JPS5657734A - Novel preparation of 4-acyloxy-beta-ionone - Google Patents
Novel preparation of 4-acyloxy-beta-iononeInfo
- Publication number
- JPS5657734A JPS5657734A JP13244979A JP13244979A JPS5657734A JP S5657734 A JPS5657734 A JP S5657734A JP 13244979 A JP13244979 A JP 13244979A JP 13244979 A JP13244979 A JP 13244979A JP S5657734 A JPS5657734 A JP S5657734A
- Authority
- JP
- Japan
- Prior art keywords
- acids
- acid
- formula
- ionone
- carboxylic
- 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
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 3
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002841 Lewis acid Substances 0.000 abstract 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- -1 etc. Chemical class 0.000 abstract 2
- 239000000796 flavoring agent Substances 0.000 abstract 2
- 235000019634 flavors Nutrition 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 150000007517 lewis acids Chemical class 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 150000003460 sulfonic acids Chemical class 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000002537 cosmetic Substances 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To prepare the titled compound useful as a flavor improving agent, etc., easily, safely, in an industrial scale, in one step, by oxidizing β-ionone with oxygen in a carboxylic acid anhydride in the presence of a catalyst selected from mineral acids, carboxylic acids, sulfonic acids, and Lewis acids.
CONSTITUTION: The compound of formula I useful as an agent for improving flavor of perfumery and cosmetics, is prepared from the compound of formula II, easily, safely, in high yield, in an industrial scale and one step, by heating β-ionone of formula II in a carboxylic acid anhydride of formula III (R is acid residue such as alkyl) in the presence of a catalyst selected from mineral acids such as concentrated sulfuric acid, concentrated hydrochloric acid, etc., carboxylic acids such as trifluoroacetic acid, trichloroacetic acid, etc., sulfonic acids such as p-toluenesulfonic acid, and Lewis acids such as aluminum chloride, at 50W70°C for 5W6hr, and then stirring for 15W20hr introducing oxygen gas into the system. When the carboxylic acid anhydride is acetic anhydride, the heating is not necessary, and oxygen can be introduced from the betinning.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13244979A JPS5834458B2 (en) | 1979-10-16 | 1979-10-16 | Novel production method of 4-acyloxy β-ionone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13244979A JPS5834458B2 (en) | 1979-10-16 | 1979-10-16 | Novel production method of 4-acyloxy β-ionone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5657734A true JPS5657734A (en) | 1981-05-20 |
| JPS5834458B2 JPS5834458B2 (en) | 1983-07-27 |
Family
ID=15081612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13244979A Expired JPS5834458B2 (en) | 1979-10-16 | 1979-10-16 | Novel production method of 4-acyloxy β-ionone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5834458B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963583A (en) * | 1987-10-05 | 1990-10-16 | Ciba-Geigy Corporation | Beta-ionone derivatives as antifungal agents |
| US4963193A (en) * | 1984-09-21 | 1990-10-16 | Givaudan Corporation | Oxo-ionyl esters useful as tobacco flavorants and tobacco products containing same |
| US5001155A (en) * | 1987-09-03 | 1991-03-19 | University Of Kentucky Research Foundation | β-ionone derivative as antifungal agent |
-
1979
- 1979-10-16 JP JP13244979A patent/JPS5834458B2/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963193A (en) * | 1984-09-21 | 1990-10-16 | Givaudan Corporation | Oxo-ionyl esters useful as tobacco flavorants and tobacco products containing same |
| US5001155A (en) * | 1987-09-03 | 1991-03-19 | University Of Kentucky Research Foundation | β-ionone derivative as antifungal agent |
| US4963583A (en) * | 1987-10-05 | 1990-10-16 | Ciba-Geigy Corporation | Beta-ionone derivatives as antifungal agents |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5834458B2 (en) | 1983-07-27 |
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