Lesquerolic acid

Lesquerolic acid is a hydroxycarboxylic acid that occurs naturally in Paysonia lasiocarpa and other Paysonia and Physaria species.^[2] The acid is typically found together with other hydroxylated fatty acids, such as densipolic, auricolic, ricinoleic, etc.^[3]

Lesquerolic acid

Stereo, skeletal formula of lesquerolic acid (Z,R)
Names
Preferred IUPAC name (11Z,14R)-14-Hydroxyicos-11-enoic acid[1]
Identifiers
CAS Number	4103-20-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:165421
ChemSpider	4472235 Y
MeSH	lesquerolic+acid
PubChem CID	5312810
UNII	87K5QW62TR Y
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/s1 Y Key: OONXYOAWMIVMCI-KWRJMZDGSA-N Y
SMILES O=C(O)CCCCCCCCC\C=C/C[C@H](O)CCCCCC
Properties
Chemical formula	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

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.^[4]

Uses

Lesquerolic acid, with other hydroxy fatty acids, has important industrial uses, including making resins, waxes, nylons and plastics.