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
ChemSpider	4942630
Jmol 3D model	Interactive image
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
Vapor pressure	{{{value}}}
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. It is found in all parts of the ponderosa pine (Pinus ponderosa), especially the needles. This gives its toxic and abortifacient effects. It is also present in the lodgepole pine (P. contorta), the jeffrey pine (P. jeffreyi) and possibly in the monterey pine (P. radiata).