JP4790143B2 - Method for removing off-flavor from food and deodorant - Google Patents
Method for removing off-flavor from food and deodorant Download PDFInfo
- Publication number
- JP4790143B2 JP4790143B2 JP2001106601A JP2001106601A JP4790143B2 JP 4790143 B2 JP4790143 B2 JP 4790143B2 JP 2001106601 A JP2001106601 A JP 2001106601A JP 2001106601 A JP2001106601 A JP 2001106601A JP 4790143 B2 JP4790143 B2 JP 4790143B2
- Authority
- JP
- Japan
- Prior art keywords
- fermentation
- reaction
- present
- fermented seasoning
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 34
- 235000013305 food Nutrition 0.000 title description 44
- 239000002781 deodorant agent Substances 0.000 title description 27
- 239000000796 flavoring agent Substances 0.000 title description 23
- -1 4-hydroxy-3-methoxyphenyl Chemical group 0.000 claims description 65
- YOMSJEATGXXYPX-UHFFFAOYSA-N 2-methoxy-4-vinylphenol Chemical compound COC1=CC(C=C)=CC=C1O YOMSJEATGXXYPX-UHFFFAOYSA-N 0.000 claims description 56
- 238000004519 manufacturing process Methods 0.000 claims description 55
- 235000011194 food seasoning agent Nutrition 0.000 claims description 52
- 239000000243 solution Substances 0.000 claims description 38
- 238000010411 cooking Methods 0.000 claims description 29
- 238000000855 fermentation Methods 0.000 claims description 27
- 230000004151 fermentation Effects 0.000 claims description 27
- 235000007164 Oryza sativa Nutrition 0.000 claims description 24
- 235000009566 rice Nutrition 0.000 claims description 24
- 102000004190 Enzymes Human genes 0.000 claims description 21
- 108090000790 Enzymes Proteins 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims description 16
- 238000007254 oxidation reaction Methods 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003504 photosensitizing agent Substances 0.000 claims description 10
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 claims description 9
- 239000002151 riboflavin Substances 0.000 claims description 9
- 235000019192 riboflavin Nutrition 0.000 claims description 9
- 229960002477 riboflavin Drugs 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 6
- 239000004310 lactic acid Substances 0.000 claims description 5
- 235000014655 lactic acid Nutrition 0.000 claims description 5
- 235000014101 wine Nutrition 0.000 claims description 5
- YBHQCJILTOVLHD-YVMONPNESA-N Mirin Chemical compound S1C(N)=NC(=O)\C1=C\C1=CC=C(O)C=C1 YBHQCJILTOVLHD-YVMONPNESA-N 0.000 claims description 4
- 244000294411 Mirabilis expansa Species 0.000 claims description 3
- 235000015429 Mirabilis expansa Nutrition 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 235000013536 miso Nutrition 0.000 claims description 3
- 235000013555 soy sauce Nutrition 0.000 claims description 3
- 239000000052 vinegar Substances 0.000 claims description 3
- 235000021419 vinegar Nutrition 0.000 claims description 3
- 241000209094 Oryza Species 0.000 claims 7
- 125000001452 riboflavin group Chemical group 0.000 claims 2
- PAYKFSAULXORES-UHFFFAOYSA-N 4-(5-ethenyl-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)-2-methoxyphenol Chemical compound O1C=2C(OC)=CC(C=C)=CC=2CC1C1=CC=C(O)C(OC)=C1 PAYKFSAULXORES-UHFFFAOYSA-N 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 71
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 39
- 235000019441 ethanol Nutrition 0.000 description 26
- 235000019645 odor Nutrition 0.000 description 20
- 229940088598 enzyme Drugs 0.000 description 19
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 18
- 240000007594 Oryza sativa Species 0.000 description 17
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 17
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 15
- 235000001785 ferulic acid Nutrition 0.000 description 15
- 229940114124 ferulic acid Drugs 0.000 description 15
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 15
- 239000002537 cosmetic Substances 0.000 description 14
- 239000003963 antioxidant agent Substances 0.000 description 13
- 235000006708 antioxidants Nutrition 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 230000003078 antioxidant effect Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 235000013311 vegetables Nutrition 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 235000019992 sake Nutrition 0.000 description 9
- 241000251468 Actinopterygii Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000013077 scoring method Methods 0.000 description 8
- 235000015170 shellfish Nutrition 0.000 description 8
- 239000003205 fragrance Substances 0.000 description 7
- 235000013372 meat Nutrition 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 235000013339 cereals Nutrition 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 244000144972 livestock Species 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- 108010056979 phenylacrylic acid decarboxylase Proteins 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000234282 Allium Species 0.000 description 5
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 5
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 5
- 238000004332 deodorization Methods 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 5
- 235000020778 linoleic acid Nutrition 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 102000003992 Peroxidases Human genes 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000001877 deodorizing effect Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 108040007629 peroxidase activity proteins Proteins 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 235000014347 soups Nutrition 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 4
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 208000035985 Body Odor Diseases 0.000 description 3
- 244000000626 Daucus carota Species 0.000 description 3
- 235000002767 Daucus carota Nutrition 0.000 description 3
- 239000004278 EU approved seasoning Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 101710121765 Endo-1,4-beta-xylanase Proteins 0.000 description 3
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 3
- 102100022624 Glucoamylase Human genes 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229910003460 diamond Inorganic materials 0.000 description 3
- 239000010432 diamond Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 3
- 235000013622 meat product Nutrition 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 3
- 235000012141 vanillin Nutrition 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000002566 Capsicum Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000006002 Pepper Substances 0.000 description 2
- 244000062780 Petroselinum sativum Species 0.000 description 2
- 235000016761 Piper aduncum Nutrition 0.000 description 2
- 240000003889 Piper guineense Species 0.000 description 2
- 235000017804 Piper guineense Nutrition 0.000 description 2
- 235000008184 Piper nigrum Nutrition 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000269851 Sarda sarda Species 0.000 description 2
- 206010040904 Skin odour abnormal Diseases 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 2
- 108090000637 alpha-Amylases Proteins 0.000 description 2
- 102000004139 alpha-Amylases Human genes 0.000 description 2
- 229940024171 alpha-amylase Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000011648 beta-carotene Substances 0.000 description 2
- 235000013734 beta-carotene Nutrition 0.000 description 2
