KR100363616B1 - Femented liquor for flavoring - Google Patents
Femented liquor for flavoring Download PDFInfo
- Publication number
- KR100363616B1 KR100363616B1 KR10-2000-0019421A KR20000019421A KR100363616B1 KR 100363616 B1 KR100363616 B1 KR 100363616B1 KR 20000019421 A KR20000019421 A KR 20000019421A KR 100363616 B1 KR100363616 B1 KR 100363616B1
- Authority
- KR
- South Korea
- Prior art keywords
- flavor
- vinyl
- ferulic acid
- fermentation
- flavor liquid
- Prior art date
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- 239000000796 flavoring agent Substances 0.000 claims abstract description 62
- 235000019634 flavors Nutrition 0.000 claims abstract description 62
- 239000007788 liquid Substances 0.000 claims abstract description 43
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims abstract description 39
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims abstract description 39
- 235000001785 ferulic acid Nutrition 0.000 claims abstract description 39
- 229940114124 ferulic acid Drugs 0.000 claims abstract description 39
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims abstract description 39
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000000855 fermentation Methods 0.000 claims abstract description 37
- 230000004151 fermentation Effects 0.000 claims abstract description 37
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 28
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 28
- 239000000243 solution Substances 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 235000013305 food Nutrition 0.000 claims abstract description 10
- 238000012545 processing Methods 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 5
- 239000011259 mixed solution Substances 0.000 claims abstract description 3
- 241000894006 Bacteria Species 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 7
- 102000004190 Enzymes Human genes 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 235000015099 wheat brans Nutrition 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 3
- 230000001737 promoting effect Effects 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 239000001963 growth medium Substances 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 230000001902 propagating effect Effects 0.000 claims 1
- 235000013555 soy sauce Nutrition 0.000 abstract description 14
- YOMSJEATGXXYPX-UHFFFAOYSA-N 2-methoxy-4-vinylphenol Chemical compound COC1=CC(C=C)=CC=C1O YOMSJEATGXXYPX-UHFFFAOYSA-N 0.000 abstract description 6
- 230000006872 improvement Effects 0.000 abstract description 6
- CHWNEIVBYREQRF-UHFFFAOYSA-N 4-Ethyl-2-methoxyphenol Chemical compound CCC1=CC=C(O)C(OC)=C1 CHWNEIVBYREQRF-UHFFFAOYSA-N 0.000 abstract description 3
- 241000235070 Saccharomyces Species 0.000 abstract description 3
- 235000021107 fermented food Nutrition 0.000 abstract description 2
- 235000019990 fruit wine Nutrition 0.000 abstract description 2
- 239000004615 ingredient Substances 0.000 abstract 1
- 235000010633 broth Nutrition 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 11
- 235000013312 flour Nutrition 0.000 description 10
- 235000014347 soups Nutrition 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- 210000005253 yeast cell Anatomy 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000267823 Hydrangea macrophylla Species 0.000 description 3
- 235000014486 Hydrangea macrophylla Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 235000015096 spirit Nutrition 0.000 description 3
- 241001513093 Aspergillus awamori Species 0.000 description 2
- 240000006439 Aspergillus oryzae Species 0.000 description 2
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 229910000462 iron(III) oxide hydroxide Inorganic materials 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 235000020095 red wine Nutrition 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 1
- IDVPUNSRRGGJIB-UHFFFAOYSA-N 5-ethyl-2-methoxyphenol Chemical compound C(C)C=1C=C(C(=CC1)OC)O.C(C)C=1C=C(C(=CC1)OC)O IDVPUNSRRGGJIB-UHFFFAOYSA-N 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241001037822 Bacillus bacterium Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 244000294411 Mirabilis expansa Species 0.000 description 1
- 235000015429 Mirabilis expansa Nutrition 0.000 description 1
- 244000299790 Rheum rhabarbarum Species 0.000 description 1
- 235000009411 Rheum rhabarbarum 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000004883 caffeic acid Nutrition 0.000 description 1
- 229940074360 caffeic acid Drugs 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 235000013536 miso Nutrition 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019997 soju Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
-
- 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
- A23L27/204—Aromatic compounds
-
- 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
- A23V2200/00—Function of food ingredients
- A23V2200/15—Flavour affecting agent
Abstract
4-비닐 구아이아콜(4-vinyl guaiacol)과 관련성분인 4-에틸 구아이아콜(4-ethyl guaiacol)은 과실주,간장 등의 발효식품에 미량(0∼5ppm) 함유되는 향미성분으로서, 식품의 향미에 크게 기여하고 있다. 그러나, 4-비닐 구아이아콜 또는 4-에틸 구아이아콜을 비교적 고농도로 함유하는 향미액(향미료)을 발효법에 의하여, 단기간에 쉽게 제조하는 방법은 알려져 있지 않다. 이와같은 관점에서, 본 발명자 등은 4-비닐 구아이아콜을 주성분으로 하는 향미액을 발효법에 의하여, 단기간에 안전하게 제조하는 방법과 그 이용에 대한 발명을 하게 되었다.4-vinyl guaiacol, 4-ethyl guaiacol, a related ingredient, is a flavor component contained in trace amounts (0-5 ppm) in fermented foods such as fruit wine and soy sauce. It contributes greatly to the flavor of the. However, a method for easily producing a flavor liquid (flavour) containing 4-vinyl gua alcohol or 4-ethyl gua alcohol in a relatively high concentration in a short time is not known. From this point of view, the inventors of the present invention have invented a method for safely producing a flavor liquid containing 4-vinyl guacol as a main component by a fermentation method in a short time and using the same.
본 발명은 밀기울에서 페룰산(ferulic acid)을 유리시켜 얻는 페룰산액과, 패룰산 변환능이 높은 사카로미세스속 호모를 증식시켜 얻는 효모배양액을 혼합하고, 이 혼합액의 발효에 의하여 4-비닐 구아이아콜을 비교적 고농도로 함유하는 향미액을 얻고, 이 향미액을 식품제조 또는 가공에 있어서, 향미개량의 재료로 사용하는 방법에 관한 것이다.The present invention mixes a ferulic acid solution obtained by releasing ferulic acid from bran and a yeast culture solution obtained by growing Saccharomyces genus having high ferulic acid conversion ability, and 4-vinyl guai by fermentation of the mixed solution. The present invention relates to a method of obtaining a flavor liquid containing acol at a relatively high concentration and using the flavor liquid as a material for flavor improvement in food production or processing.
Description
4-비닐 구아이아콜(4-vinyl guaiacol)을 주성분으로 하는 향미액(향미료)을 발효법에 의하여, 단기간에 안전하게 제조하는 기술과, 향미액을 식품제조 또는 가공의 재료로 사용하여, 식품의 향미를 개선하는 방법을 제공한다.The flavor of food using the technique of producing a flavor liquid (flavor) mainly composed of 4-vinyl guaiacol by fermentation method in a short period of time and using the flavor liquid as a material for food production or processing, Provides a way to improve.
본 발명은 결합형 페롤산(ferulic acid)을 함유하는 밀기울을 주원료로 하고, 발효법에 의하여 4-비닐 구아이아콜을 주성분으로 하는 향미액(향미료)을 제조하는 기술에 관한 것이며, 이것은 식품공업 또는 발효공업 분야의 향미료 제조기술에 속한다.The present invention relates to a technique for producing a flavor liquid (flavor) containing a bran containing ferulic acid as a main raw material, 4-vinyl gua alcohol as a main ingredient by fermentation, which is a food industry or It belongs to flavor manufacturing technology of fermentation industry.
종래, 발효법에 의하여 향미개선제(향미료)를 제조하는 기술로서는, 초산에틸 에스테르(ester)생산균을 주박 또는 주류 증류폐액으로 조제한 배지에 배양하고, 그 배양액을 가공하여 얻는 향미료의 제조법(일본 공개특허공보 소 54-126795), 쌀겨를 아밀라제(amylase)효소제, 국균(麴菌)을 배양한 국(麴) 등으로 가수분해 하여 페룰산(ferulic acid), 카페산(caffeic acid) 등의 페놀 카르복실산류를 생성시킨 향미액을 제조하고, 이 향미액을 식품에 첨가하는 향미증강법(일본 특허공보 소 55-48779) 등이 알려져 있다.Conventionally, as a technique for producing a flavor improving agent (flavor) by the fermentation method, a method of producing a flavor obtained by culturing the ethyl acetate-producing bacteria in a medium prepared with sake or liquor distillation waste, and processing the culture solution (Japanese Patent Laid-Open Publication 54-126795), rice bran is hydrolyzed with amylase enzymes, broths cultured with Korean bacteria, and phenol carboxyl such as ferulic acid and caffeic acid. The flavor enhancement method (Japanese Patent Publication No. 55-48779) etc. which manufacture the flavor liquid which produced the acid, and add this flavor liquid to food are known.
또한,4-비닐 구아이아콜과 관련성분인 4-에틸 구아이아콜(4-ethyl guaiacol)은 과실주, 간장 등의 발효제품 제조시, 장기간의 발효·숙성과정을 거쳐서, 미량(0∼5ppm) 생산되는 것이 알려져 있다.In addition, 4-ethyl guaiacol (4-ethyl guaiacol), a related component of 4-vinyl guaiacol, has a long period of fermentation and maturation during the production of fermented products such as fruit wine and soy sauce, and is a trace amount (0 to 5 ppm). It is known to be produced.
그러나, 이들 발효식품에서의 함량보다 4-비닐 구아이아콜을 고농도로 함유하는 향미액(향미료)의 제조에 관하여는 보고된 것이 없다. 이러한 실정하에서, 본 발명자들은 아스페르질루스(Aspergillus)속 균의 효소작용에 의하여, 밀기울에서 페룰산을 유리시키고, 이어서 페룰산 변환능이 높은 효모에 의하여, 4-비닐 구아이아콜을 생성시켜, 향미액을 제조하는 방법을 제시하였다.(한국 특허 출원번호 98-40406) 그러나, 향미액의 제조에 있어서 발효기간의 단축과 안전발효를 위해서는, 제조공정에 개량할 여지가 남아 있었다.However, there is no report on the preparation of flavor liquids (flavors) containing higher concentrations of 4-vinyl guiacol than those in these fermented foods. Under these circumstances, the present inventors liberated ferulic acid in bran by the enzymatic action of the genus Aspergillus , followed by production of 4-vinyl guiacol by yeast having high ferulic acid conversion ability, A method of preparing a flavor liquid is presented. (Korean Patent Application No. 98-40406) However, in the manufacture of a flavor liquid, in order to shorten the fermentation period and safe fermentation, there is room for improvement in the manufacturing process.
본 발명은 밀기울을 주원료로 하고, 발효법에 의하여 4-비닐 구아이아콜을 비교적 고농도로 함유하는 향미액(향미료)을 단기간에 안전하게 제조하는 기술을 제공하고자 하는 것이다.It is an object of the present invention to provide a technique for safely producing a flavor liquid (flavor) containing vinyl as a main raw material and containing a relatively high concentration of 4-vinyl guiacol by a fermentation method in a short time.
본 발명자 등은 상기한 과제를 해결하기 위하여, 상세히 연구·검토한 결과, 향미액 제조시, 페룰산을 4-비닐 구아이아콜로 변환하는 효모의 배양공정에서는, 효모를 낮은 pH의 산성배지에 배양하여, 잡균의 오염을 방지하고, 발효공정에서는 발효액을 교반하여, 효모와 기질인 페룰산의 접촉을 빈번하게 하므로써, 반응을 촉진하는 등의 조작이 매우 중요함을 알게 되었고, 이 식견에 의하여 본 발명을 완성하였다. 즉, 본 발명은 결합형 페룰산의 원료인 밀기울에서, 국균(Aspergillus oryzae)의 효소작용에 의하여 페룰산을 유리시킨 후, 밀기울을 분리하여 페룰산액을 얻는 공정과 페룰산 변환능이 높은 사카로미세스(Saccharomyces)속 효모를 낮은 pH의 배지에 배양하는 공정을 각각 실시하고, 이들 두 액을 혼합한 후, 혼합액을 교반하면서 발효시켜, 4-비닐 구아이아콜을 상당히 고농도로 함유하는 향미액을 단기간에 안전하게 제조하는 것이다.MEANS TO SOLVE THE PROBLEM In order to solve the above-mentioned subject, the present inventors studied and reviewed in detail, and in the culture process of yeast which converts ferulic acid to 4-vinyl guiacol at the time of preparation of a flavor liquid, yeast is transferred to the acidic medium of low pH By culturing, to prevent contamination of various bacteria, in the fermentation process, the fermentation broth was agitated, and the contact between the yeast and ferulic acid as a substrate was frequent, and the operation such as promoting the reaction was found to be very important. The present invention has been completed. That is, in the present invention, the process of obtaining ferulic acid by separating fermented bran from fermented bran by the enzyme action of Bacillus ( Aspergillus oryzae ) in the bran, which is the raw material of bound ferulic acid, and saccharomyces having high ferulic acid conversion ability. The Saccharomyces genus yeast was cultured in low pH medium, and the two liquids were mixed. The mixed solution was then fermented with stirring to prepare a flavor liquid containing a fairly high concentration of 4-vinyl gua alcohol. It is safe to manufacture.
향미액 제조에 대하여 공정별로 상세히 설명한다.(1) 페룰산액의 조제맥류, 쌀, 옥수수 등의 곡류 가공시, 부산물로 얻는 기울이나 겨에는 결합형 페룰산이 함유되므로, 이들 곡물의 기울이나 겨는 페룰산 원료로 이용할 수 있다. 그러나, 본 발명에서는 원료의 수집, 처리시의 문제점, 발효제품에 미치는 영향 등을 비교·검토하여, 밀기울을 보다 유리한 원료로 선택하였다.본 발명의 방법에서는 페룰산 원료로서, 밀기울에 100% 량의 물(v/w)을 살수·혼합하고 증자한 것을 사용하였다. 또 페룰산 유리효소의 생산균으로서는 국균 중에서 황국균(Aspergillus oryzae)을 택하고, 상법에 따라 증자한 밀기울에 배양하여 사용하였다. 이 배양물은 페률산 유리효소의 활성이 높고, 반응생성물인 페률산에는 영향을 주지 않으므로 유효하게 사용할 수 있다.페룰산액 조제에 있어서는 증자밀기울과 황국균을 배양한 밀기울국을 10:1(원료 밀기울량으로 환산)의 비율로 사용하고, 이들을 합한 양에 대하여 3.5∼5배량의 온수(v/w)를 가한 후, 45∼50℃에서 6시간 정도 보온하여, 페룰산을 유리시키고, 이어서 밀기울을 분리하여 페룰산액을 얻는다. 조제한 페룰산액은 75℃로 15분간 가열처리 후 사용하였다.(2) 효모 배양액의 제조본 발명에서는 페룰산을 4-비닐 구아이아콜로 변환하는 효모로서, ATCC 36029와 NRRL Y-1373균주를 선발하여 사용하였다. 이들 균주는 페룰산 변환능이 높고, 발효시의 발효생성물의 향미도 양호하여, 본 발명의 목적에 적합하였다. 효모의 배양에는 알콜 발효를 고도로 억제하면서 증식시키는 방법과, 효모의 증식과 함께 알콜발효를 진행시키는 방법이 있으나, 본 발명에서는 후자의 방법을 택하고, 효모배양 공정에서 잡균의 오염을 방지하기 위하여, 낮은 pH의 산성배지에서 효모를 배양하였다.본 발명의 방법에서는 밀가루에 25% 량의 물(v/w)을 살수·혼합하여 증자한 후, 이것에 백국균(Aspergillus awamori의 백색 변이주)을 번식시켜, 효소와 함께 다량의 구연산을 생성시킨 밀가루국(麴)을 만들고, 이것을 효모배지의 원료로 하였다. 밀가루국을 상법에 따라 당화하고, 여과한 국 당화액 배지 또는 물에 밀가루국을 담금한 수국(水麴) 배지를 만들었다. 이렇게 만든 배지의 pH는 3.0∼3.5이나, 산성이 약한 경우에는 양조용 젖산 또는 구연산을 첨가하여 산을 보충할 수도 있다. 이들 배지에 종효모(yeast starter)를 첨가하고, 25℃로 1∼2일간 배양하였다.(3) 페룰산을 변환시키는 발효공정상기한 효모배양액과 페룰산액을 1:1∼3(v:v)의 비율로 혼합한 후, 혼합액을 25℃에 보온하고 교반을 계속하면서, 4-비닐 구아이아콜의 생성반응을 1∼2일간 진행시킨다.본 발효공정에서는 발효액중에 페룰산 변환효모의 생균수가 많을수록, 교반에 의한 효모균과 페룰산의 접촉이 빈번할수록, 4-비닐 구아이아콜의 생성속도는 빠르게 된다. 그러나, 발효액 중에 효모균체 외의 고형의 입자가 과다하게 섞여 있으면 반응은 지체된다. 그러므로, 발효공정에서는 다수의 효모생균수를 확보하고, 충분히 교반하는 등의 방법에 의하여, 발효를 안전하게, 단기간에 완료할 수 있다. 발효액은 그대로 또는 여과하거나 수증기 증류하여 향미액으로서 사용한다.[실시예]실시예 1. 폐률산액의 조제페룰산 원료인 밀기울에 100% 량의 물(v/w)을 살수·혼합하고, 120℃에서 40분간 가압살균한 후 냉각하여 사용하고, 페룰산 유리효소 생산균으로서는 황국균을 선택하고, 상법에 따라 증자한 밀기울에 30℃로 2일간 배양한 밀기울국을 사용하였다.상기의 증자한 밀기울 100g과 황국균을 배양한 밀기울국 10g(이들의 량은 원료 밀기울로 환산)을 1ℓ 삼각 플라스크에 넣고, 이것에 물440㎖를 가하여 혼합한 후, 온수욕(water bath)에서 45℃로 3시간 → 50℃로 3시간 → 55℃로 1시간 보온하여 페룰산을 유리시키고, 삼베로 여과하여 페룰산액 494㎖를 얻었다. 페룰산액은 75℃에서 15분간 가열처리하고 냉각 후에 사용하였다.실시예 2. 국 당화액에서의 효모배양백국균(Aspergillus awamori의 백색 변이주)을 밀가루에 배양한 국을 배지원료로 사용하기 위하여, 먼저 밀가루에 25%의 물(v/w)을 살수하여 고루게 섞어주고, 이어서 뭉쳐진 덩어리를 부수고, 시루에서 증기를 통하여 1시간 증지한 후, 약 30℃까지 냉각하였다. 이것에 백국균의 종국(種麴)을 혼합하고, 상법에 따라 30℃로 42시간 배양하여 밀가루국을 얻었다.1ℓ 삼각 플라스크에 밀가루국 150g과 물 600㎖을 넣어 섞어주고, 온수욕(water bath)에서 55∼58℃로 8시간 당화시킨 후, 삼베로 여과하여 국 당화액 575㎖를 얻었다. 이 국 당화액은 75℃로 15분간 가열처리하고, 냉각 후 사용하였다.한편, 맥아즙을 조제하고, 양조용 젖산을 0.5%농도가 되게 첨가한 배지에, ATTC 36029균주를 접종하고, 25℃에서 40시간 배양하여, 이것을 종효모(yeast starter)로 하였다.1ℓ 삼각 플라스크에 상기한 국 당화액 500㎖를 넣고 종효모액 40㎖를 첨가한 후, 삼각 플라스크 주둥이를 알루미늄 호일(foil)로 덮어 씌우고, 자기교반기(magnetic stirrer)로 교반하면서 24시간 배양하였다. 배양 종료후의 배양액의 분석치는 표 1과 같고, 배양종료 후의 효모 생존균수는 ㎖당 1.78×108개 였다.실시예 3. 수국(水麴)배지에서의 효모배양효모배지의 원료로서는 실시예 2와 같이, 밀가루국을 사용하였다. 1ℓ 삼각 플라스크에 물 400㎖를 넣고, 밀가루국 200g을 첨가, 혼합하여 수국배지를 만든 후, 실시예 2와 동일하게 만든 종효모액 40㎖를 첨가하여, 25℃로 40시간 효모배양과 알콜발효를 병행시켰다. 효모배양 종료후의 배양액의 분석치는 표 2와 같고, 배양액중의 효모 생존균수는 ㎖당 2.4 ×108개 였다.실시예 4. 향미액의 제조(1)실시예 1과 동일하게 조제한 페룰산액(페룰산 농도 272.8ppm) 400㎖와 실시예 2와 동일하게 제조한 효모 배양액 200㎖를 1ℓ삼각 플라스크에 넣고, 주둥이를 알루미늄 호일로 덮어 씌운뒤 25℃의 항온기에 넣고, 액을 자기교반기로 계속 교반하면서, 1일 및 2일간 발효시켜 향미액을 얻었다. 발효액 중의 ㎖당 효모 생존균수는 발효 1일 후에 7.5×107개, 발효 2일 후에 8.3× 107개 였다. 발효액을 여과하여 얻은 향미액의 일반성분 분석치와 페놀 화합물의 분석치는 표 3 및 표 4와 같다.향미액의 발효과정에 있어서, 페룰산에서 4-비닐 구아이아콜로 변환되는 변환율은 발효 1일후에 약 82%가 되고, 발효 2일후에는 100% 가깝게 변환되었다. 발효중에는 향미성분으로서, 4-비닐 구아이아콜과 함께 4-비닐 페놀도 소량 생성 되는 데, 4-비닐 페놀은 4-비닐 구아이아콜 보다는 향미가치가 낮으므로, 4-비닐 페놀량이 적고, 4-비닐 구아이아콜이 비교적 다량(100ppm이상) 함유되는 것은 향미성분의 조성으로 볼 때 바람직한 것이다.실시예 5. 향미액의 제조(2)실시예 1과 동일하게 조제한 페룰산액(페룰산 농도 252.6ppm) 400㎖와 실시예 3과 동일하게 제조한 효모배양액 200㎖를 1ℓ 삼각 플라스크에 넣고, 실시예 4와 동일한 조건하에서 발효시켜 향미액을 얻었다. 발효액을 여과하여 얻는 향미액의 일반성분 분석치와 페놀 화합물의 분석치는 표 5 및 표 6과 같다.발효액중의 ㎖당 효모 생균수는 발효 1일 후에 1.19×108개, 발효 2일 후에 1.33×108개로 많았으나, 실시예 4의 경우에 비하여, 발효액 중에 고형 입자의 량이 많아, 페룰산을 4-비닐 구아이아콜로 변환하는 반응이 더디게 되고, 4-비닐 구아이아콜의 함량도 약간 적었다. 그러나, 본 실험에서 사용한 효모 배양법은 비교적 간단히 실시할 수 있는 장점이 있고, 향미액도 식품의 향미개선에 효과적으로 사용할 수 있다.실시예 6. 식품의 향미개선 시험(1)혼합간장 (산분해 간장과 양조간장을 9:1로 혼합한 것)에, 실시예 4 에서 2일간 발효시켜 여과한 향미액(4-비닐 구아이아콜 약 150ppm 함유)을 첨가하되, 4-비닐 구아이아콜로서 0.8-2.4ppm 범위로 첨가한 몇개의 시험구를 만들고 1주일간 실온에 보관한 후, 5명의 패널에 의하여 관능시험을 하였다. 그 결과 향미액을 첨가한 간장은 무첨가의 것에 비하여, 신분해 간장 특유의 불쾌취가 거의 소실되고, 간장맛(간장과 물을 6:4로 혼합하여 관능시험)에 감칠맛이 부여되고, 짠맛이 순화되어 부드럽다고, 패널 전원이 동의 하였다. 관능상으로는 간장에 4-비닐 구아이아콜로서 1.0∼2.0ppm 첨가한 것이 바람직하다고 판정하였다.양조간장에 상기와 같이 향미액을 첨가하여 관능시험한 결과, 향미액의 첨가효과가 유사하게 인정되었다. 또 간장양조시에, 담금한 후 2∼3개월간 발효시킨 간장 덧(mash)에 상기와 같이 향미액을 첨가하고, 이어서, 2∼3주간 발효시키면 향미가 양호한 간장을 얻을 수 있고, 양조기간도 단축되었다. 위의 처리과정에서,간장 덧 중에 존재하는 내염성 후숙효모에 의하여,4-비닐 구아이아콜이 4-에틸 구아이아콜로 변환될 수 있으나, 이 경우에도 향미개선 효과는 비슷하게 나타난다.실시예 7. 식품의 향미개선 시험(2)포도주(J사 적포도주, 에타놀 10%)에 실시예 4에서 2일간 발효시켜 얻은 향미액을 첨가하되, 4-비닐 구아이아콜로서 0.001∼0.5ppm 농도 범위로 첨가한 여러단계의 시험구를 만들어, 1주간 실온에 보관한 후, 5명의 패널에 의하여 관능검사를 하였다. 그 결과, 4-비닐 구아이아콜로서 0.001∼0.1ppm 첨가한 시험구에서도 무첨가구에 비하여 향이 부여되고, 맛이 좋아진 것으로 인정 되었으며, 향미액의 적정 첨가량은 소비층의 기호성향을 고려하여, 정할 필요가 있는 것으로 판단하였다.소주나 기타 증류주에 함유되는 4-비닐 구아이아콜은, 장기간 저장중에 바닐린등으로 변환되어, 장기숙성주의 독특한 방향을 내는 것으로 알려져 있다. 그러므로 증류주의 장기숙성주를 만들 경우, 본 발명의 향미액은 매우 유용한 재료로 사용될 수 있다.The production of flavor liquids will be described in detail in each process. (1) When processing cereals such as cereals, rice, and corn of ferulic acid liquid, the slant or bran obtained as a by-product contains bound ferulic acid. It can be used as a ferulic acid raw material. However, in the present invention, the bran is selected as a more advantageous raw material by comparing and reviewing the collection of raw materials, problems in processing, effects on fermented products, and the like. In the method of the present invention, 100% of bran is used as ferulic acid raw material. The water (v / w) of which was sprinkled, mixed and increased. As a bacterium for the production of ferulic acid free enzyme, H. germ ( Aspergillus oryzae ) was selected among the bacterium, and cultured in bran which was increased by the commercial method. This culture can be used effectively because it has high activity of ferric acid free enzyme and does not affect the reaction product, ferric acid. For preparing ferulic acid solution, 10: 1 (raw material wheat bran) prepared with steamed wheat bran and sulfur bacteria Amount, and 3.5 to 5 times the amount of hot water (v / w) was added to the sum of these amounts, and then the mixture was kept at 45 to 50 ° C for about 6 hours to liberate ferulic acid, and then bran was added. Isolate to obtain a ferulic acid solution. The prepared ferulic acid solution was used after heat treatment at 75 ° C. for 15 minutes. (2) Preparation of the yeast culture solution In the present invention, strains of ATCC 36029 and NRRL Y-1373 were selected as yeasts for converting ferulic acid to 4-vinyl guiacol. Was used. These strains had high ferulic acid conversion ability and good flavor of fermentation products during fermentation, which was suitable for the purpose of the present invention. In the cultivation of yeast, there is a method of proliferating with a high suppression of alcohol fermentation, and a method of advancing alcohol with fermentation of yeast, but in the present invention, the latter method is selected and in order to prevent contamination of various bacteria in the yeast culture process. The yeast was cultivated in an acidic medium at low pH. In the method of the present invention, 25% water (v / w) was sprinkled and mixed with flour, and