Betulin structure
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Common Name | Betulin | ||
|---|---|---|---|---|
| CAS Number | 473-98-3 | Molecular Weight | 442.717 | |
| Density | 1.0±0.1 g/cm3 | Boiling Point | 522.3±23.0 °C at 760 mmHg | |
| Molecular Formula | C30H50O2 | Melting Point | 256-257 °C(lit.) | |
| MSDS | USA | Flash Point | 210.9±17.2 °C | |
| Symbol |
GHS08 |
Signal Word | Warning | |
Use of BetulinBetulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | betulin |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. |
|---|---|
| Related Catalog | |
| 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 |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| 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 |
This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.
This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| Symbol |
GHS08 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H371 |
| Precautionary Statements | P260 |
| Hazard Codes | Xi: Irritant; |
| Risk Phrases | R36/37/38 |
| Safety Phrases | S36/37-S36-S26 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | OK5755000 |
| HS Code | 29181985 |
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 7 | |
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| DownStream 9 | |
This table shows customs‑related data including HS‑code, tariff and regulatory conditions for import and export.
| HS Code | 29181985 |
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This table lists relevant public references with title, journal and publication metadata for this compound.
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A new cycloartane nortriterpenoid from stem and leaf of Quercus variabilis.
J. Asian Nat. Prod. Res. 15(9) , 1050-4, (2013) A new compound 3-acetyloxy-epicycloeucalenol-24-one (1), with 11 known compounds 3α-acetyloxy-4α,14α-dimethyl-9β,19-cycloergost-24-oic acid (2), 3-epicycloeucalenol (3), 3-epicycloeucalenyl-24-one (4)... |
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Antidiabetic property of Aerva lanata (L.) Juss. ex Schult. is mediated by inhibition of alpha glucosidase, protein glycation and stimulation of adipogenesis.
J. Diabetes 7 , 548-61, (2015) Diabetes is the leading cause of morbidity and mortality, with a number currently diagnosed as high as 371 million. Plant-based therapy could be an ideal choice because of fewer side-effects and wider... |
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alpha-Glucosidase inhibitory activity of triterpenoids from Cichorium intybus.
J. Nat. Prod. 71 , 910-3, (2008) Two new triterpenoids, 18alpha,19beta-20(30)-taraxasten-3beta,21alpha-diol (cichoridiol) (1) and 17-epi-methyl-6-hydroxyangolensate (intybusoloid) (2), were obtained from the methanolic extract of see... |
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| Betuline |
| Lup-20(30)-ene-3b,28-diol |
| TROCHOL |
| 3b-Lup-20(29)-ene-3,28-diol |
| Betulin |
| BETULOL |
| (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxyméthyl)-5a,5b,8,8,11a-pentaméthyl-1-(1-propèn-2-yl)icosahydro-1H-cyclopenta[a]chrysén-9-ol |
| (3β)-Lup-20(29)-ene-3,28-diol |
| MFCD00016802 |
| Lup-20(29)-ene-3b,28-diol |
| betula camphor |
| BETULINOL |
| (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-ol |
| EINECS 207-475-5 |
| Lup-20(30)-ene-3β,28-diol |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What are the uses of betulin? |
| A: Main uses of betulin: Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. |
| Q: What is the boiling point of betulin? |
| A: Boiling point of betulin is 522.3±23.0 °C at 760 mmHg. |
| Q: What is the LogP of betulin? |
| A: LogP of betulin is 9.01. |
| Q: What is the safety information for betulin? |
| A: Safety information for betulin: S36/37-S36-S26. |
| Q: What are the downstream products of betulin? |
| A: Related downstream products(CAS) of betulin: 472-15-1;13159-28-9;4481-62-3;38736-77-5;488-23-3;2131-43-3;486-34-0;582-16-1;545-47-1. |
| Q: What are the storage conditions for betulin? |
| A: Storage conditions for betulin: 2-8°C. |
| Q: What is the SMILES notation of betulin? |
| A: SMILES notation of betulin is C=C(C)C1CCC2(CO)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C12. |
| Q: What are the upstream materials of betulin? |
| A: Related upstream materials(CAS) of betulin: 1721-69-3;2259-06-5;472-15-1;13159-28-9;292638-85-8;27686-35-7;107-13-1. |
| Q: What is the molecular weight of betulin? |
| A: Molecular weight of betulin is 442.717. |
| Q: What is the CAS number of betulin? |
| A: CAS number of betulin is 473-98-3. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| BioBioPha |
| Dayang Chem (Hangzhou) Co., Ltd. |
| naturewill |
| Henan Tianfu Chemical Co., Ltd. |
| Zhongshan Xingrui Chemical Co. , Ltd. |