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 2
- 229960002747 betacarotene Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 108010041969 feruloyl esterase Proteins 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940059442 hemicellulase Drugs 0.000 description 2
- 108010002430 hemicellulase Proteins 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 235000011197 perejil Nutrition 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
- 235000013580 sausages Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000020083 shōchū Nutrition 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920001221 xylan Polymers 0.000 description 2
- 150000004823 xylans Chemical class 0.000 description 2
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 1
- JOLPMPPNHIACPD-ZZXKWVIFSA-N (e)-3-(4-aminophenyl)prop-2-enoic acid Chemical compound NC1=CC=C(\C=C\C(O)=O)C=C1 JOLPMPPNHIACPD-ZZXKWVIFSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- WDMUXYQIMRDWRC-UHFFFAOYSA-N 2-hydroxy-3,4-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1O WDMUXYQIMRDWRC-UHFFFAOYSA-N 0.000 description 1
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 description 1
- SMIOEQSLJNNKQF-UHFFFAOYSA-N 4-acetoxy acetophenone Chemical compound CC(=O)OC1=CC=C(C(C)=O)C=C1 SMIOEQSLJNNKQF-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 1
- 240000002234 Allium sativum Species 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 241000237519 Bivalvia Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 1
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 1
- 108090000489 Carboxy-Lyases Proteins 0.000 description 1
- 102000004031 Carboxy-Lyases Human genes 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 241000272185 Falco Species 0.000 description 1
- 101710196208 Fibrinolytic enzyme Proteins 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 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 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 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 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 108010029541 Laccase Proteins 0.000 description 1
- 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 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- 240000000599 Lentinula edodes Species 0.000 description 1
- 235000001715 Lentinula edodes Nutrition 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 108010059896 Manganese peroxidase Proteins 0.000 description 1
- IHKNVZISLLDMOR-UHFFFAOYSA-N O-Acetylferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1OC(C)=O IHKNVZISLLDMOR-UHFFFAOYSA-N 0.000 description 1
- IHKNVZISLLDMOR-GQCTYLIASA-N O-acetylferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1OC(C)=O IHKNVZISLLDMOR-GQCTYLIASA-N 0.000 description 1
- 238000003684 Perkin reaction Methods 0.000 description 1
- 108010059820 Polygalacturonase Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- 229930006000 Sucrose Natural products 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- UGXQOOQUZRUVSS-ZZXKWVIFSA-N [5-[3,5-dihydroxy-2-(1,3,4-trihydroxy-5-oxopentan-2-yl)oxyoxan-4-yl]oxy-3,4-dihydroxyoxolan-2-yl]methyl (e)-3-(4-hydroxyphenyl)prop-2-enoate Chemical compound OC1C(OC(CO)C(O)C(O)C=O)OCC(O)C1OC1C(O)C(O)C(COC(=O)\C=C\C=2C=CC(O)=CC=2)O1 UGXQOOQUZRUVSS-ZZXKWVIFSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229920000617 arabinoxylan Polymers 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 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 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 235000013532 brandy Nutrition 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene 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
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 235000020639 clam Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- WODOUQLMOIMKAL-FJSYBICCSA-L disodium;(2s)-2-(octadecanoylamino)pentanedioate Chemical compound [Na+].[Na+].CCCCCCCCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC([O-])=O WODOUQLMOIMKAL-FJSYBICCSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 108010093305 exopolygalacturonase Proteins 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 238000002143 fast-atom bombardment mass spectrum Methods 0.000 description 1
- 238000012395 formulation development Methods 0.000 description 1
- 210000000540 fraction c Anatomy 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 235000005772 leucine Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 108010062085 ligninase Proteins 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000014102 seafood Nutrition 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 235000002374 tyrosine Nutrition 0.000 description 1
- 235000015041 whisky Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000007222 ypd medium Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- General Preparation And Processing Of Foods (AREA)
- Soy Sauces And Products Related Thereto (AREA)
- Seasonings (AREA)
- Alcoholic Beverages (AREA)
- Cosmetics (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、魚貝類、畜肉製品及び野菜類等の食品のオフフレーバーの除去方法及び消臭剤等に関する。
【０００２】
【従来の技術】
食品の品質に悪影響を及ぼす要素の一つとして魚貝類の生臭さ、畜肉類の獣臭、大豆の青臭さ等の不快臭等のいわゆるオフフレーバーがあげられる。これらオフフレーバーのマスキングを目的として、食品の加工、調理時に清酒、ワイン、焼酎、みりん等が使用されている。これらの添加による消臭効果は、エタノールによるところが大きいと考えられている。
【０００３】
消臭に有効な物質に関しては、前述のエタノールの他にアミノ酸及び有機酸［日食工誌,29(6),340(1982)］、アミノ・カルボニル反応生成物［J.Fish Sausage,212,15(1982)］、糖類[日食工誌, 46(5),319(1999)]及びフェノール化合物［日食工誌, 29(7),426(1982)］等が知られている。
食品加工技術を利用した伝統的な消臭方法の一つとして燻煙が挙げられるが、燻煙による消臭に関しては前述のフェノール化合物の関与が報告されている[日水誌,47(1),113(1981)、J.Fish Sausage,212,15(1982)]。
【０００４】
フェノール化合物の一種であるバニリンは、魚貝類のオフフレーバーであるトリメチルアミンの臭気を抑える物質としてよく知られているが、バニリンは特有の甘い香りを有するため、食品の種類によっては不快臭とされ、消臭剤として利用されていない。
フェノール化合物の一種である４−ビニルグアヤコールは該バニリンの前駆体の一つであるが、清酒、ワイン等の醸造製品の分野においてそれ自身オフフレーバー成分の一つであると考えられており、製造工程において可能な限り生成を抑制する検討がされている。
【０００５】
一方、フェルラ酸から４−ビニルグアヤコールを生成する活性を有するフェルラ酸脱炭酸酵素の酵素源として、酵母やカビの存在が知られており、酵母のフェルラ酸脱炭酸酵素遺伝子が取得されている［Gene,142,107(1994)、特開平１０−２７６７８８号公報］。
食品のオフフレーバーには元々、食品の素材に存在するものと加工、調理工程で生成するものとがある。後者の加工、調理工程で生成するオフフレーバーの一つとして、加熱による脂質の酸化反応によるものが知られている。酸化反応で生成するオフフレーバーは酸化反応を抑制することによって減少させることができるので、抗酸化活性を有する物質を存在させることがオフフレーバー除去の有効な手段の一つであると考えられている。
【０００６】
【発明が解決しようとする課題】
本発明の一つの目的は、魚貝類、畜肉製品及び野菜類等の食品のオフフレーバーを効果的に除去する食品のオフフレーバーの除去方法及び消臭剤等を提供することにある。
本発明の別の目的の一つは、本発明の消臭剤を含有する製品を提供することである。
【０００７】
本発明の別の目的の一つは、フェノール化合物を酸素の存在下で反応させる酸化反応工程を含む消臭剤の製造方法及び当該製造方法により製造された消臭剤を提供することである。
本発明の別の目的の一つは、フェノール化合物を酸素の存在下で反応させる酸化反応工程を含む調味料の製造方法及び当該製造方法により製造された調味料を提供することである。
【０００８】
本発明の別の目的の一つは、モロミを酸素の存在下で反応させる酸化反応工程を含む酒の製造方法及び当該製造方法により製造された酒を提供することである。
【０００９】
【課題を解決するための手段】
本発明は、スチレン構造を有するフェノール化合物の多量体を食品に存在させることを特徴とする食品のオフフレーバーの除去方法を提供する。
また、本発明は、スチレン構造を有するフェノール化合物の多量体を含有する消臭剤を提供する。
【００１０】
また、本発明は、スチレン構造を有するフェノール化合物の多量体を含有する調味料を提供する。
また、本発明は、スチレン構造を有するフェノール化合物の多量体を含有する化粧料を提供する。
また、本発明は、スチレン構造を有するフェノール化合物の多量体を含有する酸化防止剤を提供する。
【００１１】
また、本発明はスチレン構造を有するフェノール化合物を酸素の存在下、その多量体に変換させることを特徴とするスチレン構造を有するフェノール化合物の多量体の製造法を提供する。
また、本発明は調味料の製造法において、その製造工程のいずれかの時期にスチレン構造を有するフェノール化合物を存在させ、調味料の製造工程中または製造工程終了後に、該フェノール化合物を酸素の存在下で反応させる酸化反応工程を含むことを特徴とする調味料の製造方法を提供する。
【００１２】
また、本発明は酒の製造方法において、モロミを酸素の存在下で反応させる酸化反応工程を含む酒の製造方法を提供する。
また、本発明は、食品を上記の消臭剤を用いて調理することを特徴とする消臭された食品の製造法および該製造法により得られる食品を提供する。
また、本発明は、食品を上記の消臭剤を用いて調理することを特徴とする食品の消臭方法を提供する。
【００１３】
【発明の実施の形態】
スチレン構造を有するフェノール化合物としては、ベンゼン環上にヒドロキシル基及びビニル基を有する化合物（該ビニル基はカルボキシル基等で置換されていてもよい）であれば特に限定されないが、一般式（Ｉ）
【００１４】
【化２】
