Lesquerolic acid

Lesquerolic acid is a hydroxycarboxylic acid that occurs naturally in Paysonia lasiocarpa and other Paysonia and Physaria species.[2] 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.[3] Lesquerolic acid, with other hydroxy fatty acids, has important industrial uses, including making resins, waxes, nylons and plastics.

Lesquerolic acid
Stereo, skeletal formula of lesquerolic acid (Z,R)
Names
Preferred IUPAC name
(11Z,14R)-14-Hydroxyicos-11-enoic acid[1]
Identifiers
3D model (JSmol)
ChemSpider
MeSH lesquerolic+acid
UNII
  • 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/s1 checkY
    Key: OONXYOAWMIVMCI-KWRJMZDGSA-N checkY
  • O=C(O)CCCCCCCCC\C=C/C[C@H](O)CCCCCC
Properties
C20H38O3
Molar mass 326.521 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

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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