Betulin

SKU: orb1304514

Description

Betulin (betulinol) is a naturally abundant lupane-type triterpenoid, primarily sourced from birch bark extractives and sap. It is widely utilized in research for its studied biological activities, with applications in both in vitro and in vivo investigations across fields such as medicinal chemistry and pharmacology.

Research Area

Cell Biology, Metabolism Research

Key Properties

• CAS Number: 473-98-3
• MW: 442.72
• Purity: 99.88%
• Formula: C₃₀H₅₀O₂
• SMILES: CC(=C)[C@@H]1CC[C@]2(CO)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
• Target: Lipid,Apoptosis,Fatty Acid Synthase,Endogenous Metabolite
• Solubility: DMSO:20 mg/mL (45.18 mM)

Bioactivity

• Target IC50:
  SREBP:14.5 μM
• In Vivo:
  Betulin enhances glucose intolerance, augments basal learning performance, and notably ameliorates oxidative stress by significantly restoring SOD activity while reducing MDA levels in the hippocampus. Further, it significantly mitigates serum and hippocampal inflammatory cytokines. Betulin administration also upregulates Nrf2 and HO-1 expressions and inhibits IκB and NF-κB phosphorylations. Overall, