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PIMARIC ACID

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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
Product Categories:
  • Activators
  • Aliphatics
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
127-27-5.mol
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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
pka
4.68±0.60(Predicted)
LogP
6.731 (est)
EPA Substance Registry System
Pimaric acid (127-27-5)
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PIMARIC ACID Usage And Synthesis

Description

Pimaric 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.

Uses

A novel activators of large-conductance Ca2+-activated K+ channel α-subunit.

Definition

ChEBI: (+)-Pimaric acid is a diterpenoid.

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