Lesquerolic acid

{{Chembox

| ImageFile = Lesquerolic acid.png

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageName = Stereo, skeletal formula of lesquerolic acid (Z,R)

| PIN = (11Z,14R)-14-Hydroxyicos-11-enoic acid{{Cite web|title = CID 20980884 - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=20980884|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 20 November 2011|location = USA|date = 5 December 2007}}

|Section1={{Chembox Identifiers

| CASNo = 4103-20-2

| CASNo_Ref = {{cascite|correct|??}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 87K5QW62TR

| PubChem = 5312810

| ChEBI = 165421

| ChemSpiderID = 4472235

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| MeSHName = lesquerolic+acid

| SMILES = O=C(O)CCCCCCCCC\C=C/C[C@H](O)CCCCCC

| StdInChI =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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OONXYOAWMIVMCI-KWRJMZDGSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C=20 | H=38 | O=3

}}

}}

Lesquerolic acid is a hydroxycarboxylic acid that occurs naturally in Paysonia lasiocarpa and other Paysonia and Physaria species.{{cite journal

|author1=C. R. Smith Jr. |author2=T. L. Wilson |author3=T. K. Miwa |author4=H. Zobel |author5=R. L. Lohmar |author6=I. A. Wolff

| title = Lesquerolic Acid. A New Hydroxy Acid from Lesquerella Seed Oil1a

| journal=J. Org. Chem.

| year=1961

| volume=26

| issue=8

| pages=2903–2905

| doi=10.1021/jo01066a067

}}

The acid is typically found together with other hydroxylated fatty acids, such as densipolic, auricolic, ricinoleic, etc.{{cite journal |last1=Salywon |first1=Andrew M. |last2=Dierig |first2=David A. |last3=Rebman |first3=Jon P. |last4=de Rodríguez |first4=Diana Jasso |title=Evaluation of new Lesquerella and Physaria (Brassicaceae) oilseed germplasm |journal=American Journal of Botany |date=2005 |volume=92 |issue=1 |pages=53–62 |doi=10.3732/ajb.92.1.53 |url=https://bsapubs.onlinelibrary.wiley.com/doi/full/10.3732/ajb.92.1.53 |access-date=4 April 2025 |language=en |issn=1537-2197|url-access=subscription }}

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.{{cite web

| author=David A. Dierig

| title=Lesquerella

| publisher=New Crop FactSHEET

| year=1995

| url=http://www.hort.purdue.edu/newcrop/cropfactsheets/Lesquerella.html

}}