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Lesquerolic acid

Names
Preferred IUPAC name (11Z,14R)-14-Hydroxyicos-11-enoic acid
Identifiers
CAS Number	4103-20-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:165421
ChemSpider	4472235
MeSH	lesquerolic+acid
PubChem CID	5312810
UNII	87K5QW62TR
CompTox Dashboard (EPA)	DTXSID101029878
InChI InChI=1S/C20H38O3/c1-2-3-4-13-16-19(21)17-14-11-9-7-5-6-8-10-12-15-18-20(22)23/h11,14,19,21H,2-10,12-13,15-18H2,1H3,(H,22,23)/b14-11-/t19-/m1/s1Key: OONXYOAWMIVMCI-KWRJMZDGSA-N
SMILES O=C(O)CCCCCCCCC\C=C/C(O)CCCCCC
Properties
Chemical formula	C20H38O3
Molar mass	326.521 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Lesquerolic acid is a hydroxycarboxylic acid that occurs naturally in Paysonia lasiocarpa and other Paysonia and Physaria species. This compound has the R configuration at the alcohol-bearing stereocenter, and it is of the Z configuration at the olefin. Lesquerolic acid is chemically similar to ricinoleic acid, but with two additional carbons at the carboxyl end of the carbon chain. Lesquerolic acid, with other hydroxy fatty acids, has important industrial uses, including making resins, waxes, nylons and plastics.

References

1. "CID 20980884 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 5 December 2007. Retrieved 20 November 2011.
2. C. R. Smith Jr.; T. L. Wilson; T. K. Miwa; H. Zobel; R. L. Lohmar; I. A. Wolff (1961). "Lesquerolic Acid. A New Hydroxy Acid from Lesquerella Seed Oil1a". J. Org. Chem. 26 (8): 2903–2905. doi:10.1021/jo01066a067.
3. David A. Dierig (1995). "Lesquerella". New Crop FactSHEET.

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