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. sativa was found to have a 3R absolute configuration (i.e. (3R, 9Z)-heptadeca-1,9-diene-4,6-diyn-3-ol)
