Vernolic Acid
Title: Vernolic Acid
CAS Name: 11-(3-Pentyloxiranyl)-9-undecenoic acid
Additional Names: 12,13-epoxyoleic acid; cis-12,13-epoxyoctadec-cis-9-enoic acid; octadec-cis-12,13-epoxy-cis-9-enoic acid
Molecular Formula: C18H32O3
Molecular Weight: 296.44
Percent Composition: C 72.93%, H 10.88%, O 16.19%
Literature 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 Type: (-)-Form
CAS Registry Number: 32381-42-3
CAS Name: [2R-[2a(Z),3a]]-11-(3-Pentyloxiranyl)-9-undecenoic acid
Additional Names: (12R,13S)-(-)-12,13-epoxyoleic acid
Properties: Crystals from acetone at -25°, mp 30-31°. Liq at room temp. [a]D -8°.
Melting point: mp 30-31°
Optical Rotation: [a]D -8°
 
Derivative Type: (+)-Form
CAS Registry Number: 503-07-1
CAS Name: [2S-[2a(Z),3a]]-11-(3-Pentyloxiranyl)-9-undecenoic acid
Additional Names: (12S,13R)-(+)-12,13-epoxyoleic acid

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