Methyl betulinate

• CAT Number: R067582
• CAS Number: 2259-06-5
• PubChem Substance ID: 73493
• Molecular Formula: C31H50O3
• Molecular Weight: 470.7
• Purity: 95%
• Analysis method: HPLC
• IUPAC Name: methyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• InChI: InChI=1S/C31H50O3/c1-19(2)20-11-16-31(26(33)34-8)18-17-29(6)21(25(20)31)9-10-23-28(5)14-13-24(32)27(3,4)22(28)12-15-30(23,29)7/h20-25,32H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,28-,29+,30+,31-/m0/s1
• InChIKey: XNZIMRUZBOZIBC-JVRMVBBZSA-N
• SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)OC

Methyl betulinate(cas 2259-06-5) is the methyl ester of betulinic acid, a pentacyclic lupane terpene isolated as a constituent of various tree
species, including birch. In Australia, methyl betulinate was isolated from Akania bidwillii (syn. Akania lucens) by Ritchie and
Taylor, University of Sydney in the late 1960s. More recently, methyl betulinate has been reported to be active in a number of
bioassays, in particular against the malaria parasite, Plasmodium falciparum, and against human melanoma cell lines.

Reference

1. Some constituents of Akania lucens. Krajniak E. et al., Aust. J. Chem., 1969, 22, 1331.
2. Erythrocyte membrane modifying agents and the inhibition of Plasmodium falciparum growth: structure-activity
relationships for betulinic acid analogues. Ziegler H.L. et al., Bioorg. Med. Chem. 2004, 12, 119.
3. The potential of triterpenoids in the treatment of melanoma. Sarek J. et al., in Research on melanoma – A
glimpse into current directions and future trends 2011. DOI: 10.5772/19582