（式中、Ｒ1は水素原子またはカルボキシル基を表し、Ｒ2は水素原子または低級アルコキシ基を表す）で表される化合物が好ましい。ここで低級アルコキシ基の低級アルキル部分としては、例えば、直鎖または分岐状の炭素数１〜６のものがあげられ、具体的には、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、ペンチル基、へキシル基等があげられる。なお、一般式（Ｉ）で表される化合物の多量体においては、各化合物は同一でも異なっていてもよい。
【００１６】
スチレン構造を有するフェノール化合物の多量体としては、例えば、スチレン構造を有するフェノール化合物の２〜５量体等があげられるが、中でも２量体が好ましく、さらには以下の一般式（ＩＩ）〜（ＶＩＩ）
【００１７】
【化３】
【化４】
【化５】
（式中、Ｒ1a、Ｒ1b、Ｒ1c、Ｒ1d、Ｒ1e、Ｒ1f、Ｒ1g、Ｒ1h、Ｒ1i、Ｒ1j、Ｒ1k及びＲ1l は、同一もしくは異なって、水素原子またはカルボキシル基を表し、Ｒ2a、Ｒ2b、Ｒ2c、Ｒ2d、Ｒ2e、Ｒ2f、Ｒ2g、Ｒ2h、Ｒ2i、Ｒ2j、Ｒ2k及びＲ2lは、同一もしくは異なって水素原子または低級アルコキシ基を表す）で表されるものが好ましく、さらには、２，３−ジヒドロ−２−(４−ヒドロキシ−３−メトキシフェニル)−７−メトキシ−５−ビニルベンゾフラン（ＶＧＤ）がより好ましく使用される。
（スチレン構造を有するフェノール化合物の入手方法）
スチレン構造を有するフェノール化合物は、公知の方法により合成可能であり、例えば、４−ビニルフェノールは、４−アセトキシアセトフェノンの還元、脱水、加水分解によって得られる。フェルラ酸は、４−ヒドロキシ−３−メトキシベンズアルデヒドとマロン酸をピペリジンの存在下ピリジン中、縮合脱炭酸して得られる。ｐ−クマル酸はｐ−アミノケイ皮酸よりジアゾニウム塩を経て得るか、もしくは、ｐ−オキシベンズアルデヒドからＰｅｒｋｉｎ反応により得られる。４−ビニルグアヤコールはバニリンに無水酢酸または酢酸ナトリウムを作用させて４−アセトキシ−３−メトキシ桂皮酸とした後、加水分解し、キノリンを用いて脱炭酸することによって得られる。
【００２１】
また、フェルラ酸等、スチレン構造を有するフェノール化合物の一部のものについては、市販品として購入も可能である。
また、４−ビニルグアヤコ−ル、フェルラ酸等は天然物（食品の原料である場合もある）からも製造できる。
以下にこれらのフェノール化合物を天然物から製造する方法について例示する。
（フェルラ酸の製造方法）
フェルラ酸は、植物細胞壁の構成成分の一つであるアラビノキシラン、ペクチン等の繊維質に存在するフェルラ酸エステルをフェルラ酸エステラーゼの存在下に通常の方法で分解して得ることができる。フェルラ酸またはフェルラ酸エステルを含有する植物としては例えば米、小麦、大麦、蕎麦等の穀類、馬鈴薯、甘藷等の芋類、ブドウ、リンゴ、柑橘類等の果物類及び野菜類等が例示される。
【００２２】
また、フェルラ酸は前記の植物を繊維分解酵素例えば、キシラナーゼ、アラビナーゼ、セルラーゼ、ペクチナーゼ、ヘミセルラーゼ等を用いて、通常の方法で、処理することによっても得ることができる。
また、例えば、木材中のリグニンを熱分解、エタノール分解、加水分解酵素、例えば、リグニナーゼ、マンガンペルオキシダーゼ、ラッカーゼ等により通常の方法で分解することによってもフェルラ酸を得ることができる。
（４−ビニルグアヤコールの製造方法）
４−ビニルグアヤコールはフェルラ酸をフェルラ酸脱炭酸酵素の存在下に通常の方法で処理することによって得ることができる。
【００２３】
フェルラ酸脱炭酸酵素の酵素源としては酵素自体のみならず、該酵素活性を有する糸状菌、酵母等の菌体、あるいはそれらから適当な方法で抽出した粗酵素等を用いることができる[Appl. Environ. Microbiol., 59(7), 2244(1993)]。酵母としては該酵素活性が０．５ユニット／ｇ（ユニットの定義は以下の実施例にて説明する）菌体湿重量以上である菌株が好ましく、具体的な酵母として、サッカロマイセス セレビシエ(Saccharomyces cerevisiae)ＩＦＯ ２２６０、ＩＦＯ１９５３、ＩＦＯ ０２３３及びダイヤイースト（商品名、協和発酵工業製の圧搾酵母）等の菌株が例示される。
（１）スチレン構造を有するフェノール化合物の多量体の製造方法
以下、スチレン構造を有するフェノール化合物の多量体の製造方法について説明する。
【００２４】
スチレン構造を有するフェノール化合物の多量体への変換反応は、例えばエタノール含有溶媒等の溶媒中で酸素の存在下、１０〜８０℃で熟成させることによって行われる。具体的には、例えば、５ｐｐｍの４−ビニルグアヤコールのＶＧＤへの変換反応は、２５℃で６ヶ月以上、３７℃で４ヶ月以上または６０℃で２０日以上、熟成させて行うのが好ましい。
【００２５】
また、酸素を反応系内に、強制的に曝気させるのが、反応期間を短縮できる点で好ましい。
上記の変換反応においては、光の照射下で行うことによって反応を促進することができるが、光増感物質の存在下で行うことにより、さらに反応を促進することができる。
【００２６】
光の照射下及び光増感物質の存在下で行う場合、５〜８０℃、好ましくは１０〜３０℃において、変換に好適な光量、及び時間が選ばれるが、例えば５ｐｐｍの４−ビニルグアヤコール溶液１LのＶＧＤへの変換反応は、２０℃で２０〜４０W蛍光灯下３〜１日、３０℃で２０〜４０W蛍光灯下２〜０．５日処理するのが好ましい。
【００２７】
このときに用いられる光源としては、主として２４０〜５００ｎｍの間の波長の光を発光する光源が好ましく使用でき、その具体例としては、太陽光、蛍光灯、白熱灯、ブラックライト、殺菌灯及び捕虫灯等があげられ、光源は１種または２種以上で使用できる。中でも、ブラックライト、殺菌灯または捕虫灯がエネルギー消費効率の観点からより好ましく使用される。
【００２８】
光増感物質としては、例えばヒドロキシメチルフルフラール、リボフラビン等が挙げられる。光増感物質と光源の種類の組合わせによって変換率が異なるため、紫外光にはヒドロキシメチルフルフラール、リボフラビン等が好ましく、可視光にはリボフラビン等が好ましく用いられる。発酵液に光を照射するに際して、原料中にリボフラビンが含まれているかまたは発酵によりリボフラビンが生成される場合は、光増感物質は特に添加しなくてもよい。光増感物質の濃度は、１ｐｐｂ以上であるのが好ましく、１０〜５０００ｐｐｂであるのがより好ましい。
【００２９】
また、該変換反応は、スチレン構造を有するフェノール化合物をその多量体に変換する能力を有する酵素の存在下で行うこともできる。
該酵素の酵素源としては、例えば、パーオキシダーゼ、具体的には、ＩＣＮＢｉｏｍｅｄｉｃａｌｓ Ｉｎｃ．製のパーオキシダーゼ試薬または西洋ワサビから水抽出したパーオキシダーゼの粗酵素液等を用いることができる。
【００３０】
この反応混合物は、フェノール化合物の多量体と他の成分からなる混合物であって、それ自体で消臭剤として使用できる。
反応混合物からの該多量体（以下、スチレン構造を有するフェノール化合物の多量体を該多量体と表現することもある）の回収は、例えば、ダイヤイオンＨＰ２０（三菱化学製）等の非イオン性多孔性樹脂（ここで非イオン性多孔性樹脂とは、イオン交換基のような官能基を持たず、ファンデルワールス力により種々の有機物を吸着する樹脂を意味する）を用いて行われる。カラムに充填した非イオン性多孔性樹脂にアルコール、例えば、エタノール、メタノール等の５〜３０％の水溶液を流して平衡化させ、ついで反応液を通して多量体を樹脂に吸着させ、アルコールを供給して多量体を溶出させる。必要に応じて、溶出液を減圧下で乾固させて目的物の粉末を得る。
（２）食品のオフフレーバーの除去方法
本発明の食品のオフフレーバーの除去方法は、前記のようにして得られるスチレン構造を有するフェノール化合物の多量体や、スチレン構造を有するフェノール化合物の多量体を含有する反応混合物を、例えば、添加等により食品に存在させることによって食品のオフフレーバーを減少または完全に除去するものである。
【００３１】
該多量体を使用する際には、純粋なものだけでなく、その含有物を使用してもよい。例えば、前記反応混合物を使用したり、反応混合物の粗精製品を使用することが可能である。例えば、後述する本発明の消臭剤または調味料を食品のオフフレーバーの除去に使用する形態は、食品のオフフレーバーの除去方法の概念に含まれる。
【００３２】
本発明の食品のオフフレーバーの除去方法においては、該多量体を食品に対して、０.５ｐｐｂ以上存在させるのが好ましい。
（３）消臭剤
本発明の消臭剤は魚貝類等の生臭さ、畜肉類の獣臭、大豆の青臭さ等の食品のオフフレーバー、加齢臭、腋のにおい等の体臭等の消臭に有効である。
【００３３】
本発明の消臭剤は、スチレン構造を有するフェノール化合物の多量体を適当な溶媒（例えば、水、エタノールまたはこれらの混合液）または粉末（食品等の用途の場合は、例えば、澱粉、デキストリン、乳糖等の賦形剤、化粧料等の用途の場合は、例えば、タルク等の賦形剤)に混合することによって得られる。また、該多量体を製造する際の反応混合物そのもの、及び、当該反応混合物からの精製操作の際に得られる該多量体のエタノール溶液等をそのまま本発明の消臭剤として用いることもできる。スチレン構造を有するフェノール化合物の多量体は、前記の（１）の説明に従ってまたはそれに準じて、入手することができる。
【００３４】
本発明の消臭剤は、スチレン構造を有するフェノール化合物の多量体の他に、用途、目的に応じた種々の成分を含有することができる。本発明の消臭剤を食品の消臭に使用する場合は、例えば、エタノール等と混合した液として食品に添加するか、後述する本発明の調味料等として使用することができる。
本発明の消臭剤を食品に用いる場合は、例えば、１〜８０％、好ましくは５〜３０％エタノール水溶液に該多量体を好ましくは１０ｐｐｂ以上、より好ましくは１０ｐｐｂ〜１００ｐｐｍ含有する溶液を調製し、食品に添加することができる。
【００３５】
本発明の消臭剤を体臭の消去を目的として使用する場合は、例えば、後述する本発明の化粧料等として使用することができる。
（４）調味料
本発明の調味料は、現在、使用されている公知の、または将来開発される新規な調味料にスチレン構造を有するフェノール化合物の多量体を好ましくは１０ｐｐｂ以上、より好ましくは１０ｐｐｂ〜１００ｐｐｍ含有させることにより得ることができる。具体的には、本発明の調味料は、スチレン構造を有するフェノール化合物の多量体を調味料の最終製品または製造工程中のいずれかの時期に添加することにより得ることもできるが、調味料の製造工程中のいずれかの時期にスチレン構造を有するフェノール化合物を存在させ、調味料の製造工程中または製造工程終了後に該フェノール化合物を酸素の存在下で酸化反応させることによっても得ることができる。スチレン構造を有するフェノール化合物の多量体は、前記の（１）の説明に従ってまたはそれに準じて、入手することができるが、調味料の製造工程中または製造工程終了後に該フェノール化合物を酸素の存在下で酸化反応させる方法については、さらに後述の発酵調味料の説明で詳細に説明する。
【００３６】
本発明の調味料としては、グルタミン酸、アスパラギン酸、アラニン、アルギニン、ロイシン、チロシン、またはグリシン等のアミノ酸類、コハク酸、乳酸、リンゴ酸、クエン酸、または酢酸等の有機酸類、エタノール、１−プロパノール、２−メチルプロパノール、またはイソアミルアルコール等のアルコール類、グルコース、フルクトース、シュクロース、またはマルトース等の糖類、酢酸イソアミル、またはカプロン酸エチル等のエステル類のいずれか１種もしくは２種以上を含有するものが好ましく、例えば、その形態として、日本酒、焼酎、ウイスキーまたはブランディー等の酒類、発酵調味料あるいはエキス調味料等があげられる。
（エキス調味料）
本発明のエキス調味料は、前記の本発明の調味料の中で肉、水産物、野菜等の煮汁または蒸煮汁あるいはこれらの濃縮物等を含有する調味料のことであり、例えば、畜肉エキス調味料、水産エキス調味料または野菜エキス調味料等があげられる。畜肉エキス調味料は、牛、豚、鶏等の肉または骨等を主原料とし、水産エキス調味料は、カツオ、サバ、マグロ、イワシ、グチ、ハモ、イトヨリ、ホタテ、アサリ、カキ、オキアミ、カニ等の水産物またはその乾燥物を主原料とし、野菜エキス調味料は、オニオン、ガーリック、ニンジン、ハクサイ、キャベツ、シイタケ、コンブ等またはその乾燥物を主原料として、通常の方法で製造される。
【００３７】
さらに本発明のエキス調味料の製造法を、以下に説明する。スチレン構造を有するフェノール化合物の多量体を含むエタノール、水あるいはこれらの混合液等の溶液（例えば、以下に説明する本発明の料理酒等であるのが好ましい）を用いて、鰹節等のエキスの素より、５〜１２０℃、好ましくは２０〜８０℃で１〜１０時間抽出を行う。抽出液を固液分離した上清をエキスとして得ることができる。得られたエキスを必要に応じて、加熱濃縮、減圧濃縮、膜濃縮、凍結濃縮等に付すことによって濃縮物として本発明のエキス調味料を得ることができる。
（発酵調味料）
本発明の発酵調味料は、前記の本発明の調味料の中で微生物等の発酵作用を利用して製造したものであり、具体的な形態としては、酢、料理酒、清酒、ワイン、みりん、醤油または味噌等があげられる。
【００３８】
本発明の発酵調味料は、スチレン構造を有するフェノール化合物の多量体を発酵調味料の最終製品または製造工程中のいずれかの時期に添加することにより得ることもできるが、発酵調味料の製造工程中のいずれかの時期にスチレン構造を有するフェノール化合物を存在させ、発酵調味料の製造工程中または製造工程終了後に該フェノール化合物を酸素の存在下で酸化反応させて得るのが好ましい。
【００３９】
発酵調味料の製造工程終了後に該酸化反応を行い、本発明の発酵調味料を製造する方法として、例えば、製造工程中において、４−ビニルグアヤコ−ルを生成させ、発酵調味料の製造工程終了後、さらに、この発酵調味料中の４−ビニルグアヤコ−ルをＶＧＤに変換させる方法等があげられる。以下、料理酒の場合をその具体例として説明する。
【００４０】
まず、米等の穀類（通常、フェルラ酸またはそのエステル等を含む）を原料として用い、これを米麹等の糸状菌によって液化し、糖化する。この際に、必要に応じてα−アミラーゼ等の液化酵素、及び／又はグルコアミラーゼ等の糖化酵素を添加してもよい。次いで、酵母を加えて発酵させ、得られた発酵液（モロミ）をろ過し、ろ液として料理酒が得られる。ここで、糸状菌は繊維分解酵素活性及びフェルラ酸エステラーゼ活性も有し、穀類中の繊維の分解またはフェルラ酸の遊離にも寄与する。
【００４１】
この工程において、グルコアミラーゼと共にキシラナーゼを存在させることによって穀類からフェルラ酸が生成され、このフェルラ酸が特定の酵母〔前記の４−ビニルグアヤコールの製造方法の説明で例示された酵母等〕が有するフェルラ酸脱炭酸酵素によって４−ビニルグアヤコールに変換され、これが得られた料理酒に含まれる。またこの時、糸状菌のフェルラ酸脱炭酸酵素を用いることもできる。
【００４２】
さらに、この４−ビニルグアヤコールを含む料理酒を用いて４−ビニルグアヤコールのＶＧＤ等の多量体への変換反応〔４−ビニルグアヤコールのその多量体への変換反応は、前記の（１）の説明に従ってまたはそれに準じて行うことができる〕を行うことにより、ＶＧＤを含有する本発明の料理酒が得られる。
また、発酵調味料の製造工程中において該多量体を生成させる方法としては、スチレン構造を有するフェノール化合物を製造工程の適当な時期に添加するかまたは生成させ、前記と同様にして、製造工程中の適当な時期に、その多量体への変換反応を行う方法等があげられる。
（５）化粧料
本発明の化粧料は、スチレン構造を有するフェノール化合物の多量体を化粧料全量に対して、好ましくは１０ｐｐｂ以上、より好ましくは、１０ｐｐｂ〜１ｐｐｍの濃度になるように配合すること等により得ることができる。スチレン構造を有するフェノール化合物の多量体及び当該多量体を含有する反応混合物は、前記の該多量体の製造法の説明に従ってまたはそれに準じて、入手することができる。
【００４３】
本発明の化粧料は、必要に応じて、化粧料用基剤、例えば、顔料、香料、防腐剤、界面活性剤、抗酸化剤、紫外線吸収剤等を含有してもよく、これらを、例えば、「経皮適用製剤開発マニュアル」松本光雄監修 第１版（清至書院 1985年発行）等に記載の方法に準じて、調製することにより、得ることができる。
顔料としては、タール系色素、酸化鉄、酸化チタン、酸化亜鉛等の顔料があげられる。香料としては、じゃ香等の動物性香料、ペパーミント油、レモン油、ローズ油等の植物性香料、ベンジルアルコール、アニソール等の合成香料等があげられる。防腐剤としては、パラベン、メチルパラベン、ｐ−オキシ安息香酸エチル、ｐ−オキシ安息香酸ブチル等があげられる。界面活性剤としては、セチル硫酸ナトリウム等の陰イオン性界面活性剤、ポリオキシエチレンアルキルエーテル、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレン多価アルコール脂肪酸エステル、脂肪酸エステル硬化ヒマシ油、多価アルコール脂肪酸エステル、ポリグリセリン脂肪酸エステル等の非イオン性界面活性剤、テトラアルキルアンモニウム塩等の陽イオン性界面活性剤、ベタイン型、スルホベタイン型、スルホアミノ酸型、Ｎ−ステアロイル−Ｌ−グルタミン酸ナトリウム等の両イオン性界面活性剤等があげられる。抗酸化剤としては、ジブチルヒドロキシトルエン等があげられる。紫外線吸収剤としては、パラメトキシケイ皮酸２−エチルヘキシル、４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン等があげられる。
【００４４】
化粧料の剤型としては、クリーム、乳液、化粧水、美容液、パック等があげられる。例えば、乳液の場合は、油相及び水相をそれぞれ加熱したものを乳化分散して冷却する公知の方法により製造することができる。
本発明の化粧料は、体臭の除去等に有用である。
（６）酸化防止剤
本発明の酸化防止剤は、スチレン構造を有するフェノール化合物の多量体を好ましくは１０ｐｐｂ以上、より好ましくは１０ｐｐｂ 〜１００ｐｐｍ含む。
【００４５】
本発明の酸化防止剤は、スチレン構造を有するフェノール化合物の多量体を適当な溶媒（例えば、水、エタノールまたはこれらの混合液）または粉末〔ここで、該粉末の具体例としては、（３）の説明であげたもの等があげられる〕に混合することによって得られる。また、該多量体を製造する際の反応混合物からの精製操作の際に得られる該多量体のエタノール溶液等をそのまま本発明の酸化防止剤として用いることもできる。スチレン構造を有するフェノール化合物の多量体は、前記の該多量体の製造方法の説明に従ってまたはそれに準じて、入手することができる。
【００４６】
本発明の酸化防止剤は、例えば、食品、調味料、化粧料等の製造工程中、最終製品または食品の調理の際等に添加等することにより使用することができる。
本発明の酸化防止剤は、食品、調味料、化粧料等の酸化防止、例えば、食品中のリノール酸等の酸化防止に有用である。
（７）食品を上記の消臭剤で調理することを特徴とする消臭された食品の製造法及び該製造法により得られる食品
食品を上記の消臭剤で調理することを特徴とする消臭された消臭された食品の製造法は、例えば、前記の（３）で説明される消臭剤を魚貝類等、畜肉類等、大豆等の野菜等の調理に好ましくは食品中のスチレン構造を有するフェノール化合物の多量体の濃度が０．５ｐｐｂ以上になるように使用することにより実施することができる。本発明の食品は、該製造法により得られ、オフフレーバーが除去されているという食品として有用な性質を有する。
（８）食品を上記の消臭剤で調理することを特徴とする食品の消臭方法
食品を上記の消臭剤で調理することを特徴とする食品の消臭方法は、例えば、前記の（３）で説明される消臭剤を魚貝類等、畜肉類等、大豆等の野菜等の調理に好ましくは食品中のスチレン構造を有するフェノール化合物の多量体の濃度が０．５ｐｐｂ以上になるように使用することにより実施することができる。
【００４７】
以下に実施例をあげて本発明を説明する。
【００４８】
【実施例】
以下の実施例に用いられる高速液体クロマトグラフィー（ＨＰＬＣ）の分析条件は下記のとおりである。
カラム： Inertsil ＯＤＳ−２ ４．６×２５０ｍｍ（ＧＬサイエンス社製）検出器：ＯＤ ２８０ｎｍ
以下の実施例における酵素の酵素活性の定義は下記のとおりである。
（フェルラ酸脱炭酸酵素の酵素活性）
ＹＰＤ培地で３０℃一晩振とう培養した被験酵母培養液０．９ｍLに１ｇ／Lフェルラ酸(一丸ファルコス社製)水溶液を０．１ｍL加え、２５℃静置条件下で反応させた。反応液の上清中の４−ビニルグアヤコール量を高速液体クロマトグラフィーを用いて、定量し、１時間当りに１ｐｐｍの４−ビニルグアヤコールを生成する酵素量を１ユニット（単位）と定義した。
（キシラナーゼの酵素活性）
カラス麦由来のキシラン(半井化学製)１００ｍｇを５０mol/L酢酸緩衝液(ｐＨ４．５)９．０ｍLに加えた溶液に、被験酵素液１．０ｍLを添加した後、５２℃で攪拌条件下で反応させた。反応液中の還元糖当量の変化をジニトロサリチル酸法で定量し、１分間にキシランから１μｍｏｌの還元糖当量を遊離する酵素量を１ユニット（単位）と定義した。
（フェノール化合物の定量法）
以下の実施例においてに、スチレン構造を有するフェノール化合物の分析は以下のとおり行った。
【００４９】
被験物質について次のとおりＨＰＬＣ分析を行った。ＶＧＤの分析は試料を濃縮して被験液とした。試料５０ｍLをＨＰＬＣ前処理用Ｃ18カートリッジに通した後、アセトニトリル０．８ｍLで溶出させ１．０ｍLにしたものについて、上記条件で分析を行った。
高速液体クロマトグラフィーによる分画条件移動相：Ａ液 ２０mmol/L酢酸ナトリウム水溶液、Ｂ液 アセトニトリル
Ｂ液／Ａ液（容量比）を３０〜８０％／２５分のリニアグラジエントで溶出させた。
カラム温度：４０℃流速：１．０ｍL／分
（７点評点法及び有意差検定について）
以下の実施例において、７点評点法とは、生臭いにおいの強度について１点（弱い）から７点（強い）までの点数をつけることにより評価する方法で、スチューデントのｔ検定を行い有意差の有無を調べた。各実施例におけるｎは人数を示す。
【００５０】
実施例１
５０ｐｐｍ ４−ビニルグアヤコール（４−ＶＧ）及び４１．６ｐｐｍヒドロキシメチルフルフラールを含有する７．７５％エタノール水溶液 ８００ｍLに紫外線を４０分間照射した。得られた反応液を７．７５％エタノール水溶液で平衡化したダイヤイオンＨＰ２０（商品名、三菱化学株式会社製）に通し、８０％メタノール水溶液で洗浄後、メタノール８ｍLで溶出される画分（画分Ａとする）を粗精製物として取得した。
【００５１】
別途、５０ｐｐｍ ４−ビニルグアヤコール及び０．５ｐｐｍ リボフラビンを含有する７．７５％エタノール水溶液２０Ｌを蛍光灯照明付きの恒温庫内で反応温度２５℃で２４時間保存した。反応液を７．７５％エタノール水溶液で平衡化したダイヤイオンＨＰ２０（商品名、三菱化学株式会社製）に通し、８０％メタノール水溶液で洗浄後、メタノール２００ｍLで溶出される画分（画分Ｂとする）を粗精製物として取得した。
【００５２】
得られた両画分を減圧下で１０倍濃縮した後、Ｃ18高速液体クロマトグラフィーにて分画を行い、両画分にＶＧＤの精製画分（画分Ｃとする）を得た。さらに、このＶＧＤについて同定を行った。
高速液体クロマトグラフィーによる分画条件とＶＧＤの同定の結果を以下に示す。
（高速液体クロマトグラフィーによる分画条件）移動相：２０mmol/L酢酸ナトリウム水溶液／アセトニトリル＝４５／５５カラム温度：４０℃流速：１．０ｍL／分（ＶＧＤの物性）ＦＡＢマススペクトル：
ポジティブモード： m/z 299 (M+H)+
ネガティブモード： m/z 297 (M-H)-１Ｈ−ＮＭＲ（４００ＭＨｚ、ＣＤ３ＯＤ）；［δ ｐｐｍ（積分、多重度、結合定数Ｊ（Ｈｚ）］； 6.98 (1H, d, 2.0), 6.92 (1H, br.s), 6.91 (1H, br.s), 6.84 (1H, dd, 8.1, 2.0), 6.78 (1H, d, 8.1), 6.64 (1H, dd, 17.6, 11.0), 5.69 (1H, t, 8.9), 5.60 (1H, dd, 17.6, 1.1), 5.06 (1H, dd, 11.0, 1.1), 3.86 (3H, s), 3.82 (3H, s), 3.55 (1H,dd, 15.6, 9.3), 3.16 (1H, dd, 15.6, 8.5)１３Ｃ−ＮＭＲ（１００ＭＨｚ、ＣＤ３ＯＤ）；δ ｐｐｍ（多重度）； 149.1 (s), 149.1 (s), 147.7 (s), 145.4 (s), 138.1 (d), 134.5 (s), 133.2 (s), 129.7 (s), 120.0 (d), 116.4 (d), 116.2 (d), 111.4 (d), 111.4 (t), 110.7 (d), 86.7 (d), 56.7 (q), 56.4 (q), 39.4 (t)
実施例２
５０ｐｐｍ ４−ビニルグアヤコール及び０．５ｐｐｍリボフラビンを含有する７．７５％エタノール水溶液２０Lを蛍光灯照明付きの恒温庫内で反応温度２５℃で２４時間保存した。反応液を７．７５％エタノール水溶液で平衡化したダイヤイオンＨＰ２０（商品名、三菱化学株式会社製）に通し、８０％エタノール水溶液で洗浄後、エタノール２００ｍLで溶出し、本発明の消臭剤を得た。この消臭剤のＶＧＤ濃度は４０．４ｐｐｍであった。
【００５３】
実施例３
玉ねぎ１００ｇ、人参１５ｇ、長ねぎ１５ｇ、パセリ１０ｇ、粒胡椒０．５ｇ、ローリエ１枚、食塩２．５ｇ、水７００ｍL、及び鯛のアラ２５０ｇの混合物を２つ用意し、一方に、実施例２で得た本発明の消臭剤（ＶＧＤ濃度は４０．４ｐｐｍ）１００ｍLを加え、他方(対照区)にエタノールを１００ｍL加えて２０分間煮た。得られた混合物を布でろ過し、スープを６０℃に保温して、容器の蓋を開けた時の生臭みを７点評点法で評価した。その結果を表１に示す。
本発明のＶＧＤ添加区では対照区と比較して有意に生臭みが抑制されていた。
【００５４】
【表１】
実施例４
１次仕込みとして水２．０Ｌに米麹３７０ｇ、酵母（ダイヤイースト、商品名、協和発酵工業株式会社製)１．５ｇ及び乳酸７ｇを加えて、２０℃で２日間発酵して酒母を得た。２次仕込みとして、水１．３Ｌに米６６０ｇ、スピターゼＣＰ−４０Ｇ（α−アミラーゼ製剤、商品名、ナガセ生化学工業株式会社製：４００，０００ユニット／ｇ）２ｇを加え９０℃、３０分間加熱して液化を行い５０℃まで冷却後、スミチーム３０００（グルコアミラーゼ、商品名、新日本化学株式会社製、３０００ユニット／ｇ）２ｇ及びスミチームＡＣ（ヘミセルラーゼ、商品名、新日本化学株式会社製、６４００ユニット／ｇ）２ｇを添加して５０℃で１６時間反応させて得た米糖化液と米麹３７０ｇを酒母に加え２０℃で２日間発酵させた。
【００５６】
３次仕込みとして、水４．４Ｌに米１８００ｇ、スピターゼＣＰ−４０Ｇを７ｇ加え９０℃、３０分間加熱して液化を行い５０℃まで冷却後、スミチーム３０００を７ｇ及びスミチームＡＣを７ｇ添加して５０℃で１６時間反応させて得た米糖化液を２次仕込み発酵液に加えて２０℃で７日間発酵させた。得られた発酵物をろ過し、ろ液（１０Ｌ）を火入した（以後この方法によって調製したろ液をモロミという）。
【００５７】
発酵工程における４−ビニルグアヤコールの生成量は３次仕込時２．１ｐｐｍ、７日経過後５．１ｐｐｍであった。
上記モロミ（５ｐｐｍの４−ビニルグアヤコール含有）を蛍光灯照明付恒温庫内（２５℃）で２４時間保存して本発明の料理酒を得た。本発明の料理酒中の４−ビニルグアヤコールは、０．１ｐｐｍであり、ＶＧＤは、６７ｐｐｂであった。
【００５８】
実施例５
実施例４で調製したモロミ１Ｌにパーオキシダーゼ試薬（８１．８ユニット／ｍｇ）１．２ｇ（ＩＣＮ Ｂｉｏｍｅｄｉｃａｌｓ Ｉｎｃ．製）を添加し、２５℃で４８時間反応させ本発明の料理酒を得た。本発明の料理酒中の４ＶＧは、０．２ｐｐｍであり、ＶＧＤは、６６ｐｐｂであった。
【００５９】
実施例６
市販おでん種（汁つき）を用いて、汁に対し実施例４で得られた本発明の料理酒を１０重量％添加して調理した後、なべの蓋を開けたときの生臭みを７点評点法で評価した。対照として、本発明の料理酒の代わりに市販の料理酒を用いるほかは同様に実施した。その結果を表２に示す。本発明の料理酒は市販料理酒と比較して有意に生臭みを抑制した。
【００６０】
【表２】
実施例７
玉ねぎ１００ｇ、人参１５ｇ、長ねぎ１５ｇ、パセリ１０ｇ、粒胡椒０．５ｇ、ローリエ１枚、食塩２．５ｇ、水７００ｍL、及び鯛のアラ２５０ｇの混合物を２つ用意し、一方に実施例４で得られた本発明の料理酒１００ｍLを加え、他方に市販料理酒１００ｍLを加え、２０分間煮た。布でろ過したスープを容器で６０℃に保温して、容器の蓋を開けたときの生臭みを７点評点法で評価した。その結果を表３に示す。本発明の料理酒は市販料理酒と比較して有意に生臭みを抑制した。
【００６２】
【表３】
実施例８
よく洗浄した殻つきアサリ３５０ｇに実施例４で得られた本発明の料理酒５０ｍLまたは市販料理酒を加えて強火にかけて沸騰させた後、弱火で１分間加熱して調製したアサリ酒蒸しを６０℃に保温し、容器の蓋を開けたときの生臭みを７点評点法で評価した。その結果を表４に示す。本発明の料理酒は市販料理酒と比較して有意に生臭みを抑制した。
【００６４】
【表４】
実施例９
鰹荒本節５ｋｇ、実施例４で得られた本発明の料理酒または市販料理酒１L、５９％変性アルコール１．４Ｌ及び水７．６Ｌを混合し、混合物を４０℃で２時間抽出し、固液分離してカツオエキスを得た。カツオエキスを６０℃に保温した状態で生臭みを７点評点法で評価した。その結果を表５に示す。本発明の料理酒は市販料理酒と比較して有意に生臭みを抑制した。
【００６６】
【表５】
実施例１０
パラオキシ安息香酸メチル０．２ｇ、１，３−ブチレングリコール３．０ｇ、クエン酸ナトリウム０．８ｇ、エチレンジアミン四酢酸（ＥＤＴＡ）２Ｎａ塩０．１ｇ、ポリオキシエチレン硬化ヒマシ油０．４ｇ、変性アルコール５．０ｇ、香料０．０５ｇ、実施例２で得られた本発明の消臭剤０．５ｍLを混合して全量を精製水で１００ｍLとして、本発明の化粧水を調製した。成人男性１０名をパネラーとして、化粧水１．０ｍLを脱脂綿浸して被験者の腋に塗布し、そのにおいを７点評点法で評価した。結果を表６に示す。ＶＧＤを含有しない対照化粧水と比較し本発明の化粧水は有意に腋の不快臭を抑制した。
【００６８】
【表６】
実施例１１
津志田ら［日食科工誌，４１（９），６１１（１９９４）］の方法に準じて、本発明の酸化防止剤（ＶＧＤ溶液）の抗酸化試験を行った。
被検化合物含有液についてリノール酸自動酸化抑制能をβ−カロチンの退色抑制を指標として試験した。β-カロチン１０ｍｇ、リノール酸１ｇ、ツイーン８０ ２ｇをクロロホルム１０ｍLにそれぞれ溶解した。各溶液０．５ｍL、０．２ｍL、１．０ｍLを２００ｍL三角フラスコに入れ、系内を窒素で置換し、乾固した後、蒸留水１００ｍLに溶解し、得られた溶液４５ｍLを０．２mol/Lリン酸緩衝液（ｐＨ６．０）４ｍLと混合し基質溶液を調製した。基質溶液２．９ｍLと実施例４で得られた本発明の料理酒０．１ｍLを混合後、６０℃恒温器で加熱して４７０ｎｍにおける吸光度（ＯＤ）の変化を測定した。また、７９０ｐｐｍのＶＧＤのアセトニトリル溶液及び市販清酒を同様にして、基質溶液に添加してＯＤの変化を調べた。リノール酸の酸化開始時のＯＤ値に対する２４時間後のＯＤ値の比（％）を表７に示す。本発明の料理酒及びＶＧＤ添加によりリノール酸の酸化が抑制された。
【００７０】
【表７】
実施例１２
実施例４で得られたモロミを遮光下に６０℃、１４日間保持しＶＧＤ２５ｐｐｂを含有する本発明の料理酒を得た。当該料理酒中の４ＶＧの濃度は０．０１ｐｐｍであった。
実施例１３
清酒の製造蒸米35g、米麹65g、汲み水100ml、ダイヤイースト(協和発酵工業株式会社製)0.1g及び乳酸1mlを仕込み、２日間発酵させ（第１発酵）、酒母を得た。添え仕込において蒸米135g、米麹65g、スミチームAC（新日本化学株式会社製）0.8ｇ及び汲み水200ml、仲仕込において蒸米235g、米麹65g及び汲み水400ml、留仕込において蒸米330g、米麹70g及び汲み水500mlを仕込み並行複発酵（第２発酵）を行った。なお、添え仕込の汲み水には圧搾酵母ダイヤイースト（協和醗酵工業株式会社製）及び乳酸1mlを添加した。なお発酵は終始15℃で行った。添え仕込みから２日後に仲仕込み、さらにその２日後に留め仕込みを行い、留め仕込みから１９日後に圧搾ろ過して、発酵物を得た。得られた発酵物をろ過し、ろ液を火入し、モロミを得た。当該モロミを蛍光灯照明付恒温庫内で２５℃で２４時間保存して本発明の清酒を得た。この実施例において、第２発酵は、添え仕込み、中仕込み及び留め仕込みから構成されているが、仕込みの回数は特に制限されない。例えば、添え仕込み及び留め仕込みの２回で構成することもできる。
【００７２】
【発明の効果】
本発明により魚貝類、畜肉製品及び野菜類等の食品のオフフレーバーを効果的に除去する食品のオフフレーバーの除去方法及び消臭剤等が提供される。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for removing off-flavors from foods such as fish and shellfish, livestock meat products and vegetables, and a deodorant.
