JP2005521716A5 - - Google Patents
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- Publication number
- JP2005521716A5 JP2005521716A5 JP2003580257A JP2003580257A JP2005521716A5 JP 2005521716 A5 JP2005521716 A5 JP 2005521716A5 JP 2003580257 A JP2003580257 A JP 2003580257A JP 2003580257 A JP2003580257 A JP 2003580257A JP 2005521716 A5 JP2005521716 A5 JP 2005521716A5
- Authority
- JP
- Japan
- Prior art keywords
- asarone
- organic solvent
- process according
- formula
- residue
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000012267 brine Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- OUIUORSUNABXEN-GZBFAFLISA-N Isoacolamone Natural products C1CC=C(C)[C@@H]2C(=O)[C@H](C(C)C)CC[C@]21C OUIUORSUNABXEN-GZBFAFLISA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 42
- RKFAZBXYICVSKP-AATRIKPKSA-N alpha-asarone Chemical compound COC1=CC(OC)=C(\C=C\C)C=C1OC RKFAZBXYICVSKP-AATRIKPKSA-N 0.000 claims 29
- 239000003960 organic solvent Substances 0.000 claims 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 9
- RKFAZBXYICVSKP-UHFFFAOYSA-N beta- asarone Natural products COC1=CC(OC)=C(C=CC)C=C1OC RKFAZBXYICVSKP-UHFFFAOYSA-N 0.000 claims 9
- RKFAZBXYICVSKP-WAYWQWQTSA-N beta-asarone Chemical compound COC1=CC(OC)=C(\C=C/C)C=C1OC RKFAZBXYICVSKP-WAYWQWQTSA-N 0.000 claims 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- 239000000741 silica gel Substances 0.000 claims 6
- 229910002027 silica gel Inorganic materials 0.000 claims 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- 239000012024 dehydrating agents Substances 0.000 claims 3
- 239000000284 extract Substances 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- 239000010410 layer Substances 0.000 claims 3
- 238000005406 washing Methods 0.000 claims 3
- DNAVOCNYHNNEQI-SNAWJCMRSA-N (e)-3-(2,4,5-trimethoxyphenyl)prop-2-enal Chemical compound COC1=CC(OC)=C(\C=C\C=O)C=C1OC DNAVOCNYHNNEQI-SNAWJCMRSA-N 0.000 claims 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims 2
- AUNAUZZQBAIQFJ-UHFFFAOYSA-N 2,4,5-Trimethoxy-1-allylbenzene Chemical compound COC1=CC(OC)=C(OC)C=C1CC=C AUNAUZZQBAIQFJ-UHFFFAOYSA-N 0.000 claims 2
- 241000209495 Acorus Species 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims 2
- DNAVOCNYHNNEQI-UHFFFAOYSA-N asaronaldehyde Natural products COC1=CC(OC)=C(C=CC=O)C=C1OC DNAVOCNYHNNEQI-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000004440 column chromatography Methods 0.000 claims 2
- 239000010649 ginger oil Substances 0.000 claims 2
- 239000003921 oil Substances 0.000 claims 2
- 239000012044 organic layer Substances 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- 231100000331 toxic Toxicity 0.000 claims 2
- 230000002588 toxic effect Effects 0.000 claims 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims 1
