ChemicalBook Product Catalog Natural Products Terpenes PIMARIC ACID

PIMARIC ACID

PIMARIC ACID Basic information
Product Name:PIMARIC ACID
Synonyms:(1R,4aR,4bS,7S,10aR)-7-Ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-triMethyl-1-phenanthrenecarboxylic Acid;13α-Methyl-13-vinylpodocarp-8(14)-en-15-oic acid;PIMARIC ACID;1-phenanthrenecarboxylicacid,7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahyd;7-trimethyl-,[1theta-(1alpha,4abeta,4balpha,7beta,10aalpha)]-ro-4a;13-alpha-methyl-13-vinylpodocarp-8(14)-en-15-oic acid;1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-, (1R,4aR,4bS,7S,10aR)-;8(14),15-PiMaradien-18-oic Acid
CAS:127-27-5
MF:C20H30O2
MW:302.45
EINECS:
Product Categories:Activators;Aliphatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:127-27-5.mol
PIMARIC ACID Structure
PIMARIC ACID Chemical Properties
Melting point 217-219°
alpha D18 +74.7° (c = 0.4 in chloroform); D20 +87.3° (in chloroform)
Boiling point bp18 282°
density 1.0434 (rough estimate)
refractive index 1.4800 (estimate)
storage temp. Store at -20°C
solubility DMSO: soluble,Water: soluble
pka4.68±0.60(Predicted)
LogP6.731 (est)
EPA Substance Registry SystemPimaric acid (127-27-5)
Safety Information
MSDS Information
PIMARIC ACID Usage And Synthesis
DescriptionPimaric acid is a resin acid that has been found in A. cordata and various pines. It reduces mRNA expression, protein levels, and promoter activity of matrix metalloproteinase-9 (MMP-9) in TNF-α-stimulated human aortic smooth muscle cells (HASMCs) in a concentration-dependent manner when used at concentrations ranging from 5 to 20 μM. Pimaric acid (10-20 μM) reduces nuclear expression and binding of the transcription factors NF-κB and AP-1 to the MMP-9 promoter in HASMCs. Pimaric acid also reduces TNF-α-induced HASMC migration to control levels when used at a concentration of 20 μg/ml.
UsesA novel activators of large-conductance Ca2+-activated K+ channel α-subunit.
DefinitionChEBI: (+)-Pimaric acid is a diterpenoid.
PIMARIC ACID Preparation Products And Raw materials
Preparation ProductsPIMAROL-->(1R)-7β-Ethenyl-1,2,3,4,4a,5,6,7,8,9,10,10aα-dodecahydro-1,4aβ,7-trimethyl-1α-phenanthrenecarboxylic acid methyl ester
2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one Sodium tungstate Hydroxyecdysone (4E,6E)-1,7-Diphenyl-4,6-heptadien-3-one Artemether beta-Sitosterol hydroxygenkwanin cis-1,2,3,6-Tetrahydrophthalic anhydride alpha-Terpineol beta-Eudesmol MOSLOFLAVONE alpha-Cyperone PIMARIC ACID sandaracopimaric acid (CIS)-8-METHYLNON-6-ENOIC ACID
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