JPS6328591B2 - - Google Patents
Info
- Publication number
- JPS6328591B2 JPS6328591B2 JP13222884A JP13222884A JPS6328591B2 JP S6328591 B2 JPS6328591 B2 JP S6328591B2 JP 13222884 A JP13222884 A JP 13222884A JP 13222884 A JP13222884 A JP 13222884A JP S6328591 B2 JPS6328591 B2 JP S6328591B2
- Authority
- JP
- Japan
- Prior art keywords
- substituted phenyl
- phenylethane
- propionic acid
- culture
- represented
- 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
Links
- -1 1-(substituted phenyl)-1-phenylethane Chemical class 0.000 claims description 22
- 241000894006 Bacteria Species 0.000 claims description 13
- 241000589516 Pseudomonas Species 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000012258 culturing Methods 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 230000001580 bacterial effect Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- UXDXFLFOBWPAFT-UHFFFAOYSA-N 1-(2-methylpropyl)-4-(1-phenylethyl)benzene Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C1=CC=CC=C1 UXDXFLFOBWPAFT-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 239000013076 target substance Substances 0.000 description 3
- YRZGPGIJDFEJCZ-UHFFFAOYSA-N 1-(1-phenylethyl)-4-(3,3,3-trifluoro-2-methylpropyl)benzene Chemical compound C1=CC(CC(C)C(F)(F)F)=CC=C1C(C)C1=CC=CC=C1 YRZGPGIJDFEJCZ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QHIYHGLUFKNDHJ-UHFFFAOYSA-N C(C)(C)C1(CC=CC=C1)C(C)C1=CC=CC=C1 Chemical compound C(C)(C)C1(CC=CC=C1)C(C)C1=CC=CC=C1 QHIYHGLUFKNDHJ-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- PTPSJAAAKGKENT-UHFFFAOYSA-N 1-(1-phenylethyl)-4-(3,3,3-trifluoropropyl)benzene Chemical compound C=1C=C(CCC(F)(F)F)C=CC=1C(C)C1=CC=CC=C1 PTPSJAAAKGKENT-UHFFFAOYSA-N 0.000 description 1
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical class C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 1
- FTXZNKAZMHJDLA-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)propanoic acid Chemical compound CC(C)C1=CC=CC=C1C(C)C(O)=O FTXZNKAZMHJDLA-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 241000589513 Burkholderia cepacia Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- QLULGSLAHXLKSR-UHFFFAOYSA-N azane;phosphane Chemical compound N.P QLULGSLAHXLKSR-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 238000012364 cultivation method Methods 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 150000005599 propionic acid derivatives Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13222884A JPS6112294A (ja) | 1984-06-26 | 1984-06-26 | ２−（置換フエニル）プロピオン酸の製造方法 |
| CH254885A CH664767A5 (de) | 1984-06-26 | 1985-06-17 | Verfahren zur herstellung von 2-(substituiertphenyl)-propionsaeure durch mikroorganismen. |
| GB08515270A GB2160866B (en) | 1984-06-26 | 1985-06-17 | Preparing 2-arylpropionic acids |
| FR8509759A FR2566425B1 (fr) | 1984-06-26 | 1985-06-20 | Procede pour la production de 2-(phenyl substitue) acide propionique par micro-organisme |
| DE19853523082 DE3523082C2 (de) | 1984-06-26 | 1985-06-25 | Verfahren zur Herstellung von 2-(4-Isobutylphenyl)-propionsäure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13222884A JPS6112294A (ja) | 1984-06-26 | 1984-06-26 | ２−（置換フエニル）プロピオン酸の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6112294A JPS6112294A (ja) | 1986-01-20 |
| JPS6328591B2 true JPS6328591B2 (pl) | 1988-06-09 |
Family
ID=15076371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13222884A Granted JPS6112294A (ja) | 1984-06-26 | 1984-06-26 | ２−（置換フエニル）プロピオン酸の製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS6112294A (pl) |
| CH (1) | CH664767A5 (pl) |
| DE (1) | DE3523082C2 (pl) |
| FR (1) | FR2566425B1 (pl) |
| GB (1) | GB2160866B (pl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU599438B2 (en) * | 1986-12-01 | 1990-07-19 | Gist-Brocades N.V. | Process for the preparation of 2-arylpropionic acids |
| GB8728064D0 (en) * | 1987-12-01 | 1988-01-06 | Shell Int Research | Process for preparation of substituted phenoxy propanoic acids |
| FI902435A0 (fi) * | 1989-05-16 | 1990-05-16 | Puetter Medice Chem Pharm | Foerfarande foer framstaellning av 2-asylalkanoinsyror. |
| US5434302A (en) * | 1994-02-18 | 1995-07-18 | Paradies; H. Henrich | Method for the preparation of optically active 2-aryl alkyl aldehydes and formation of 2-aryl-alkanoic acids therefrom |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419469A (en) * | 1965-12-08 | 1968-12-31 | Sun Oil Co | Production of carboxylic acids by microbiological oxidation of hydrocarbons |
| JPS5439043A (en) * | 1977-09-01 | 1979-03-24 | Ajinomoto Co Inc | Preparation of phenylalkane carboxylic acids |
| GB2045748A (en) * | 1979-03-09 | 1980-11-05 | Ici Ltd | Biotransformations using methane-utilizing bacteria |
-
1984
- 1984-06-26 JP JP13222884A patent/JPS6112294A/ja active Granted
-
1985
- 1985-06-17 GB GB08515270A patent/GB2160866B/en not_active Expired
- 1985-06-17 CH CH254885A patent/CH664767A5/de not_active IP Right Cessation
- 1985-06-20 FR FR8509759A patent/FR2566425B1/fr not_active Expired
- 1985-06-25 DE DE19853523082 patent/DE3523082C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3523082A1 (de) | 1986-02-13 |
| FR2566425B1 (fr) | 1988-02-05 |
| DE3523082C2 (de) | 1986-10-02 |
| GB2160866A (en) | 1986-01-02 |
| GB8515270D0 (en) | 1985-07-17 |
| JPS6112294A (ja) | 1986-01-20 |
| GB2160866B (en) | 1987-11-11 |
| CH664767A5 (de) | 1988-03-31 |
| FR2566425A1 (fr) | 1985-12-27 |
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