Isocupressic acid

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Isocupressic acid

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
	PubChem	6438138
ChemSpider	4942630
Jmol-3D images	{{#if:O=C(O)[C@]1(CCC[C@@]2([C@H](/C(=C)CC[C@@H]12)CCC(=C/CO)/C)C)C\|Image 1
SMILES O=C(O)[C@]1(CCC[C@@]2([C@H](/C(=C)CC[C@@H]12)CCC(=C/CO)/C)C)C
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
Properties
Molecular formula	C₂₀H₃₂O₃
Molar mass	320.47 g mol⁻¹
Except where noted otherwise, 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]

References

↑ Wang, S; Panter, KE; Gardner, DR; Evans, RC; Bunch, TD (2004). "Efects 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.

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