JPS59231048A - ｌ（−）―カルニチンの製造法 - Google Patents
ｌ（−）―カルニチンの製造法Info
- Publication number
- JPS59231048A JPS59231048A JP10459683A JP10459683A JPS59231048A JP S59231048 A JPS59231048 A JP S59231048A JP 10459683 A JP10459683 A JP 10459683A JP 10459683 A JP10459683 A JP 10459683A JP S59231048 A JPS59231048 A JP S59231048A
- Authority
- JP
- Japan
- Prior art keywords
- carnitine
- mandelic acid
- acid
- resolving
- ion exchange
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- PHIQHXFUZVPYII-LURJTMIESA-N (S)-carnitine Chemical compound C[N+](C)(C)C[C@@H](O)CC([O-])=O PHIQHXFUZVPYII-LURJTMIESA-N 0.000 title abstract description 4
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 title abstract description 3
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 claims abstract description 5
- 229960002510 mandelic acid Drugs 0.000 claims abstract description 4
- 229960004203 carnitine Drugs 0.000 abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 9
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 abstract description 8
- 239000003456 ion exchange resin Substances 0.000 abstract description 7
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 6
- 235000019441 ethanol Nutrition 0.000 abstract description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 5
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- -1 carnitine mandelic acid salt Chemical class 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- ACZVSMNFVFBOTM-UHFFFAOYSA-O 2-carboxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCC(O)=O ACZVSMNFVFBOTM-UHFFFAOYSA-O 0.000 abstract 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000004060 metabolic process Effects 0.000 abstract 1
- 238000010606 normalization Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229960001518 levocarnitine Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10459683A JPS59231048A (ja) | 1983-06-11 | 1983-06-11 | ｌ（−）―カルニチンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10459683A JPS59231048A (ja) | 1983-06-11 | 1983-06-11 | ｌ（−）―カルニチンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59231048A true JPS59231048A (ja) | 1984-12-25 |
| JPH0471063B2 JPH0471063B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-11-12 |
Family
ID=14384804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10459683A Granted JPS59231048A (ja) | 1983-06-11 | 1983-06-11 | ｌ（−）―カルニチンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59231048A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6342034B1 (en) | 1997-07-28 | 2002-01-29 | Samsung Fine Chemicals Co., Ltd. | Process for the preparation of L-carnitine |
| WO2021122876A1 (en) * | 2019-12-20 | 2021-06-24 | L'oreal | Process for treating keratin fibers using a composition comprising a carnitine salt or carnitine-based salt comprising an aromatic organic anion |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53119844A (en) * | 1977-03-24 | 1978-10-19 | Nippon Kayaku Co Ltd | Optically active amino acid-mandelic acid complexes and theire preparation |
-
1983
- 1983-06-11 JP JP10459683A patent/JPS59231048A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53119844A (en) * | 1977-03-24 | 1978-10-19 | Nippon Kayaku Co Ltd | Optically active amino acid-mandelic acid complexes and theire preparation |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6342034B1 (en) | 1997-07-28 | 2002-01-29 | Samsung Fine Chemicals Co., Ltd. | Process for the preparation of L-carnitine |
| WO2021122876A1 (en) * | 2019-12-20 | 2021-06-24 | L'oreal | Process for treating keratin fibers using a composition comprising a carnitine salt or carnitine-based salt comprising an aromatic organic anion |
| FR3104969A1 (fr) * | 2019-12-20 | 2021-06-25 | L'oreal | Procédé de traitement des fibres kératiniques mettant en œuvre une composition comprenant un sel de carnitine ou de dérivé de carnitine comprenant un anion organique aromatique |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0471063B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-11-12 |
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