Isocupressic acid

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Isocupressic acid
Isocupressic acid.svg
Names
IUPAC name
(1S,4aR,5S,8aR)-5-[(3E)-5-Hydroxy-3-methyl-3-penten-1-yl]-1,4a-dimethyl-6-methylenedecahydro-1-naphthalenecarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
Properties
C20H32O3
Molar mass 320.473 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Isocupressic acid is a diterpene acid present in a variety of conifer needles. It induces abortion in cattle.[1] It is found in all parts of the ponderosa pine (Pinus ponderosa), especially the needles. This gives its toxic and abortifacient effects.[2] It is also present in the lodgepole pine (P. contorta), the jeffrey pine (P. jeffreyi) and possibly in the monterey pine (P. radiata).[3]

References[edit]

  1. ^ Wang, S; Panter, KE; Gardner, DR; Evans, RC; Bunch, TD (2004). "Effects of the pine needle abortifacient, isocupressic acid, on bovine oocyte maturation and preimplantation embryo development". Animal Reproduction Science. 81 (3–4): 237–44. doi:10.1016/j.anireprosci.2003.10.008. PMID 14998650.
  2. ^ Stegelmeier, BL; Gardner, DR; James, LF; Panter, KE; Molyneux, RJ (1996). "The toxic and abortifacient effects of ponderosa pine". Vet. Pathol. 33 (1): 22–8. doi:10.1177/030098589603300103. PMID 8826003.
  3. ^ Burrows, George E.; Tyrl, Ronald J. (2012). Toxic Plants of North America (2nd ed.). John Wiley & Sons. ISBN 9781118413388.