Absolute configuration of falcarinol (9Z-heptadeca-1,9-diene-4,6-diyn-3-ol) from Pastinaca sativa.
Falcarinol (9Z-heptadeca-1,9-diene-4,6-diyn-3-ol; (1) is a polyacetylene commonly found in several plant families. The absolute configuration of naturally occurring 1 is not clear and contradictory results have been reported in the literature. Determination of the absolute configuration of 1 from Pastinaca sativa L. was carried out. Isolation of 95% pure 1 was performed via successive fractionation and preparative-HPLC. A racemic mixture comprised of 3R-1 and 3S-1 was synthesized in order to confirm the absolute configuration of the isolated natural product using chiral HPLC. Based on a combination of chiral HPLC and specific rotation, 1 present in P. saliva was found to have a 3R absolute configuration (i.e. (3R, 9Z)-heptadeca-1,9-diene-4,6-diyn-3-ol).
Department of Agroforestry Sciences, School of Technical Agricultural Engineering, University of Seville, Ctra de Utrera, C.P. 41013, Spain.
Mireia
M
Corell
Emile
E
Sheehy
Paul
P
Evans
Nigel
N
Brunton
Juan
J
Valverde
D002851:Chromatography, High Pressure Liquid; D053280:Diynes / Q000737:chemistry* / Q000302:isolation & purification*; D005233:Fatty Alcohols / Q000737:chemistry* / Q000302:isolation & purification*; D008968:Molecular Conformation; D028529:Pastinaca / Q000737:chemistry*; D018517:Plant Roots / Q000737:chemistry; D013237:Stereoisomerism
D053280:Diynes; D005233:Fatty Alcohols; C018541:falcarinol