CN103932145A - Method for enhancing meat flavor of food by adopting 2-glycosylated thiazolidine-4-carboxylic acid - Google Patents

Method for enhancing meat flavor of food by adopting 2-glycosylated thiazolidine-4-carboxylic acid Download PDF

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Publication number
CN103932145A
CN103932145A CN201410165454.4A CN201410165454A CN103932145A CN 103932145 A CN103932145 A CN 103932145A CN 201410165454 A CN201410165454 A CN 201410165454A CN 103932145 A CN103932145 A CN 103932145A
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China
Prior art keywords
thiazolidine
carboxylic acid
glycosylation
sugar
food
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CN201410165454.4A
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Chinese (zh)
Inventor
谢建春
公敬欣
曹长春
张玲
都荣强
孙宝国
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Beijing Technology and Business University
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Beijing Technology and Business University
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Priority to CN201410165454.4A priority Critical patent/CN103932145A/en
Publication of CN103932145A publication Critical patent/CN103932145A/en
Pending legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/21Synthetic spices, flavouring agents or condiments containing amino acids
    • A23L27/215Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/26Meat flavours
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00Food compositions, function of food ingredients or processes for food or foodstuffs

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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)

Abstract

The invention provides a method for enhancing the meat flavor of a food by adopting 2-glycosylated thiazolidine-4-carboxylic acid. According to the method, a certain amount of 2-glycosylated thiazolidine-4-carboxylic acid is used in thermal-reaction meat flavor essence or other food manufacture relevant to thermal processing, the meat flavor of a food can be effectively enhanced, and the obtained food has the advantages of natural and rich smell, smell durability and good stability.

