CAS 4439-98-9 Betulonal (HCID 473111)

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Basic information

CAS: 4439-98-9
Standard SMILES: C=C(C)[C@@H]1CC[C@]2(C=O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
InChIKey: MHAVMNJPXLZEIG-CNRMHUMKSA-N
Molecular formula: C30H46O2
Average molar mass: 438.7 g/mol
Monoisotopic mass: 438.34978071

Overview

Betulonal has been reported in Phoradendron reichenbachianum, Boronia gracilipes, and Quercus suber with data available.

Names & identifiers

Preferred name: Betulonal
IUPAC: (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carbaldehyde
English name: betulonic aldehyde
Molecular formula: C30H46O2
Molecular weight: 438.69

Names & synonyms

betulonaldehydeBetulonal4439-98-9DTXSID301346531(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carbaldehyde(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta(a)chrysene-3a-carbaldehydeBetulonolic aldehydeRefChem:119571DTXCID301775194Betulonic Aldehyde3-oxolup-20(29)-en-28-alBetulonic aldehyde, betulonal

Show more names

lup-28-al-20(29)-en-3-oneLup-20(29)-en-28-al, 3-oxo-Betulonic aldehyde, 97%, Semi-Synthetic(1R,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxoicosahydro-3aH-cyclopenta[a]chrysene-3a-carbaldehyde

(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carbaldehydeLup-20(29)-en-28-al-3-oneCHEMBL297478orb1740236SCHEMBL5956547SCHEMBL9353806MHAVMNJPXLZEIG-CNRMHUMKSA-N3,28-Dideoxy-3,28-dioxobetulin

Properties

Computed structural properties

XLogP: 7.8
Topological polar surface area: 34.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 32
Formal charge: 0
Complexity: 855

Physicochemical properties

Melting point: 165 · 165-166 °C
Boiling point: 511.7 · 511.7±33.0 °C(Predicted)
Density: 1.037 · 1.037±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
solubility: 10 mg/ml · DMF: 10 mg/ml
form: A crystalline solid

Chemistry & industry

Applications · 1 item

UsesBetulonaldehyde is a pentacyclic triterpenoid that can be isolated from Diospyros filipendula. Betulonaldehyde has antiplasmodial activity (IC50: 3.36μg/mL). Betulonaldehyde has cytotoxic to NCI H187 lung cancer cells and non-cancerous Vero cells (IC50s: 19.23 and 17.09 μg/mL, respectively). Betulonaldehyde inhibits Phorbol 12-myristate 13-acetate (HY-18739) induced inflammation in mice[1][2].