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B8936

Sigma-Aldrich

Betulinic acid

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C30H48O3
Numéro CAS:
472-15-1
Poids moléculaire :
456.70
Numéro CE :
207-448-8
Numéro MDL:
MFCD00009619
Code UNSPSC :
12352205
ID de substance PubChem :
329773146
Nomenclature NACRES :
NA.25

Pureté

≥98% (HPLC)

Forme

powder

Pf

295-298 °C (dec.) (lit.)

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

2-8°C

Chaîne 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

Clé InChI

QGJZLNKBHJESQX-FZFNOLFKSA-N

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Catégories apparentées

Description générale

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..

Application

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Les clients ont également consulté

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SREBP Processing Inhibitor, Betulin The SREBP Processing Inhibitor, Betulin, also referenced under CAS 473-98-3, controls the biological activity of SCAP (SREBP cleavage activating protein). This small molecule/inhibitor is primarily used for Cell Signaling applications.

Sigma-Aldrich

569371

SREBP Processing Inhibitor, Betulin

Hirsutenone ≥95% (LC/MS-ELSD)

Sigma-Aldrich

SMB00096

Hirsutenone

Betulonic acid phyproof® Reference Substance

PHL83839

Betulonic acid

Lupeol analytical standard

Supelco

18692

Lupeol

Oregonin ≥95% (LC/MS-ELSD)

Sigma-Aldrich

SMB00088

Oregonin

Betulin phyproof® Reference Substance

PHL89581

Betulin

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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