Skip to Content
Merck
All Photos(1)

Documents

B8936

Sigma-Aldrich

Betulinic acid

≥98% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
Molecular Weight:
456.70
EC Number:
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.25

Quality Level

Assay

≥98% (HPLC)

form

powder

mp

295-298 °C (dec.) (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

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

InChI key

QGJZLNKBHJESQX-FZFNOLFKSA-N

Looking for similar products? Visit Product Comparison Guide

General description

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

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Biological activity of betulinic acid: a review
Moghaddam M G, et al.,
Pharmacology & Pharmacy (2012)
Jimin Shin et al.
PloS one, 6(6), e21492-e21492 (2011-07-07)
Signal transducer and activator of transcription 3 (STAT3) is a transcription factor that regulates various cellular processes such as cell survival, angiogenesis and proliferation. In the present study, we examined that betulinic acid (BA), a triterpene from the bark of
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service