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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-[(3E )-5-Hydroxy-3-methylpent-3-en-1-yl]-1,4a-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylic acid
Identifiers
ChEMBL
ChemSpider
UNII
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
O=C(O)[C@]1(CCC[C@@]2([C@H](/C(=C)CC[C@@H]12)CCC(=C/CO)/C)C)C
Properties
C 20 H 32 O 3
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).
Chemical compound
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
^ 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 .
^ 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 .
^ Burrows, George E.; Tyrl, Ronald J. (2012). Toxic Plants of North America (2nd ed.). John Wiley & Sons.
ISBN
9781118413388 .