WO2019093738A1 - Arôme de réaction comprenant de l'allulose et son procédé de production - Google Patents
Arôme de réaction comprenant de l'allulose et son procédé de production Download PDFInfo
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- 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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- Prior art keywords
- flavor
- reaction
- compound
- reactive
- present application
- Prior art date
Links
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 117
- 235000019634 flavors Nutrition 0.000 title claims abstract description 93
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 72
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- LKDRXBCSQODPBY-JDJSBBGDSA-N D-allulose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@H]1O LKDRXBCSQODPBY-JDJSBBGDSA-N 0.000 title abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 25
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 claims description 20
- 235000013355 food flavoring agent Nutrition 0.000 claims description 18
- 235000013372 meat Nutrition 0.000 claims description 16
- RUYNUXHHUVUINQ-UHFFFAOYSA-N 2-Methyl-3-furanthiol Chemical compound CC=1OC=CC=1S RUYNUXHHUVUINQ-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 10
- CLSLQQCDHOZMDT-UHFFFAOYSA-N (2-Furanylmethyl) methyl disulfide Chemical compound CSSCC1=CC=CO1 CLSLQQCDHOZMDT-UHFFFAOYSA-N 0.000 claims description 8
- 239000000539 dimer Substances 0.000 claims description 8
- -1 methyldisulfanyl Chemical group 0.000 claims description 8
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 241000544912 Melanoides Species 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 235000013305 food Nutrition 0.000 abstract description 33
- 239000000203 mixture Substances 0.000 abstract description 16
- 239000000463 material Substances 0.000 abstract description 2
- 125000000151 cysteine group Chemical class N[C@@H](CS)C(=O)* 0.000 abstract 1
- 150000001945 cysteines Chemical class 0.000 description 25
- 235000000346 sugar Nutrition 0.000 description 25
- 235000001014 amino acid Nutrition 0.000 description 19
- 150000001413 amino acids Chemical class 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 17
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical class SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 13
- 235000015278 beef Nutrition 0.000 description 13
- 235000018417 cysteine Nutrition 0.000 description 13
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 10
- 239000008103 glucose Substances 0.000 description 10
- 239000003205 fragrance Substances 0.000 description 9
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 8
- 229930091371 Fructose Natural products 0.000 description 8
- 239000005715 Fructose Substances 0.000 description 8
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 150000001720 carbohydrates Chemical class 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000001953 sensory effect Effects 0.000 description 5
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- 235000008429 bread Nutrition 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 235000016213 coffee Nutrition 0.000 description 4
- 235000013353 coffee beverage Nutrition 0.000 description 4
- 235000009508 confectionery Nutrition 0.000 description 4
- 235000011194 food seasoning agent Nutrition 0.000 description 4
- 239000002304 perfume Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000013555 soy sauce Nutrition 0.000 description 4
- 235000013599 spices Nutrition 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000002470 solid-phase micro-extraction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 244000299461 Theobroma cacao Species 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 125000004989 dicarbonyl group Chemical group 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 235000014347 soups Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 239000003021 water soluble solvent Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- 108010005094 Advanced Glycation End Products Proteins 0.000 description 1
- 238000003691 Amadori rearrangement reaction Methods 0.000 description 1
- 208000035404 Autolysis Diseases 0.000 description 1
- 206010057248 Cell death Diseases 0.000 description 1
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 235000015429 Mirabilis expansa Nutrition 0.000 description 1
- 244000294411 Mirabilis expansa Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 238000012443 analytical study Methods 0.000 description 1
- 239000007961 artificial flavoring substance Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001058 brown pigment Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000013736 caramel Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 235000016019 chocolate confectionery Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
- 235000015071 dressings Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000021107 fermented food Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 235000013611 frozen food Nutrition 0.000 description 1
- MWFFRFMPYAKXEY-UHFFFAOYSA-N furan-3-thiol Chemical compound SC=1C=COC=1 MWFFRFMPYAKXEY-UHFFFAOYSA-N 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002641 glycemic effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000013536 miso Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 230000028043 self proteolysis Effects 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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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Abstract
La présente invention concerne : un procédé de production d'un arôme de réaction, le procédé comprenant une étape de mise en contact d'allulose et d'un analogue de cystéine, et une étape de chauffage du matériau résultant obtenu par mise en contact de celui-ci; un arôme de réaction produit par celui-ci; et une composition alimentaire comprenant l'arôme de réaction.
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Non-Patent Citations (5)
Title |
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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 |
KR102346711B1 (ko) | 2022-01-04 |
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