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Betulinic acid

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Betulinic acid Basic information

Product Name:
Betulinic acid
Synonyms:
  • Betulinic acid technical grade, 90%
  • 3BETA-HYDROXY-20(29)-LUPENE-28-OIC ACID
  • 3BETA-HYDROXY-20(29)-LUPAENE-28-OIC ACID
  • 3B-HYDROXY-20(29)-LUPENE-28-OIC ACID
  • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentaMethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
  • Birch bark extract/β-Amyrin/betulinic acid
  • 3-B-HYDROXY-LUPA-20(30)-ENE 28-OIC ACID
  • BETULINIC ACID
CAS:
472-15-1
MF:
C30H48O3
MW:
456.71
EINECS:
207-448-8
Product Categories:
  • Tri-Terpenoids
  • sy
  • Pentacyclic Triterpenes
  • chemical reagent
  • Inhibitors
  • Triterpenoids
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Antineoplastic
  • natural product
  • 472-15-1
Mol File:
472-15-1.mol
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Betulinic acid Chemical Properties

Melting point:
295-298 °C (dec.) (lit.)
alpha 
D25 +7.5° (c = 0.37 in pyridine)
Boiling point:
550.0±33.0 °C(Predicted)
Density 
1.065±0.06 g/cm3(Predicted)
refractive index 
7.8 ° (C=0.9, Pyridine)
storage temp. 
2-8°C
solubility 
Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
pka
4.61±0.70(Predicted)
color 
White or off-white
optical activity
[α]20/D +7.8°, c = 0.9 in pyridine
Merck 
14,1190
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
InChIKey
QGJZLNKBHJESQX-FZFNOLFKSA-N
LogP
7.653 (est)
CAS DataBase Reference
472-15-1(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Safety Statements 
24/25
WGK Germany 
3
HS Code 
29181985

MSDS

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Betulinic acid Usage And Synthesis

Description

Betulinic acid (472-15-1) is a natural Lupane triterpenoid from white birch tree (Betula pubescens). Induces apoptosis in a variety of cell lines.1 Induces mitochondrial permeability transition pore opening.2 ?Acts as a chemosensitizer for anticancer drug treatment in chemoresistant colon cancer cell lines.3 Cell permeable.

Chemical Properties

colorless Needles

Uses

antineoplastic

Uses

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

Uses

Betulinic Acid is a natural pentacyclic triterpenoid. Betulinic Acid displays anti-inflammatory and anti-HIV activity. Betulinic Acid selectively induces apoptosis in tumor cells by directly activati ng the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism. Betulinic Acid also exhibits TGR5 agonist activity

Definition

ChEBI: A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium cla iflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties.

General Description

Betulinic acid is a lupane-type triterpene, which can be prepared from betulin via oxidation using chromium oxide (VI). Along with anti-HIV-1 and anti-tumor activity, it also shows other bioactivities such as anti-inflammatory, antibacterial, in vitro antimalarial, anthelmintic and antioxidant activities.

Biological Activity

Natural triterpenoid that displays anti-HIV and antitumor activity. Induces the production of reactive oxygen species (ROS) and activates NF- κ B. Exhibits TRG5 agonist activity (EC 50 = 1.04 μ M).

Biochem/physiol Actions

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.

Anticancer Research

This compound is a pentacyclic triterpene obtained from Betula and Zizyphus species,which shows selective cytotoxicity against human melanoma cells (Shoeb2006). It generates reactive oxygen species, activates MAPK cascade, inhibitstopoisomerase I, inhibits angiogenesis, modulates pro-growth transcriptionalactivators, modulates the activity of aminopeptidase-N, and thereby inducesapoptosis in cancer cells (Desai et al. 2008; Fulda 2008).

storage

+4°C

References

1) Ehrhardt et al. (2004) Betulinic acid-induced apoptosis in leukemia cells; Leukemia, 18 1406 2) Mullauer et al. (2009) Betulinic acid induces cytochrome c release and apoptosis in Bax/Bak-independent, permeability transition pore dependent fashion.; Apoptosis, 14 191 3) Jung et al. (2007) Effect of betulinic acid on anticancer drug-resistant colon cancer cells; Basic Clin. Pharmacol. Toxicol., 101 277

Betulinic acid Supplier

Aktin Chemicals, Inc. Gold
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028-85159085
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info@aktinchem.com
Nanjing Spring & Autumn Biological Engineering Co., Ltd. Gold
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025-84430028 13815430202
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sale02@cqherb.com
J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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jkinfo@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
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4006608290; 18621169109
Email
market03@meryer.com
INTATRADE GmbH
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+49 3493/605464
Email
sales@intatrade.de