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
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). 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 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

Species	% of kernel oil	Notes
S. spicatum	34	^[1]
S. obtusifolium	71.5	^[3]
S. acuminatum	?

Patents

It was the subject of a 2003 European patent (for use in food).^[5] The patent application was deemed withdrawn in August 2012.^[6]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

It is used in some skincare products.^[7]^{[better source needed]}

References

^ ^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)

[Yandi1996-1] 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.

[Lightelm1952-2] 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.

[MPiA-3] Medicinal Plants in Australia, Volume 1. Cheryll Williams page 274. ISBN 978-1-877058-79-0

[Okada2013-4] 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.

[5] EP 1402787 A1:Ximenynic acid

[6] Ximenynic acid

[7] Sandalwood Nut CO2 Oil (product)

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