[0002]
[Prior art]
One of the factors that adversely affect the quality of food is so-called off-flavor such as unpleasant odors such as the raw odor of fish and shellfish, the animal odor of livestock meat, and the blue odor of soybeans. For the purpose of masking these off-flavors, sake, wine, shochu, mirin, etc. are used during processing and cooking of food. It is considered that the deodorizing effect due to these additions is largely due to ethanol.
[0003]
Regarding substances effective for deodorization, in addition to the aforementioned ethanol, amino acids and organic acids [eclipse,29(6), 340 (1982)], amino carbonyl reaction product [J. Fish Sausage,212, 15 (1982)], sugar [eclipse magazine,46(5), 319 (1999)] and phenolic compounds [Eclipse Journal,29(7), 426 (1982)] and the like are known.
Smoke is one of the traditional deodorization methods using food processing technology, but the participation of the aforementioned phenolic compounds has been reported for deodorization by smoke [Nissui Journal,47(1), 113 (1981), J. Fish Sausage,212, 15 (1982)].
[0004]
Vanillin, a kind of phenolic compound, is well known as a substance that suppresses the odor of trimethylamine, an off-flavor of fish and shellfish. Not used as a deodorant.
4-Vinylguaiacol, a kind of phenolic compound, is one of the precursors of the vanillin, but is considered to be one of off-flavor components in the field of brewing products such as sake and wine. Studies are underway to suppress production as much as possible in the process.
[0005]
On the other hand, the presence of yeast and fungi is known as an enzyme source of ferulic acid decarboxylase having the activity of producing 4-vinylguaiacol from ferulic acid, and the ferulic acid decarboxylase gene of yeast has been obtained [ Gene,142107 (1994), Japanese Patent Laid-Open No. 10-276788].
There are two types of food off-flavors, one that is originally present in food materials and one that is produced by processing and cooking processes. One of the off-flavors generated in the latter processing and cooking process is known to be due to lipid oxidation reaction by heating. Since the off-flavor produced by the oxidation reaction can be reduced by suppressing the oxidation reaction, the presence of a substance having an antioxidant activity is considered to be one of the effective means for removing the off-flavor. .
[0006]
[Problems to be solved by the invention]
One object of the present invention is to provide a food off-flavor removal method, a deodorant, and the like that effectively remove off-flavor from foods such as fish and shellfish, livestock meat products and vegetables.
Another object of the present invention is to provide a product containing the deodorant of the present invention.
[0007]
Another object of the present invention is to provide a method for producing a deodorant comprising an oxidation reaction step in which a phenol compound is reacted in the presence of oxygen, and a deodorant produced by the production method.
Another object of the present invention is to provide a seasoning production method including an oxidation reaction step in which a phenol compound is reacted in the presence of oxygen, and a seasoning produced by the production method.
[0008]
Another object of the present invention is to provide a method for producing liquor comprising an oxidation reaction step in which moromi is reacted in the presence of oxygen, and liquor produced by the production method.
[0009]
[Means for Solving the Problems]
The present invention provides a method for removing off-flavours of food, characterized in that a multimer of a phenol compound having a styrene structure is present in the food.
The present invention also provides a deodorant containing a multimer of a phenol compound having a styrene structure.
[0010]
Moreover, this invention provides the seasoning containing the multimer of the phenol compound which has a styrene structure.
Moreover, this invention provides the cosmetics containing the multimer of the phenol compound which has a styrene structure.
The present invention also provides an antioxidant containing a multimer of a phenol compound having a styrene structure.
[0011]
The present invention also provides a method for producing a multimer of a phenol compound having a styrene structure, wherein the phenol compound having a styrene structure is converted to the multimer in the presence of oxygen.
Further, the present invention provides a seasoning production method in which a phenol compound having a styrene structure is present at any time during the production process, and the phenol compound is present in the presence of oxygen during or after the seasoning production process. There is provided a method for producing a seasoning characterized in that it comprises an oxidation reaction step to be reacted below.
[0012]
Moreover, this invention provides the manufacturing method of liquor including the oxidation reaction process which reacts moromi in presence of oxygen in the manufacturing method of liquor.
Moreover, this invention provides the foodstuff obtained by the manufacturing method of the deodorized foodstuff characterized by cooking a foodstuff using said deodorizer, and this manufacturing method.
In addition, the present invention provides a method for deodorizing foods, which comprises cooking foods using the above deodorant.
[0013]
DETAILED DESCRIPTION OF THE INVENTION
The phenol compound having a styrene structure is not particularly limited as long as it is a compound having a hydroxyl group and a vinyl group on the benzene ring (the vinyl group may be substituted with a carboxyl group or the like).
[0014]
[Chemical 2]
(Wherein R1Represents a hydrogen atom or a carboxyl group, R2Represents a hydrogen atom or a lower alkoxy group). Here, examples of the lower alkyl part of the lower alkoxy group include linear or branched ones having 1 to 6 carbon atoms, specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group. , A pentyl group, a hexyl group, and the like. In the multimer of the compound represented by the general formula (I), each compound may be the same or different.
[0016]
Examples of the multimer of the phenol compound having a styrene structure include a 2 to 5 mer of a phenol compound having a styrene structure. Among them, a dimer is preferable, and the following general formulas (II) to ( VII)
[0017]
[Chemical Formula 3]
[Formula 4]
[Chemical formula 5]
(Wherein R1a, R1b, R1c, R1d, R1e, R1f, R1g, R1h, R1i, R1j, R1kAnd R1l Are the same or different and each represents a hydrogen atom or a carboxyl group;2a, R2b, R2c, R2d, R2e, R2f, R2g, R2h, R2i, R2j, R2kAnd R2lAre the same or different and each represents a hydrogen atom or a lower alkoxy group), and 2,3-dihydro-2- (4-hydroxy-3-methoxyphenyl) -7-methoxy-5 is preferred. -Vinylbenzofuran (VGD) is more preferably used.
(Method for obtaining phenolic compound having styrene structure)
A phenol compound having a styrene structure can be synthesized by a known method. For example, 4-vinylphenol can be obtained by reduction, dehydration, and hydrolysis of 4-acetoxyacetophenone. Ferulic acid is obtained by condensation decarboxylation of 4-hydroxy-3-methoxybenzaldehyde and malonic acid in pyridine in the presence of piperidine. p-Coumaric acid can be obtained from p-aminocinnamic acid via a diazonium salt or can be obtained from p-oxybenzaldehyde by the Perkin reaction. 4-Vinylguaiacol is obtained by reacting vanillin with acetic anhydride or sodium acetate to give 4-acetoxy-3-methoxycinnamic acid, followed by hydrolysis and decarboxylation with quinoline.
[0021]
Some of the phenolic compounds having a styrene structure such as ferulic acid can be purchased as commercial products.
Moreover, 4-vinyl guaiacol, ferulic acid, etc. can be manufactured also from a natural product (it may be a raw material of a foodstuff).
Hereinafter, a method for producing these phenol compounds from natural products will be exemplified.
(Method for producing ferulic acid)
Ferulic acid can be obtained by decomposing ferulic acid esters present in fibers such as arabinoxylan and pectin, which are one of the components of the plant cell wall, by a conventional method in the presence of ferulic acid esterase. Examples of plants containing ferulic acid or ferulic acid esters include grains such as rice, wheat, barley and buckwheat, potatoes such as potato and sweet potato, fruits such as grapes, apples and citrus, and vegetables.
[0022]
Ferulic acid can also be obtained by treating the above-mentioned plant with a fiber-degrading enzyme such as xylanase, arabinase, cellulase, pectinase, hemicellulase and the like by a usual method.
Further, for example, ferulic acid can also be obtained by decomposing lignin in wood by thermal decomposition, ethanol decomposition, hydrolase, for example, ligninase, manganese peroxidase, laccase and the like by a usual method.
(Method for producing 4-vinyl guaiacol)
4-Vinylguaiacol can be obtained by treating ferulic acid in the usual manner in the presence of ferulic acid decarboxylase.
[0023]
As an enzyme source of ferulic acid decarboxylase, not only the enzyme itself, but also fungal cells having the enzyme activity, fungal bodies such as yeast, or crude enzymes extracted from them by an appropriate method can be used [Appl. Environ. Microbiol.,59(7), 2244 (1993)]. As the yeast, a strain having the enzyme activity of 0.5 unit / g or more (unit definition will be described in the following examples) is preferably a wet cell weight or more. As a specific yeast, Saccharomyces cerevisiae (Saccharomyces cerevisiae) Strains such as IFO 2260, IFO 1953, IFO 0233 and diamond yeast (trade name, pressed yeast manufactured by Kyowa Hakko Kogyo Co., Ltd.) are exemplified.
(1) Method for producing a multimer of a phenol compound having a styrene structure
Hereinafter, the manufacturing method of the multimer of the phenol compound which has a styrene structure is demonstrated.
[0024]
The conversion reaction of a phenol compound having a styrene structure into a multimer is performed by aging at 10 to 80 ° C. in the presence of oxygen in a solvent such as an ethanol-containing solvent. Specifically, for example, the conversion reaction of 5 ppm 4-vinylguaiacol to VGD is preferably carried out by aging at 25 ° C. for 6 months or longer, 37 ° C. for 4 months or longer, or 60 ° C. for 20 days or longer.
[0025]
In addition, it is preferable to forcibly aerate oxygen into the reaction system because the reaction period can be shortened.
In the above conversion reaction, the reaction can be promoted by carrying out under light irradiation, but the reaction can be further promoted by carrying out in the presence of a photosensitizer.
