CAS Number472-15-1
Synonyms(3β)-3-Hydroxylup-20(29)-en-28-oic acid; Gratiolone; betulic acid; Platanol; 3β-Hydroxy-20(29)-lupaene-28-oic Acid; (3b)-3-hydroxylup-20(29)-en-28-oic Acid; Betulinic acid; MFCD00009619; MAIRIN; Melaleucin; ALS-357; EINECS 207-448-8; Betulinic
Molecular FormulaC30H48O3
Molecular Weight456.70
Purity≥98 (HPLC)%
Density1.1±0.1 g/cm3
Boiling Point550.0±33.0 °C at 760 mmHg
Melting Point295-298 °C (dec.) (lit.)
Appearancepowder
EINECS207-448-8
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 472-15-1 |
| Catalog No. | 2A-9009389 |
| Chinese Name | 白桦脂酸 |
| Synonyms | (3β)-3-Hydroxylup-20(29)-en-28-oic acid; Gratiolone; betulic acid; Platanol; 3β-Hydroxy-20(29)-lupaene-28-oic Acid; (3b)-3-hydroxylup-20(29)-en-28-oic Acid; Betulinic acid; MFCD00009619; MAIRIN; Melaleucin; ALS-357; EINECS 207-448-8; Betulinic |
| Molecular Formula | C30H48O3 |
| Molecular Weight | 456.70 |
| Purity | ≥98 (HPLC) |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 550.0±33.0 °C at 760 mmHg |
| Melting Point | 295-298 °C (dec.) (lit.) |
| Appearance | powder |
| Water Solubility | Water solubility: Practically insoluble; soluble i |
| Storage Condition | Store in a sealed container in a ventilated and dr |
| Application | Betulinic acid is a natural pentacyclic triterpenoid compound. It is an inhibitor of eukaryotic topoisomerase I (topoisomerase I) with an IC50 value of 5 μM. It has anti-inflammatory, anti-malarial, a |
| EINECS | 207-448-8 |
| HTC | 2942000000 |
| PubChem ID | 329773146 |
| MDL Number | MFCD00009619 |
| 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 |
| InChI Key | QGJZLNKBHJESQX-FZFNOLFKSA-N |
| NACRES Code | NA.25 |
| UNSPSC | 12352205 |
| Hazard Symbols | Transport |
| MSDS | msds/9389_1_472_15_1.pdf |
| Bioactivity | Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties. Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Anti-infection >> HIV Signaling Pathways >> Autophagy >> Mitophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Natural Products >> Terpenoids and Glycosides Research Areas >> Cancer Research Areas >> Inflammation/Immunology Research Areas >> Infection Target Topoisomerase I:5 μM (IC50) HIV-1:1.4 μM (EC50) In Vitro Betulinic acid is a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and prevents topoisomerase I-DNA interaction[1]. Betulinic acid (10, 20, 40, 80, and 160 µM) significantly suppresses MDA-MB-231 cell viability in a time- and dose-dependent manner after treatment for 24 or 48 h. Betulinic acid (20, 40 µM) causes decrease in Bcl-2 expression of MDA-MB-231 cells. Betulinic acid also induces morphological changes of MDA-MB-231 cells at 20 µM, and leads to ultrastructure changes of MDA-MB-231 cells at 40 µM[2]. Betulinic acid shows anti-HIV activities, with an EC50 of 1.4 µM in acutely infected H9 lymphocytes[4]. In Vivo Betulinic acid (10 and 30 mg/kg, p.o.) significantly abrogates colon shortening, and reduces malondialdehyde (MDA) and lipid hydroperoxide levels in dextran sulfate sodium (DSS)-induced colitis in mice. Betulinic acid (30 mg/kg, p.o.) restores superoxide dismutase (SOD), catalase activity and glutathione (GSH) content to control levels in DSS-induced colitis in mice. Betulinic acid (30 mg/kg, p.o.) also inhibits the DSS-induced increase in inflammatory markers. Betulinic acid (3, 10, 30 mg/kg, p.o.) suppresses acetic acid-induced writhing responses and mustard oil (MO)-induced visceral nociception in mice[3]. Cell Assay CCK-8 is used in the assay. MDA-MB-231 cells are cultured in 96-well plates at a density of 2 × 103 cells/well and then treated with DMSO vehicle or various concentrations of