WO2019093738A1 - 알룰로스를 포함하는 반응 향미제 및 이의 제조방법 - Google Patents

알룰로스를 포함하는 반응 향미제 및 이의 제조방법 Download PDF

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Publication number
WO2019093738A1
WO2019093738A1 PCT/KR2018/013385 KR2018013385W WO2019093738A1 WO 2019093738 A1 WO2019093738 A1 WO 2019093738A1 KR 2018013385 W KR2018013385 W KR 2018013385W WO 2019093738 A1 WO2019093738 A1 WO 2019093738A1
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WO
WIPO (PCT)
Prior art keywords
flavor
reaction
compound
reactive
present application
Prior art date
Application number
PCT/KR2018/013385
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English (en)
French (fr)
Korean (ko)
Inventor
김수정
박윤경
임주희
최종민
변성배
정동철
Original Assignee
씨제이제일제당 (주)
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Publication of WO2019093738A1 publication Critical patent/WO2019093738A1/ko

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Classifications

    • 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
    • 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
    • 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
    • A23L27/26—Meat flavours
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/02—Acid
    • A23V2250/06—Amino acid
    • A23V2250/0616—Cysteine
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/02—Acid
    • A23V2250/06—Amino acid
    • A23V2250/0652—Tyrosine

Definitions

  • the present application relates to a method for preparing a reaction flavor comprising contacting an allylose and a cysteine analog and heating the contacted product; A reaction flavor produced thereby; And a food composition comprising the reactive flavor.
  • the flavor of a food determines its quality along with the physical properties and appearance of the food, and is one of the important factors for the consumer to select foods. Furthermore, the flavor of the food is the quality of the deterioration and corruption Is considered to be an important index of deterioration.
  • the mechanism by which the flavor components are generated during processing is very diverse and has not been clearly identified.
  • the components of the raw material itself may be changed by microorganisms and enzymes, or flavor components may be expressed by newly produced metabolites.
  • the interest and demand for the reaction fragrance produced from the food ingredient or the food through the heat treatment based on the Maillard reaction is increasing.
  • the structure of the raw materials used for the reaction in particular, the structure of the aroma component, which is the metabolite produced depending on the type of the protein or the sugar on which the chemical reaction is based
  • the perfume ingredient itself may vary depending on the temperature and pressure conditions used for processing the perfume ingredient, or the degree of expression of the desired perfume ingredient may be different. Studies on processing conditions capable of excellently expressing a perfume component in consideration of both the kind of the raw materials and the reaction conditions are still insufficient.
  • the present inventors confirmed the expression of beef flavor and found that when alulose was selected as a sugar source, the beef flavor was lower than that of other kinds of sugar sources such as sugar, glucose and lactose And thus the present invention has been completed.
  • One object of the present application is to provide a method for the preparation of a pharmaceutical composition comprising contacting allylose and a cysteine analogue; And heating the resultant of the contacting step.
  • the present invention also provides a method for producing a reaction flavor.
  • Another object of the present application is a process for the preparation of (i) 2-methylfuran-3-thiol; And (ii) at least one of 2-methylcyclopentan-1-one and 2 - [(methyldisulfanyl) methyl] furan) To provide a reactive flavor.
  • One aspect of the present application for achieving the above object is a method for producing a cysteine analogue comprising: contacting an allylose and a cysteine analog; And heating the contact resultant.
  • the present invention also provides a method for producing a reaction flavor.
  • a method for preparing a pharmaceutical composition comprising: (i) contacting an alulose, and (ii) a compound represented by the following formula (1), a salt thereof or a dimer thereof; And heating the contacted product.
  • the method comprises the steps of:
  • n is an integer from 1 to 4, and R is H, CH 3 , CH 2 CH 3 or -SH.
  • a reactive flavoring agent exhibiting beef flavor can be prepared through the above-described method for producing a reactive flavoring agent.
  • flavor agent in the present application is a food additive used to impart a specific odor and taste to a food, and includes natural flavors, artificial flavors, spices, spices and the like using extracts obtained from plants, leaves, It is a component that directly affects consumers' palatability.
  • the 'reaction flavor' raw material component of the present application when heated, it is mixed with the term 'reaction flavor' as a flavor agent using a flavor ingredient expressed through a chemical reaction between raw ingredients.
  • the chemical reaction includes Caramelization, Maillard reaction, heating reaction of a sulfur compound, and pyrolysis reaction of lipid.
  • the reactive flavoring agent of the present application may mean that the saccharide and the amino acid show a flavor expressed by Maillard reaction, and specifically, a meat flavor, more specifically, a beef flavor.
  • alulose is a type of sugar having the formula C 6 H 12 O 6 and a molecular weight of 180.16, which is known to exist in small quantities in figs, grapes, and the like, and is also called psicose.
  • the above-mentioned alulose is a concept including both D-alulose and L-alulose, and may be purchased from commercially available aluloses, directly extracted from natural products, and produced by chemical or microbiological methods, But is not limited thereto.
  • aluloses are rarely metabolized in the body, and the calorie is 0 to 0.2 kcal / g, which is very low to 0 to 5% as compared with the same amount of common sugars (fructose, glucose, sugar, etc.).
