Methyl ursolate

Base Information

• Chemical Name: Methyl ursolate
• CAS No.: 32208-45-0
• Molecular Formula: C₃₁H₅₀O₃
• Molecular Weight: 470.736
• European Community (EC) Number: 250-953-3
• DSSTox Substance ID: DTXSID60348374
• Nikkaji Number: J120.805E
• Wikidata: Q82123127
• Metabolomics Workbench ID: 129889
• ChEMBL ID: CHEMBL260673
• Mol file: 32208-45-0.mol

Synonyms:methyl ursolate

Chemical Property of Methyl ursolate

Chemical Property:

• Melting Point: 286 °C
• Boiling Point: 526.1 °C at 760 mmHg
• PKA: 15.15±0.70(Predicted)
• Flash Point: 190.7 °C
• PSA: 46.53000
• Density: 1.07 g/cm ³
• LogP: 7.17790
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 470.37599545
• Heavy Atom Count: 34
• Complexity: 889

Purity/Quality:

98%Min ^*data from raw suppliers

UrsolicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1C)C)C(=O)OC
• Isomeric SMILES: C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)C(=O)OC

Technology Process of Methyl ursolate

There total 33 articles about Methyl ursolate 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%

diazomethane (186581-53-3,908094-01-9,334-88-3) + ursolic acid (77-52-1) → methyl (3β)-3-hydroxyurs-12-en-28-oate (915-32-2,26532-60-5,32208-45-0,74984-68-2,94482-47-0,121468-30-2)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 ℃;

DOI:10.1016/j.bioorg.2019.103054

Reference yield: 99.0%

ursolic acid (77-52-1) + methyl iodide (74-88-4) → methyl (3β)-3-hydroxyurs-12-en-28-oate (915-32-2,26532-60-5,32208-45-0,74984-68-2,94482-47-0,121468-30-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c4ob00679h

Reference yield: 97.0%

ursolic acid (77-52-1) + diazomethyl-trimethyl-silane (18107-18-1) → methyl (3β)-3-hydroxyurs-12-en-28-oate (915-32-2,26532-60-5,32208-45-0,74984-68-2,94482-47-0,121468-30-2)

Guidance literature:

In methanol; benzene;

DOI:10.1248/cpb.47.141

upstream raw materials:

diazomethane

ursolic acid

dimethyl sulfate

cynarasaponin A methyl ester

Downstream raw materials:

3α-hydroxyurs-12-en-28-oic acid methyl ester

α-amyrin

3β-O-[4-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl]ursolic-28-methyl ester

methyl (3β,13ζ)-3-(benzoyloxy)-12-oxours-9(11)-en-28-oate

Refernces

• 1、 Elsbaey, Marwa,Mwakalukwa, Rogers,Shimizu, Kuniyoshi,Miyamoto, Tomofumi. "Pentacylic triterpenes from Lavandula coronopifolia: structure related inhibitory activity on α-glucosidase". . p. 1436 - 1444. Retrieved 2019/08/26.
• 2、 Fontana, Gianfranco,Bruno, Maurizio,Notarbartolo, Monica,Labbozzetta, Manuela,Poma, Paola,Spinella, Alberto,Rosselli, Sergio. "Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement". . . Retrieved 2019/06/19.