Ximenynic acid

Ximenynic acid
Names
	Preferred IUPAC name (11E)-Octadec-11-en-9-ynoic acid
	Other names Santalbic acid
Identifiers
CAS Number	557-58-4;
3D model (JSmol)	Interactive image;
ChemSpider	83781;
ECHA InfoCard	100.008.346
EC Number	209-179-1;
PubChem CID	5312688;
UNII	IA0Z48P13W;
CompTox Dashboard (EPA)	DTXSID501317249 ;
	InChI InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,11-17H2,1H3,(H,19,20)/b8-7+ Key: VENIIVIRETXKSV-BQYQJAHWSA-N;
	SMILES CCCCCCC=CC#CCCCCCCCC(=O)O;
Properties
Chemical formula	C18H30O2
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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 3 South American ximenia species (and so 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

It was the subject of a 2003 European patent (for use in food).^[5] The patent application was deemed withdrawn in August 2012.^[6]

It is used in some skincare products.^[7]

^ ^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.
^ ^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. 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
^ EP 1402787 A1:Ximenynic acid
^ Ximenynic acid
^ Sandalwood Nut CO2 Oil (product)

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