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Merck

B8936

Sigma-Aldrich

Betulinic acid

≥98% (HPLC)

Sinónimos:

3β-Hydroxy-20(29)-lupaene-28-oic acid, Lupatic acid, Mairin

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About This Item

Fórmula empírica (notación de Hill):
C30H48O3
Número de CAS:
Peso molecular:
456.70
Número CE:
Número MDL:
Código UNSPSC:
12352205
ID de la sustancia en PubChem:
NACRES:
NA.25

Nivel de calidad

Ensayo

≥98% (HPLC)

Formulario

powder

mp

295-298 °C (dec.) (lit.)

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

temp. de almacenamiento

2-8°C

cadena SMILES

CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O

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

Clave InChI

QGJZLNKBHJESQX-FZFNOLFKSA-N

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Descripción general

Betulinic acid (BetA) is a natural product mostly sourced from the birch tree (Betula spp.). This pentacyclic lupanetype triterpenoid is also associated with other species such as Syzygium spp., Diospyros spp., Ziziphus spp., and Paeonia spp..

Aplicación

Betulinic acid (BetA) has been used:
  • to test its effects as an antiviral agent against Dengue virus (DENV)
  • as a sterol regulatory element-binding protein (SREBP) inhibitor to repress the lipid metabolism and proliferation of clear cell renal cell carcinoma (ccRCC) cells
  • as a treatment to test its anti-tumor properties for cell viability and apoptotic cell death assays in multiple myeloma models

Acciones bioquímicas o fisiológicas

Betulinic acid displays many biological and pharmacological properties such as anticancer, anti-inflammatory, anti-bacterial, anti-human immunodeficiency virus (HIV), and anti-malarial properties.
Betulinic acid, a pentacyclic triterpene, selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Los clientes también vieron

Sami Alakurtti et al.
Bioorganic & medicinal chemistry, 18(4), 1573-1582 (2010-02-02)
Betulin, a naturally occurring abundant triterpene is converted in four steps to 3,28-di-O-acetyllupa-12,18-diene. When various 4-substituted urazoles were oxidized to the corresponding urazines with iodobenzene diacetate in the presence of 3,28-di-O-acetyllupa-12,18-diene, new heterocyclic betulin derivatives were produced. These betulin derivatives
Sasithon Senamontree et al.
PeerJ, 9, e12321-e12321 (2021-11-02)
Controlling cellular functions, including stem cell growth and differentiation, can be the key for the treatment of metabolic disorders, such as type II diabetes mellitus (T2DM). Previously identified as peroxisome proliferator-activated receptor gamma (PPARγ) antagonist, betulinic acid (BA) may have
Franziska B Mullauer et al.
Anti-cancer drugs, 22(3), 223-233 (2011-01-26)
Betulinic acid (BetA) is a plant-derived pentacyclic triterpenoid with potent anticancer capacity that targets the mitochondrial pathway of apoptosis. BetA has a broad efficacy in vitro against prevalent cancer types, including lung, colorectal, prostate, cervix and breast cancer, melanomas, neuroblastomas
Rita C Santos et al.
Bioorganic & medicinal chemistry, 17(17), 6241-6250 (2009-08-14)
A series of new imidazole carboxylic esters (carbamates) and N-acylimidazole derivatives of betulin and betulinic acid (14-29) have been synthesized. The new compounds were screened for in vitro cytotoxicity activity against human cancer cell lines HepG2, Jurkat and HeLa. A
Yan-Fang Sun et al.
Food chemistry, 138(2-3), 1998-2007 (2013-02-16)
Betulinic acid (BA), a natural pentacyclic triterpenoid, was isolated from sour jujube fruits for the first time. An inclusion complex comprising BA and β-cyclodextrin (β-CD) was formed to improve the dissolution of BA, but little is known about its anticancer

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