Betulonaldehyde

Name: Betulonaldehyde
CAS#: 4439-98-9
Chemical Formula: C30H46O2
Exact Mass: 438.3498
Molecular Weight: 438.696
Elemental Analysis: C, 82.14; H, 10.57; O, 7.29

Description: Betulonaldehyde is a pentacyclic triterpenoid and derivative of the cholesterol biosynthesis inhibitor betulin that has been found in Betula. It is active against P. falciparum (IC50 = 3.36 µg/ml) and cytotoxic to NCI H187 lung cancer cells and non-cancerous Vero cells (IC50s = 19.23 and 17.09 µg/ml, respectively). Topical application of betulonaldehyde (1 mg/ear) reduces ear edema induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in mice. It has also been used a precursor in the semisynthesis of C-2 and C-28 betulonic aldehyde derivatives.

IUPAC/Chemical Name: (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carbaldehyde

InChi Key: MHAVMNJPXLZEIG-CNRMHUMKSA-N

InChi Code: InChI=1S/C30H46O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h18,20-23,25H,1,8-17H2,2-7H3/t20-,21+,22-,23+,25+,27-,28+,29+,30+/m0/s1

SMILES Code: C[C@]12[C@@]3(C)[C@]([H])(CC[C@@]1([C@@]4([H])[C@H](C(C)=C)CC[C@@]4(CC2)C=O)[H])[C@]5(C)[C@@]([H])(CC3)C(C(CC5)=O)(C)C

Appearance: Solid powder