Lesquerolic acid

Lesquerolic acid

Names
IUPAC name (11Z, 14R)-14-Hydroxyicos-11-enoic acid[1]
Identifiers
CAS Registry Number	4103-20-2 Y
ChemSpider	4472235 Y
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/s1 Y Key: OONXYOAWMIVMCI-KWRJMZDGSA-N Y
Jmol-3D images	Image
MeSH	lesquerolic+acid
PubChem	5312810
SMILES O=C(O)CCCCCCCCC\C=C/C[C@H](O)CCCCCC
Properties
Molecular formula	C20H38O3
Molar mass	326.51 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Lesquerolic acid is a hydroxy acid that occurs naturally in Paysonia lasiocarpa and other Paysonia and Physaria species. It was first isolated in 1961 by a team from the Northern Regional Research Laboratory.^[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.

References