Betulinic acid ranging from 5 µM to 160 µM in 100 µL of medium for the indicated times. After the treatment period, the medium in each well is replaced with 110 µL of medium containing 10 µL of the CCK-8 mixture, and the plates are incubated for 1 h and 30 min at 37°C. The absorbance at a wavelength of 450 nm is measured with a microplate reader[2]. Animal Admin Female Swiss albino mice are administered vehicle (5% v/v DMSO in peanut oil) or Betulinic acid (3, 10 or 30 mg/kg) in vehicle, orally. After 1 h, acetic acid (300 mg/kg) is administered by intraperitoneal route and number of writhing response of each animal is counted for 20 min by an observer who is blind to the treatments. Writhing response is when animal rubs its abdomen on surface of table/floor with elongation of the body and extension of the hind limbs[3]. References [1]. Chowdhury AR, et al. Betulinic acid, a potent inhibitor of eukaryotic topoisomerase I: identification of the inhibitory step, the major functional group responsible and development of more potent derivatives. Med Sci Monit. 2002 Jul;8(7):BR254-65. [2]. Gao Y, et al. Betulinic acid induces apoptosis and ultrastructural changes in MDA-MB-231 breast cancer cells. Ultrastruct Pathol. 2018 Jan-Feb;42(1):49-54. [3]. Kalra J, et al. Betulinic acid alleviates dextran sulfate sodium-induced colitis and visceral pain in mice. Naunyn Schmiedebergs Arch Pharmacol. 2017 Dec 26. [4]. Hashimoto F, et al. Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Bioorg Med Chem. 1997 Dec;5(12):2133-43. Chemical & Physical Properties Density 1.1±0.1 g/cm3 Boiling Point 550.0±33.0 °C at 760 mmHg Melting Point 295-298 °C (dec.)(lit.) Molecular Formula C30H48O3 Molecular Weight 456.700 Flash Point 300.5±21.9 °C Exact Mass 456.360352 PSA 57.53000 LogP 8.94 Vapour Pressure 0.0±3.4 mmHg at 25°C Index of Refraction 1.533 InChIKey QGJZLNKBHJESQX-FZFNOLFKSA-N SMILES C=C(C)C1CCC2(C(=O)O)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C12 Storage condition Store at +4°C |
| Use of | Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties. Properties Articles110 Name betulinic acid Synonym More Synonyms Betulinic acid Biological Activity Description Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties. Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Anti-infection >> HIV Signaling Pathways >> Autophagy >> Mitophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Natural Products >> Terpenoids and Glycosides Research Areas >> Cancer Research Areas >> Inflammation/Immunology Research Areas >> Infection Topoisomerase I:5 μM (IC50) HIV-1:1.4 μM (EC50) References [1]. Chowdhury AR, et al. Betulinic acid, a potent inhibitor of eukaryotic topoisomerase I: identification of the inhibitory step, the major functional group responsible and development of more potent derivatives. Med Sci Monit. 2002 Jul;8(7):BR254-65. [2]. Gao Y, et al. Betulinic acid induces apoptosis and ultrastructural changes in MDA-MB-231 breast cancer cells. Ultrastruct Pathol. 2018 Jan-Feb;42(1):49-54. [3]. Kalra J, et al. Betulinic acid alleviates dextran sulfate sodium-induced colitis and visceral pain in mice. Naunyn Schmiedebergs Arch Pharmacol. 2017 Dec 26. [4]. Hashimoto F, et al. Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Bioorg Med Chem. 1997 Dec;5(12):2133-43. Chemical & Physical Properties Molecular Formula C30H48O3 Exact Mass 456.360352 PSA 57.53000 Index of Refraction 1.533 InChIKey QGJZLNKBHJESQX-FZFNOLFKSA-N |
| Tax Rebate | 9.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 30.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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