CN102057047B - 通过用霉菌对十一烯酸进行生物转化来生产天然9-癸烯-2-酮的方法及其在香料和食品调味剂领域中的用途 - Google Patents
通过用霉菌对十一烯酸进行生物转化来生产天然9-癸烯-2-酮的方法及其在香料和食品调味剂领域中的用途 Download PDFInfo
- Publication number
- CN102057047B CN102057047B CN200980120746.3A CN200980120746A CN102057047B CN 102057047 B CN102057047 B CN 102057047B CN 200980120746 A CN200980120746 A CN 200980120746A CN 102057047 B CN102057047 B CN 102057047B
- Authority
- CN
- China
- Prior art keywords
- acid
- decen
- oil
- undecylenic acid
- feed rate
- 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.)
- Active
Links
- DZECLZDTSQJBSU-UHFFFAOYSA-N dec-9-en-2-one Chemical compound CC(=O)CCCCCCC=C DZECLZDTSQJBSU-UHFFFAOYSA-N 0.000 title claims abstract description 50
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 title claims abstract description 35
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229960002703 undecylenic acid Drugs 0.000 title claims abstract description 35
- 235000013305 food Nutrition 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 239000002304 perfume Substances 0.000 title abstract description 15
- 238000000034 method Methods 0.000 claims description 34
- 230000036983 biotransformation Effects 0.000 claims description 27
- 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 claims description 13
- 239000008103 glucose Substances 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 8
- 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 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 241000235527 Rhizopus Species 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 238000009423 ventilation Methods 0.000 claims description 6
- 241000235575 Mortierella Species 0.000 claims description 5
- 241000235395 Mucor Species 0.000 claims description 5
- 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 claims description 5
- 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 claims description 5
- 241000639924 Aspergillaceae Species 0.000 claims description 4
- 241000228212 Aspergillus Species 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 241000235557 Mortierellaceae Species 0.000 claims description 4
- 241000228143 Penicillium Species 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 238000004900 laundering Methods 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 150000004666 short chain fatty acids Chemical class 0.000 claims description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004519 grease Substances 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 27
- 235000019198 oils Nutrition 0.000 description 27
- 239000000203 mixture Substances 0.000 description 25
- 241000306282 Umbelopsis isabellina Species 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 240000006439 Aspergillus oryzae Species 0.000 description 15
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 15
- 235000013599 spices Nutrition 0.000 description 14
- 244000099147 Ananas comosus Species 0.000 description 13
- 235000007119 Ananas comosus Nutrition 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 241000134363 Umbelopsis ramanniana Species 0.000 description 9
- 235000013399 edible fruits Nutrition 0.000 description 9
- 239000003205 fragrance Substances 0.000 description 8
- 241000220324 Pyrus Species 0.000 description 7
- 230000001580 bacterial effect Effects 0.000 description 7
- 235000021017 pears Nutrition 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 235000011194 food seasoning agent Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000004321 preservation Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 241000228245 Aspergillus niger Species 0.000 description 5
- 239000004278 EU approved seasoning Substances 0.000 description 5
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 5
- 240000005384 Rhizopus oryzae Species 0.000 description 5
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 244000271379 Penicillium camembertii Species 0.000 description 4
