Description
Betulinic acid is a pentacyclic lupane-type triterpene derivative of betulin with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation. Betulinic acid is a natural compound found in the herbs of Ziziphus jujuba. It can be used in cosmetics material.
Synonyms
ALS357; ALS 357; ALS-357; Mairin; Lupatic Acid; 3beta-Hydroxy-20(29)-lupaene-28-oic acid
IUPAC Name
(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-carboxylic acid
Molecular Formula
C30H48O3
Canonical SMILES
CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O
InChI
InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
InChIKey
QGJZLNKBHJESQX-FZFNOLFKSA-N
Boiling Point
550.0±33.0 °C at 760 mmHg
Melting Point
295-298 °C (dec.)(lit.)
Flash Point
300.5±21.9 °C
Solubility
In Vitro:
DMSO : 35.71 mg/mL(78.19 mM;Need ultrasonic)
In Vivo:
1.Add each solvent one by one:10% DMSO >> 40%PEG300 >> 5%Tween-80 >> 45% saline
Solubility: 2.5 mg/mL (5.47 mM); Suspended solution; Need ultrasonic
2.Add each solvent one by one:10% DMSO >> 90% (20%SBE-β-CDin saline)
Solubility: 2.5 mg/mL (5.47 mM); Suspended solution; Need ultrasonic
3.Add each solvent one by one:10% DMSO >> 90%corn oil
Solubility: ≥ 2.08 mg/mL (4.55 mM); Clear solution
Appearance
White to off-white Solid
Application
Anti-melanogenic/antitumor/anti-HIV
Storage
4°C, protect from light
* In solvent :
-80°C, 6 months
-20°C, 1 month (protect from light)
Vapor Pressure
0.0±3.4 mmHg at 25°C