Methyl 15-hydroxy-7-oxodehydroabietate

Base Information

• Chemical Name: Methyl 15-hydroxy-7-oxodehydroabietate
• CAS No.: 60188-95-6
• Molecular Formula: C21H28O4
• Molecular Weight: 344.44
• UNII: 8685KPY2HH
• ChEMBL ID: CHEMBL498067
• Nikkaji Number: J587.936A
• Wikidata: Q27269715
• Mol file: 60188-95-6.mol

Synonyms:Methyl 15-hydroxy-7-oxodehydroabietate;60188-95-6;8685KPY2HH;methyl (1R,4aS,10aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylate;Methyl 15-hydroxy-7-oxodehydroabietate, (+)-;Abietic acid, dehydro-14-hydroxy-9-oxo-, methyl ester;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-9-oxo-, methyl ester, (1R,4aS,10aR)-;UNII-8685KPY2HH;CHEMBL498067;AKOS040734668;Q27269715;1-PHENANTHRENECARBOXYLIC ACID, 1,2,3,4,4A,9,10,10A-OCTAHYDRO-7-(1-HYDROXY-1-METHYLETHYL)-1,4A-DIMETHYL-9-OXO-, METHYL ESTER, (1R-(1.ALPHA.,4A.BETA.,10A.ALPHA.))-;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-9-oxo-, methyl ester, (1R-(1alpha,4abeta,10aalpha))-

Chemical Property of Methyl 15-hydroxy-7-oxodehydroabietate

Chemical Property:

• Boiling Point: 477.5±45.0 °C(Predicted)
• PKA: 14.43±0.29(Predicted)
• PSA: 63.60000
• Density: 1.135±0.06 g/cm3(Predicted)
• LogP: 3.73750
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 344.19875937
• Heavy Atom Count: 25
• Complexity: 568

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(C1CC(=O)C3=C2C=CC(=C3)C(C)(C)O)(C)C(=O)OC
• Isomeric SMILES: C[C@]12CCC[C@@]([C@@H]1CC(=O)C3=C2C=CC(=C3)C(C)(C)O)(C)C(=O)OC

Technology Process of Methyl 15-hydroxy-7-oxodehydroabietate

There total 11 articles about Methyl 15-hydroxy-7-oxodehydroabietate 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: 99.0%

C21H28O5 (864060-47-9) → methyl 15-hydroxy-7-oxo-8,11,13-abietatrien-18-oate (60188-95-6)

Guidance literature:

With phosphorous acid trimethyl ester; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2010.05.090

Reference yield: 96.8%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 15-hydroxy-7-oxo-8,11,13-abietatrien-18-oic acid (95416-25-4) → methyl 15-hydroxy-7-oxo-8,11,13-abietatrien-18-oate (60188-95-6)

Guidance literature:

In diethyl ether; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.61.723

Reference yield: 84.0%

15-hydroxydehydroabietic acid methyl ester (29461-23-2) → methyl 15-hydroxy-7-oxo-8,11,13-abietatrien-18-oate (60188-95-6)

Guidance literature:

With tert.-butylhydroperoxide; dipyridinium dichromate; Celite; In benzene; 1.) 10 deg C, 15 min, 2.) 25 deg C, 3 h;

upstream raw materials:

diazomethane

15-hydroxy-7-oxo-8,11,13-abietatrien-18-oic acid

Methyl dehydroabietate

15-hydroxydehydroabietic acid methyl ester

Downstream raw materials:

15-hydroxy-7-oxo-8,11,13-abietatrien-18-oic acid

7β,15-dihydroxydehydroabietic acid methyl ester

((1R,4aS,10aR)-7-Methoxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-yl)-diphenyl-methanol

Refernces

• 1、 Alvarez-Manzaneda,Chahboun,Guardia,Lachkar,Dahdouh,Lara,Messouri. "New route to 15-hydroxydehydroabietic acid derivatives: Application to the first synthesis of some bioactive abietane and nor-abietane type terpenoids". . p. 2577 - 2580. Retrieved 2007/10/03.
• 2、 Krohn, Karsten,Budianto, Emil,Floerke, Ulrich,Hausen, Bjoern M.. "Investigation of the Allergenic Principles from Colophony: Autoxidation, Synthesis, and Sensitization". . p. 911 - 920. Retrieved 2007/10/02.