JP2007222110A5 - - Google Patents
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- Publication number
- JP2007222110A5 JP2007222110A5 JP2006048804A JP2006048804A JP2007222110A5 JP 2007222110 A5 JP2007222110 A5 JP 2007222110A5 JP 2006048804 A JP2006048804 A JP 2006048804A JP 2006048804 A JP2006048804 A JP 2006048804A JP 2007222110 A5 JP2007222110 A5 JP 2007222110A5
- Authority
- JP
- Japan
- Prior art keywords
- tetramethylnaphtho
- furan
- dodecahydro
- sclareol
- microorganism
- 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.)
- Granted
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- 244000005700 microbiome Species 0.000 claims description 70
- XVULBTBTFGYVRC-HHUCQEJWSA-N (13R)-Labd-14-ene-8,13-diol Chemical compound CC1(C)CCC[C@]2(C)[C@@H](CC[C@](O)(C)C=C)[C@](C)(O)CC[C@H]21 XVULBTBTFGYVRC-HHUCQEJWSA-N 0.000 claims description 58
- YPZUZOLGGMJZJO-UHFFFAOYSA-N Ambronide Chemical compound C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 claims description 52
- 241001337994 Cryptococcus <scale insect> Species 0.000 claims description 19
- IMKJGXCIJJXALX-SHUKQUCYSA-N Sclareolide Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OC(=O)C1 IMKJGXCIJJXALX-SHUKQUCYSA-N 0.000 claims description 14
- 229940096995 sclareolide Drugs 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 108020001027 Ribosomal DNA Proteins 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 10
- AIALTZSQORJYNJ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol Chemical compound OCCC1C(C)(O)CCC2C(C)(C)CCCC21C AIALTZSQORJYNJ-UHFFFAOYSA-N 0.000 claims description 7
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 6
- 230000002194 synthesizing Effects 0.000 claims description 6
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 description 50
- 239000002609 media Substances 0.000 description 26
- 241000894007 species Species 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cells Anatomy 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241000694959 Cryptococcus sp. Species 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N furane Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- DVARTQFDIMZBAA-UHFFFAOYSA-O Ammonium nitrate Chemical compound [NH4+].[O-][N+]([O-])=O DVARTQFDIMZBAA-UHFFFAOYSA-O 0.000 description 4
- 229940041514 Candida albicans extract Drugs 0.000 description 4
- 229940061634 Magnesium sulfate heptahydrate Drugs 0.000 description 4
- 241001443590 Naganishia albida Species 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000002054 inoculum Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000001954 sterilising Effects 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- -1 tetramethylnaphtho [2,1-b] furan (dodecahydro-3a, 6,6,9a-tetramethylnaphtho [2,1-b] furan) Chemical compound 0.000 description 4
- 239000012138 yeast extract Substances 0.000 description 4
- IMKJGXCIJJXALX-UHFFFAOYSA-N 3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphtho[8,7-d]furan-2-one Chemical compound C1CC2C(C)(C)CCCC2(C)C2C1(C)OC(=O)C2 IMKJGXCIJJXALX-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 241001491901 Filobasidium magnum Species 0.000 description 3
- GNSKLFRGEWLPPA-UHFFFAOYSA-M Monopotassium phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 3
- 229920001850 Nucleic acid sequence Polymers 0.000 description 3
- 241000222051 Papiliotrema laurentii Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DDJDOFNJCINQQL-UHFFFAOYSA-N 1,2,4,5-tetramethylbenzo[e][1]benzofuran Chemical compound C1=CC=CC2=C(C(=C(C)O3)C)C3=C(C)C(C)=C21 DDJDOFNJCINQQL-UHFFFAOYSA-N 0.000 description 2
- WCXIYSNGVSMUKA-UHFFFAOYSA-N 1-methylbenzo[e][1]benzofuran Chemical compound C1=CC=CC2=C3C(C)=COC3=CC=C21 WCXIYSNGVSMUKA-UHFFFAOYSA-N 0.000 description 2
- 241001491949 Filobasidium elegans Species 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M Lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940029983 VITAMINS Drugs 0.000 description 2
- 229940021016 Vitamin IV solution additives Drugs 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 2
- 230000000721 bacterilogical Effects 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 230000034303 cell budding Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 230000002538 fungal Effects 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 230000001568 sexual Effects 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229930003231 vitamins Natural products 0.000 description 2
