sandaracopimaradiene
(-)-8(14),15-isopimaradiene
Identification
| Name | sandaracopimaradiene |
| IUPAC | (4aS,4bS,7R,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene |
| CAS Number | 21738-16-9 |
| FDA UNII | Search |
| Molecular Formula | C20 H32 |
| Molecular Weight | 272.47504000 |
| Nikkaji Number | J112.498F |
Regulatory
Physical Properties
| Appearance | white crystalline solid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 37.00 to 40.00 °C. @ 760.00 mm Hg |
| Boiling Point | 336.00 to 337.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.000211 mmHg @ 25.00 °C. (est) |
| Flash Point | 303.00 °F. TCC ( 150.56 °C. ) |
| logP (o/w) | 8.630 (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 | flavor and fragrance agents |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(4aS,4bS,7R,10aS)-7-
ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene
(-)-iso
pimara-8(14),15-diene
(13a)-
pimara-8(14),15-diene
iso
pimara-8(14),15-diene
(-)-8(14),15-iso
pimaradiene
(+)-
sandaracopimaradiene
sandracopimaradiene
(4aS,4bS,7R,10aS)-1,1,4a,7-
tetramethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene
PubMed:
Picking sides: distinct roles for CYP76M6 and CYP76M8 in rice oryzalexin biosynthesis.
PubMed:
Asymmetric total synthesis of ent-sandaracopimaradiene, a biosynthetic intermediate of oryzalexins.
PubMed:
Active principles of Tetradenia riparia. I. Antimicrobial activity of 8(14),15-sandaracopimaradiene-7 alpha,18-diol.
PubMed:
Identification of (+)-phyllocladene, (--)-sandaracopimaradiene, and (+)-kaurene as new fungal metabolites from fusicoccin-producing Phomopsis amygdali F6.
PubMed:
Active principles of Tetradenia riparia; II. Antispasmodic activity of 8(14),15-sandaracopimaradiene-7 alpha,18-diol.
PubMed:
The synthesis of (-)-sandaracopimaradiene from androstane derivatives.
PubMed:
Molecular evolution of the substrate specificity of ent-kaurene synthases to adapt to gibberellin biosynthesis in land plants.
PubMed:
Diterpenes drive Th1 polarization depending on IL-12.
PubMed:
CYP701A8: a rice ent-kaurene oxidase paralog diverted to more specialized diterpenoid metabolism.
PubMed:
Xanthine oxidase inhibitory terpenoids of Amentotaxus formosana protect cisplatin-induced cell death by reducing reactive oxygen species (ROS) in normal human urothelial and bladder cancer cells.
PubMed:
Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals.
PubMed:
Terpenoids from Guarea rhophalocarpa.
PubMed:
New phenylpropane and anti-inflammatory diterpene derivatives from Amentotaxus formosana.
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:
Functional plasticity of paralogous diterpene synthases involved in conifer defense.
PubMed:
Mechanism of abietadiene synthase catalysis: stereochemistry and stabilization of the cryptic pimarenyl carbocation intermediates.
PubMed:
Diterpene cyclases responsible for the biosynthesis of phytoalexins, momilactones A, B, and oryzalexins A-F in rice.
PubMed:
Abietadiene synthase catalysis: mutational analysis of a prenyl diphosphate ionization-initiated cyclization and rearrangement.
PubMed:
Wheat rootlet growth inhibition test of Rwandese medicinal plants: active principles of Tetradenia riparia and Diplolophium africanum.