pinusolide
1-naphthalenecarboxylic acid, 5-[2-(2,5-dihydro-2-oxo-3-furanyl)ethyl]decahydro-1,4a-dimethyl-6-methylene-, methyl ester, (1S,4aR,5S,8aR)-
Identification
| Name | pinusolide |
| IUPAC | methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate |
| CAS Number | 31685-80-0 |
| FDA UNII | Search |
| Molecular Formula | C21 H30 O4 |
| Molecular Weight | 346.46690000 |
| Nikkaji Number | J17.758J |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 465.30 °C. @ 760.00 mm Hg (est) |
| Flash Point | 443.00 °F. TCC ( 228.50 °C. ) (est) |
| logP (o/w) | 4.520 (est) |
| Soluble in | water, 0.2962 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 pinusolide usage levels up to | not for fragrance use. |
| Recommendation for pinusolide flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(1S-(1alpha,4aalpha,5alpha,8abeta))-5-(2-(2,5-
dihydro-2-oxo-3-furanyl)ethyl) decahydro-1,4a-dimethyl-6-methylene-1-naphthalene carboxylic acid methyl ester
methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylene-5-[2-(2-oxo-2,5-dihydro-3-furanyl)ethyl]decahydro-1-naphthalenecarboxylate
methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-2,5-dihydrofuran-3-yl)ethyl]decahydronaphthalene-1-carboxylate
methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
1-
naphthalenecarboxylic acid, 5-(2-(2,5-dihydro-2-oxo-3-furanyl)ethyl)decahydro-1,4a-dimethyl-6-methylene-, methyl ester, (1S-(1a,4aa,5a,8ab))-
1-
naphthalenecarboxylic acid, 5-[2-(2,5-dihydro-2-oxo-3-furanyl)ethyl]decahydro-1,4a-dimethyl-6-methylene-, methyl ester, (1S,4aR,5S,8aR)-
PubMed:
Pinusolide improves high glucose-induced insulin resistance via activation of AMP-activated protein kinase.
PubMed:
Pinusolide isolated from Biota orientalis inhibits 5-lipoxygenase dependent leukotriene C4 generation by blocking c-Jun N-terminal kinase pathway in mast cells.
PubMed:
Methylene chloride fraction of the leaves of Thuja orientalis inhibits in vitro inflammatory biomarkers by blocking NF-κB and p38 MAPK signaling and protects mice from lethal endotoxemia.
PubMed:
Suppression of adipocyte differentiation by 15-methoxypinusolidic acid through inhibition of PPARγ activity.
PubMed:
A pinusolide derivative, 15-methoxypinusolidic acid from Biota orientalis inhibits inducible nitric oxide synthase in microglial cells: implication for a potential anti-inflammatory effect.
PubMed:
Pinusolide and 15-methoxypinusolidic acid attenuate the neurotoxic effect of staurosporine in primary cultures of rat cortical cells.
PubMed:
Gram-scale synthesis of pinusolide and evaluation of its antileukemic potential.
PubMed:
15-Methoxypinusolidic acid from Biota orientalis attenuates glutamate-induced neurotoxicity in primary cultured rat cortical cells.
PubMed:
A new neuroprotective pinusolide derivative from the leaves of Biota orientalis.
PubMed:
Pinusolide from the leaves of Biota orientalis as potent platelet activating factor antagonist.
PubMed:
In vitro platelet-activating factor receptor binding inhibitory activity of pinusolide derivatives: a structure-activity study.
PubMed:
Platelet-activating factor antagonists.
PubMed:
Biological and pharmacological effects of pinusolide, a novel platelet activating factor antagonist.
PubMed:
Isolation and characterization of platelet-activating factor receptor binding antagonists from Biota orientalis.