4102-96-9Relevant academic research and scientific papers
Configurational Purity of Lesquerolic Acid
Sonnet, Philip E.,Hayes, Douglas
, p. 1069 - 1071 (1995)
Conversion of the methyl ester of lesquerolic acid, (R)-14-hydroxy-Z-11-eicosenoic acid, to a carbamate with (S)-1-(1'-naphthyl)ethylisocyanate gave a single diastereomer.Comparisons of elution orders of the relevant diastereomers obtained from the racemic ester and from a sample of lesquerolic acid synthesized from ricinoleic acid, (R)-12-hydroxy-Z-9-octadecenoic acid, were consistent with the original assignment of (R)-configuration for the longer-chain acid.Although the configuration had not been in doubt, this work demonstrates the configurational purity of the lesquerolic acid.KEY WORDS: Configuration, 1H NMR (of diastereomers), HPLC (of diastereomers), lesquerolic acid, ricinoleic acid.
Increased selectivity in the formation of the phenoxy ether of methyl lesquerolate over chloroalkyl-modified SBA-15-SO3H catalysts
Jackson, Michael A.,Appell, Michael
, p. 90 - 97 (2010)
A novel synthetic catalysis was developed for selective modification of useful bioproducts from the oil of Lesquerella fendlerii, an agricultural commodity of increasing importance. Modification of the surface of the solid acid catalyst SBA-15-SO3H with the chloroalkyl groups CH2CH2Cl, has improved the selectivity in the synthesis of the phenoxy ether of methyl 14-hydroxy-11-eicosenoate (methyl lesquerolate). A series of catalysts, SBA-15(EtCl)xSO3H where x = 0, 2, 4, 8, have been prepared and characterized by 13C CPNMR, surface properties, and elemental analyses. Selectivity increased with increased loading of the chloroalkyl group. This selectivity can be attributed to the decrease in the rate of conversion of the phenoxy ether to the Friedel-Crafts adducts. This study demonstrates synthetic approaches can develop novel catalysts to increase yields and selectivity for value-added bioproducts from new crops.
