Methyl abieta-8,11,13-trien-18-oate

Base Information

• Chemical Name: Methyl abieta-8,11,13-trien-18-oate
• CAS No.: 7151-00-0
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.468
• NSC Number: 62514
• DSSTox Substance ID: DTXSID40289635,DTXSID10880714
• Nikkaji Number: J2.997.717H
• Wikidata: Q82027027
• Mol file: 7151-00-0.mol

Synonyms:Methyl abieta-8,11,13-trien-18-oate;METHYL DEHYDROABIETATE;7151-00-0;Dehydroabietic acid methyl ester;Podocarpa-8,11,13-trien-15-oic acid, 13-isopropyl-, methyl ester;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, methyl ester, [1R-(1.alpha.,4a.beta.,10a.alpha.)]-;NSC 81596;NSC 146198;Methyl 8,11,13-abietatrien-18-oate;NCIOpen2_008041;SCHEMBL2603428;DTXSID10880714;DTXSID40289635;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, methyl ester, (1R,4aS,10aR)-;NSC62514;NSC-62514;Phenanthrene-1-carboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethyl-, methyl ester, , [1R-(1.alpha.,4a.beta.,10a.alpha.)]-

Chemical Property of Methyl abieta-8,11,13-trien-18-oate

Chemical Property:

• Vapor Pressure: 2.7E-06mmHg at 25°C
• Boiling Point: 390.2°Cat760mmHg
• Flash Point: 184.3°C
• Density: 1.017g/cm³
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 457

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=CC2=C(C=C1)C3(CCCC(C3CC2)(C)C(=O)OC)C

Technology Process of Methyl abieta-8,11,13-trien-18-oate

There total 40 articles about Methyl abieta-8,11,13-trien-18-oate 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: 100.0%

dehydroabietic acid (1740-19-8) → Methyl dehydroabietate (1235-74-1,1757-97-7,2756-34-5,7151-00-0,10178-27-5,10178-29-7,21699-55-8,24035-60-7)

Guidance literature:

With diazomethane;

DOI:10.1016/j.tetlet.2010.05.090

Reference yield: 100.0%

dehydroabietic acid (1740-19-8) + diazomethyl-trimethyl-silane (18107-18-1) → Methyl dehydroabietate (1235-74-1,1757-97-7,2756-34-5,7151-00-0,10178-27-5,10178-29-7,21699-55-8,24035-60-7)

Guidance literature:

In methanol; benzene;

DOI:10.1016/j.bmcl.2003.08.072

Reference yield: 98.0%

dehydroabietic acid (1740-19-8) + dimethyl sulfate (77-78-1) → Methyl dehydroabietate (1235-74-1,1757-97-7,2756-34-5,7151-00-0,10178-27-5,10178-29-7,21699-55-8,24035-60-7)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 3h;

DOI:10.1016/j.ejmech.2017.07.049

upstream raw materials:

diazomethane

dehydroabietic acid

methanol

methyl ester of levopimaric acid

Downstream raw materials:

methyl (1R,4aS,10aR)-6-acetyl-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenantrene-1-carboxylate

(1R,4aS,10aR)-methyl 6-bromo-1,2,3,4,4a,9,10,10aoctahydro-7-isopropyl-1,4a-dimethylphenanthrene-1-carboxylate

methyl 14-bromodehydroabietate

13-isopropyl-14-acetyl-podocarpatrien-(C)-oic acid-⁽¹⁵⁾-methyl ester

Refernces

• 1、 Tahara,Harigaya,Onda. "Conversion of dehydroabietic acid into a steroid skeleton: Formation of the A ring. II". . p. 1996 - 2000. Retrieved 1975.
• 2、 Chen, Nai-Yuan,Xie, Yu-Lan,Lu, Guo-Dong,Ye, Fang,Li, Xin-Yu,Huang, Yu-Wen,Huang, Ming-Li,Chen, Tie-Yu,Li, Cui-Ping. "Synthesis and antitumor evaluation of (aryl)methyl-amine derivatives of dehydroabietic acid-based B ring-fused-thiazole as potential PI3K/AKT/mTOR signaling pathway inhibitors". . p. 967 - 979. Retrieved 2020/04/24.
• 3、 Li, A-Liang,Yang, Ya-Qun,Wang, Wen-Yan,Liu, Qing-Song,Sun, Yue,Gu, Wen. "Synthesis, cytotoxicity and apoptosis-inducing activity of novel 1H-benzo[d]imidazole derivatives of dehydroabietic acid". . p. 1668 - 1678. Retrieved 2020/07/30.