Betulinic acid

Category	Human immunodeficiency Virus (HIV)
CAS	472-15-1
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.

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Product Information

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 Weight	456.70
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
Purity	98%
Density	1.1±0.1 g/cm3
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)
Animal Admin	Female Swiss albinism mice are given orally to the vehicle (5% v/v DMSO in peanut oil) or birch acid (3, 10 or 30 mg/kg) in the vehicle. Acetic acid (300 mg/kg) is administered by the intraperitoneal route and the number of twist responses per animal is counted by observers who ignore the treatment for 20 min.
Complexity	861
Exact Mass	456.36034539
Index Of Refraction	1.533
In Vitro	Chagic acid is a eukaryotic topoisomerase I inhibitor with an IC50 of 5 μM that blocks topoisomerase I-DNA interactions. After 24 or 48 h of treatment, birch acid (10, 20, 40, 8 and 160 μM) significantly inhibits MDA-MB-231 cell viability. Birch acid (20,40 μM) causes a decrease in Bcl-2 expression in MDA-MB-231 cells. Birch acid also induces morphological changes in MDA-MB-231 cells. Chagic acid has shown anti-HIV activity, with EC50 of 1.4 μM in acutely infected H9 lymphocytes.
In Vivo	Birch acid (10 and 30 mg/kg, po) significantly eliminates colon shortening and reduces the levels of malonaldehyde (MDA) and lipid hydroperoxide in dextran sulfate (DSS)-induced colitis in mice. Birch acid (30 mg / kg, orally) also inhibits the increase of DSS-induced inflammatory markers. Birch acid (3, 10, 30 mg/kg, po) inhibits acetic acid-induced twisting reactions and mustard oil (MO)-induced visceral nociception in mice.
PSA	57.53000
Target	Topoisomerase I:5 μM (IC50) HIV-1:1.4 μM (EC50)
Vapor Pressure	0.0±3.4 mmHg at 25°C
XLogP3-AA	8.2