JP2577261C - - Google Patents
Info
- Publication number
- JP2577261C JP2577261C JP2577261C JP 2577261 C JP2577261 C JP 2577261C JP 2577261 C JP2577261 C JP 2577261C
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydroxy fatty
- fatty acid
- lactone
- ester
- 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
- -1 hydroxy fatty acid Chemical group 0.000 claims description 37
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 31
- 239000000194 fatty acid Substances 0.000 claims description 31
- 238000000855 fermentation Methods 0.000 claims description 27
- 230000004151 fermentation Effects 0.000 claims description 27
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
- 239000004359 castor oil Substances 0.000 claims description 17
- 235000019438 castor oil Nutrition 0.000 claims description 17
- WBHHMMIMDMUBKC-QJWNTBNXSA-N Ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 claims description 16
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 16
- WBHHMMIMDMUBKC-GKUQOKNUSA-N Ricinoleic acid Natural products CCCCCC[C@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-GKUQOKNUSA-N 0.000 claims description 15
- 229960003656 ricinoleic acid Drugs 0.000 claims description 15
- JUKPWJGBANNWMW-VWBFHTRKSA-N Eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 claims description 13
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 11
- 150000002596 lactones Chemical class 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims description 3
- FEIUPFRYFFTGFY-UHFFFAOYSA-N 3,12-dihydroxyhexadecanoic acid Chemical compound CCCCC(O)CCCCCCCCC(O)CC(O)=O FEIUPFRYFFTGFY-UHFFFAOYSA-N 0.000 claims description 2
- FSZLBXAVPUVPDY-UHFFFAOYSA-N 3,12-dihydroxypentadecanoic acid Chemical compound CCCC(O)CCCCCCCCC(O)CC(O)=O FSZLBXAVPUVPDY-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 241000894007 species Species 0.000 claims description 2
- IFYYFLINQYPWGJ-SECBINFHSA-N (5R)-5-hexyloxolan-2-one Chemical compound CCCCCC[C@@H]1CCC(=O)O1 IFYYFLINQYPWGJ-SECBINFHSA-N 0.000 description 11
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 11
- 239000000796 flavoring agent Substances 0.000 description 8
- 235000019634 flavors Nutrition 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 235000003534 Saccharomyces carlsbergensis Nutrition 0.000 description 5
- 229940081969 Saccharomyces cerevisiae Drugs 0.000 description 5
- 230000000813 microbial Effects 0.000 description 5
- 229940041514 Candida albicans extract Drugs 0.000 description 4
- 229940088598 Enzyme Drugs 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000012138 yeast extract Substances 0.000 description 4
- 239000001888 Peptone Substances 0.000 description 3
- 108010080698 Peptones Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 235000019319 peptone Nutrition 0.000 description 3
- BVDRUCCQKHGCRX-UHFFFAOYSA-N 2,3-dihydroxypropyl formate Chemical compound OCC(O)COC=O BVDRUCCQKHGCRX-UHFFFAOYSA-N 0.000 description 2
- 229940040461 Lipase Drugs 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 230000035633 Metabolized Effects 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 102000004882 lipase Human genes 0.000 description 2
- 108090001060 lipase Proteins 0.000 description 2
- 235000019626 lipase activity Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- 239000001730 (5R)-5-butyloxolan-2-one Substances 0.000 description 1
- QQAVZEYXLCYOKO-UHFFFAOYSA-N 4-hydroxydecanoic acid Chemical compound CCCCCCC(O)CCC(O)=O QQAVZEYXLCYOKO-UHFFFAOYSA-N 0.000 description 1
- IPBFYZQJXZJBFQ-UHFFFAOYSA-N 5-butyloxolan-2-one Chemical compound CCCCC1CCC(=O)O1 IPBFYZQJXZJBFQ-UHFFFAOYSA-N 0.000 description 1
- VLSVVMPLPMNWBH-UHFFFAOYSA-N 5-propyloxolan-2-one Chemical compound CCCC1CCC(=O)O1 VLSVVMPLPMNWBH-UHFFFAOYSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000235646 Cyberlindnera jadinii Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000286779 Hansenula anomala Species 0.000 description 1
- 235000014683 Hansenula anomala Nutrition 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N Hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L Iron(II) sulfate Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- 241000235042 Millerozyma farinosa Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 210000003491 Skin Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229940029983 VITAMINS Drugs 0.000 description 1
- 229940021016 Vitamin IV solution additives Drugs 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000019993 champagne Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005824 corn Nutrition 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamins Natural products 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- PAZZVPKITDJCPV-UHFFFAOYSA-N ξ-10-Hydroxyoctadecanoic acid Chemical compound CCCCCCCCC(O)CCCCCCCCC(O)=O PAZZVPKITDJCPV-UHFFFAOYSA-N 0.000 description 1
Family
ID=
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