana, and combinations thereof;
  • Vegetable-derived products for example, those derived from peas, carrots, com, potatoes, beans, cabbage, tomatoes, celery, broccoli, cauliflower, and leeks, nuts and nut products, processed foods, vegetable products, and food compositions thereof;
  • Cereals and cereal-derived products for example, farinaceous matter including grains such as, rice, com, milo, sorghum, barley, and wheat, and the like, and products derived therefrom; tapioca products, sago products, and food compositions thereof; pasta (for example, ground pasta), breading, and food compositions, dough derived from any of a variety of dough sources, including
  • Confectionery and dessert products for example, hard and soft candies, chocolate, ice creams, chewing gums, jellies and jams;
  • Milk and dairy products for example, yoghurts, cheese products, butter and butter substitute products, milk and milk substitute products, milk powders, soy products, edible oils and fat products and food compositions thereof;
  • Beverages for example, carbonated and non-carbonated beverages, alcoholic drinks such as beers, wines and spirits, non-alcoholic drinks such as soft drinks and sodas, including forms requiring reconstitution including, without limitation, beverage powder, milk-based beverage powder, sugar-free beverage powder, beverage syrup, beverage concentrate, coffee and tea, and food extracts;
  • Oral care compositions for example, mouthwashes, toothpastes and tooth gels, malodo counteractants and breath fresheners in solid, liquid and aerosol form;
  • Food additives and ingredients for example, yeast products, salt and spice products, snack foods, savory products, mustard products, vinegar products, seasonings, plant extracts, meat extracts, condiments, and gelatins;
  • Prepared food products including such products preserved by being, for example, dried, powdered, baked, refrigerated, frozen, fermented, pasteurized, sterilized, brined, for example, sauces (condiments), gravies, soups, prepared meat and vegetable products, pizzas, pre-cooked and oven-ready meals and microwave meals.
  • concentration of the flavor composition obtained through the process as hereinabove described required may vary over a wide range, depending on the desired taste and aroma effects, but as a general guide, they are employed in concentrations of from 1 to 2000 ppm by weight of the product in consumable form. Good results are obtained by using from 5 to 1000 ppm, e.g. about 10 - about 200 ppm in the final product. However, these values are given only by way of example, since the experienced flavorist may also achieve effects with lower or higher concentrations.
  • Amino acid source was a mixture of Leucine, Alanine and Phenylalanine (2 :1 :1) ** : Amino acid source was a mixture of Serine, Threonine, Proline and Cystine
  • Composition A Basmatic rice, tortilla note, roasted note.
  • Composition B Strong roast brown note, burnt, chocolate.
  • Composition C popcorn, nutty, chocolate.
  • Composition D creamy, dairy, slight roasted.
  • Composition E malty, chocolate-like, ashy, grilled
  • Composition F ashy, coffee-like, seared meat
  • L-Tyrosine 165 mM was admixed with a carbohydrate in a weight to weight ratio of approximately 3:1.
  • the pH of the reaction mixture was adjusted to pH 3 prior to heating at 140°C for 30 minutes in a pressure reactor.
  • Ribose 67 mM Earthy pyrazine-iike As can be seen from the table above the reaction product obtained from DXX compared to the reaction product obtained by using reducing sugars such as Xylose, Glucose, Fructose or Ribose is more intense and possesses superior flavor profiles i.e. dairy, and metallic, bioody notes which is desirable, for example, for savory and diary products.
  • L-Alanine (337 mM) was admixed with a carbohydrate In a weight to weight ratio of approximately 3:1.
  • the pH of the reaction mixture was adjusted to pH 6 prior to heating at 140°C for 30 minutes in a pressure reactor.
  • reaction product obtained from DXX compared to the reaction product obtained by using reducing sugars such as Xylose, Glucose, Fructose or Ribose is more intense with unique flavor profile such as bloody, metallic which is desirable for, for example for savory products.
  • Sample 4A Sample 4B % by weight % by weight
  • Sample 4A and 4B were tested by a group of 9 trained panelists. Sample 6b was described to be creamier, burnt ending, less bitter, more rounded, slightly nutty, pleasant note, more chocolate aroma compared to sample 6A.
  • Sample 5a and 5B were tested by a group of 8 trained panelists. Sample 5B was described to be tastier (i.e. more flavor, more aroma, more buttery, more creamy, more nutty/tortilla).

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Seasonings (AREA)

Abstract

L'invention concerne un procédé pour la préparation de compositions de saveurs avec des profils aromatiques uniques obtenues en effectuant une réaction de 3,4,5-trihydroxypentan-2-one avec une source d'acides aminés.
PCT/EP2011/071286 2010-11-29 2011-11-29 Procédé de production de saveurs WO2012072630A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US41759910P 2010-11-29 2010-11-29
US61/417,599 2010-11-29

Publications (1)

Publication Number Publication Date
WO2012072630A1 true WO2012072630A1 (fr) 2012-06-07

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PCT/EP2011/071286 WO2012072630A1 (fr) 2010-11-29 2011-11-29 Procédé de production de saveurs

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107404920A (zh) * 2015-03-19 2017-11-28 雀巢产品技术援助有限公司 奶精组合物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4022920A (en) * 1974-07-02 1977-05-10 Lever Brothers Company Flavoring with Amadori compounds
DE3722129A1 (de) * 1987-07-03 1989-01-12 Bat Cigarettenfab Gmbh Verfahren zur kontinuierlichen herstellung von aromastoffen, insbesondere tabakaromastoffen
EP1252825A1 (fr) * 2001-04-25 2002-10-30 Société des Produits Nestlé S.A. Compositions aromatisantes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4022920A (en) * 1974-07-02 1977-05-10 Lever Brothers Company Flavoring with Amadori compounds
DE3722129A1 (de) * 1987-07-03 1989-01-12 Bat Cigarettenfab Gmbh Verfahren zur kontinuierlichen herstellung von aromastoffen, insbesondere tabakaromastoffen
EP1252825A1 (fr) * 2001-04-25 2002-10-30 Société des Produits Nestlé S.A. Compositions aromatisantes

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BRAMMER; MEYERS., ORGANIC LETTERS., vol. 11, no. 20, 2009, pages 4748 - 4751
GINER ET AL., TETRAHEDRON LETT., 1998, pages 2479 - 2482
MEYER O.; J.F.HOEFFLER; C.GROSDEMANGE-BILLIARD; M. ROHMER, TETRAHEDRON, vol. 60, 2004, pages 12153 - 12162
ROHMER, M., PURE APPLIED CHEMISTRY., vol. 79, no. 4, 2007, pages 739 - 751

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107404920A (zh) * 2015-03-19 2017-11-28 雀巢产品技术援助有限公司 奶精组合物
US20180055079A1 (en) * 2015-03-19 2018-03-01 Nestec S.A. Creamer compositions
US10687548B2 (en) * 2015-03-19 2020-06-23 Societe Des Produits Nestle S.A. Creamer compositions

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