methyl (4aS,6aR,6bS,12aS,14aR,14bR)-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,11,12,14a,14b-dodecahydropicene-4a-carboxylate

Base Information

• Chemical Name: methyl (4aS,6aR,6bS,12aS,14aR,14bR)-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,11,12,14a,14b-dodecahydropicene-4a-carboxylate
• CAS No.: 218600-50-1
• Molecular Formula: C31H46O4
• Molecular Weight: 482.704
• European Community (EC) Number: 606-849-9
• DSSTox Substance ID: DTXSID70705454
• Mol file: 218600-50-1.mol

Synonyms:218600-50-1;Methyl 3,12-dioxoolean-9(11)-en-28-oate;CID 53488152;methyl (4aS,6aR,6bS,12aS,14aR,14bR)-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,11,12,14a,14b-dodecahydropicene-4a-carboxylate;3,12-Dioxo-olean-9(11)-en-28-oic acid methyl ester;DTXSID70705454;AKOS015999232;CS-13924;Methyl3,12-dioxoolean-9(11)-en-28-oate;Q-101074;Methyl (5xi,18alpha)-3,12-dioxoolean-9(11)-en-28-oate;(4aS,6aR,6bS,12aS,14aR,14bR)-methyl-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate;2,2,6a,6b,9,9,12a-Heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester

Chemical Property of methyl (4aS,6aR,6bS,12aS,14aR,14bR)-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,11,12,14a,14b-dodecahydropicene-4a-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 557.072°C at 760 mmHg
• Flash Point: 232.707°C
• PSA: 60.44000
• Density: 1.10
• LogP: 6.70920
• Storage Temp.: 2-8°C
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 482.33960994
• Heavy Atom Count: 35
• Complexity: 1020

Purity/Quality:

97% ^*data from raw suppliers

Methyl 3,12-dioxoolean-9(11)-en-28-oate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(C2C1)C(=O)C=C4C3(CCC5C4(CCC(=O)C5(C)C)C)C)C)C(=O)OC)C
• Isomeric SMILES: C[C@@]12CC[C@]3(CCC(C[C@@H]3[C@H]1C(=O)C=C4[C@]2(CCC5[C@@]4(CCC(=O)C5(C)C)C)C)(C)C)C(=O)OC

Technology Process of methyl (4aS,6aR,6bS,12aS,14aR,14bR)-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,11,12,14a,14b-dodecahydropicene-4a-carboxylate

There total 8 articles about methyl (4aS,6aR,6bS,12aS,14aR,14bR)-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,11,12,14a,14b-dodecahydropicene-4a-carboxylate 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%

methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate (65023-19-0) → methyl 3,12-dioxoolean-9(11)-en-28-oate (218600-50-1)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; for 24h; Inert atmosphere; Reflux;

DOI:10.1021/ol400399x

Reference yield:

methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate (65023-20-3) → methyl 3,12-dioxoolean-9(11)-en-28-oate (218600-50-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / methanolic KOH / 0.5 h / Heating

2: 92 percent / Jones reagent / acetone / 0.17 h / 20 °C

With potassium hydroxide; jones reagent; In acetone; 2: Jones oxidation;

DOI:10.1021/jm0002230

Reference yield:

Oleanolic acid (508-02-1) → methyl 3,12-dioxoolean-9(11)-en-28-oate (218600-50-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

2.2: 24 h / 35 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 24 h / Inert atmosphere; Reflux

With potassium carbonate; 3-chloro-benzenecarboperoxoic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol400399x

upstream raw materials:

methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate

methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate

methyl 3-O-β-acetyl-11-dehydro-12-oxo-18β-oleanolate

oleanolic acid methyl ester

Downstream raw materials:

methyl 2-hydroxymethylene-3,12-dioxoolean-9⁽¹¹⁾-en-28-oate

1,2-dihydro-2-cyano-3,12-dioxooleana-1,9⁽¹¹⁾-dien-28-oic acid methyl ester

bardoxolone methyl

bardoxolone