CAS Number473-98-3
SynonymsBetuline; Lup-20(30)-ene-3b,28-diol; TROCHOL; 3b-Lup-20(29)-ene-3,28-diol; Betulin; BETULOL; (3β)-Lup-20(29)-ene-3,28-diol; MFCD00016802; Lup-20(29)-ene-3b,28-diol; betula camphor; BETULINOL; EINECS 207-475-5; Lup-20(30)-ene-3β,28-diol
Molecular FormulaC30H50O2
Molecular Weight442.72
Purity≥98%
Density1.0±0.1 g/cm3
Boiling Point522.3±23.0 °C at 760 mmHg
Melting Point256-257 °C (lit.)
Appearancepowder
EINECS207-475-5
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 473-98-3 |
| Catalog No. | 2A-9009390 |
| Chinese Name | 白桦脂醇； 桦木醇 |
| Synonyms | Betuline; Lup-20(30)-ene-3b,28-diol; TROCHOL; 3b-Lup-20(29)-ene-3,28-diol; Betulin; BETULOL; (3β)-Lup-20(29)-ene-3,28-diol; MFCD00016802; Lup-20(29)-ene-3b,28-diol; betula camphor; BETULINOL; EINECS 207-475-5; Lup-20(30)-ene-3β,28-diol |
| Molecular Formula | C30H50O2 |
| Molecular Weight | 442.72 |
| Purity | ≥98 |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 522.3±23.0 °C at 760 mmHg |
| Melting Point | 256-257 °C (lit.) |
| Appearance | powder |
| Storage Condition | Store sealed at 2-8°C, placed in a ventilated, dry |
| Application | Betulin is a SREBP inhibitor with an IC50 value of 14.5 μM in K562 cells. |
| EINECS | 207-475-5 |
| HTC | 29181985 |
| PubChem ID | 57653970 |
| MDL Number | MFCD00016802 |
| SMILES | [H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@@]5(CO)CC[C@@H](C(C)=C)[C@]25[H] |
| InChI | 1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1 |
| InChI Key | FVWJYYTZTCVBKE-ROUWMTJPSA-N |
| NACRES Code | NA.22 |
| UNSPSC | 12352002 |
| Hazard Symbols | Transport |
| MSDS | msds/9390_1_473_98_3.pdf |
| Bioactivity | Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Natural Products >> Terpenoids and Glycosides Target IC50: 14.5 μM (SREBP, K562 cell), 74.1 μM (SREBP, HeLa cell), 17.1 μM (SREBP, GOTO cell)[1], 21.09 μM (SREBP, 181P cell), 20.62 μM (SREBP, HeLa cell)[2] In Vitro Betulin (BE) displays a broad spectrum of biological and pharmacological properties, among which the anticancer and chemopreventive activity attract most of the attention. BE has been shown to elicit anticancer properties by inhibiting cancer cells growth. BE has exhibited quite a different range of its antiproliferative activity, depending on cancer cells type, from a weak inhibition of cell proliferation in human erythroleukaemia cell line (K562) to a strong inhibition in human neuroblastoma cells (SK-N-AS), where the effect has been most pronounced. Additionally, BE has also been found to express significant cytotoxicity against primary cancer cells cultures isolated from tumour samples obtained from ovarian, cervical carcinoma, and glioblastoma patients, where the IC50 values have ranged from 2.8 to 3.4 μM, being significantly lower, when compared with established cell lines[1]. The cytotoxic activity of crude birch bark extract and purified betulin and betulinic acid towards human gastric carcinoma (EPG85-257) and human pancreatic carcinoma (EPP85-181) drug-sensitive and drug-resistant (daunorubicin and mitoxantrone) cell lines are compared. Significant differences in sensitivity between cell lines depending on the compound used are shown, suggesting that both betulin and betulinic acid can be considered as a promising leads in the treatment of cancer[2]. In Vivo Betulin could improve glucose intolerance and modify basal learning performance. Treatment with betulin significantly restores SOD activity and decreased MDA content in hippocampus. Betulin also markedly reduces the contents of inflammatory cytokines in serum and hippocampus. Furthermore, administration of BE effectively upregulated the expressions of Nrf2, HO-1 and blocked the phosphorylations of IκB, NF-κB. In summary, BE might exhibit protective effect on cognitive decline in STZ-induced diabetic rats through HO-1/Nrf-2/ NF-κB pathway[3]. Cell Assay Chemoresistance is tested using a proliferation assay based on sulphorhodamine B staining. Briefly, 800 cells per well are seeded in triplicate in 96-well plates. After attachment for 24 h, substances are added in dilution series for a 5-day incubation, before SRB staining is performed. Incubation is terminated by replacing the medium with 10% trichloroacetic acid, followed by further incubation at 4°C for 1h. Subsequently, the