JP2009531353A5 - - Google Patents
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- Publication number
- JP2009531353A5 JP2009531353A5 JP2009501908A JP2009501908A JP2009531353A5 JP 2009531353 A5 JP2009531353 A5 JP 2009531353A5 JP 2009501908 A JP2009501908 A JP 2009501908A JP 2009501908 A JP2009501908 A JP 2009501908A JP 2009531353 A5 JP2009531353 A5 JP 2009531353A5
- Authority
- JP
- Japan
- Prior art keywords
- process according
- vanillin
- acetylacetone
- respect
- curcumin
- 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
- 238000000034 method Methods 0.000 claims description 19
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 claims description 18
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 235000012754 curcumin Nutrition 0.000 claims description 9
- 229940109262 curcumin Drugs 0.000 claims description 9
- 239000004148 curcumin Substances 0.000 claims description 9
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 claims description 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004327 boric acid Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 235000012141 vanillin Nutrition 0.000 claims description 6
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 6
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 2
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- -1 alkyl borate Chemical compound 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06006519 | 2006-03-29 | ||
| EP06006519.0 | 2006-03-29 | ||
| PCT/EP2007/002403 WO2007110168A1 (en) | 2006-03-29 | 2007-03-19 | Curcumin synthesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009531353A JP2009531353A (ja) | 2009-09-03 |
| JP2009531353A5 true JP2009531353A5 (enExample) | 2013-01-10 |
| JP5341747B2 JP5341747B2 (ja) | 2013-11-13 |
Family
ID=38093544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009501908A Expired - Fee Related JP5341747B2 (ja) | 2006-03-29 | 2007-03-19 | クルクミンの合成 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7964755B2 (enExample) |
| EP (1) | EP1999097B1 (enExample) |
| JP (1) | JP5341747B2 (enExample) |
| KR (1) | KR20080112340A (enExample) |
| CN (1) | CN101454267B (enExample) |
| AT (1) | ATE538080T1 (enExample) |
| WO (1) | WO2007110168A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ585835A (en) | 2007-12-27 | 2012-07-27 | Baxter Int | Chemically modified factor IX comprising a hydrophilic polymer attached via a releasable linker |
| US8680143B2 (en) | 2008-07-07 | 2014-03-25 | Laila Pharmaceuticals Pvt. Ltd. | Orally active curcuminoid compounds |
| EP2857379B1 (en) * | 2012-05-08 | 2020-09-02 | Asac Compañía De Biotecnología E Investigación SA | Method for the synthesis of curcumin |
| CN102701933A (zh) * | 2012-05-30 | 2012-10-03 | 江南大学 | 一种采用氧化铝负载氟化钾固体碱催化合成姜黄素的方法 |
| CN102701934A (zh) * | 2012-05-30 | 2012-10-03 | 江南大学 | 一种以氧化锌负载氧化镁为催化剂催化合成姜黄素的方法 |
| CN102911022B (zh) * | 2012-10-25 | 2015-12-09 | 山东鲁诺动物药业有限公司 | 一种天然姜黄素类物的人工合成方法 |
| CN103910615A (zh) * | 2014-04-09 | 2014-07-09 | 西安雅森生物技术有限公司 | 一种合成姜黄素的方法 |
| CN108101761B (zh) * | 2017-12-08 | 2021-08-03 | 陕西嘉禾生物科技股份有限公司 | 一种姜黄素的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL255427A (enExample) * | 1959-08-31 | |||
| DE3821197A1 (de) * | 1988-06-23 | 1989-12-28 | Basf Ag | Verfahren zur herstellung von (alpha),(beta)-ungesaettigten ketonen |
| US5679864A (en) * | 1995-11-03 | 1997-10-21 | Gene Print Inc. | Process for the synthesis of curcumin-related compounds |
-
2007
- 2007-03-19 WO PCT/EP2007/002403 patent/WO2007110168A1/en not_active Ceased
- 2007-03-19 KR KR1020087026287A patent/KR20080112340A/ko not_active Ceased
- 2007-03-19 US US12/295,010 patent/US7964755B2/en not_active Expired - Fee Related
- 2007-03-19 EP EP07723370A patent/EP1999097B1/en not_active Not-in-force
- 2007-03-19 AT AT07723370T patent/ATE538080T1/de active
- 2007-03-19 JP JP2009501908A patent/JP5341747B2/ja not_active Expired - Fee Related
- 2007-03-19 CN CN2007800198805A patent/CN101454267B/zh not_active Expired - Fee Related
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