JPS5569535A - Preparation of dihydro-coenzyme q analog compound - Google Patents
Preparation of dihydro-coenzyme q analog compoundInfo
- Publication number
- JPS5569535A JPS5569535A JP14208278A JP14208278A JPS5569535A JP S5569535 A JPS5569535 A JP S5569535A JP 14208278 A JP14208278 A JP 14208278A JP 14208278 A JP14208278 A JP 14208278A JP S5569535 A JPS5569535 A JP S5569535A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- reaction
- coenzyme
- pulenol
- reacting
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 239000005515 coenzyme Substances 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 3
- 230000002378 acidificating effect Effects 0.000 abstract 2
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 abstract 2
- 150000002828 nitro derivatives Chemical class 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000007810 chemical reaction solvent Substances 0.000 abstract 1
- 235000017471 coenzyme Q10 Nutrition 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- DSBZYDDWLLIJJS-UHFFFAOYSA-N ubiquinol-0 Chemical compound COC1=C(O)C=C(C)C(O)=C1OC DSBZYDDWLLIJJS-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To prepare the title compound useful as a raw material of coenzyme Q, easily, safely, and in high yield, by reacting a hydroquinone derivative with pulenol in the presence of an acidic condensation catalyst in a nitro compound as a reaction solvent.
CONSTITUTION: The objective compound V (R1 is IV; A, B are H or A-B is a bond; R2 is H or acyl; R3 is H or alkyl), e.g. co-enzyme Q10, is prepared by reacting a hydroquinone derivative of formula I (e.g. 2,3-dimethoxy-5-methylbenzohydroquinone) with pulenol or its reactive derivative of formula II or III (e.g. isodecapulenol or its ester, halide, etc.), in a nitro compound such as nitromethane, nitrobenzene, etc., in the presence of an acidic condensation catalyst.
EFFECT: High reaction yield, high production ratio of Δ2-trans compound in the main products, high rate of reaction, reduced amount of the catalyst, and suppressed corrosion of the reaction apparatus.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14208278A JPS5929173B2 (en) | 1978-11-17 | 1978-11-17 | Method for producing dihydrocoenzyme Q compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14208278A JPS5929173B2 (en) | 1978-11-17 | 1978-11-17 | Method for producing dihydrocoenzyme Q compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5569535A true JPS5569535A (en) | 1980-05-26 |
| JPS5929173B2 JPS5929173B2 (en) | 1984-07-18 |
Family
ID=15307008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14208278A Expired JPS5929173B2 (en) | 1978-11-17 | 1978-11-17 | Method for producing dihydrocoenzyme Q compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5929173B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009505969A (en) * | 2005-08-10 | 2009-02-12 | ディーエスエム アイピー アセッツ ビー．ブイ． | Preparation method of ubihydroquinone and ubiquinone |
-
1978
- 1978-11-17 JP JP14208278A patent/JPS5929173B2/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009505969A (en) * | 2005-08-10 | 2009-02-12 | ディーエスエム アイピー アセッツ ビー．ブイ． | Preparation method of ubihydroquinone and ubiquinone |
| KR101366958B1 (en) * | 2005-08-10 | 2014-03-12 | 디에스엠 아이피 어셋츠 비.브이. | Process for the preparation of ubihydroquinones and ubiquinones |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5929173B2 (en) | 1984-07-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5679628A (en) | Preparation of isoprene | |
| JPS5655355A (en) | Preparation of alkylenediamine derivative | |
| JPS5695142A (en) | Preparation of aliphatic aldehyde | |
| JPS57144252A (en) | Preparation of aminoalkylthiol | |
| JPS55111468A (en) | Preparation of n-benzyl-tetrahydro isoquinoline derivative | |
| JPS56123927A (en) | Preparation of hydroquinone and quinone derivative | |
| JPS5562040A (en) | Preparation of alpha-ketocarboxylic acids or their esters | |
| JPS5527161A (en) | Production of alcohol or its ether derivative | |
| JPS5618936A (en) | Production of phenylacetic acid | |
| JPS5538347A (en) | Preparation of indazoleacetic acids | |
| JPS57144253A (en) | Preparation of crude aminoalkylthiol | |
| JPS55108898A (en) | 25-hydroxy-24-oxocholesterol derivative and its preparation | |
| JPS5257142A (en) | Process for preparing dihalovinyl-cyclopropanecarboxylic acid derivati ves | |
| JPS55151548A (en) | Production of guanidinocaproic ester | |
| JPS5522613A (en) | Preparation of 2-hydroxy-3-butenoic acid derivative | |
| JPS5498754A (en) | 3-hydroxy-3-bromomethylphthalide derivative | |
| JPS5564538A (en) | Preparation of dihydrocoenzyme q compound | |
| JPS5262234A (en) | Process for preparation of n_3'-hydroxyphenyl-2-methylbenzamide | |
| JPS57149283A (en) | Long-chain fatty acid lactol | |
| JPS5772963A (en) | Alpha-(2-pyridyl)arylacetaldehyde | |
| JPS56161388A (en) | Novel vincamine derivative | |
| JPS57149270A (en) | Preparation of 3,4,5,6,7,8-hexahydrocarbostyril-5-one | |
| JPS5520706A (en) | Preparation of metoclopramide | |
| JPS57116032A (en) | Preparation of alpha,beta-dehydro-alpha-amino acid ester | |
| JPS5527113A (en) | Preparation of dihydrocoenzyme q compound |