- 239000001147 (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran Substances 0.000 description 1
- 229920002483 18S ribosomal RNA Polymers 0.000 description 1
- 229920002652 28S ribosomal RNA Polymers 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-Toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-LQKXBSAESA-N Ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- PRKQVKDSMLBJBJ-UHFFFAOYSA-N Ammonium carbonate Chemical compound N.N.OC(O)=O PRKQVKDSMLBJBJ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000235114 Bensingtonia Species 0.000 description 1
- GKVGNBJMSKJSKF-LAPMDVQOSA-N C[C@@](CC1)([C@H](CC2=O)[C@]3(C)C1C(C)(C)CCC3)[O]2=C Chemical compound C[C@@](CC1)([C@H](CC2=O)[C@]3(C)C1C(C)(C)CCC3)[O]2=C GKVGNBJMSKJSKF-LAPMDVQOSA-N 0.000 description 1
- 229960003563 Calcium Carbonate Drugs 0.000 description 1
- 240000004439 Cistus albidus Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 229960002989 Glutamic Acid Drugs 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 241000766694 Hyphozyma Species 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
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-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
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 240000003489 Salvia sclarea Species 0.000 description 1
- 235000002911 Salvia sclarea Nutrition 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L Zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 210000004748 cultured cells Anatomy 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- TZBCMHLFINVTGO-UHFFFAOYSA-N ethanol;naphthalene Chemical compound CCO.C1=CC=CC2=CC=CC=C21 TZBCMHLFINVTGO-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229960001781 ferrous sulfate Drugs 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 150000004676 glycans Polymers 0.000 description 1
- 239000001963 growth media Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 1
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 229960003390 magnesium sulfate Drugs 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- ISPYRSDWRDQNSW-UHFFFAOYSA-L manganese(II) sulfate monohydrate Chemical compound O.[Mn+2].[O-]S([O-])(=O)=O ISPYRSDWRDQNSW-UHFFFAOYSA-L 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 235000006109 methionine Nutrition 0.000 description 1
- 230000000394 mitotic Effects 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 230000000877 morphologic Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000000056 organs Anatomy 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- HHUJLKPGQMFFMS-UHFFFAOYSA-N potassium;boron(1-) Chemical compound [B-].[K+] HHUJLKPGQMFFMS-UHFFFAOYSA-N 0.000 description 1
- 230000001850 reproductive Effects 0.000 description 1
- 230000000284 resting Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000001691 salvia sclarea Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- DLRVVLDZNNYCBX-ZZFZYMBESA-N β-melibiose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 DLRVVLDZNNYCBX-ZZFZYMBESA-N 0.000 description 1
Images
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006048804A JP4598692B2 (ja) | 2006-02-24 | 2006-02-24 | 新規微生物、当該新規微生物を用いたドデカヒドロ−３ａ，６，６，９ａ−テトラメチルナフト［２，１−ｂ］フラン中間体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006048804A JP4598692B2 (ja) | 2006-02-24 | 2006-02-24 | 新規微生物、当該新規微生物を用いたドデカヒドロ−３ａ，６，６，９ａ−テトラメチルナフト［２，１−ｂ］フラン中間体の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007222110A JP2007222110A (ja) | 2007-09-06 |
| JP2007222110A5 true JP2007222110A5 (de) | 2007-10-18 |
| JP4598692B2 JP4598692B2 (ja) | 2010-12-15 |
Family
ID=38544498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006048804A Expired - Fee Related JP4598692B2 (ja) | 2006-02-24 | 2006-02-24 | 新規微生物、当該新規微生物を用いたドデカヒドロ−３ａ，６，６，９ａ−テトラメチルナフト［２，１−ｂ］フラン中間体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4598692B2 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5317488B2 (ja) * | 2008-02-01 | 2013-10-16 | 花王株式会社 | 新規微生物、当該新規微生物を用いたドデカヒドロ−３ａ，６，６，９ａ−テトラメチルナフト［２，１−ｂ］フラン中間体の製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0779682B2 (ja) * | 1989-08-28 | 1995-08-30 | インターナショナル フレーバーズ アンド フレーグランシィズ インコーポレーテッド | 微生物の生物学的に純粋な培養物、ラクトン生成方法、ジオール生成方法、化合物生成方法および環状エーテルの生成方法 |
| JP2802588B2 (ja) * | 1994-08-05 | 1998-09-24 | インターナショナル フレーバーズ アンド フレー グランシィズ インコーポレーテッド | 微生物の生物学的に純粋な培養物、並びにそれを用いるジオール製造方法および環状エーテル製造方法 |
-
2006
- 2006-02-24 JP JP2006048804A patent/JP4598692B2/ja not_active Expired - Fee Related
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