- 235000002245 Penicillium camembertii Nutrition 0.000 description 4
- 235000019486 Sunflower oil Nutrition 0.000 description 4
- MLFHJEHSLIIPHL-UHFFFAOYSA-N acetic acid isopentyl ester Natural products CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000002600 sunflower oil Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000011430 Malus pumila Nutrition 0.000 description 3
- 235000015103 Malus silvestris Nutrition 0.000 description 3
- 241000235526 Mucor racemosus Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000235403 Rhizomucor miehei Species 0.000 description 3
- 238000005273 aeration Methods 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000000481 breast Anatomy 0.000 description 3
- -1 breast frost Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- 241000220225 Malus Species 0.000 description 2
- 244000062730 Melissa officinalis Species 0.000 description 2
- 235000010654 Melissa officinalis Nutrition 0.000 description 2
- 241000498617 Mucor javanicus Species 0.000 description 2
- 241001480490 Mucoraceae Species 0.000 description 2
- 241000235388 Mucorales Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 240000008474 Pimenta dioica Species 0.000 description 2
- 235000006990 Pimenta dioica Nutrition 0.000 description 2
- 241000235545 Rhizopus niveus Species 0.000 description 2
- 241000758405 Zoopagomycotina Species 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 235000015243 ice cream Nutrition 0.000 description 2
- PQLMXFQTAMDXIZ-UHFFFAOYSA-N isoamyl butyrate Chemical compound CCCC(=O)OCCC(C)C PQLMXFQTAMDXIZ-UHFFFAOYSA-N 0.000 description 2
- 239000000865 liniment Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940041616 menthol Drugs 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000020238 sunflower seed Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- ANLABNUUYWRCRP-UHFFFAOYSA-N 1-(4-nitrophenyl)cyclopentane-1-carbonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1(C#N)CCCC1 ANLABNUUYWRCRP-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241001149952 Amylomyces rouxii Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000208308 Coriandrum Species 0.000 description 1
- 231100000911 LD50 test Toxicity 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 240000000064 Penicillium roqueforti Species 0.000 description 1
- 235000002233 Penicillium roqueforti Nutrition 0.000 description 1
- 241000303962 Rhizopus delemar Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 241000235033 Zygosaccharomyces rouxii Species 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 230000003570 biosynthesizing effect Effects 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- JRPDANVNRUIUAB-UHFFFAOYSA-N dec-3-en-2-one Chemical compound CCCCCCC=CC(C)=O JRPDANVNRUIUAB-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HCRBXQFHJMCTLF-UHFFFAOYSA-N ethyl 2-methylbutyrate Chemical compound CCOC(=O)C(C)CC HCRBXQFHJMCTLF-UHFFFAOYSA-N 0.000 description 1
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 description 1
- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 1
- 230000001339 gustatory effect Effects 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940094941 isoamyl butyrate Drugs 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 239000008257 shaving cream Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- XPQPWPZFBULGKT-UHFFFAOYSA-N undecanoic acid methyl ester Natural products CCCCCCCCCCC(=O)OC XPQPWPZFBULGKT-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/24—Synthetic spices, flavouring agents or condiments prepared by fermentation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/29—Fruit flavours
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Wood Science & Technology (AREA)
