Methyl betulinate

Base Information

• Chemical Name: Methyl betulinate
• CAS No.: 2259-06-5
• Molecular Formula: C₃₁H₅₀O₃
• Molecular Weight: 470.736
• European Community (EC) Number: 218-857-6
• Nikkaji Number: J109.369J
• Wikidata: Q105337617
• Metabolomics Workbench ID: 130072
• ChEMBL ID: CHEMBL295602
• Mol file: 2259-06-5.mol

Synonyms:betulinic acid methyl ester

Chemical Property of Methyl betulinate

Chemical Property:

• Melting Point: 222-223°C
• Boiling Point: 523.5°Cat760mmHg
• PKA: 15.16±0.70(Predicted)
• Flash Point: 189.5°C
• PSA: 46.53000
• Density: 1.036g/cm³
• LogP: 7.17790
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 470.37599545
• Heavy Atom Count: 34
• Complexity: 876

Purity/Quality:

99% ^*data from raw suppliers

BetulinicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)OC
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C(=O)OC
• Description: Betulinic acid methyl ester is a lupane-type triterpenoid and an esterified version of betulinic acid that has been found in Helicteres hirsuta and has diverse biological activities. It inhibits HIV-1 reverse transcriptase (IC50 = 11 μM). Betulinic acid methyl ester is active against L. braziliensis and T. cruzi (IC50s = 69.9 and 93.3 μM, respectively). It induces melanogenesis in (EC50 = 2.5 μM) and inhibits the growth of B16 2F2 melanoma cells in vitro (IC50 = 4.9 μM). Betulinic acid methyl ester is cytotoxic to SK-LU-1, HepG2, HeLa, SK-MEL-2, and AGS cells (IC50s = 60.84, 77.43, 80.17, 66.17, and 69.94 μg/ml, respectively).

Technology Process of Methyl betulinate

There total 31 articles about Methyl betulinate 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%

Betulinic acid (472-15-1) + diazomethyl-trimethyl-silane (18107-18-1) → methyl betulinate (2259-06-5,25493-95-2)

Guidance literature:

In methanol; benzene;

DOI:10.1248/cpb.47.141

Reference yield: 98.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Betulinic acid (472-15-1) → methyl betulinate (2259-06-5,25493-95-2)

Guidance literature:

diazomethane; Betulinic acid; In diethyl ether; at 0 - 5 ℃;

With acetic acid;

DOI:10.1080/10286020.2011.640774

Reference yield: 95.0%

methanol (67-56-1) + Betulinic acid (472-15-1) → methyl betulinate (2259-06-5,25493-95-2)

Guidance literature:

With diazomethyl-trimethyl-silane; In hexane; toluene; at 20 ℃;

DOI:10.3390/pharmaceutics11080422

upstream raw materials:

betulinic acid

methyl iodide

3β-hydroxy-lup-20(29)-en-28-oic acid

diazomethane

Downstream raw materials:

Acetylmethylbetulinate

betulin

dihydrobetulinic acid

methyl (3β)-3-hydroxy-20-oxo-30-norlupan-28-oate

Refernces

• 1、 Courtney et al.. "". . p. 591. Retrieved 1965.
• 2、 Herz et al.. "-". . p. 3061,3063. Retrieved 1972.
• 3、 Uzenkova,Petrenko,Shakirov,Shul ts,Tolstikov. "Synthesis of 30-amino derivatives of lupane triterpenoids". . p. 692 - 700. Retrieved 2005.
• 4、 Martin, Glenroy D.A.,Reynolds, William F.,Reese, Paul B.. "Investigation of the importance of the C-2 oxygen function in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145". . p. 701 - 710. Retrieved 2004.
• 5、 Eyong, Kenneth O.,Bairy, Guerisson,Eno, Anna A.,Taube, Joseph,Hull, Kenneth G.,Folefoc, Gabriel N.,Foyet, Harquin S.,Romo, Daniel. "Triterpenoids from the stem bark of Vitellaria paradoxa (Sapotaceae) and derived esters exhibit cytotoxicity against a breast cancer cell line". . p. 268 - 277. Retrieved 2018.
• 6、 Rasul, Mohammed Golam. "Synthesis of oxadiazole derivative of pentacyclic triterpenoid and its biological activity". . p. 1143 - 1147. Retrieved 2019/07/12.