Ximenynic acid
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Names | |
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Preferred IUPAC name
(11E)-Octadec-11-en-9-ynoic acid | |
Other names
Santalbic acid
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.008.346 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C18H30O2 | |
Molar mass | 278.436 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ximenynic acid is trans-11-octadecen-9-ynoic acid,[1] a long-chain acetylenic fatty acid.[1]
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]
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]
Sources
[edit]Species | % of kernel oil | Notes |
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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[edit]It was the subject of a 2003 European patent (for use in food).[5] The patent application was deemed withdrawn in August 2012.[6]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][better source needed]
References
[edit]- ^ a b c d 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.
- ^ a b 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.
- ^ a b 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
- ^ Ximenynic acid
- ^ Sandalwood Nut CO2 Oil (product)