Isocupressic acid

Isocupressic acid

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 (Jmol)	Interactive image
ChemSpider	4942630
PubChem	6438138
InChI InChI=1S/C20H32O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h10,16-17,21H,2,5-9,11-13H2,1,3-4H3,(H,22,23)/b14-10+/t16-,17+,19+,20-/m0/s1 Key: DOYKMKZYLAAOGH-DOEMEAPXSA-N InChI=1/C20H32O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h10,16-17,21H,2,5-9,11-13H2,1,3-4H3,(H,22,23)/b14-10+/t16-,17+,19+,20-/m0/s1 Key: DOYKMKZYLAAOGH-DOEMEAPXBD
SMILES O=C(O)[C@]1(CCC[C@@]2([C@H](/C(=C)CC[C@@H]12)CCC(=C/CO)/C)C)C
Properties
Chemical formula	C20H32O3
Molar mass	320.47 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

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: 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.