Description

A kind of method that adopts 2-glycosylation thiazolidine-4-carboxylic acid to strengthen food meat Flavor
Technical field
The invention belongs to technical field of food science, provide a kind of 2-of employing glycosylation thiazolidine-4-carboxylic acid to strengthen the method for food meat Flavor.
Background technology
Between amino acid and reduced sugar, occurring that Maillard reacts is one of important channel of forming of flavour of food products.In the elementary Maillard stage of reaction, amino acid-Amadori compound that amino acid and reduced sugar effect form is the important intermediate that causes food flavor substances to produce.In meat fragrance forms, cysteine is important raw material, under certain pH, cysteine reacts and forms cysteine-Amadori compound through elementary Maillard with reduced sugar, the further reaction under heating condition of cysteine-Amadori compound can form the important meat fragrance matters such as sulfur-containing compound, nitrogen heterocyclic ring, oxygen heterocycle, and (Xia Yanbin etc. write, flavour of food products chemistry, Chemical Industry Press, 2008.).Different from other amino acid, because cysteine contains sulfydryl reaction active groups, while there is elementary Maillard and react in cysteine and reduced sugar, except cysteine-Amadori compound, also forming 2-glycosylation thiazolidine-4-carboxylic acid intermediate, there is competition in the formation of 2-glycosyl thiazolidine-4-carboxylic acid intermediate and the formation of cysteine-Amadori compound.
Patent US20060280854A1 has reported and has utilized cysteine-Amadori compound to replace Maillard reaction raw material cysteine and sugar, to improve the utilization rate of cysteine and to promote meat Flavor to form.But in this patented method, the preparation process of cysteine-Amadori compound is loaded down with trivial details, and reaction temperature is high, cysteine-Amadori compound part in preparation process resolves into volatile flavor substance, make cysteine-Amadori compound to prepare productive rate low.The invention provides a kind of with 2-glycosylation-4-thiazolidinecarboxylic acid replacement Maillard reaction raw material cysteine and sugar, to improve cysteine utilization rate and to promote the method that meat Flavor forms, the method has overcome defect and the deficiency that productive rate is low of preparing of cysteine-Amadori compound, and in prior art, has no the report that adopts 2-glycosylation thiazolidine-4-carboxylic acid to strengthen food meat Flavor.
Summary of the invention
The invention provides a kind of method that the 2-of employing glycosylation thiazolidine-4-carboxylic acid strengthens food meat Flavor, technical scheme is as follows:
A kind of method that adopts 2-glycosylation thiazolidine-4-carboxylic acid to strengthen food meat Flavor, using 2-glycosylation thiazolidine-4-carboxylic acid as a kind of raw material, make an addition to thermal processing meat flavour or other relates in hot worked food manufacturing, can effectively strengthen food meat Flavor.
Wherein, 2-position carbon is chirality or achirality structure, and 2-glycosylation thiazolidine-4-carboxylic acid is reacted and obtains with sugar by cysteine.Sugar is the sugar that contains aldehyde radical, can be monose as glucose, wood sugar, or polysaccharide is as maltose, or by sugar degrade and the compound that contains aldehyde radical that comes as glyceraldehyde, pyroracemic aldehyde, glycolaldehyde, acetaldehyde etc., in the time that sugar is monose, structure can be expressed as follows:
R is hydrogen atom, n=4~5
Relate in hot worked food manufacturing at thermal processing meat flavour or other, a kind of 2-glycosylation thiazolidine-4-carboxylic acid can be added separately to use, also multiple 2-glycosylation thiazolidine-4-carboxylic acid can be mixed to add uses, and also can first be mixed and add and use again with starch, sugar, amino acid or other edible raw material.
The 2-glycosylation thiazolidine-4-carboxylic acid using can reference literature method be prepared (Process and Reaction Flavors, Weerasinghe, D., et al, Eds.; ACS Symposium Series.2005:117-129; Radomski J, Temeriusz A.Thiazolidine-4 (R)-carboxylic acids derived from sugars:Part I, C-2-epimerisation in aqueous solutions.Carbohydrate Research, 1989,187 (2): 223-237; De Roos K B.Meat flavor generation from cysteine and sugars.In Flavor Precursors, Teranishi, R., et al.Eds.; ACS Symposium Series; American Chemical Society:Washington, DC, 1992:203-216.), preparation process is simple, mild condition, yield is high, for example " cysteine and wood sugar in pH5 phosphate buffer 50 DEG C react 1h, in product, 2-xylosyl thiazolidine-4-carboxylic acid content can reach 90% ".2-glycosylation thiazolidine-4-carboxylic acid in product can use after separation and purification, can not edible raw material if do not use in preparation feedback, also can use without separating.
In the time that the Multiple components such as solutions of weak acidity and protein, amino acid exist, 2-glycosylation thiazolidine-4-carboxylic acid compound is heated and can constantly changes into cysteine-Amadori compound, cysteine-Amadori compound important meat fragrances such as discharging sulfur-containing compound, nitrogen heterocyclic ring, oxygen heterocycle that reacts, thus meat fragrance produced.Meanwhile, 2-glycosylation thiazolidine-4-carboxylic acid also can be heated self to degrade and produce meat fragrance.Because 2-glycosylation thiazolidine-4-carboxylic acid is the product of cysteine and sugar combination in advance, compare with sugar with using cysteine, add and use 2-glycosylation thiazolidine-4-carboxylic acid can improve the utilization rate of cysteine, strengthen meat Flavor.
Relate in hot worked food manufacturing at thermal processing meat flavour or other, a kind of 2-glycosylation thiazolidine-4-carboxylic acid can be added separately to use, also multiple 2-glycosylation thiazolidine-4-carboxylic acid can be mixed to add and use, also can with starch, sugar, after amino acid or other edible raw material mix, add and use, the adding method of 2-glycosylation thiazolidine-4-carboxylic acid and addition need to determine according to food technology and final local flavor, 2-glycosylation thiazolidine-4-carboxylic acid will react and produce meat fragrance in the time of heating, the generation speed of the higher meat fragrance of temperature is faster, the general 80-180 of heating-up temperature DEG C better.
Replace cysteine and sugar to prepare thermal processing meat flavour 2-glycosylation thiazolidine-4-carboxylic acid, can significantly improve the utilization rate of cysteine, prepared meat flavor meat is aromatic strongly fragrant; Hot-working by 2-glycosylation thiazolidine-4-carboxylic acid for food such as dilated food, ham sausage, roast chicken, gained food aroma is naturally full, lasting lasting, good stability.
Detailed description of the invention
Embodiment 1
20mmol cysteine hydrochloride and 20mmol wood sugar, 10mL water, 25 DEG C of room temperatures reaction 20h, add pyridine neutralization reaction liquid, then add 100mL ethanol to leave standstill to separate out solid, and vacuum drying obtains 2.0 grams of 2-xylosyl thiazolidine-4-carboxylic acids.Get 0.1 gram and join in 100 grams of pork protein enzymolysis liquids, add 0.2 gram of green onion, 0.1 gram, Chinese prickly ash, 0.5 gram of Chinese cassia tree again, 100 DEG C add thermal response 1 hour, obtain dense meat fragrant and have a roasting fragrant thermal processing meat flavour.The online detection of gas-matter, compares with wood sugar with the cysteine that uses a great deal of, and important meat fragrance 2-methyl-3-furanthiol content improves 3 times, and furfurylmercaptan content improves 2 times.
Embodiment 2
0.1mol cysteine and 0.1mol glucose, 50mL water, 50 DEG C of reaction 4h, adopt sulfonic acid ion exchange resin to separate, and freeze drying, obtains 18 grams of 2-glucosyl group thiazolidine-4-carboxylic acids.2-glucosyl group thiazolidine-4-carboxylic acid 0.5g is added in 400 grams of beef enzymolysis extract liquid, then add alanine and each 0.1 gram of glycine, 2 grams, butter, 2 grams of green onions, 1 gram, Chinese prickly ash, 4 grams of Chinese cassia trees, 90 DEG C of reaction 1.5h, obtain the aromatic strongly fragrant thermal Reaction for Beef Flavoring Production of meat.
Embodiment 3
According to pork 52%, show condition 11%, ice cube 24%, salt 1.5%, spices 0.8%, natrium nitrosum 0.01%, monosodium glutamate 0.12%, starch 2.1%, sugar 0.2%, composite phosphate 0.31%, the refrigerator that is placed in 4 DEG C is pickled 2 days, then meat is rubbed, and adds 2-xylosyl thiazolidine-4-carboxylic acid in 0.05% ratio of meat, record in casing, high-temperature sterilization can obtain the full ham sausage of local flavor.