- SNDHRSZUZCBJPB-UHFFFAOYSA-N 1,2,4-trimethoxy-5-propylbenzene Chemical compound CCCC1=CC(OC)=C(OC)C=C1OC SNDHRSZUZCBJPB-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229940117916 cinnamic aldehyde Drugs 0.000 claims 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- YOXCYXPIIFUVDQ-UHFFFAOYSA-N pyridine;thionyl dichloride Chemical compound ClS(Cl)=O.C1=CC=NC=C1 YOXCYXPIIFUVDQ-UHFFFAOYSA-N 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NHBUFOXGCPTIOH-UHFFFAOYSA-N 1-(2,4,5-trimethoxyphenyl)propan-1-ol Chemical compound CCC(O)C1=CC(OC)=C(OC)C=C1OC NHBUFOXGCPTIOH-UHFFFAOYSA-N 0.000 description 1
- 0 C**(c(c(OC)c1)cc(OC)c1OC)OC Chemical compound C**(c(c(OC)c1)cc(OC)c1OC)OC 0.000 description 1
- CAWFXYMATJZILQ-UHFFFAOYSA-N CCC(c(cc(c(C)c1)OC)c1OC)O Chemical compound CCC(c(cc(c(C)c1)OC)c1OC)O CAWFXYMATJZILQ-UHFFFAOYSA-N 0.000 description 1
- JWNWZWRUHGREEU-UHFFFAOYSA-N COc(c(C(C1)C1=C)c1)cc(OC)c1OC Chemical compound COc(c(C(C1)C1=C)c1)cc(OC)c1OC JWNWZWRUHGREEU-UHFFFAOYSA-N 0.000 description 1
- OKQDAQFRBDQLBK-UHFFFAOYSA-N Cc1cc(OC)c(CCC=O)cc1OC Chemical compound Cc1cc(OC)c(CCC=O)cc1OC OKQDAQFRBDQLBK-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2002/000094 WO2003082786A1 (en) | 2002-03-28 | 2002-03-28 | A process for the preparation of pharmacologically active alpha-asarone from toxic beta-asarone rich acorus calamus oil |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008101982A Division JP2008208134A (ja) | 2008-04-09 | 2008-04-09 | 毒性β−アサロンリッチなショウブ油由来の薬学的に活性なα−アサロンの調製のためのプロセス |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005521716A JP2005521716A (ja) | 2005-07-21 |
| JP2005521716A5 true JP2005521716A5 (enrdf_load_stackoverflow) | 2008-05-29 |
| JP4187660B2 JP4187660B2 (ja) | 2008-11-26 |
Family
ID=28460468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003580257A Expired - Fee Related JP4187660B2 (ja) | 2002-03-28 | 2002-03-28 | 毒性β−アサロンリッチなショウブ油由来の薬学的に活性なα−アサロンの調製のためのプロセス |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4187660B2 (enrdf_load_stackoverflow) |
| AU (1) | AU2002249562A1 (enrdf_load_stackoverflow) |
| DE (1) | DE10297696T5 (enrdf_load_stackoverflow) |
| WO (1) | WO2003082786A1 (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1318367C (zh) * | 2005-10-24 | 2007-05-30 | 丽珠医药集团股份有限公司 | β－细辛醚的精制方法 |
| CN112679324B (zh) * | 2020-12-07 | 2022-04-05 | 山东大学 | 一种低含量α-细辛醚光催化富集的方法及其应用 |
| CN114858944B (zh) * | 2022-05-31 | 2023-02-03 | 石家庄四药有限公司 | 一种对甲氧基苯丙酮有关物质的检测方法 |
| CN114938780A (zh) * | 2022-06-23 | 2022-08-26 | 章丽 | 一种石菖蒲的高产高品质无性繁殖技术 |
| CN119118838B (zh) * | 2024-11-12 | 2025-02-11 | 安徽中医药大学 | 一种苯丙素类化合物及其提取纯化方法和应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1250505C (zh) * | 2000-08-31 | 2006-04-12 | 科学工业研究院 | 制备1－丙基－2，4，5－三甲氧基苯的改进方法 |
-
2002
- 2002-03-28 AU AU2002249562A patent/AU2002249562A1/en not_active Abandoned
- 2002-03-28 WO PCT/IN2002/000094 patent/WO2003082786A1/en not_active Ceased
- 2002-03-28 JP JP2003580257A patent/JP4187660B2/ja not_active Expired - Fee Related
- 2002-03-28 DE DE10297696T patent/DE10297696T5/de not_active Withdrawn
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