[0026]
When performed in the presence of light and in the presence of a photosensitizer, the light amount and time suitable for the conversion are selected at 5 to 80 ° C., preferably 10 to 30 ° C., for example, 5 ppm 4-vinyl guaiacol solution The conversion reaction to 1 L of VGD is preferably performed at 20 ° C. for 3 to 1 day under 20 to 40 W fluorescent lamp, and at 30 ° C. for 2 to 0.5 day under 20 to 40 W fluorescent lamp.
[0027]
As the light source used at this time, a light source that mainly emits light having a wavelength of 240 to 500 nm can be preferably used. Specific examples thereof include sunlight, fluorescent lamp, incandescent lamp, black light, germicidal lamp, and insect trap. A light etc. are mention | raise | lifted and the light source can be used by 1 type (s) or 2 or more types. Among these, a black light, a germicidal lamp or a trap lamp is more preferably used from the viewpoint of energy consumption efficiency.
[0028]
Examples of the photosensitizer include hydroxymethylfurfural and riboflavin. Since the conversion rate varies depending on the combination of the photosensitizer and the type of light source, hydroxymethylfurfural, riboflavin and the like are preferable for ultraviolet light, and riboflavin and the like are preferably used for visible light. When irradiating the fermentation broth with light, if the raw material contains riboflavin or riboflavin is produced by fermentation, the photosensitizer may not be added. The concentration of the photosensitizer is preferably 1 ppb or more, and more preferably 10 to 5000 ppb.
[0029]
Moreover, this conversion reaction can also be performed in presence of the enzyme which has the capability to convert the phenol compound which has a styrene structure into the multimer.
Examples of the enzyme source of the enzyme include peroxidase, specifically, ICN Biomedicals Inc. A peroxidase reagent manufactured or a peroxidase crude enzyme solution extracted from horseradish with water can be used.
[0030]
This reaction mixture is a mixture comprising a multimer of a phenol compound and other components, and can be used as a deodorant by itself.
Recovery of the multimer from the reaction mixture (hereinafter, a multimer of a phenol compound having a styrene structure may be expressed as the multimer) is, for example, a nonionic porous material such as Diaion HP20 (manufactured by Mitsubishi Chemical). The nonionic porous resin (herein, nonionic porous resin means a resin that does not have a functional group such as an ion exchange group and that adsorbs various organic substances by van der Waals force). A nonionic porous resin packed in a column is allowed to equilibrate with a 5-30% aqueous solution of alcohol, for example, ethanol, methanol, etc., and then the multimer is adsorbed to the resin through the reaction solution and supplied with alcohol. Elute multimers. If necessary, the eluate is dried under reduced pressure to obtain the target powder.
(2) Food off-flavor removal method
The method for removing off-flavours of the food product of the present invention includes, for example, adding a multimer of a phenol compound having a styrene structure obtained as described above, or a reaction mixture containing a multimer of a phenol compound having a styrene structure. Present in foods to reduce or completely eliminate off-flavors of food.
[0031]
When the multimer is used, not only a pure one but also its content may be used. For example, the reaction mixture can be used, or a crude product of the reaction mixture can be used. For example, a form in which the deodorant or seasoning of the present invention described later is used for removal of food off-flavor is included in the concept of a method for removing food off-flavor.
[0032]
In the method for removing off-flavours of food of the present invention, the multimer is preferably present in an amount of 0.5 ppb or more relative to the food.
(3) Deodorant
The deodorizer of the present invention is effective for deodorizing body odors such as off-flavors of foods such as fish and shellfish, animal odors of livestock meat, and blue odor of soybeans, aging odors, and scents of straw.
[0033]
The deodorant of the present invention is a compound of a phenol compound having a styrene structure, which is a suitable solvent (for example, water, ethanol or a mixture thereof) or powder (for food applications, such as starch, dextrin, In the case of uses such as lactose and other cosmetics and cosmetics, for example, it can be obtained by mixing with excipients such as talc. In addition, the reaction mixture itself for producing the multimer, the ethanol solution of the multimer obtained in the purification operation from the reaction mixture, and the like can be used as the deodorant of the present invention as they are. A multimer of a phenol compound having a styrene structure can be obtained according to or in accordance with the explanation of (1) above.
[0034]
The deodorant of this invention can contain the various component according to a use and the objective other than the multimer of the phenol compound which has a styrene structure. When using the deodorizer of this invention for the deodorization of foodstuffs, it can add to a foodstuff as a liquid mixed with ethanol etc., or can be used as a seasoning etc. of this invention mentioned later, for example.
When the deodorant of the present invention is used in foods, for example, a solution containing the multimer is preferably 10 ppb or more, more preferably 10 ppb to 100 ppm, in an ethanol solution of 1 to 80%, preferably 5 to 30%. Can be added to food.
[0035]
When the deodorant of the present invention is used for the purpose of eliminating body odor, it can be used, for example, as a cosmetic of the present invention described later.
(4) Seasoning
The seasoning of the present invention preferably contains 10 ppm or more, more preferably 10 ppb to 100 ppm of a multimer of a phenol compound having a styrene structure in a known seasoning currently used or developed in the future. Can be obtained. Specifically, the seasoning of the present invention can be obtained by adding a multimer of a phenol compound having a styrene structure at any time during the final product of the seasoning or the manufacturing process. It can also be obtained by causing a phenol compound having a styrene structure to exist at any time during the production process and oxidizing the phenol compound in the presence of oxygen during the seasoning production process or after the completion of the production process. A multimer of a phenol compound having a styrene structure can be obtained according to or in accordance with the explanation of (1) above, but the phenol compound is added in the presence of oxygen during the seasoning production process or after the production process is completed. The method of causing the oxidation reaction in will be described in detail in the description of the fermented seasoning described below.
[0036]
Examples of the seasoning of the present invention include amino acids such as glutamic acid, aspartic acid, alanine, arginine, leucine, tyrosine, or glycine, organic acids such as succinic acid, lactic acid, malic acid, citric acid, or acetic acid, ethanol, 1- Contains one or more alcohols such as propanol, 2-methylpropanol, or isoamyl alcohol, sugars such as glucose, fructose, sucrose, or maltose, esters such as isoamyl acetate, or ethyl caproate For example, alcohol, such as sake, shochu, whiskey or brandy, fermented seasoning or extract seasoning, etc. can be mentioned as its form.
(Extract seasoning)
The extract seasoning of the present invention is a seasoning containing meat, marine products, boiled or steamed juice of vegetables, or a concentrate thereof among the seasonings of the present invention, for example, meat extract seasoning , Seafood extract seasoning or vegetable extract seasoning. The meat extract seasoning is mainly made from meat such as beef, pork and chicken, or bones, etc. Marine extract such as crab or dried product thereof is used as a main raw material, and vegetable extract seasoning is produced by a usual method using onion, garlic, carrot, Chinese cabbage, cabbage, shiitake, kombu or the like as a main raw material.
[0037]
Furthermore, the manufacturing method of the extract seasoning of this invention is demonstrated below. Using a solution such as ethanol, water or a mixture thereof containing a multimer of a phenol compound having a styrene structure (for example, the liquor of the present invention described below) is preferable. Extraction is performed at 5 to 120 ° C., preferably 20 to 80 ° C. for 1 to 10 hours. The supernatant obtained by solid-liquid separation of the extract can be obtained as an extract. The extract seasoning of the present invention can be obtained as a concentrate by subjecting the obtained extract to heat concentration, reduced pressure concentration, membrane concentration, freeze concentration, and the like, if necessary.
(Fermented seasoning)
The fermented seasoning of the present invention is manufactured using the fermenting action of microorganisms or the like in the seasoning of the present invention, and specific examples thereof include vinegar, cooking liquor, sake, wine, mirin. , Soy sauce or miso.
[0038]
The fermented seasoning of the present invention can be obtained by adding a multimer of phenolic compounds having a styrene structure at any time during the final product of the fermented seasoning or the production process, but the process for producing the fermented seasoning It is preferable to obtain a phenol compound having a styrene structure at any time in the middle and to oxidize the phenol compound in the presence of oxygen during or after the production process of the fermented seasoning.
[0039]
As the method for producing the fermented seasoning of the present invention by performing the oxidation reaction after completion of the fermented seasoning production process, for example, in the production process, 4-vinyl guaiacol is generated, and after the fermented seasoning production process is completed. Furthermore, the method etc. which convert 4-vinyl guaiacol in this fermented seasoning into VGD, etc. are mention | raise | lifted. Hereinafter, the case of cooking liquor will be described as a specific example.
[0040]
First, cereals such as rice (usually containing ferulic acid or an ester thereof) are used as raw materials, which are liquefied and saccharified by filamentous fungi such as rice bran. At this time, a liquefying enzyme such as α-amylase and / or a saccharifying enzyme such as glucoamylase may be added as necessary. Next, yeast is added for fermentation, and the resulting fermented liquid (moromi) is filtered to obtain a cooking liquor as the filtrate. Here, the filamentous fungus also has a fibrinolytic enzyme activity and a ferulic acid esterase activity, and contributes to the degradation of fiber in cereals or the release of ferulic acid.
[0041]
In this step, ferulic acid is produced from cereals by the presence of xylanase together with glucoamylase, and this ferulic acid is contained in a specific yeast [the yeast etc. exemplified in the description of the method for producing 4-vinyl guaiacol]. It is converted into 4-vinyl guaiacol by acid decarboxylase, which is contained in the resulting cooking liquor. At this time, the ferulic acid decarboxylase of filamentous fungi can also be used.
[0042]
Furthermore, the conversion reaction of 4-vinyl guaiacol into a multimer such as VGD using the cooking liquor containing 4-vinyl guaiacol [the conversion reaction of 4-vinyl guaiacol into the multimer is described in (1) above] The cooking liquor of the present invention containing VGD can be obtained.
In addition, as a method for producing the multimer during the production process of the fermented seasoning, a phenol compound having a styrene structure is added or produced at an appropriate time in the production process, and in the same manner as described above, And a method for carrying out a conversion reaction to the multimer at an appropriate time.
(5) Cosmetics
The cosmetic of the present invention can be obtained by blending a multimeric compound of a phenol compound having a styrene structure with a concentration of preferably 10 ppb or more, more preferably 10 ppb to 1 ppm with respect to the total amount of the cosmetic. it can. A multimer of a phenol compound having a styrene structure and a reaction mixture containing the multimer can be obtained according to or in accordance with the description of the method for producing the multimer.
[0043]
The cosmetic of the present invention may contain a cosmetic base, for example, a pigment, a fragrance, an antiseptic, a surfactant, an antioxidant, an ultraviolet absorber, etc., if necessary. It can be obtained by preparing according to the method described in “Transdermal Formulation Development Manual” supervised by Mitsuo Matsumoto, 1st Edition (published by Seiki Shoin 1985).
Examples of the pigment include pigments such as tar dyes, iron oxide, titanium oxide, and zinc oxide. Examples of the fragrances include animal fragrances such as fragrance, vegetable fragrances such as peppermint oil, lemon oil and rose oil, and synthetic fragrances such as benzyl alcohol and anisole. Examples of the preservative include paraben, methyl paraben, ethyl p-oxybenzoate, butyl p-oxybenzoate and the like. Surfactants include anionic surfactants such as sodium cetyl sulfate, polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, polyoxyethylene polyhydric alcohol fatty acid ester, fatty acid ester hardened castor oil, polyhydric alcohol fatty acid ester , Nonionic surfactants such as polyglycerin fatty acid esters, cationic surfactants such as tetraalkylammonium salts, betaines such as betaine type, sulfobetaine type, sulfoamino acid type, sodium N-stearoyl-L-glutamate Surfactants and the like. Examples of the antioxidant include dibutylhydroxytoluene. Examples of the ultraviolet absorber include 2-methoxyhexyl paramethoxycinnamate, 4-tert-butyl-4'-methoxydibenzoylmethane, and the like.
[0044]
Cosmetic dosage forms include creams, milky lotions, lotions, cosmetic liquids, packs and the like. For example, in the case of an emulsion, it can be produced by a known method in which an oil phase and an aqueous phase, respectively heated, are emulsified and dispersed and cooled.
The cosmetic of the present invention is useful for removing body odor and the like.
(6) Antioxidants
The antioxidant of the present invention preferably contains 10 ppb or more, more preferably 10 ppb to 100 ppm, of a multimer of a phenol compound having a styrene structure.