Claims (6)

1. a method that adopts 2-glycosylation thiazolidine-4-carboxylic acid to strengthen food meat Flavor, it is characterized in that: 2-glycosylation thiazolidine-4-carboxylic acid is as a kind of raw material, make an addition to thermal processing meat flavour or other relates in hot worked food manufacturing, can effectively strengthen meat Flavor.
2. a kind of method that adopts 2-glycosylation thiazolidine-4-carboxylic acid to strengthen food meat Flavor according to claim 1, it is characterized in that: the 2-position carbon in 2-glycosylation thiazolidine-4-carboxylic acid is chirality or achirality structure, 2-glycosylation thiazolidine-4-carboxylic acid is reacted and obtains with sugar by cysteine, described sugar is the sugar that contains aldehyde radical, or is degraded and the next compound that contains aldehyde radical by sugar.
3. according to a kind of method that adopts 2-glycosylation thiazolidine-4-carboxylic acid to strengthen food meat Flavor described in claim 1 or 2, it is characterized in that: described sugar is monose or polysaccharide, by sugar degrade and come the compound that contains aldehyde radical be glyceraldehyde, pyroracemic aldehyde, glycolaldehyde or acetaldehyde.
4. a kind of method that adopts 2-glycosylation thiazolidine-4-carboxylic acid to strengthen food meat Flavor according to claim 3, is characterized in that: described monose is glucose or wood sugar, described polysaccharide is maltose.
5. a kind of method that adopts 2-glycosylation thiazolidine-4-carboxylic acid to strengthen food meat Flavor according to claim 3, is characterized in that: the structure of described monose can be expressed as follows:
r is hydrogen atom, n=4~5.
6. according to a kind of method that adopts 2-glycosylation thiazolidine-4-carboxylic acid to strengthen food meat Flavor described in claim 1 or 2, it is characterized in that: relate in hot worked food manufacturing at thermal processing meat flavour or other, 2-glycosylation thiazolidine-4-carboxylic acid is added separately to use, or multiple 2-glycosylation thiazolidine-4-carboxylic acid is mixed and adds use, or be first mixed and add and use again with starch, sugar, amino acid or other edible raw material.
CN201410165454.4A 2014-04-22 2014-04-22 Method for enhancing meat flavor of food by adopting 2-glycosylated thiazolidine-4-carboxylic acid Pending CN103932145A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5726597A (en) * 1980-07-22 1982-02-12 Meiji Seika Kaisha Ltd Preparation of l-cysteine
JP2003265142A (en) * 2002-03-15 2003-09-24 Ajinomoto Co Inc Method for improving quality of sausage
US20060280854A1 (en) * 2003-08-20 2006-12-14 Kris De Roos Maillard reaction compounds of cysteine and a sugar having meatlike flavour
CN101664157A (en) * 2009-08-24 2010-03-10 天津春发食品配料有限公司 Preparation method of pork essence

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5726597A (en) * 1980-07-22 1982-02-12 Meiji Seika Kaisha Ltd Preparation of l-cysteine
JP2003265142A (en) * 2002-03-15 2003-09-24 Ajinomoto Co Inc Method for improving quality of sausage
US20060280854A1 (en) * 2003-08-20 2006-12-14 Kris De Roos Maillard reaction compounds of cysteine and a sugar having meatlike flavour
CN101664157A (en) * 2009-08-24 2010-03-10 天津春发食品配料有限公司 Preparation method of pork essence

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