Ximenynic acid
| Names | |
|---|---|
| Preferred IUPAC name
(11E)-Octadec-11-en-9-ynoic acid | |
| Other names
Santalbic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.008.346 Edit this at Wikidata |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C18H30O2 | |
| Molar mass | 278.436g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25°C [77°F], 100kPa).
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Ximenynic acid is trans-11-octadecen-9-ynoic acid,[1] a long-chain acetylenic fatty acid.[1]
Discovery
[edit ]It was discovered in the fruit kernels of three species of South American plants in the genus Ximenia , after which it is named.[2] and found to have the formula C18H30O2.[2]
Natural occurence
[edit ]It can be extracted from the fruit kernels of the Santalum obtusifolium (Sandalwood)[3] and the Australian sandalwood Santalum spicatum [1]
It is also found in seed oil of other plants in the Santalaceae family, including the native cherry Exocarpos cupressiformis and sweet quandong Santalum acuminatum .[4]
| Species | % of kernel oil | Notes |
|---|---|---|
| S. spicatum | 34 | [1] |
| S. obtusifolium | 71.5 | [3] |
| S. acuminatum | ? |
Patents
[edit ]It was the subject of a 2003 European patent (for use in food).[5] The patent application was deemed withdrawn in August 2012.[6]
Uses
[edit ]It is used in some skincare products.[7] [bettersourceneeded ]
See also
[edit ]References
[edit ]- 1 2 3 4 Liu, Yandi D.; Longmore, Robert B.; Fox, John E. D. (December 1996). "Separation and identification of ximenynic acid isomers in the seed oil of Santalum spicatum R.Br. as their 4,4-dimethyloxazoline derivatives" . Journal of the American Oil Chemists' Society. 73 (12): 1729–1731. doi:10.1007/BF02517979. ISSN 0003-021X. S2CID 83483921.
- 1 2 Lightelm, S. P.; Schwartz, H. M.; von Holdt, M. M. (1952). "193. The chemistry of ximenynic acid" . Journal of the Chemical Society (Resumed): 1088–1093. doi:10.1039/jr9520001088. ISSN 0368-1769.
- 1 2 Medicinal Plants in Australia, Volume 1. Cheryll Williams page 274. ISBN 978-1-877058-79-0
- ↑ Okada, Shoko; Zhou, Xue-Rong; Damcevski, Katherine; Gibb, Nerida; Wood, Craig; Hamberg, Mats; Haritos, Victoria S. (November 2013). "Diversity of Δ12 Fatty Acid Desaturases in Santalaceae and Their Role in Production of Seed Oil Acetylenic Fatty Acids". Journal of Biological Chemistry. 288 (45): 32405–32413. doi:10.1074/jbc.M113.511931 . PMC 3820875 . PMID 24062307.
- ↑ "EP 1402787 A1:Ximenynic acid". Archived from the original on 2024年12月30日. Retrieved 2016年02月03日.
- ↑ Ximenynic acid
- ↑ "Sandalwood Nut CO2 Oil (product)". Archived from the original on 2016年03月06日. Retrieved 2016年02月03日.