  • the aluloside can be used in solid form such as solid phase, powder, crystal and the like, and may be used in the form of crystalline alulose, but is not limited thereto.
  • the alulos may be aluloses having a purity of 90% or more (containing 90 wt% or more of alulose based on dry solids), a purity of 95% or more, a purity of 98% or more, or a purity of 98% to 99.5%.
  • the alulose of the present application has an advantage in that it exhibits a superior flavor as compared to glucose, fructose, which is the same hexabody, have. Specifically, in the present application, it was confirmed that not only the content of the chemical component expressing the beef flavor was excellent but also the sensory evaluation was excellent.
  • cyste analogue in the present application is used to collectively refer to components added to cause a Maillard reaction by reacting with a reducing sugar. Although other amino acids generally known can be used, cysteine or an analogue thereof is suitable for the purpose of the present application .
  • a compound of the following formula 1, a salt thereof or a dimer thereof can be used:
  • n is an integer from 1 to 4, and R is H, CH 3 , CH 2 CH 3 or -SH.
  • the compound of Formula 1 includes an amine and sulfur, and is a compound having two to five carbons between an amine and a sulfur.
  • a carboxyl group carboxyl group, COOH
  • cysteine homocysteine, methionine
  • cystine its dimeric form, cystine, may be included.
  • cysteine is an amino acid involved in the expression of representative beef flavor including sulfur, which can affect the flavor characteristics. Therefore, the cysteine is not necessarily limited to cysteine itself, but may be defined as a substance containing a primary amine and a thiol, and the other substance in the form of a primary amine and a thiol It is obvious to those skilled in the art that it is suitable for the production of the reaction flavor of the present application.
  • cysteine is an amino acid having a carboxyl group with 3 carbon atoms, but the site is not directly involved in the reaction, so it is not limited thereto.
  • the cysteine analogue may be purchased from a commercially available cysteine analogue itself generally used by a person skilled in the art in food production, or may be a cysteine analogue component originating from a raw material contained in the food, but is not limited thereto.
  • the contact means that the alurus and the cysteine analogue are in contact with each other, and there is no limitation on the form of the contact so long as the reaction can occur through heating after the contact. For example, it may be to mix aluloses and cysteine analogs in one space.
  • the heating may be to cause a Maillard reaction of the allyl and cysteine analogs.
  • the Maillard reaction in this application is also known as an amino-carbonyl reaction as a representative non-enzymatic browning reaction. Occurs between a reducing sugar and a compound having an amino group such as an amino acid, a peptide, or a protein.
  • the Maillard reaction was first reported by the French biochemist L. C. Maillard in 1912 and involved in the formation of browning and aroma during heat treatment, cooking or storage of food.
  • the carbonyl group and the amino group of the reducing sugar are condensed to form an amadori rearrangement composition through the nitrogen glycoside and then decomposed to form a reactive group such as 3-deoxyosone Rich dicarbonyl is produced, which in turn reacts with the amino compound to form a brown melanoidin with various fragrance components.
  • Melanoidin is a very stable substance having antioxidant activity and is a main cause of browning in almost all foods such as fermented foods such as soybean paste and soy sauce and roasted coffee. Browning by Mailler reaction occurs for a long time in general food, and the intensity of color is not high enough to be used as a coloring matter. However, high intensity color tone can be obtained by controlling reaction conditions. Browned foods such as soy sauce, miso, bread, cookies, and coffee probably contain Maillard reaction products such as retinoid compounds, dicarbonyl, and melanoidins.
  • the heating temperature may be 50 ° C to 200 ° C, 60 ° C to 150 ° C, 60 ° C to 100 ° C, specifically 80 ° C to 100 ° C, but is not limited thereto.
  • the reaction can be carried out without limitation as long as the allylose and the cysteine analogue react with each other to sufficiently express the flavor, and the Maillard reaction may occur at 60 ° C or higher.
  • the heating may be performed for 30 minutes to 2 hours, and may be performed for 30 minutes to 60 minutes, but is not limited thereto.
  • the progress of the Maillard reaction and the intensity of flavor expression may vary.
  • the Mailler reaction is generally carried out at 100 ° C for 30 minutes to 60 minutes.
  • a Maillard reaction was caused by a reaction at a temperature of 100 ° C for 2 hours.
  • the step of contacting the allylose and cysteine analog may be further contacting an aqueous solvent.
  • the alulose and cysteine analogue can be contacted, dissolved in a water-soluble solvent, and then heated.
  • the water-soluble solvent may be, but is not limited to, water, ethanol or methanol.
  • the progress of the Maillard reaction and the intensity of flavor expression may vary depending on the contact ratio of the alulose and cysteine analogues.
  • the allylose and amino acid may be contacted in a ratio of from 0.5: 1 to 5: 1, but not limited thereto, specifically 0.5: 1 to 4: 1, and more specifically, 1: : 1 to 2: 1, and even more specifically 2: 1.
  • the production method of the reactive flavoring agent of the present application may further comprise a step of cooling after the heating step.
  • the heated mixture is allowed to stand at room temperature for 30 minutes to produce a final product, a reactive flavor.
  • the reactive flavoring agent produced by the method of producing a reactive flavoring agent of the present application may be one comprising an aromatic compound.
  • the aroma compound is selected from the group consisting of 2-methylcyclopentan-1-one, 2-methylfuran-3-thiol, Sulfanyl) methyl] furan (2 - [(methyldisulfanyl) methyl] furan), but the present invention is not limited thereto.
