9963. Vernolic Acid
Nomenclature
11-(3-Pentyloxiranyl)-9-undecenoic acid; 12,13-epoxyoleic acid; cis-12,13-epoxyoctadec-cis-9-enoic acid; octadec-cis-12,13-epoxy-cis-9-enoic acid.C18H32O3; mol wt 296.44.
C 72.93%, H 10.88%, O 16.19%.
Description and references
Naturally occurring as the (+) and () forms. Principal seed-oil acid from Vernonia anthelmintica Willd. (Serratula anthelmintica Roxb., Conyza anthelmintica Linn.) Compositae. Isoln and structure: Gunstone, J. Chem. Soc. 1954, 1611; from Plectranthus spp.: C. M. J. Daulatabad, A. M. Mirajkur, J. Chem. Technol. Biotechnol. 45, 143 (1989). Synthesis and absorption spectrum: Osbond, ibid. 1961, 5270; idem, GB 909354 (1962 to Roche). Enantiospecific synthesis of ()-form: C. A. Moustakis et al., Tetrahedron Lett. 27, 303 (1986).
Derivative
()-Form.Nomenclature
CAS number: 32381-42-3
[2R-[2α(Z),3α]]-11-(3-Pentyloxiranyl)-9-undecenoic
acid; (12R,13S)-()-12,13-epoxyoleic
acid. Properties
Crystals from acetone at 25°, mp 30-31°. Liquid at room temp. [α]D 8°.Derivative
(+)-Form.Nomenclature
CAS number: 503-07-1
[2S-[2α(Z),3α]]-11-(3-Pentyloxiranyl)-9-undecenoic
acid; (12S,13R)-(+)-12,13-epoxyoleic acid.