ChemicalBook > CAS DataBase List > Betulinic acid

Betulinic acid

Product Name
Betulinic acid
CAS No.
472-15-1
Chemical Name
Betulinic acid
Synonyms
MAIRIN;BETULIC ACID;Betulinic;ALS-357;Betulinic acid technical grade, 90%;(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;Platanol;Ccris 6748;Nsc 113090;Nsc 677578
CBNumber
CB4667160
Molecular Formula
C30H48O3
Formula Weight
456.71
MOL File
472-15-1.mol
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Betulinic acid Property

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).
form 
Solid
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

Hazard Codes 
Xi
Safety Statements 
24/25
WGK Germany 
3
HS Code 
29181985
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P273Avoid release to the environment.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
855057
Product name
Betulinic acid
Purity
technical grade, 90%
Packaging
100mg
Price
$129
Updated
2024/03/01
Sigma-Aldrich
Product number
855057
Product name
Betulinic acid
Purity
technical grade, 90%
Packaging
500mg
Price
$435
Updated
2024/03/01
TCI Chemical
Product number
B2836
Product name
Betulinic Acid
Purity
>97.0%(GC)(T)
Packaging
1g
Price
$640
Updated
2024/03/01
TCI Chemical
Product number
B2836
Product name
Betulinic Acid
Purity
>97.0%(GC)(T)
Packaging
100mg
Price
$139
Updated
2024/03/01
Cayman Chemical
Product number
11686
Product name
Betulinic Acid
Purity
≥97%
Packaging
50mg
Price
$36
Updated
2024/03/01
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Betulinic acid Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Betulinic acid manufacturers

Baoji Guokang Bio-Technology Co., Ltd.
Product
Betulinic acid 472-15-1
Price
US $15.60/KG
Min. Order
1KG
Purity
99%
Supply Ability
100kg
Release date
2021-06-08
Chongqing Zhihe Biopharmaceutical Co., Ltd.
Product
Betulinic acid 472-15-1
Price
US $0.00-0.00/kg
Min. Order
0.10000000149011612kg
Purity
≥98%HPLC
Supply Ability
20tons
Release date
2024-01-03
Wuhan Senwayer Century Chemical Co.,Ltd
Product
Betulinic acid 472-15-1
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99% HPLC
Supply Ability
20 tons
Release date
2022-10-20

472-15-1, Betulinic acid Related Search:

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  • 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
  • BETULIC ACID
  • MAIRIN
  • LUP-20(29)-EN-28-OIC ACID, 3-HYDROXY-, (3B)-
  • Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)-
  • BETULINIC ACID, TECH., 90%
  • BETULICACID: LUP-20(29)-EN-28-OICACID, 3-HYDROXY-, (3B)-,
  • Betulinic
  • 3β-hydroxy-20(29)-lupaene-28-oic acid
  • BETULINIC ACID(P)
  • BETULINIC ACID hplc
  • BETULINIC ACID WITH HPLC
  • Betulinic Acid(98%)
  • Ccris 6748
  • Einecs 207-448-8
  • Lup-20(29)-en-28-oic acid, 3beta-hydroxy- (8ci)
  • Nsc 113090
  • Nsc 677578
  • Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3β)-
  • (+)-(3β)-3-Hydroxylup-20(29)-en-28-oicacid
  • Lupatic Acid
  • ALS-357
  • Gratiolone
  • Melaleucin
  • Platanol
  • Platanolic acid
  • 3β-hydroxy-lup-20(29)-ene-28-oicacid
  • Betulinic acid 472-15-1
  • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
  • Top Quality Betulinic Acid 98% HPLC 472-15-1
  • Betulinic a
  • BetulinicAcid&gt
  • betulinicaci
  • Betulinic acid USP/EP/BP
  • (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
  • Betulinic acid (ALS357
  • (3β)-3-Hydroxylup-20(29)-en-28-oic acid
  • ALS-357|||Lupatic acid|||Betulic acid
  • Betulinic acid (Mairin
  • Betulinic acid-RM
  • 472-15-1
  • 471-15-1
  • Chemopreventive Agents
  • Cancer Research
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  • Anti-proliferative Agents
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  • Pentacyclic Triterpenes
  • Triterpenoids
  • Inhibitors