  • Another aspect of the present application to accomplish the above object is a process for the preparation of (i) 2-methylfuran-3-thiol; And (ii) at least one of 2-methylcyclopentan-1-one and 2 - [(methyldisulfanyl) methyl] furan) To provide a reactive flavor.
  • the reactive flavoring agent may be one in which the allylose and cysteine analogue are subjected to the Meier reaction, and may represent meat, specifically, beef flavor.
  • aroma compounds may be further included.
  • aluloses cysteine analogues, Maillard reaction and aromatic compounds are as described above.
  • the reaction flavor comprises 2-methylcyclopentan-1-one and / or 2- [(methyldisulfanyl) methyl] furan in addition to 2-methylfuran- It may be that the flavor intensity is higher than that of the reaction flavor containing only furan-3-thiol.
  • the 2-methylcyclopentan-1-one may be used in an amount of 10 to 100 parts by weight, 10 to 50 parts by weight, and 10 to 30 parts by weight, based on 100 parts by weight of 2-methylfuran- 13 to 20 parts by weight, more specifically 15 to 19 parts by weight, of the 2 - [(methyldisulfanyl) methyl] furan may be contained in 100 parts by weight of 2-methylfuran- May be 90 to 300 parts by weight, 100 to 250 parts by weight, more preferably 110 to 240 parts by weight, and more preferably 120 to 230 parts by weight.
  • the reactive flavoring agent may further include melanoid.
  • Melanoidin is a term used to refer to the final product resulting from the Maillard reaction. Most of the melanoidins contained in actual foods are polymers. Fermentation of fermented soy sauce or soy sauce, roasted coffee, and so on. It has a strong antioxidant activity, is known to prevent cancer, is a brown pigment containing nitrogen in the molecule, and can be a major component of the characteristic brown of foods such as coffee, cocoa, bread, malt and honey.
  • the reactive flavor comprises the steps of: (i) contacting an alulose, and (ii) a compound of formula 1, a salt thereof or a dimer thereof; And heating the contacted product. ≪ IMAGE >
  • the flavor intensity of the reaction flavor of the present application may vary depending on the ratio of contact between the alulose and the cysteine analogue.
  • the allylose and cysteine analogues are present in a ratio of from 0.5: 1 to 5: 1, specifically from 0.5: 1 to 4: 1, more specifically from 1: 1 to 2: 1, But is not limited thereto.
  • Another aspect of the present application for achieving the above object is to provide a food composition comprising the reactive flavoring agent.
  • the particular ingredients may be provided in many distinct physical forms, such as, for example, in solid, liquid or encapsulated form.
  • the encapsulated form refers to a form in which a substance or component is contained within a capsule material and is protected, allowing it to progressively or completely release.
  • the reactive flavoring agent can be used together with other food compositions or components, and the amount of the reaction flavoring agent contained in the food composition can be appropriately determined in consideration of the taste of the food, the purpose of use, health, and the like.
  • the food composition containing the reactive flavoring agent of the present application may include various foods such as sauces, soups, soups, dressings, cooked and frozen foods, seasonings, complex seasonings, confections, breads, .
  • the seasoning food includes a soybean paste, a soybean paste, a kochujang, a mixed potato, and the like, and the complex seasoning food is prepared by mixing powder, salt, salt, spice, protein hydrolyzate, sodium L-glutamate, And may be processed by a method such as drying in the form of granules or solid.
  • the confectionery include chocolate, chocolate confectionery, gum, jelly, and caramel.
  • the breads include pastries, cakes, sandwiches, and crackers, and the confectionery may include cereals, flakes, muesli But is not limited thereto.
  • the composition can be freely used as long as it is a composition capable of producing food including a reaction flavoring agent.
  • aluloses, cysteine analogues and reactive flavors are as described above.
  • Another aspect of the present application for achieving the above object is a method for preparing a cysteine analogue comprising: contacting allylose and a cysteine analog; And heating the contacted product.
  • the present invention also provides a method for increasing the reaction flavor.
  • the flavor may be meat, in particular beef flavor.
  • Another aspect of the present application for achieving the above object is a method for producing a cysteine analogue comprising: contacting alulose with a food comprising a cysteine analog; And heating the contacted product.
  • the present invention also provides a method for increasing the flavor of a food product.
  • the flavor may be meat, in particular beef flavor.
  • Glycemic acid and amino acid were used for the preparation of reaction flavor.
  • Sugar, glucose, fructose, xylose and alulose were used as the party members, and cysteine, which is a typical amino acid involved in the expression of beef flavor, was contained by including sulfur as an amino acid.
  • the saccharide source and the amino acid were quantitatively measured in a sealed glass bottle, and then purified water was added thereto to dissolve the saccharide and the amino acid so as to obtain the desired concentration.
  • the prepared solution was sealed and heated in a preheated constant temperature water bath (100 DEG C) for 2 hours. The heated solution was allowed to stand at room temperature for 30 minutes to prepare a flavoring agent.
  • glycosides used and the ratio of amino acid to saccharide (weight ratio) used in each experimental group are shown in Tables 1 and 2 below.
  • reaction flavor 4 g was added to the vial for analysis and used as an analytical sample.
  • the conditions were as follows.
  • the GC / MS analysis conditions are as follows.
  • Example 3 it was confirmed that beef flavor could be expressed when alulose was used as a source of sugar, and it was tried to determine at which ratio meat flavor could be detected by varying the ratio of sugar source to amino acid.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Seasonings (AREA)
PCT/KR2018/013385 2017-11-10 2018-11-06 알룰로스를 포함하는 반응 향미제 및 이의 제조방법 WO2019093738A1 (ko)

