Methyl glycyrrhetinate

Base Information

• Chemical Name: Methyl glycyrrhetinate
• CAS No.: 1477-44-7
• Molecular Formula: C₃₁H₄₈O₄
• Molecular Weight: 484.72
• DSSTox Substance ID: DTXSID90933191
• Nikkaji Number: J109.360F
• Wikidata: Q76009819
• Metabolomics Workbench ID: 123164
• ChEMBL ID: CHEMBL1271483
• Mol file: 1477-44-7.mol

Synonyms:Methyl glycyrrhetinate;1477-44-7;18-beta-Glycyrrhetinic acid methyl ester;Methyl glycyrrhetate;Methyl 18-beta-glycyrrhetate;Methyl 18-beta-glycyrrhetinate;CHEMBL1271483;methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate;Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo-, methyl ester;C31H48O4;SCHEMBL13393872;DTXSID90933191;BDBM50058817;AKOS016036158;LS-98305;18-BETA-GLYCYRRHETINICACIDMETHYLESTER;Methyl 3-hydroxy-11-oxoolean-12-en-29-oate;(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-methyl 10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate

Chemical Property of Methyl glycyrrhetinate

Chemical Property:

• Vapor Pressure: 8E-15mmHg at 25°C
• Melting Point: 253～255℃
• Refractive Index: 1.547
• Boiling Point: 559 °C at 760 mmHg
• PKA: 15.11±0.70(Predicted)
• Flash Point: 170.8 °C
• PSA: 63.60000
• Density: 1.11 g/cm³
• LogP: 6.50100
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 484.35526001
• Heavy Atom Count: 35
• Complexity: 981

Purity/Quality:

99% ^*data from raw suppliers

18-B-GLYCYRRHETINIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC3(C(C2(CCC1O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)OC)C)C)C)C
• Isomeric SMILES: C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)(C)C(=O)OC

Technology Process of Methyl glycyrrhetinate

There total 52 articles about Methyl glycyrrhetinate 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%

enoxolone (471-53-4) + methyl iodide (74-88-4) → methyl glycyrrhetinate (1477-44-7,5092-01-3,7558-31-8,10379-74-5,10379-79-0,21857-94-3,118492-16-3)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 24h;

DOI:10.1002/ardp.200900051

Reference yield: 99.54%

enoxolone (471-53-4) + diazomethyl-trimethyl-silane (18107-18-1) → methyl glycyrrhetinate (1477-44-7,5092-01-3,7558-31-8,10379-74-5,10379-79-0,21857-94-3,118492-16-3)

Guidance literature:

In methanol; diethyl ether; at 0 - 20 ℃; for 2h;

DOI:10.1002/anie.201910051

Reference yield: 99.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + enoxolone (471-53-4) → methyl glycyrrhetinate (1477-44-7,5092-01-3,7558-31-8,10379-74-5,10379-79-0,21857-94-3,118492-16-3)

Guidance literature:

In methanol; diethyl ether; at 0 ℃;

DOI:10.1016/j.tet.2008.10.035

upstream raw materials:

enoxolone

18β-glycyrrhetinic acid

methyl iodide

glycyrrhetinic acid 30-methylester

Downstream raw materials:

1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid

C₄₈H₆₆O₁₂

C₅₃H₇₁FO₉

C₅₃H₇₁FO₉

Refernces

• 1、 Zhang, Wei,Wang, He-Ying,Wang, Huai-Xu,Zhu, Zhen-Yuan. "Synthesis and inhibition of α-glucosidase of methyl glycyrrhetinate glycosides". supporting information. p. 1874 - 1880. Retrieved 2019/07/22.
• 2、 -. "Application of acetyl glycyrrhetinic acid methyl ester in preparation of medicine for treating viral hepatitis B". Paragraph 0025; 0028-0031. . Retrieved 2020/11/25.