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CAS

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127-27-5

Pimaric acid is a resin acid that has been found in A. cordata and various pines. It possesses the ability to reduce 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. Pimaric acid also has the capability to reduce nuclear expression and binding of transcription factors NF-κB and AP-1 to the MMP-9 promoter in HASMCs, as well as reduce TNF-α-induced HASMC migration to control levels.

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  • 1-Phenanthrenecarboxylicacid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-,(1R,4aR,4bS,7S,10aR)-

    Cas No: 127-27-5

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  • 127-27-5 Structure

  • Basic information

    1. Product Name: PIMARIC ACID
    2. Synonyms: 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)-;(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;8(14),15-PiMaradien-18-oic Acid
    3. CAS NO:127-27-5
    4. Molecular Formula: C20H30O2
    5. Molecular Weight: 302.451
    6. EINECS: N/A
    7. Product Categories: Activators;Aliphatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
    8. Mol File: 127-27-5.mol

  • Chemical Properties

    1. Melting Point: 217-219°
    2. Boiling Point: bp18 282°
    3. Flash Point: 198.7°C
    4. Appearance: /
    5. Density: 1.0434 (rough estimate)
    6. Vapor Pressure: 5.52E-08mmHg at 25°C
    7. Refractive Index: 1.4800 (estimate)
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 4.68±0.60(Predicted)
    11. CAS DataBase Reference: PIMARIC ACID(CAS DataBase Reference)
    12. NIST Chemistry Reference: PIMARIC ACID(127-27-5)
    13. EPA Substance Registry System: PIMARIC ACID(127-27-5)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 127-27-5(Hazardous Substances Data)

127-27-5 Usage

Uses

Used in Pharmaceutical Industry:
Pimaric acid is used as a novel activator of large-conductance Ca2+-activated K+ channel α-subunit for its potential therapeutic applications.
Used in Cardiovascular Research:
Pimaric acid is used as a regulator of matrix metalloproteinase-9 (MMP-9) expression and activity in human aortic smooth muscle cells (HASMCs) for its potential role in cardiovascular health and disease prevention.
Used in Anti-inflammatory Applications:
Pimaric acid is used to reduce the nuclear expression and binding of transcription factors NF-κB and AP-1 to the MMP-9 promoter in HASMCs, which may contribute to its anti-inflammatory properties.
Used in Cell Migration Studies:
Pimaric acid is used to reduce TNF-α-induced HASMC migration to control levels, which may have implications for understanding and treating conditions involving abnormal cell migration.

Check Digit Verification of cas no

The CAS Registry Mumber 127-27-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 7 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 127-27:
(5*1)+(4*2)+(3*7)+(2*2)+(1*7)=45
45 % 10 = 5
So 127-27-5 is a valid CAS Registry Number.
InChI:InChI=1/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20+/m0/s1

127-27-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name PIMARIC ACID

1.2 Other means of identification

Product number -
Other names 1-phenanthrenecarboxylicacid,7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahyd

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:127-27-5 SDS

127-27-5Related news

PIMARIC ACID (cas 127-27-5) from Aralia cordata has an inhibitory effect on TNF-α-induced MMP-9 production and HASMC migration via down-regulated NF-κB and AP-109/10/2019

Many studies have indicated that activation of matrix metalloproteinase (MMP)-9 and smooth muscle cell (SMC) migration are involved in neointimal formation and atherosclerosis. In this study, we revealed that pimaric acid (PiMA) purified from Aralia cordata had an inhibitory effect on MMP-9 prod...detailed

127-27-5Relevant articles and documents

Inhibition of platelet aggregation by diterpene acids from Pinus massoniana resin

Cheung,Fu,Smal

, p. 17 - 25 (2007/10/02)

The acidic fraction of the resin of Pinus massoniana Lamb. from China was converted to the p-nitrophenyl esters, and the esters separated by chromatography. The separated p-nitrophenyl esters were individually hydrolysed by potassium hydroxide in acetone-water at room temperature to 8 diterpene acids of the pimarane and abietane groups: pimaric acid (8(14),15-pimaradien-18-oic acid) (1), levopimaric acid (8(14),12-abietadien-18-oic acid (2), palustric acid (8,13-abietadien-18-oic acid) (3), neoabietic acid (8(14),13(15)-abietadien-18-oic acid) (4), abietic acid (7,13-abietadien-18-oic acid) (5), dehydroabietic acid (8,11,13-abietatrien-18-oic acid) (6), 7-oxodehydroabietic acid (7-oxo-8,11,13-abietatrien-18-oic acid) (7) and 7α-hydroxydehydroabietic acid (7α-hydroxy-8,11,13-abietatrien-18-oic acid) (8). The structure (and stereochemistry) of the diterpene acids were substantiated by nulear magnetic resonance spectroscopy (proton and carbon-13, one and two dimensional), by mass spectrometry (electron impact and methane chemical ionization) and by rotation measurements. The 8 diterpene acids were tested for their ability to inhibit the aggregation of washed rabbit platelets induced by platelet activating factor (PAF), adenosine diphosphate (ADP) and by calcium ionophore A23187. With platelet aggregation induced by the latter two agonists, activities comparable with or higher than linolenic acid were given by the first 4 acids. With aggregation induced by PAF, the first 3 acids show activity, but at a level significantly lower than that of linolenic acid. Levopimaric acid has the highest activity among the diterpene acids tested. It is proposed that this activity is related to the folded shape of the molecule.

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