[0045]
The antioxidant of the present invention comprises a multimer of a phenol compound having a styrene structure in an appropriate solvent (for example, water, ethanol or a mixture thereof) or powder [wherein, specific examples of the powder include (3) And the like mentioned in the explanation of the above. In addition, an ethanol solution of the multimer obtained in the purification operation from the reaction mixture for producing the multimer can be used as it is as the antioxidant of the present invention. A multimer of a phenol compound having a styrene structure can be obtained according to or in accordance with the description of the method for producing the multimer.
[0046]
The antioxidant of the present invention can be used, for example, by being added during the production process of foods, seasonings, cosmetics, etc., when the final product or food is cooked.
The antioxidant of the present invention is useful for antioxidants such as foods, seasonings and cosmetics, for example, antioxidants such as linoleic acid in foods.
(7) A method for producing a deodorized food, characterized by cooking the food with the above deodorant, and a food obtained by the production method
The method for producing a deodorized food product characterized by cooking the food product with the above deodorant is, for example, a fish and shellfish or the like for the deodorant described in (3) above. For example, it can be carried out by cooking so that vegetables such as soybeans can be used so that the concentration of the multimeric phenol compound having a styrene structure in the food is 0.5 ppb or more. The food of the present invention is obtained by the production method and has a useful property as a food from which off-flavor is removed.
(8) A method for deodorizing a food, characterized by cooking the food with the above deodorant.
The food deodorization method characterized by cooking the food with the above deodorant is, for example, fish shellfish etc., livestock meats, vegetables such as soybeans, etc. as the deodorizer described in (3) above Preferably, the concentration of the phenol compound having a styrene structure in the food is 0.5 ppb or more.
[0047]
Hereinafter, the present invention will be described with reference to examples.
[0048]
【Example】
Analytical conditions for high performance liquid chromatography (HPLC) used in the following examples are as follows.
Column: Inertsil ODS-2 4.6 × 250 mm (manufactured by GL Sciences) Detector: OD 280 nm
The definition of the enzyme activity of the enzyme in the following examples is as follows.
(Enzyme activity of ferulic acid decarboxylase)
0.1 mL of 1 g / L ferulic acid (manufactured by Ichimaru Falcos) aqueous solution was added to 0.9 mL of a test yeast culture broth cultured at 30 ° C. overnight in a YPD medium, and reacted at 25 ° C. under static conditions. The amount of 4-vinyl guaiacol in the supernatant of the reaction solution was quantified using high performance liquid chromatography, and the amount of enzyme that produced 1 ppm of 4-vinyl guaiacol per hour was defined as 1 unit (unit).
(Enzymatic activity of xylanase)
After adding 1.0 mL of the test enzyme solution to a solution obtained by adding 100 mg of xylan derived from crow barley (manufactured by Hanai Chemical) to 9.0 mL of 50 mol / L acetate buffer (pH 4.5), the mixture was stirred at 52 ° C. Reacted. The change in reducing sugar equivalent in the reaction solution was quantified by the dinitrosalicylic acid method, and the amount of enzyme that liberates 1 μmol of reducing sugar equivalent from xylan per minute was defined as 1 unit (unit).
(Quantitative determination of phenolic compounds)
In the following examples, the analysis of the phenol compound having a styrene structure was performed as follows.
[0049]
The test substance was subjected to HPLC analysis as follows. For the analysis of VGD, the sample was concentrated to prepare a test solution. Sample 50 mL for HPLC pretreatment C18After passing through the cartridge, the sample eluted with 0.8 mL of acetonitrile to 1.0 mL was analyzed under the above conditions.
Fractionation conditions by high performance liquid chromatography Mobile phase: Liquid A 20 mmol / L sodium acetate aqueous solution, liquid B acetonitrile
Liquid B / liquid A (volume ratio) was eluted with a linear gradient of 30 to 80% / 25 minutes.
Column temperature: 40 ° C. Flow rate: 1.0 mL / min
(7-point scoring method and significant difference test)
In the following examples, the 7-point scoring method is a method for evaluating the intensity of the odor by assigning a score from 1 point (weak) to 7 points (strong). The presence or absence was examined. In each example, n represents the number of people.
[0050]
Example 1
800 mL of a 7.75% aqueous ethanol solution containing 50 ppm 4-vinyl guaiacol (4-VG) and 41.6 ppm hydroxymethylfurfural was irradiated with ultraviolet rays for 40 minutes. The obtained reaction solution was passed through Diaion HP20 (trade name, manufactured by Mitsubishi Chemical Corporation) equilibrated with 7.75% aqueous ethanol solution, washed with 80% aqueous methanol solution, and fraction eluted with 8 mL of methanol (fraction) Min A) was obtained as a crude product.
[0051]
Separately, 20 L of a 7.75% aqueous ethanol solution containing 50 ppm 4-vinyl guaiacol and 0.5 ppm riboflavin was stored at a reaction temperature of 25 ° C. for 24 hours in a thermostatic chamber equipped with a fluorescent lamp. The reaction solution was passed through Diaion HP20 (trade name, manufactured by Mitsubishi Chemical Corporation) equilibrated with an aqueous 7.75% ethanol solution, washed with an 80% aqueous methanol solution, and fractions eluted with 200 mL of methanol (fractions B and B). Was obtained as a crude product.
[0052]
ObtainedBothAfter concentrating the fraction 10 times under reduced pressure, C18Fractionation was performed by high performance liquid chromatography, and a purified fraction of VGD (referred to as fraction C) was obtained in both fractions. Furthermore, this VGD was identified.
The fractionation conditions by high performance liquid chromatography and the results of VGD identification are shown below.
(Fractionation conditions by high performance liquid chromatography) Mobile phase: 20 mmol / L sodium acetate aqueous solution / acetonitrile = 45/55 Column temperature: 40 ° C. Flow rate: 1.0 mL / min (physical properties of VGD) FAB mass spectrum:
Positive mode: m / z 299 (M + H) +
Negative mode: m / z 297 (M-H)-1H-NMR (400 MHz, CD3OD); [δ ppm (integral, multiplicity, coupling constant J (Hz)]; 6.98 (1H, d, 2.0), 6.92 (1H, br.s), 6.91 (1H, br.s), 6.84 (1H , dd, 8.1, 2.0), 6.78 (1H, d, 8.1), 6.64 (1H, dd, 17.6, 11.0), 5.69 (1H, t, 8.9), 5.60 (1H, dd, 17.6, 1.1), 5.06 ( 1H, dd, 11.0, 1.1), 3.86 (3H, s), 3.82 (3H, s), 3.55 (1H, dd, 15.6, 9.3), 3.16 (1H, dd, 15.6, 8.5)13C-NMR (100 MHz, CD3OD); δ ppm (multiplicity); 149.1 (s), 149.1 (s), 147.7 (s), 145.4 (s), 138.1 (d), 134.5 (s), 133.2 (s), 129.7 (s), 120.0 (d), 116.4 (d), 116.2 (d), 111.4 (d), 111.4 (t), 110.7 (d), 86.7 (d), 56.7 (q), 56.4 (q), 39.4 (t)
Example 2
20 L of a 7.75% aqueous ethanol solution containing 50 ppm 4-vinylguaiacol and 0.5 ppm riboflavin was stored at a reaction temperature of 25 ° C. for 24 hours in a thermostatic chamber equipped with a fluorescent lamp. The reaction solution is passed through Diaion HP20 (trade name, manufactured by Mitsubishi Chemical Corporation) equilibrated with an aqueous 7.75% ethanol solution, washed with an 80% aqueous ethanol solution, and then eluted with 200 mL of ethanol to obtain the deodorant of the present invention. Obtained. The VGD concentration of this deodorant was 40.4 ppm.
[0053]
Example 3
Prepare 2 mixtures of 100g onion, 15g carrot, 15g long onion, 10g parsley, 0.5g grain pepper, 1 bay leaf, 2.5g salt, 700ml water and 250g ara. 100 mL of the deodorant of the present invention (VGD concentration: 40.4 ppm) obtained in 1 above was added, and 100 mL of ethanol was added to the other (control group) and boiled for 20 minutes. The obtained mixture was filtered with a cloth, the soup was kept at 60 ° C., and the raw odor when the container lid was opened was evaluated by a 7-point scoring method. The results are shown in Table 1.
In the VGD addition group of the present invention, the live smell was significantly suppressed as compared with the control group.
[0054]
[Table 1]
Example 4
As a first charge, 370 g of rice bran, 1.5 g of yeast (Dia Yeast, trade name, manufactured by Kyowa Hakko Kogyo Co., Ltd.) and 7 g of lactic acid were added to 2.0 L of water and fermented at 20 ° C. for 2 days to obtain a liquor mother. . As a secondary charge, add 660 g of rice and 1.3 g of spitase CP-40G (α-amylase preparation, trade name, manufactured by Nagase Seikagaku Corporation: 400,000 units / g) to 1.3 L of water, and heat at 90 ° C. for 30 minutes. After liquefaction and cooling to 50 ° C., Sumiteam 3000 (glucoamylase, trade name, manufactured by Shin Nippon Chemical Co., Ltd., 3000 units / g) 2 g and Sumiteam AC (hemicellulase, trade name, manufactured by Shin Nippon Chemical Co., Ltd.) 6400 units / g) 2 g was added, and the rice saccharified solution obtained by reacting at 50 ° C. for 16 hours and 370 g of rice bran were added to the sake mother and fermented at 20 ° C. for 2 days.
[0056]
As a third charge, 1800 g of rice and 7 g of spitase CP-40G were added to 4.4 L of water, heated at 90 ° C. for 30 minutes for liquefaction, cooled to 50 ° C., then added 7 g of Sumiteam 3000 and 7 g of Sumiteam AC. The rice saccharified solution obtained by reacting at 16 ° C. for 16 hours was added to the secondary charging fermentation solution and fermented at 20 ° C. for 7 days. The obtained fermented product was filtered, and the filtrate (10 L) was fired (hereinafter, the filtrate prepared by this method is referred to as Moromi).
[0057]
The production amount of 4-vinyl guaiacol in the fermentation process was 2.1 ppm at the time of the third charge, and 5.1 ppm after 7 days.
The above moromi (containing 5 ppm of 4-vinyl guaiacol) was stored for 24 hours in a thermostatic chamber (25 ° C.) with fluorescent lamp illumination to obtain the cooked liquor of the present invention. 4-vinyl guaiacol in the cooking liquor of the present invention was 0.1 ppm, and VGD was 67 ppb.
[0058]
Example 5
To 1 L of moromi prepared in Example 4, 1.2 g of a peroxidase reagent (81.8 units / mg) (ICN Biomedicals Inc.) was added and reacted at 25 ° C. for 48 hours to obtain the cooking liquor of the present invention. 4VG in the cooking liquor of the present invention was 0.2 ppm, and VGD was 66 ppb.
[0059]
Example 6
Using a commercially available oden seed (with soup), adding 10% by weight of the cooking liquor of the present invention obtained in Example 4 to the soup, cooking, and then adding 7 raw odors when the pan lid is opened Evaluation was made by the scoring method. As a control, the same procedure was carried out except that a commercial liquor was used instead of the liquor of the present invention. The results are shown in Table 2. The cooked liquor of the present invention significantly suppressed the raw odor compared with the commercial cooked liquor.
[0060]
[Table 2]
Example 7
Prepare a mixture of 100 g of onion, 15 g of carrot, 15 g of long onion, 10 g of parsley, 0.5 g of grain pepper, 1 bay leaf, 2.5 g of salt, 700 ml of water, and 250 g of ara. 100 mL of the obtained cooking liquor of the present invention was added, and 100 mL of commercial cooking liquor was added to the other and boiled for 20 minutes. The soup filtered with a cloth was kept at 60 ° C. in a container, and the raw odor when the container lid was opened was evaluated by a 7-point scoring method. The results are shown in Table 3. The cooked liquor of the present invention significantly suppressed the raw odor compared with the commercial cooked liquor.
[0062]
[Table 3]
Example 8
After adding 50 mL of the cooked liquor of the present invention obtained in Example 4 or a commercial cooked liquor to 350 g of well-washed clams, the mixture was boiled over high heat and then heated for 1 minute on low heat. The raw odor when the container lid was opened was evaluated by a 7-point scoring method. The results are shown in Table 4. The cooked liquor of the present invention significantly suppressed the raw odor compared with the commercial cooked liquor.
