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)-

CAS: 31685-80-0 C21 H30 O4 MW: 346.46690000

Identification

Namepinusolide
IUPACmethyl (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 Number31685-80-0
FDA UNIISearch
Molecular FormulaC21 H30 O4
Molecular Weight346.46690000
Nikkaji NumberJ17.758J

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 ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for pinusolide usage levels up tonot for fragrance use.
Recommendation for pinusolide flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

pinus koraiensis oleorosin

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.