Pimaric acid

Base Information

• Chemical Name: Pimaric acid
• CAS No.: 127-27-5
• Deprecated CAS: 26341-61-7
• Molecular Formula: C20H30 O2
• Molecular Weight: 302.457
• NSC Number: 2956
• UNII: 88R98Z71NI
• DSSTox Substance ID: DTXSID80858728
• Nikkaji Number: J5.391K
• Wikipedia: Pimaric_acid
• Wikidata: Q418035
• Metabolomics Workbench ID: 68410
• ChEMBL ID: CHEMBL1410398
• Mol file: 127-27-5.mol

Synonyms:pimara-8(14),15-dien-19-oic acid;pimaradienoic acid;pimaric acid;pimaric acid, (L)-isomer;Usic acid

Chemical Property of Pimaric acid

Chemical Property:

• Vapor Pressure: 5.52E-08mmHg at 25°C
• Melting Point: 217-219°
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 413.2°Cat760mmHg
• PKA: 4.68±0.60(Predicted)
• Flash Point: 198.7°C
• PSA: 37.30000
• Density: 1.05g/cm³
• LogP: 5.20620
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 302.224580195
• Heavy Atom Count: 22
• Complexity: 534

Purity/Quality:

99%, ^*data from raw suppliers

Pimaric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2C(=C1)CCC3C2(CCCC3(C)C(=O)O)C)C=C
• Isomeric SMILES: C[C@]1(CC[C@H]2C(=C1)CC[C@@H]3[C@@]2(CCC[C@@]3(C)C(=O)O)C)C=C
• 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.

Technology Process of Pimaric acid

There total 6 articles about Pimaric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ pimaric acid (127-27-5)

Guidance literature:

With chromium(VI) oxide; acetic acid;

DOI:10.1021/ja01191a100

Reference yield:

p-nitrophenyl pimarate → pimaric acid (127-27-5)

Guidance literature:

With potassium hydroxide; In acetone; for 2h; Ambient temperature;

Reference yield:

8(14),15-pimaradien-18-al (472-39-9) + acetic acid (64-19-7,77671-22-8) → pimaric acid (127-27-5)

Guidance literature:

DOI:10.1021/ja01191a100 DOI:10.1021/ja01597a061

upstream raw materials:

8⁽¹⁴⁾,15-pimaradien-18-al

acetic acid

Downstream raw materials:

(1R,4aR,4bS,7S,10aR)-1,4a,7-Trimethyl-1-phenylsulfanylmethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthrene

Methyl pimara-8,15-dien-18-oate

8⁽¹⁴⁾,15-pimaradien-18-ol

Dihydro-pimarsaeure

Refernces

• 1、 Cheung,Fu,Smal. "Inhibition of platelet aggregation by diterpene acids from Pinus massoniana resin". . p. 17 - 25. Retrieved 2007/10/02.