- Nutrition Science (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0853672A FR2931839B1 (fr) | 2008-06-03 | 2008-06-03 | Procede de production de la 9-decen-2-one naturelle par bioconversion de l'acide undecylenique a l'aide d'une moisissure et utilisation en parfumerie et aromatique alimentaire |
| FR0853672 | 2008-06-03 | ||
| PCT/FR2009/000646 WO2009147319A2 (fr) | 2008-06-03 | 2009-06-03 | Procede de production de la 9-decen-2-one naturelle par bioconversion de l'acide undecylenique a l'aide d'une moisissure et utilisation en parfumerie et aromatique alimentaire |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102057047A CN102057047A (zh) | 2011-05-11 |
| CN102057047B true CN102057047B (zh) | 2015-06-17 |
Family
ID=40546013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980120746.3A Active CN102057047B (zh) | 2008-06-03 | 2009-06-03 | 通过用霉菌对十一烯酸进行生物转化来生产天然9-癸烯-2-酮的方法及其在香料和食品调味剂领域中的用途 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8481789B2 (enExample) |
| EP (1) | EP2297328B1 (enExample) |
| JP (2) | JP2011521664A (enExample) |
| KR (1) | KR101694672B1 (enExample) |
| CN (1) | CN102057047B (enExample) |
| BR (1) | BRPI0913339B1 (enExample) |
| DK (1) | DK2297328T3 (enExample) |
| ES (1) | ES2628178T3 (enExample) |
| FR (2) | FR2931839B1 (enExample) |
| MX (1) | MX2010013197A (enExample) |
| PL (1) | PL2297328T3 (enExample) |
| PT (1) | PT2297328T (enExample) |
| RU (1) | RU2542388C2 (enExample) |
| WO (1) | WO2009147319A2 (enExample) |
| ZA (1) | ZA201008529B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102703527A (zh) * | 2012-05-16 | 2012-10-03 | 深圳波顿香料有限公司 | 一种c5~c13的脂肪族甲基酮的制备方法 |
| JP2015534053A (ja) * | 2012-09-07 | 2015-11-26 | ザ ブリガム アンド ウィメンズ ホスピタル インコーポレイテッドＴｈｅ Ｂｒｉｇｈａｍ ａｎｄ Ｗｏｍｅｎ’ｓ Ｈｏｓｐｉｔａｌ， Ｉｎｃ． | 侵襲性アスペルギルス症の診断及び治療 |
| GB201407383D0 (en) | 2014-04-28 | 2014-06-11 | Givaudan Sa | Improvements in or relating to organic compounds |
| WO2015187938A1 (en) | 2014-06-05 | 2015-12-10 | The Brigham And Women's Hospital, Inc. | Diagnosis and treatment of invasive aspergillosis |
| CA2992805A1 (en) * | 2015-08-07 | 2017-02-16 | V. Mane Fils | Composition comprising taste modulation compounds, their use and foodstuff comprising them |
| CN112021546B (zh) * | 2020-09-04 | 2022-07-01 | 恒枫食品科技有限公司 | 一种杏仁味香精的制备方法 |
| CN115590135B (zh) * | 2022-10-12 | 2024-04-26 | 恒枫食品科技有限公司 | 一种香精及其应用、含该香精的碳酸饮料 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4832964A (en) * | 1987-10-22 | 1989-05-23 | Nestec S.A. | Preparation of a blue cheese flavour |
| US4957862A (en) * | 1989-02-27 | 1990-09-18 | Sanofi | Microbiological process for the preparation of methyl ketones |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5939822A (ja) * | 1982-08-31 | 1984-03-05 | Meiji Milk Prod Co Ltd | ω−アルケニルメチルケトンを含有する香料組成物 |
| JP2826748B2 (ja) * | 1988-09-09 | 1998-11-18 | 昭和産業株式会社 | 発酵法によるメチルケトン及び／またはその対応アルコールの製造法、及び培養液の使用 |
| JPH03247291A (ja) * | 1990-02-27 | 1991-11-05 | Showa Sangyo Co Ltd | 発酵法によるメチルケトン及び／またはその対応アルコールの製造法、及び培養液の使用 |
| JPH04148688A (ja) * | 1990-10-09 | 1992-05-21 | Showa Sangyo Co Ltd | メチルケトンの製造方法 |
| JP4148688B2 (ja) | 2001-03-07 | 2008-09-10 | 株式会社リコー | マルチビーム走査装置 |
| FR2877340B1 (fr) * | 2004-11-03 | 2008-10-10 | Mane Fils Sa | Preparation stereoselective de gamma-lactones |
| FR2877339B1 (fr) * | 2004-11-03 | 2008-10-31 | Mane Fils Sa V | Gamma-undecenolactone, procede de preparation et utilisations |
-
2008
- 2008-06-03 FR FR0853672A patent/FR2931839B1/fr active Active
- 2008-12-18 FR FR0858747A patent/FR2931840A1/fr active Pending
-
2009
- 2009-06-03 JP JP2011512171A patent/JP2011521664A/ja active Pending
- 2009-06-03 CN CN200980120746.3A patent/CN102057047B/zh active Active
- 2009-06-03 BR BRPI0913339A patent/BRPI0913339B1/pt active IP Right Grant
- 2009-06-03 US US12/995,289 patent/US8481789B2/en active Active
- 2009-06-03 PT PT97576953T patent/PT2297328T/pt unknown
- 2009-06-03 PL PL09757695T patent/PL2297328T3/pl unknown