then, white mutant strain of Aspergillus awamori was added thereto. Reproduction was carried out to make wheat flour soup in which a large amount of citric acid was produced together with an enzyme, which was used as a raw material for yeast medium. Wheat flour soup was saccharified according to the conventional method, and filtered broth saccharified liquid medium or hydrangea medium in which wheat flour soup was immersed in water. The pH of the medium thus produced is 3.0-3.5, but if the acid is weak, the acid may be supplemented by adding brewing lactic acid or citric acid. The yeast starter was added to these mediums, and cultured at 25 ° C. for 1 to 2 days. (3) Fermentation step for converting ferulic acid The above-mentioned yeast culture solution and ferulic acid solution were 1: 1 to 3 (v: v). After mixing at a ratio of), the mixture is kept at 25 ° C. and stirring is continued, and the reaction of producing 4-vinyl gua alcohol is allowed to proceed for 1 to 2 days. In this fermentation process, the number of live bacteria of ferulic acid-converted yeast is The more, the more frequent the contact between the yeast and ferulic acid by stirring, the faster the production rate of 4-vinyl guiacol. However, if the solid particles other than the yeast cells are mixed excessively in the fermentation broth, the reaction will be delayed. Therefore, in the fermentation step, the fermentation can be completed safely and in a short time by a method such as securing a large number of viable yeast cells and stirring sufficiently. The fermentation broth is used as it is, or filtered or steam distilled to be used as a flavor liquid. EXAMPLE 1 Preparation of Waste Acid Solution A 100% amount of water (v / w) was sprinkled and mixed with wheat bran, a ferulic acid raw material, and 120 After sterilization under pressure at 40 ° C. for 40 minutes, the mixture was cooled and used. As a ferulic acid free enzyme producing bacterium, a yellow bran bacterium was selected, and bran soup incubated at 30 ° C. for 2 days was added to the increased bran according to the commercial method. 100 g and 10 g of wheat bran soup incubated with rhubarb bacteria (the amount is converted into raw bran) into a 1 L Erlenmeyer flask, 440 ml of water was added to the mixture, and then mixed at 45 ° C. in a water bath for 3 hours → 50 It heated at 3 degreeC to 55 degreeC for 1 hour, liberated ferulic acid, and filtered with hemp, and obtained 494 ml of ferulic acid liquids. The ferulic acid solution was heat-treated at 75 ° C. for 15 minutes and used after cooling. Example 2 In order to use a broth cultured with yeast cultured white sugar strain of Aspergillus awamori in flour solution, First, 25% water (v / w) was sprinkled on the flour, mixed evenly, and then the agglomerated mass was crushed, and then steamed for 1 hour through steam in a shiru, and then cooled to about 30 ° C. The seed of the Bacillus bacterium was mixed and incubated for 42 hours at 30 ° C. according to the conventional method to obtain a flour soup. 150 liters of flour soup and 600 ml of water were mixed in a 1-liter Erlenmeyer flask, followed by a water bath. After saccharification at 55-58 ° C. for 8 hours, the mixture was filtered through burlap to give 575 ml of the saccharified solution. The broth saccharified solution was heat-treated at 75 ° C. for 15 minutes, and used after cooling. Meanwhile, ATTC 36029 strain was inoculated into a medium in which wort was prepared and brewing lactic acid was added at a concentration of 0.5%, and 25 ° C. was used. Incubated for 40 hours at, and made this as a yeast starter. 