Absolute configuration of a hydroxyfuranoid acid from the pelage of the genus Bos, 18-(6S,9R,10R)-bovidic acid.
Pelage extracts of the banteng (Bos javanicus), the domestic cattle (B. taurus), the gaur (B. frontalis), and the yak (B. grunniens) were investigated by FABMS and NMR. An 18-carbon hydroxyfuranoid acid, 1 (10-hydroxy-6,9-oxidooctadecanoic acid), first reported from the wool of the domestic sheep (Ovis aries) was confirmed in B. frontalis; we suspend judgment on the occurrence of this compound in the other species we examined. The stereochemistry of 1, determined by Mosher NMR and CD tweezer methods, was assigned as 6S, 9R, 10R. We propose the name bovidic acid for this and homologous alpha-hydroxylated 2,5-tetrahydrofuranoid carboxylic acids, in reference to the family Bovidae, which represents their sole known natural source.
Ishii
Hideki
H
Department of Chemistry, Columbia University, 3000 Broadway, New York, New York 10027, USA.
Krane
Sonja
S
Itagaki
Yasuhiro
Y
Berova
Nina
N
Nakanishi
Koji
K
Weldon
Paul J
PJ
D000818:Animals; D002417:Cattle; D002942:Circular Dichroism; D006197:Hair / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012756:Sheep; D013229:Stearic Acids / Q000737:chemistry* / Q000302:isolation & purification*; D013237:Stereoisomerism
C492421:10-hydroxy-6,9-oxidooctadecanoic acid; D013229:Stearic Acids