FR2302992A1 - PROCESS FOR PREPARING STEREOSPECIFIC ISOMERS OF GERANYLACETONE - Google Patents
PROCESS FOR PREPARING STEREOSPECIFIC ISOMERS OF GERANYLACETONEInfo
- Publication number
- FR2302992A1 FR2302992A1 FR7614799A FR7614799A FR2302992A1 FR 2302992 A1 FR2302992 A1 FR 2302992A1 FR 7614799 A FR7614799 A FR 7614799A FR 7614799 A FR7614799 A FR 7614799A FR 2302992 A1 FR2302992 A1 FR 2302992A1
- Authority
- FR
- France
- Prior art keywords
- delta4
- cis
- isomers
- iii
- trans
- 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
- HNZUNIKWNYHEJJ-FMIVXFBMSA-N geranyl acetone Chemical class CC(C)=CCC\C(C)=C\CCC(C)=O HNZUNIKWNYHEJJ-FMIVXFBMSA-N 0.000 title 1
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 230000000707 stereoselective effect Effects 0.000 title 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 abstract 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000002304 perfume Substances 0.000 abstract 2
- 238000011084 recovery Methods 0.000 abstract 2
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 abstract 1
- KEVYVLWNCKMXJX-ZCNNSNEGSA-N Isophytol Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)C=C KEVYVLWNCKMXJX-ZCNNSNEGSA-N 0.000 abstract 1
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 abstract 1
- 229930003427 Vitamin E Natural products 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003699 antiulcer agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 abstract 1
- 230000003054 hormonal effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229930014550 juvenile hormone Natural products 0.000 abstract 1
- 239000002949 juvenile hormone Substances 0.000 abstract 1
- 150000003633 juvenile hormone derivatives Chemical class 0.000 abstract 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229940046009 vitamin E Drugs 0.000 abstract 1
- 235000019165 vitamin E Nutrition 0.000 abstract 1
- 239000011709 vitamin E Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
Process for prepg. specific stereoisomers of farnesylacetic aced or its esters of formula (I): CH3. C(CH3)=CH.CH2CH2. C(CH3)DELTA8=CH. CH2CH2. C(CH3)DELTA4= CHCH2CH2COOR2 (I) (R2 = H, 1-6C alkyl, 3-6C cycloalkyl, 2-6C alkenyl or 3-6C cycloalkenyl)comprises rectifying a mixt. of (i) DELTA4,8-cis and DELTA4-trans-DELTA-cis (I); (ii) DELTA4,8-trans (I) or (III) all 4 isomers to recovery from mixts. (i) and (ii) both components and from (iii) the DELTA4,8-cis isomers. Similar processes for separg. DELTA6-cis and DELTA6-trans isomers of nerolidol (II) and DELTA5-cis and DELTA5-trans geranylacetone (III) are also new. (I) are anti-ulcer agents (for which purpose individual isomers are pref), perfumes and aroma agents. (II) and (III) are intermediates for (I), perfumes and cpds. with juvenile hormone activity; (II) is also used to make isophytol a starting material for Vitamin E. Recovery of individual isomers is almost quantitative.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49104062A JPS5132511A (en) | 1974-09-10 | 1974-09-10 | Ritsutaikiseisareta geraniruaseton no seizohoho |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2302992A1 true FR2302992A1 (en) | 1976-10-01 |
| FR2302992B3 FR2302992B3 (en) | 1980-10-24 |
Family
ID=14370676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7614799A Granted FR2302992A1 (en) | 1974-09-10 | 1976-05-17 | PROCESS FOR PREPARING STEREOSPECIFIC ISOMERS OF GERANYLACETONE |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5132511A (en) |
| FR (1) | FR2302992A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014096067A1 (en) * | 2012-12-18 | 2014-06-26 | Dsm Ip Assets B.V. | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from (r)-6,10,14-trimetylpentadec-5-en-2-one |
| WO2014096098A1 (en) * | 2012-12-18 | 2014-06-26 | Dsm Ip Assets B.V. | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5578576A (en) * | 1978-12-08 | 1980-06-13 | Nec Corp | Semiconductor device |
| BR112015014256B1 (en) * | 2012-12-18 | 2021-02-23 | Dsm Ip Assets B.V | unsaturated compound cis / trans isomerization process, unsaturated compound isomer production process, composition comprising nitrogen monoxide and unsaturated compound, and ketal or acetal |
| JP6442782B2 (en) * | 2012-12-18 | 2018-12-26 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | Polythiols as cis / trans isomerization catalysts for unsaturated compounds |
-
1974
- 1974-09-10 JP JP49104062A patent/JPS5132511A/en active Pending
-
1976
- 1976-05-17 FR FR7614799A patent/FR2302992A1/en active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014096067A1 (en) * | 2012-12-18 | 2014-06-26 | Dsm Ip Assets B.V. | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from (r)-6,10,14-trimetylpentadec-5-en-2-one |
| WO2014096098A1 (en) * | 2012-12-18 | 2014-06-26 | Dsm Ip Assets B.V. | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one |
| US9611200B2 (en) | 2012-12-18 | 2017-04-04 | Dsm Ip Assets B.V. | (6R,10R)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14 trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one |
| EA033302B1 (en) * | 2012-12-18 | 2019-09-30 | ДСМ АйПи АССЕТС Б.В. | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one |
| EA033302B9 (en) * | 2012-12-18 | 2020-01-22 | ДСМ АйПи АССЕТС Б.В. | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5132511A (en) | 1976-03-19 |
| FR2302992B3 (en) | 1980-10-24 |
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