[0064]
[Table 4]
Example 9
鰹 Aramotobu 5 kg, 1 L of the cooking liquor or commercial cooking liquor obtained in Example 4, 1.4 L of 59% denatured alcohol and 7.6 L of water are mixed, and the mixture is extracted at 40 ° C. for 2 hours. The bonito extract was obtained by liquid separation. The raw odor was evaluated by a 7-point scoring method with the bonito extract kept at 60 ° C. The results are shown in Table 5. The cooked liquor of the present invention significantly suppressed the raw odor compared with the commercial cooked liquor.
[0066]
[Table 5]
Example 10
0.2 g of methyl paraoxybenzoate, 3.0 g of 1,3-butylene glycol, 0.8 g of sodium citrate, 0.1 g of ethylenediaminetetraacetic acid (EDTA) 2Na salt, 0.4 g of polyoxyethylene hydrogenated castor oil, denatured alcohol 5 0.0 g, 0.05 g of fragrance, and 0.5 mL of the deodorant of the present invention obtained in Example 2 were mixed to make the total amount 100 mL with purified water to prepare the lotion of the present invention. Using 10 adult men as panelists, 1.0 ml of skin lotion was soaked in cotton wool and applied to the subject's eyelids, and the odor was evaluated by a 7-point scoring method. The results are shown in Table 6. Compared with the control lotion containing no VGD, the lotion of the present invention significantly suppressed the unpleasant odor of wrinkles.
[0068]
[Table 6]
Example 11
Tsushida et al.41(9), 611 (1994)], an antioxidant test of the antioxidant (VGD solution) of the present invention was conducted.
The test compound-containing solution was tested for its ability to inhibit linoleic acid autooxidation using the inhibition of fading of β-carotene as an index. 10 mg of β-carotene, 1 g of linoleic acid and 802 g of Tween 802 were dissolved in 10 mL of chloroform. Place 0.5 mL, 0.2 mL, and 1.0 mL of each solution into a 200 mL Erlenmeyer flask, replace the interior with nitrogen, dry, and dissolve in 100 mL of distilled water. 45 mL of the resulting solution is 0.2 mol / mol. A substrate solution was prepared by mixing with 4 mL of L phosphate buffer (pH 6.0). After mixing 2.9 mL of the substrate solution and 0.1 mL of the cooking liquor of the present invention obtained in Example 4, the change in absorbance (OD) at 470 nm was measured by heating with a 60 ° C. incubator. Moreover, the acetonitrile solution of 790 ppm and commercially available sake were added to the substrate solution in the same manner, and the change in OD was examined. Table 7 shows the ratio (%) of the OD value after 24 hours to the OD value at the start of linoleic acid oxidation. Addition of the cooking liquor and VGD of the present invention suppressed the oxidation of linoleic acid.
[0070]
[Table 7]
Example 12
The moromi obtained in Example 4 was kept at 60 ° C. for 14 days under shading to obtain a cooking liquor of the present invention containing VGD25ppb. The concentration of 4VG in the cooked liquor was 0.01 ppm.
Example 13
Production of refined sake 35 g of steamed rice, 65 g of rice bran, 100 ml of drawn water, 0.1 g of diamond yeast (manufactured by Kyowa Hakko Kogyo Co., Ltd.) and 1 ml of lactic acid were charged and fermented for 2 days (first fermentation) to obtain a sake mother. Steamed rice 135g, rice bran 65g, Sumiteam AC (manufactured by Shin Nippon Chemical Co., Ltd.) 0.8g and pumped water 200ml, steamed rice 235g, rice bran 65g, pumped water 400ml, steamed rice 330g, rice bran 70g And 500 ml of pumping water was charged and parallel double fermentation (second fermentation) was performed. It should be noted that pressed yeast diamond yeast (manufactured by Kyowa Hakko Kogyo Co., Ltd.) and 1 ml of lactic acid were added to the pumped water supplied. Fermentation was performed at 15 ° C throughout. Two days after the supplementary preparation, the intermediate preparation was carried out, and further two days later, the stop preparation was carried out, and after 19 days from the stop preparation, press filtration was performed to obtain a fermented product. The obtained fermented product was filtered and the filtrate was ignited to obtain moromi. The moromi was stored for 24 hours at 25 ° C. in a thermostatic chamber with fluorescent lamp illumination to obtain the sake of the present invention. In this example, the second fermentation is composed of supplementary charging, medium charging, and fastening charging, but the number of times of charging is not particularly limited. For example, it can also be constituted by two times of supplementary preparation and fastening preparation.
[0072]
【The invention's effect】
The present invention provides a food off-flavor removal method, a deodorant, and the like that effectively remove off-flavors from foods such as fish and shellfish, livestock meat products, and vegetables.
Claims (13)
（ａ）水に米と液化酵素を加え液化反応させた後、得られた液化した混合液に糖化酵素を添加し糖化反応させることにより糖化液を調製する工程と、
（ｂ）水に米麹と酵母と乳酸とを加え発酵反応させる１次発酵工程と、
（ｃ）１次発酵工程で得られた酒母に（ａ）工程で得られた糖化液と米麹とを加え発酵反応させる２次発酵工程と、
（ｄ）２次発酵工程で得られた発酵液に（ａ）工程で得られた糖化液を加え発酵反応させる３次発酵工程と、
（ｅ）３次発酵工程で得られた発酵液を濾過する工程The manufacturing method according to claim 10, wherein the moromi is moromi obtained by the following steps (a) to (e).
(A) a step of preparing a saccharified solution by adding saccharifying enzyme to the obtained liquefied mixed solution after adding rice and liquefying enzyme to water and causing a liquefaction reaction;
(B) a primary fermentation process in which rice bran, yeast and lactic acid are added to water and subjected to a fermentation reaction;
(C) a secondary fermentation process in which the saccharified solution obtained in the process (a) and rice bran are added to the liquor obtained in the primary fermentation process and subjected to a fermentation reaction;
(D) a tertiary fermentation step in which the saccharified solution obtained in the step (a) is added to the fermentation broth obtained in the secondary fermentation step to cause a fermentation reaction;
(E) Filtering the fermentation broth obtained in the tertiary fermentation process
（ａ）水に米と米麹と酵母とを加え発酵反応させる１次発酵工程と、
（ｂ）１次発酵工程で得られた酒母に、水と米及び米麹とを断続的に加えて段仕込みを行う２次発酵工程と、
（ｃ）２次発酵工程で得られた発酵液を濾過する工程The manufacturing method according to claim 10, wherein the moromi is moromi obtained by the following steps (a) to (c).
(A) a primary fermentation process in which rice, rice bran and yeast are added to water and subjected to a fermentation reaction;
(B) a secondary fermentation process in which water, rice, and rice bran are intermittently added to the liquor obtained in the primary fermentation process to prepare a step;
(C) Filtering the fermentation broth obtained in the secondary fermentation process
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001106601A JP4790143B2 (en) | 2000-04-06 | 2001-04-05 | Method for removing off-flavor from food and deodorant |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000104277 | 2000-04-06 | ||
| JP2000-104277 | 2000-04-06 | ||
| JP2000104277 | 2000-04-06 | ||
| JP2001106601A JP4790143B2 (en) | 2000-04-06 | 2001-04-05 | Method for removing off-flavor from food and deodorant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001352914A JP2001352914A (en) | 2001-12-25 |
| JP2001352914A5 JP2001352914A5 (en) | 2008-04-24 |
| JP4790143B2 true JP4790143B2 (en) | 2011-10-12 |
Family
ID=26589549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001106601A Expired - Lifetime JP4790143B2 (en) | 2000-04-06 | 2001-04-05 | Method for removing off-flavor from food and deodorant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4790143B2 (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060134197A1 (en) * | 2002-12-27 | 2006-06-22 | Yukio Uchida | Method of reducing unpleasant taste and/or unpleasant odor |
| JPWO2005120253A1 (en) * | 2004-06-11 | 2008-04-03 | ベストアメニティ株式会社 | Liquid seasoning and method for producing the same |
| WO2006062174A1 (en) * | 2004-12-08 | 2006-06-15 | San-Ei Gen F.F.I., Inc. | Masking agent for livestock meat odor |
| JP2008523806A (en) | 2004-12-16 | 2008-07-10 | ダウ・コーニング・コーポレイション | Method for inhibiting or reducing off-flavors in beverages using silane-treated silica filter media |
| JP4948384B2 (en) * | 2007-12-26 | 2012-06-06 | キッコーマン株式会社 | Liquid seasoning in containers |
| JP5089446B2 (en) * | 2008-03-11 | 2012-12-05 | 宝酒造株式会社 | Cooking liquors and their uses, and processed foods |
| JP2010011795A (en) * | 2008-07-04 | 2010-01-21 | Kikkoman Corp | Mirin (sweet sake for seasoning) |
| JP6080287B2 (en) * | 2010-03-30 | 2017-02-15 | 宝酒造株式会社 | Shochu, food processing method, processed food manufacturing method, and fermented seasoning |
| JP7162351B2 (en) * | 2020-05-01 | 2022-10-28 | 株式会社東洋発酵 | Composition for external use and method for producing composition for external use |
| JP7466426B2 (en) * | 2020-10-14 | 2024-04-12 | サントリーホールディングス株式会社 | Zinc-containing green tea drink |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2951341B2 (en) * | 1989-11-16 | 1999-09-20 | タマ生化学株式会社 | Food deodorant and food deodorizing method |
| JP2951353B2 (en) * | 1990-03-15 | 1999-09-20 | タマ生化学株式会社 | How to deodorize meat |
| AU693988B2 (en) * | 1995-01-25 | 1998-07-09 | Quest International B.V. | Process for the preparation of a flavouring component |
-
2001
- 2001-04-05 JP JP2001106601A patent/JP4790143B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001352914A (en) | 2001-12-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7125575B2 (en) | Method of removing off-flavor from foods and deodorizer | |
| Baqueiro-Peña et al. | Vanilla (Vanilla planifolia Andr.), its residues and other industrial by-products for recovering high value flavor molecules: A review | |
| Othman et al. | Antioxidant phenolic compounds loss during the fermentation of Chétoui olives | |
| Sefton et al. | Norisoprenoids in Vitis vinifera white wine grapes and the identification of a precursor of damascenone in these fruits | |
| Lin et al. | Biologically active components and nutraceuticals in the Monascus-fermented rice: a review | |
| Lee et al. | Comparative volatile profiles in soy sauce according to inoculated microorganisms | |
| JP4790143B2 (en) | Method for removing off-flavor from food and deodorant | |
| JP5089446B2 (en) | Cooking liquors and their uses, and processed foods | |
| KR101138783B1 (en) | Process of fermentated tomato using lactic acid bacteria and its product | |
| EP0012246A1 (en) | Aromatic and flavouring substances, their preparation by fermentation, their use and products containing them | |
| Mao et al. | Research progress on flavor and quality of Chinese rice wine in the brewing process | |
| JP6945282B2 (en) | Deodorizing method for unpleasant odors and manufacturing method for processed foods | |
| Giri et al. | Antioxidative properties of aqueous and aroma extracts of squid miso prepared with Aspergillus oryzae-inoculated koji | |
| US20110177181A1 (en) | Modified grape seed oils | |
| Herkenhoff et al. | Aroma component analysis by HS-SPME/GC–MS to characterize Lager, Ale, and sour beer styles | |
| JP4372820B2 (en) | Preparation method of long-life red doraji, long-life red doraji prepared by this preparation method, and functional food material containing the same | |
| Zhu et al. | Optimization of ultrasonic-assisted enzymatic hydrolysis to extract soluble substances from edible fungi by-products | |
| Li et al. | Salinity plays a dual role in broad bean paste-meju fermentation | |
| Zhong et al. | Effects of stabilization combined with fermentation treatments on the volatile composition and flavor profile of cooked black rice | |
| KR102510719B1 (en) | Manufacturing method for seasoning sauce for ribs using sarcodon aspratus and seasoning sauce for ribs manufactured by the same | |
| JP2011162457A (en) | Plant fermentation extract, method for producing the same and cosmetic | |
| US5948453A (en) | Food flavorant preparation via bioconversion of elemental sulphur | |
| Nunomura et al. | Soy sauce | |
| Chalier et al. | Production of volatile components by Penicillium roqueforti cultivated in the presence of soya bean oil | |
| Zhang et al. | Evaluation of differences in volatile flavor compounds between liquid-state and solid-state fermented Tartary buckwheat by Monascus purpureus |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A712 Effective date: 20050808 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20051108 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080307 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080307 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20080912 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20081128 |
|
| RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20090421 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110215 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110405 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110426 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110621 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20110712 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110720 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140729 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 4790143 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |