Absolute configuration of a hydroxyfuranoid acid from the pelage of the genus Bos, 18-(6S,9R,10R)-bovidic acid.

@article{Ishii2004AbsoluteCO,
  title={Absolute configuration of a hydroxyfuranoid acid from the pelage of the genus Bos, 18-(6S,9R,10R)-bovidic acid.},
  author={Hideki Ishii and Sonja Krane and Yasuhiro Itagaki and Nina Berova and Kōji Nakanishi and Paul J. Weldon},
  journal={Journal of natural products},
  year={2004},
  volume={67 8},
  pages={
          1426-30
        }
}
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… Expand
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References

SHOWING 1-2 OF 2 REFERENCES
Mammalian Semiochemistry: The Investigation of Chemical Signals Between Mammals
Mammalian Semiochemistry. Chemistry's Contribution. The Skin. Scent Glands. Microogranisms in Mammalian Semiochemistry. Urine. Secretions of the Reproductive Tract. Breath, Saliva and the Pig.Expand