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Isocupressic acid

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Isocupressic acid
Names
IUPAC name (13E)-15-Hydroxylabda-8(20),13-dien-19-oic acid
Systematic IUPAC name (1S,4aR,5S,8aR)-5--1,4a-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: DOYKMKZYLAAOGH-DOEMEAPXBD
SMILES
  • O=C(O)1(CCC2((/C(=C)CC12)CCC(=C/CO)/C)C)C
Properties
Chemical formula C20H32O3
Molar mass 320.473 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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).

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. Archived from the original on 2021-06-05. Retrieved 2018-12-29.
  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. S2CID 19523938.
  3. Burrows, George E.; Tyrl, Ronald J. (2012). Toxic Plants of North America (2nd ed.). John Wiley & Sons. ISBN 9781118413388.


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