500 ml of the above-described Korean saccharification solution was added to a 1 L Erlenmeyer flask, 40 mL of the Yeast Solution was added, and the Erlenmeyer flask was covered with aluminum foil. Incubated for 24 hours while stirring with a magnetic stirrer. The analytical value of the culture solution after the completion of the culture is shown in Table 1, and the number of viable yeasts after the end of the culture was 1.78 × 10 8 per ml. Example 3 Yeast Culture in Hydrangea Medium As a raw material of yeast medium, wheat flour soup was used as in Example 2. 400 ml of water was added to a 1-liter Erlenmeyer flask, 200 g of wheat flour soup was added and mixed to make a hydrangea medium, and 40 ml of the seed yeast solution prepared in the same manner as in Example 2 was added. It was parallel. The analytical value of the culture solution after the completion of the yeast culture is shown in Table 2, and the number of viable yeasts in the culture solution was 2.4 × 10 8 per ml. Example 4 Preparation of Flavor Liquid (1) 400 ml of ferulic acid solution (ferulic acid concentration 272.8 ppm) prepared in the same manner as in Example 1 and 200 ml of the yeast culture solution prepared in the same manner as in Example 2 were placed in a 1 L triangle flask, and the spout was Was covered with aluminum foil and placed in a thermostat at 25 ° C., and the solution was fermented for 1 day and 2 days while continuing stirring with a magnetic stirrer to obtain a flavor liquid. The number of viable yeast cells per ml in the fermentation broth was 7.5 × 10 7 after 1 day of fermentation and 8.3 × 10 7 cells after 2 days of fermentation. The analysis values of the general components and the phenolic compounds of the flavor liquid obtained by filtering the fermentation broth are shown in Tables 3 and 4. During the fermentation of the flavor liquid, the conversion rate of ferulic acid to 4-vinyl guiacol was about 82% after 1 day of fermentation, and nearly 100% after 2 days of fermentation. During the fermentation, a small amount of 4-vinyl phenol is produced together with 4-vinyl guiacol as a flavor component. Since 4-vinyl phenol has a lower flavor value than 4-vinyl guiacol, the amount of 4-vinyl phenol is less, 4 A relatively large amount of vinyl guacol (more than 100 ppm) is preferable in view of the composition of the flavor component. Example 5 Preparation of Flavor Liquid (2) Ferulic acid liquid prepared in the same manner as in Example 1 (ferulic acid concentration 252.6) ppm) 400 ml and 200 ml of the yeast culture solution prepared in the same manner as in Example 3 were placed in a 1 L Erlenmeyer flask and fermented under the same conditions as in Example 4 to obtain a flavor liquid. The analysis values of the general components of the flavor liquid obtained by filtering the fermentation broth and the analysis values of the phenolic compounds are shown in Tables 5 and 6. The number of viable yeast cells per ml in the fermentation broth was 1.19 × 10 8 after 1 day of fermentation and 1.33 × 10 8 after 2 days of fermentation, but the amount of solid particles in fermentation broth was higher than that of Example 4 The reaction to convert to 4-vinyl guiacol was slow, and the content of 4-vinyl guiacol was also slightly low. However, the yeast culture method used in this experiment has the advantage of being relatively simple to carry out, and the flavor liquid can also be effectively used to improve the flavor of food. Example 6 Flavor Improvement Test of Food (1) Mixed Soy Sauce To the mixture of brewed soy sauce and 9: 1 soy sauce, the flavored liquid (containing about 