Ximenynic acid

Ximenynic acid is trans-11-octadecen-9-ynoic acid,[1] a long-chain acetylenic fatty acid.[1]

Not to be confused with Ximenic acid, a 26 carbon Omega-9 fatty acid.
Ximenynic acid
Names
Preferred IUPAC name
(11E)-Octadec-11-en-9-ynoic acid
Other names
Santalbic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.346
EC Number
  • 209-179-1
UNII
  • 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
  • CCCCCCC=CC#CCCCCCCCC(=O)O
Properties
C18H30O2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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
Species % of kernel oilNotes
S. spicatum34[1]
S. obtusifolium71.5[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It was the subject of a 2003 European patent (for use in food).[5] The patent application was deemed withdrawn in August 2012.[6]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]

References
  1. Separation and identification of ximenynic acid isomers in the seed oil of Santalum spicatum R.Br. as their 4,4-dimethyloxazoline derivatives. Yandi et al. 1996
  2. The chemistry of ximenynic acid. J. Chem. Soc., 1952, 1088-1093 DOI: 10.1039/JR9520001088
  3. Medicinal Plants in Australia, Volume 1. Cheryll Williams page 274. ISBN 978-1-877058-79-0
  4. Diversity of Δ12 fatty acid desaturases in santalaceae and their role in production of seed oil acetylenic fatty acids. Okada et al. 2013. J Biol Chem 2013 Nov 23;288(45):32405-13. Epub 2013 Sep 23.
  5. EP 1402787 A1:Ximenynic acid
  6. Ximenynic acid
  7. Sandalwood Nut CO2 Oil (product)


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