plates are ished five times with water and stained by adding 100 μL 0.4% SRB in 1% acetic acid for 10 min at room temperature. Ishing the plates five times with 1% acetic acid eliminated unbound dye. After air-drying and re-solubization of the protein bound dye in 10 mM Tris-HCl (pH=8.0), absorbance is read at 562 nm[2]. Animal Admin Rats: The rats are randomLy divided into five groups (n=10): control group, STZ group, STZ+betulin (20 mg/kg) group, STZ+betulin (40 mg/kg) group. Diabetes is induced by STZ (30 mg/kg, i.p.) dissolved in citrate buffer (pH 4.4, 0.1 M) using 1 mL syringe for 4 weeks, meanwhile the control rats receive an equal volume of citrate buffer. Thereafter, the diabetic rats are treated with betulin (20 mg/kg, 40 mg/kg) for another 4 weeks[3]. References [1]. Król SK, et al. Comprehensive review on betulin as a potent anticancer agent. Biomed Res Int. 2015;2015:584189. [2]. Drag M, et al. Comparision of the Cytotoxic Effects of Birch Bark Extract, Betulin and Betulinic Acid Towards Human Gastric Carcinoma and Pancreatic Carcinoma Drug-sensitive and Drug-Resistant Cell Lines. Molecules. 2009 Apr 24;14(4):1639-51. [3]. Ma C, et al. Protective effect of betulin on cognitive decline in streptozotocin (STZ)-induced diabetic rats. Neurotoxicology. 2016 Dec;57:104-111. Chemical & Physical Properties Density 1.0±0.1 g/cm3 Boiling Point 522.3±23.0 °C at 760 mmHg Melting Point 256-257 °C(lit.) Molecular Formula C30H50O2 Molecular Weight 442.717 Flash Point 210.9±17.2 °C Exact Mass 442.381073 PSA 40.46000 LogP 9.01 Vapour Pressure 0.0±3.1 mmHg at 25°C Index of Refraction 1.525 InChIKey FVWJYYTZTCVBKE-ROUWMTJPSA-N SMILES C=C(C)C1CCC2(CO)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C12 Storage condition 2-8°C |
| Use of | Properties Articles47 Name betulin Synonym More Synonyms Betulin Biological Activity Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Natural Products >> Terpenoids and Glycosides In Vitro Betulin (BE) displays a broad spectrum of biological and pharmacological properties, among which the anticancer and chemopreventive activity attract most of the attention. BE has been shown to elicit anticancer properties by inhibiting cancer cells growth. BE has exhibited quite a different range of its antiproliferative activity, depending on cancer cells type, from a weak inhibition of cell proliferation in human erythroleukaemia cell line (K562) to a strong inhibition in human neuroblastoma cells (SK-N-AS), where the effect has been most pronounced. Additionally, BE has also been found to express significant cytotoxicity against primary cancer cells cultures isolated from tumour samples obtained from ovarian, cervical carcinoma, and glioblastoma patients, where the IC50 values have ranged from 2.8 to 3.4 μM, being significantly lower, when compared with established cell lines[1]. The cytotoxic activity of crude birch bark extract and purified betulin and betulinic acid towards human gastric carcinoma (EPG85-257) and human pancreatic carcinoma (EPP85-181) drug-sensitive and drug-resistant (daunorubicin and mitoxantrone) cell lines are compared. Significant differences in sensitivity between cell lines depending on the compound used are shown, suggesting that both betulin and betulinic acid can be considered as a promising leads in the treatment of cancer[2]. References [1]. Król SK, et al. Comprehensive review on betulin as a potent anticancer agent. Biomed Res Int. 2015;2015:584189. [2]. Drag M, et al. Comparision of the Cytotoxic Effects of Birch Bark Extract, Betulin and Betulinic Acid Towards Human Gastric Carcinoma and Pancreatic Carcinoma Drug-sensitive and Drug-Resistant Cell Lines. Molecules. 2009 Apr 24;14(4):1639-51. [3]. Ma C, et al. Protective effect of betulin on cognitive decline in streptozotocin (STZ)-induced diabetic rats. Neurotoxicology. 2016 Dec;57:104-111. Chemical & Physical Properties Molecular Formula C30H50O2 Exact Mass 442.381073 PSA 40.46000 Index of Refraction 1.525 InChIKey FVWJYYTZTCVBKE-ROUWMTJPSA-N |
| 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 If applicable, the chemical meets the requirements of the Regulations on the Safety Management of Hazardous Chemicals (adopted by the State Council on January 9, 2002). |
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