150 ppm of 4-vinyl guaicol) which was fermented and filtered for 2 days in Example 4 was added. Several test spheres added in the 2.4 ppm range were made and stored at room temperature for one week, followed by sensory tests by five panelists. As a result, the soy sauce added with the flavor liquid almost lost the unpleasant odor peculiar to the newly resolved soy sauce, and the rich taste was given to the soy sauce taste (sensory test by mixing soy sauce and water at 6: 4). The panel was agreed to be smooth and smooth. It was judged that it was preferable to add 1.0-2.0 ppm of 4-vinyl guiacol to soy sauce as a functional aspect. As a result of the sensory test by adding the flavor liquid to the brewing soy sauce as described above, the effect of adding the flavor liquid was similarly recognized. When the soy sauce is brewed, the flavoring liquid is added to the soy sauce mash which has been soaked for 2 to 3 months, and then fermented for 2 to 3 weeks to obtain soy sauce with good flavor. Shortened. In the above treatment process, 4-vinyl guiacol may be converted into 4-ethyl guiacol by the salt tolerant post-gum yeast present in the soy sauce, but the flavor improvement effect is similar in this case. Flavor improvement test of food (2) To the wine (red wine, J company red wine, ethanol 10%), the flavor liquid obtained by fermentation in Example 4 for 2 days was added, but 4-vinyl guiacol was added in 0.001-0.5 ppm concentration range. Several stages were prepared, stored at room temperature for one week, and then sensory tested by five panels. As a result, it was recognized that the taste was given to the taste and the taste was better than the non-added even in the test group added with 0.001 to 0.1 ppm of 4-vinyl guacol, and the appropriate amount of the flavor liquid was determined in consideration of the preference of the consumer. It is known that 4-vinyl guai alcohol contained in soju and other distilled spirits is converted into vanillin and the like during long-term storage, and it is known to give a unique direction of long-term ripening liquor. Therefore, when making long-term matured liquor of distilled spirit, the flavor liquid of the present invention can be used as a very useful material.
본 발명에 의하여, 4-비닐 구아이아콜을 상당히 고농도로 함유하는 향미액(향미료)을 쉽게 제조할 수 있게 되었고, 이 향미액을 증류주, 발효주 등의 각종 주류, 간강, 된장 등의 장류, 조미액, 훈제품 등의 제조에 있어서, 향미개량 또는 향미 부여를 위한 재료로 유효하게 이용할 수 있다.According to the present invention, it is possible to easily prepare a flavor liquid (flavor) containing 4-vinyl gua alcohol at a considerably high concentration, and the flavor liquid is prepared by various liquors such as distilled spirits, fermented spirits, enteric liquors such as liver rivers, miso, and seasoning liquids. In the manufacture of smoked products, etc., it can be effectively used as a material for flavor improvement or flavor provision.
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996034971A1 (en) * | 1995-05-05 | 1996-11-07 | Orsan | Method for producing vanillin using the bioconversion of benzene precursors |
JPH09238673A (en) * | 1996-03-07 | 1997-09-16 | Sanwa Shiyurui Kk | Production of distilled liquor |
KR19980070757A (en) * | 1997-02-07 | 1998-10-26 | 히라따다다시 | Ferulic acid decarboxylase |
EP0885968A1 (en) * | 1997-06-19 | 1998-12-23 | Givaudan-Roure (International) S.A. | Process for the production of vanillin |
KR100280270B1 (en) * | 1998-09-29 | 2001-02-01 | 박윤중 | Food flavor improvement method |
WO2000050622A1 (en) * | 1999-02-24 | 2000-08-31 | Zylepsis Limited | Flavour/aroma materials and their preparation |
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