isocupressic acid
15-hydroxylabda-8(17),13-dien-19-oic acid
Identification
| Name | isocupressic acid |
| IUPAC | (1S,4aR,5S,8aR)-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid |
| CAS Number | 1909-91-7 |
| FDA UNII | Search |
| Molecular Formula | C20 H32 O3 |
| Molecular Weight | 320.47264000 |
| Nikkaji Number | J148.791D |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 454.00 to 455.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 469.00 °F. TCC ( 242.60 °C. ) (est) |
| logP (o/w) | 4.867 (est) |
| Soluble in | water, 0.6267 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for isocupressic acid usage levels up to | not for fragrance use. |
| Recommendation for isocupressic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(1S,4aR,5S,8aR)-5-[(3E)-5-
hydroxy-3-methylpent-3-en-1-yl]-1,4a-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylic acid
(1S,4aR,5S,8aR)-5-[(E)-5-
hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
15-
hydroxylabda-8(17),13-dien-19-oic acid
1-
naphthalenecarboxylic acid, decahydro-5-((3E)-5-hydroxy-3-methyl-3-pentenyl)-1,4a-dimethyl-6-methylene-, (1S,4aR,5S,8aR)-
1-
naphthalenecarboxylic acid, decahydro-5-[(3E)-5-hydroxy-3-methyl-3-penten-1-yl]-1,4a-dimethyl-6-methylene-, (1S,4aR,5S,8aR)-
PubMed:
[Study on chemical constituents from petroleum ether-soluble parts of cones of Platycladus orientalis].
PubMed:
Activation of transient receptor potential ankyrin-1 (TRPA1) in lung cells by wood smoke particulate material.
PubMed:
Anti-mycobacterial natural products from the Canadian medicinal plant Juniperus communis.
PubMed:
A comparison of the metabolism of the abortifacient compounds from Ponderosa pine needles in conditioned versus naive cattle.
PubMed:
Molecular Mechanism of Isocupressic Acid Supresses MA-10 Cell Steroidogenesis.
PubMed:
A new lignan glycoside from Juniperus rigida.
PubMed:
Isolation, chemical, and biotransformation routes of labdane-type diterpenes.
PubMed:
Implication of agathic acid from Utah juniper bark as an abortifacient compound in cattle.
PubMed:
Efects of the pine needle abortifacient, isocupressic acid, on bovine oocyte maturation and preimplantation embryo development.
PubMed:
Development of enzyme-linked immunosorbent assays for isocupressic acid and serum metabolites of isocupressic acid.
PubMed:
Isocupressic acid blocks progesterone production from bovine luteal cells.
PubMed:
Potential antitumor promoting diterpenoids from the stem bark of Thuja standishii.
PubMed:
Preparation of tetrahydroagathic acid: a serum metabolite of isocupressic acid, a cattle abortifacient in ponderosa pine.
PubMed:
Pine needle abortion in cattle: metabolism of isocupressic acid.
PubMed:
Abortifacient effects of a unique class of vasoactive lipids from Pinus ponderosa needles.
PubMed:
Ponderosa pine and broom snakeweed: poisonous plants that affect livestock.
PubMed:
Abortifacient effects of lodgepole pine (Pinus contorta) and common juniper (Juniperus communis) on cattle.
PubMed:
Microbial transformations of isocupressic acid.
PubMed:
In vitro biotransformations of isocupressic acid by cow rumen preparations: formation of agathic and dihydroagathic acids.
PubMed:
Isocupressic acid, an abortifacient component of Cupressus macrocarpa.
PubMed:
The toxic and abortifacient effects of ponderosa pine.
PubMed:
Platelet aggregation inhibitors in a Bhutanese medicinal plant, shug chher.