pimaradiene
sandaracopimara-8(14),15-diene
Identification
| Name | pimaradiene |
| IUPAC | (4aS,4bS,7S,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene |
| CAS Number | 1686-61-9 |
| FDA UNII | Search |
| Molecular Formula | C20 H32 |
| Molecular Weight | 272.47504000 |
| Nikkaji Number | J440.693A |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 337.00 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 0.000211 mmHg @ 25.00 °C. (est) |
| Flash Point | 303.00 °F. TCC ( 150.50 °C. ) (est) |
| logP (o/w) | 8.709 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
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 pimaradiene usage levels up to | not for fragrance use. |
| Recommendation for pimaradiene flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(4aS,4bS,7S,10aS)-7-
ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene
pimara-8(14),15-diene
sandaracopimara-8(14),15-diene
8(14),15-
sandaracopimaradiene
PubMed:
Optimization of recombinant expression enables discovery of novel cytochrome P450 activity in rice diterpenoid biosynthesis.
PubMed:
Acanthoic acid ameliorates lipopolysaccharide-induced acute lung injury.
PubMed:
Chenopodolin: a phytotoxic unrearranged ent-pimaradiene diterpene produced by Phoma chenopodicola, a fungal pathogen for Chenopodium album biocontrol.
PubMed:
Tyrosinase inhibitors from Calceolaria integrifolia s.l.: Calceolaria talcana aerial parts.
PubMed:
Evolution of conifer diterpene synthases: diterpene resin acid biosynthesis in lodgepole pine and jack pine involves monofunctional and bifunctional diterpene synthases.
PubMed:
Identification and characterization of a novel diterpene gene cluster in Aspergillus nidulans.
PubMed:
Limonoids and Diterpenoids from Toona ciliata Roem. var. yunnanensis.
PubMed:
CYP99A3: functional identification of a diterpene oxidase from the momilactone biosynthetic gene cluster in rice.
PubMed:
Attenuation of experimental murine colitis by acanthoic acid from Acanthopanax koreanum.
PubMed:
Terpenoids from Toona ciliata.
PubMed:
Trypanocidal activity of pimarane diterpenes from Viguiera arenaria (Asteraceae).
PubMed:
Increasing complexity of a diterpene synthase reaction with a single residue switch.
PubMed:
A single residue switch converts abietadiene synthase into a pimaradiene specific cyclase.
PubMed:
Following evolution's lead to a single residue switch for diterpene synthase product outcome.
PubMed:
Inhibition of trypsin-induced mast cell activation by acanthoic acid.
PubMed:
Metabolic flux analysis of diterpene biosynthesis pathway in rice.
PubMed:
Mechanism of abietadiene synthase catalysis: stereochemistry and stabilization of the cryptic pimarenyl carbocation intermediates.
PubMed:
Diterpenes from Sideritis trojana.
PubMed:
Effects of acanthoic acid on TNF-alpha gene expression and haptoglobin synthesis.
PubMed:
Suppression of interleukin-1 and tumor necrosis factor-alpha production by acanthoic acid, (-)-pimara-9(11),15-dien-19-oic acid, and it antifibrotic effects in vivo.
PubMed:
Biosynthesis of cyclic diterpene hydrocarbons in rice cell suspensions: conversion of 9,10-syn-labda-8(17),13-dienyl diphosphate to 9beta-pimara-7,15-diene and stemar-13-ene.
PubMed:
Diterpenoid resin acid biosynthesis in conifers: enzymatic cyclization of geranylgeranyl pyrophosphate to abietadiene, the precursor of abietic acid.
PubMed:
Biosynthesis of rice phytoalexins: identification of putative diterpene hydrocarbon precursors.