Basic information
- CAS
472-15-1- Standard SMILES
C=C(C)C1CCC2(C(=O)O)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C12- InChIKey
QGJZLNKBHJESQX-UHFFFAOYSA-N- Molecular formula
- C30H48O3
- Average molar mass
- 456.7 g/mol
- Monoisotopic mass
- 456.36034539
Overview
Lup-20(29)-en-28-oic acid, 3beta-hydroxy- has been reported in Salvia miltiorrhiza, Pongamia pinnata var. pinnata, and other organisms with data available.
Names & identifiers
- Preferred name
- Lup-20(29)-en-28-oic acid, 3beta-hydroxy-
- IUPAC
- 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
- English name
- Betulinic acid
- Molecular formula
- C30H48O3
- Molecular weight
- 456.71
Names & synonyms
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 acid9-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 acidLup-20(29)-en-28-oic acid, 3beta-hydroxy-RefChem:108859038736-77-5Lup-20(29)-en-28-oic acid, 3.beta.-hydroxy-3beta-Hydroxy-20(29)-lupaene-28-oic acidalpha-Betulinic acidbetulinic acid [M+H]+Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3.beta.)-SCHEMBL4143519QGJZLNKBHJESQX-UHFFFAOYSA-N
Show more names
MAIRINBETULIC ACIDBetulinicALS-357Betulinic 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 acidPlatanolCcris 6748Nsc 113090
Properties
Computed structural properties
- XLogP
- 8.2
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 861
Physicochemical properties
- Melting point
- 295 · 295-298 °C (dec.) (lit.)
- alpha
- 25 · D25 +7.5° (c = 0.37 in pyridine)
- Boiling point
- 550 · 550.0±33.0 °C(Predicted)
- Density
- 1.065 · 1.065±0.06 g/cm3(Predicted)
- refractive index
- 7.8 ° · 7.8 ° (C=0.9, Pyridine)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
- pka
- 4.61 · 4.61±0.70(Predicted)
- form
- Solid
- color
- White or off-white
- optical activity
- 20 · [α]20/D +7.8°, c = 0.9 in pyridine
- Merck
- 14 · 14,1190
- Stability
- 2 years · 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.
- Major Application
- food and beverages
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- hs_code
- 29181985
- Signal word
- Warning
- Symbol(GHS)
- GHS06
- hazard_code
- Xi
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H413
- Precautionary statements
- P501-P273
Chemistry & industry
Applications
DescriptionBetulinic 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.
Usesantineoplastic
UsesBetulinic 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) cellsas a treatment to test its anti-tumor properties for cell viability and apoptotic cell death assays in multiple myeloma models
UsesBetulinic 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
General DescriptionBetulinic 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…