Levopimaric acid

Base Information

• Chemical Name: Levopimaric acid
• CAS No.: 79-54-9
• Molecular Formula: C20H30 O2
• Molecular Weight: 302.457
• NSC Number: 4827
• UNII: 6073C2A77I
• DSSTox Substance ID: DTXSID20878526
• Nikkaji Number: J4.233A
• Wikipedia: Levopimaric_acid
• Wikidata: Q6535822
• Metabolomics Workbench ID: 68412
• Mol file: 79-54-9.mol

Synonyms:Levopimaric acid;l-Pimaric acid;l-Sapietic acid;79-54-9;beta-Pimaric acid;.beta.-Pimaric acid;NSC4827;(1R,4aR,4bS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,9,10,10a-octahydrophenanthrene-1-carboxylic acid;UNII-6073C2A77I;delta6,8(14)-Abietadienoic acid;NSC 4827;NSC-4827;.DELTA.6,8(14)-Abietadienoic acid;6073C2A77I;(1R,4aS,4bR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,9,10,10a-octahydro phenanthrene-1-carboxylic acid;Podocarpa-8(14),12-dien-15-oic acid, 13-isopropyl-;(-)-LEVOPIMARIC ACID;LEVOPIMARIC ACID [MI];SCHEMBL152258;13-isopropylpodocarpa-8(14),12-dien-15-oic acid;CHEBI:29615;DTXSID20878526;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,9,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R-(1.alpha.,4a.beta., 4b.alpha.,10a.alpha.))-;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,9,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1theta-(1alpha,4abeta,4balpha,10aalpha))-;HY-N7431;Podocarpa-8(14), 13-isopropyl-;CS-0128313;Q6535822;13-isopropylpodocar-pa-8(14),12-dien-15-oic acid;(1R,4aR,4bS)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,9,10,10a-octahydrophenanthrene-1-carboxylic acid;(1R,4aR,4bS,10aR)-7-isopropyl-1,4a-dimethyl-2,3,4,4b,5,9,10,10a-octahydrophenanthrene-1-carboxylic acid;1-PHENANTHRENECARBOXYLIC ACID, 1,2,3,4,4A,4B,5,9,10,10A-DECAHYDRO-1,4A-DIMETHYL-7-(1-METHYLETHYL)-, (1R,4AR,4BS,10AR)-;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,9,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R-(1alpha,4abeta, 4balpha,10aalpha))-;1-Phenanthrenecarboxylic acid,2,3,4,4a,4b,5,9,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, [1R-(1.alpha.,4a.beta.,4b.alpha.,10a.alpha.)]-

Chemical Property of Levopimaric acid

Chemical Property:

• Vapor Pressure: 1.41E-08mmHg at 25°C
• Melting Point: 150°
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 429.4°C at 760 mmHg
• PKA: 4.68±0.60(Predicted)
• Flash Point: 204.6°C
• PSA: 37.30000
• Density: 1.06g/cm³
• LogP: 5.20620
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 302.224580195
• Heavy Atom Count: 22
• Complexity: 542

Purity/Quality:

99.5% ^*data from raw suppliers

LevopimaricAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=CCC2C(=C1)CCC3C2(CCCC3(C)C(=O)O)C
• Isomeric SMILES: CC(C)C1=CC[C@H]2C(=C1)CC[C@@H]3[C@@]2(CCC[C@@]3(C)C(=O)O)C
• Uses: Levopimaric Acid is a major component of pine oleoresin. It is an abietane-type of diterpene resin acid and has antibacterial, cardiovascular, and antioxidant properties.

Technology Process of Levopimaric acid

There total 1 articles about Levopimaric 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:

maleopimaric acid (510-39-4) → abietic acid (514-10-3) + levopimaric acid (79-54-9)

Guidance literature:

at 260 ℃; under 20 Torr;

Reference yield: 90.5%

Levopimaric Acid (79-54-9) + propynoic acid ethyl ester (623-47-2) → 2-[2-((1R,2R,6R)-2-Ethoxycarbonyl-2,6-dimethyl-6-vinyl-cyclohexyl)-ethyl]-4-isopropyl-benzoic acid ethyl ester (75399-78-9)

Guidance literature:

at 150 - 160 ℃; for 15h;

DOI:10.1021/jo01314a055

Reference yield: 3.0%

levopimaric acid (79-54-9) → dehydroabietic acid (1740-19-8) + abietic acid (514-10-3) + <1R-(1α,4aβ,4bα,6α,10aα)>-1,2,3,4,4a,4b,5,6,10,10a-Decahydro-6-hydroxy-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrencarbonsaeure-methylester (3484-53-5) + 15-hydroxydehydroabietic acid methyl ester (29461-23-2)

Guidance literature:

In dichloromethane; for 720h; Product distribution; autoxidation, daylight; partially identification after esterification with diazomethane;

upstream raw materials:

maleopimaric acid

Downstream raw materials:

methyl ester of levopimaric acid

maleopimaric acid

abietic acid

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