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KR20170149928 2017-11-10
KR10-2017-0149928 2017-11-10

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CN110771853B (zh) * 2019-11-08 2023-01-20 北京味食源食品科技有限责任公司 一种贻贝膏状香精的制备

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KR100830886B1 (ko) * 2006-07-25 2008-05-21 단국대학교 산학협력단 쓴맛이 없고 고기 향이 강한 소고기 조미 분말의 제조 방법
KR101274395B1 (ko) * 2011-02-14 2013-06-24 주식회사 후드원 쇠고기 향미를 가지는 조미 소재의 제조방법

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BAEK, S. H. ET AL.: "Maillard Browning Reaction ofD-psicose as Affected by Reaction Factors", FOOD SCIENCE AND BIOTECHNOLOGY, vol. 17, no. 6, 2008, pages 1349 - 1351, XP055449512 *
MOTTRAM, D. S. ET AL.: "important Sulfur-containing Aroma Volatiles in Meat", ACS SYMPOSIUM SERIES, vol. 564, 29 July 1994 (1994-07-29), pages 180 - 187, XP055606906, ISSN: 1947-5918, DOI: 10.1021/bk-1994-0564.ch015 *
ONG, O. X.H. ET AL.: "High-intensity Ultrasound Production of Maillard Reaction Flavor Compounds in a Cysteine--xylose Model System", ULTRASONICS SONOCHEMISTRY, vol. 26, 2015, pages 399 - 407, XP055606912, ISSN: 1350-4177, DOI: 10.1016/j.ultsonch.2015.01.001 *
YANG, C. ET AL.: "Response Surface Methodology for Meat-like Odorants from Maillard Reaction with Glutathione 1: the Optimization Analysis and the General Pathway Exploration", JOURNAL OF FOOD SCIENCE, vol. 77, no. 9, 13 August 2012 (2012-08-13) - September 2012 (2012-09-01), pages C966 - C974, XP055606915, ISSN: 0022-1147, DOI: 10.1111/j.1750-3841.2012.02863.x *
ZHANG, Y. ET AL.: "Formation of Meatlike Aroma Compounds from Thermal Reaction of Inosine 5'-monophosphate with Cysteine and Glutathione", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 39, no. 6, 1 June 1991 (1991-06-01), pages 1145 - 1148, XP055606918, ISSN: 0021-8561, DOI: 10.1021/jf00006a031 *

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KR20210025555A (ko) 2021-03-09
TWI690273B (zh) 2020-04-11
KR20190053789A (ko) 2019-05-20
TW201934022A (zh) 2019-09-01
KR102346711B1 (ko) 2022-01-04

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