- 2009-06-03 EP EP09757695.3A patent/EP2297328B1/fr active Active
- 2009-06-03 RU RU2010153903/10A patent/RU2542388C2/ru active
- 2009-06-03 MX MX2010013197A patent/MX2010013197A/es active IP Right Grant
- 2009-06-03 WO PCT/FR2009/000646 patent/WO2009147319A2/fr not_active Ceased
- 2009-06-03 DK DK09757695.3T patent/DK2297328T3/da active
- 2009-06-03 ES ES09757695.3T patent/ES2628178T3/es active Active
- 2009-06-03 KR KR1020107028601A patent/KR101694672B1/ko active Active
-
2010
- 2010-11-29 ZA ZA2010/08529A patent/ZA201008529B/en unknown
-
2015
- 2015-03-03 JP JP2015041171A patent/JP2015130873A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4832964A (en) * | 1987-10-22 | 1989-05-23 | Nestec S.A. | Preparation of a blue cheese flavour |
| US4957862A (en) * | 1989-02-27 | 1990-09-18 | Sanofi | Microbiological process for the preparation of methyl ketones |
Non-Patent Citations (2)
| Title |
|---|
| Methyl Ketone Formation by Penici//ium camembert/in Model Systems;J, OKUMURA and J. E. KINSELLA;《J Dairy Sci》;19851231;全文 * |
| Methyl Ketone Formation During Germination of Penicillium roqueforti;Tsai Y. Fan et al.;《METHYL KETONE FORMATION》;19761231;第24卷(第3期);全文 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201008529B (en) | 2012-01-25 |
| BRPI0913339B1 (pt) | 2018-10-09 |
| WO2009147319A2 (fr) | 2009-12-10 |
| EP2297328A2 (fr) | 2011-03-23 |
| PL2297328T3 (pl) | 2017-10-31 |
| JP2011521664A (ja) | 2011-07-28 |
| RU2542388C2 (ru) | 2015-02-20 |
| PT2297328T (pt) | 2017-06-26 |
| ES2628178T3 (es) | 2017-08-02 |
| BRPI0913339A2 (pt) | 2015-11-24 |
| WO2009147319A3 (fr) | 2010-04-08 |
| RU2010153903A (ru) | 2012-07-20 |
| US20110077431A1 (en) | 2011-03-31 |
| US8481789B2 (en) | 2013-07-09 |
| FR2931840A1 (fr) | 2009-12-04 |
| CN102057047A (zh) | 2011-05-11 |
| KR101694672B1 (ko) | 2017-01-10 |
| MX2010013197A (es) | 2011-03-21 |
| JP2015130873A (ja) | 2015-07-23 |
| EP2297328B1 (fr) | 2017-03-22 |
| FR2931839A1 (fr) | 2009-12-04 |
| FR2931839B1 (fr) | 2011-07-15 |
| DK2297328T3 (da) | 2017-07-03 |
| KR20110025918A (ko) | 2011-03-14 |
| HK1156985A1 (en) | 2012-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102057047B (zh) | 通过用霉菌对十一烯酸进行生物转化来生产天然9-癸烯-2-酮的方法及其在香料和食品调味剂领域中的用途 | |
| Baqueiro-Peña et al. | Vanilla (Vanilla planifolia Andr.), its residues and other industrial by-products for recovering high value flavor molecules: A review | |
| CN101965964A (zh) | 一种奶味香精制备方法、由其制备的奶味香精及相关的饲料香味剂 | |
| CN101218222A (zh) | 香兰素缩醛以及含有香兰素缩醛的感官刺激剂组合物 | |
| CN101056543B (zh) | γ-十一烯内酯，其制备方法及其在化妆品中和以食品添加剂形式的用途 | |
| JP7154719B2 (ja) | ４－メルカプト－１－オクタノールまたはその脂肪酸エステル、および香味付与剤 | |
| CA2251440C (en) | Process for the production of degradation products of fatty acids | |
| RU2406410C2 (ru) | Стереоселективный способ получения гамма-лактонов | |
| JP6827687B1 (ja) | 香味付与剤としてのジエチル メルカプトサクシネート | |
| HK1156985B (en) | Method for producing natural 9-decen-2-one by bioconverting undecylenic acid using a mold, and use in the perfume and food flavoring fields | |
| JP2021143150A (ja) | 含硫化合物および香味付与剤 | |
| JP6282189B2 (ja) | アセタール基を有するチオール化合物および該化合物を含有する香料組成物 | |
| JP7179431B2 (ja) | 含硫化合物および香味付与剤 | |
| US10392672B2 (en) | Yeast strain and method for producing natural cinnamic acid using the yeast strain for fermentation | |
| Yadav et al. | Microbial biotransformation for production of valuable aroma compounds: Current research and future challenges | |
| WO2025176277A1 (en) | Fermented essential oils | |
| JP5897048B2 (ja) | 新規アルカン酸誘導体および該化合物を含有する香料組成物 | |
| JP2024110039A (ja) | 香気徐放化合物およびこれを用いた香料組成物 | |
| DE112006002442T5 (de) | Verfahren zur Herstellung von optisch aktivem Theaspiran | |
| CN112438419A (zh) | 芽苞茶提取物的制备方法及在香精和电子烟油中的应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1156985 Country of ref document: HK |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: GR Ref document number: 1156985 Country of ref document: HK |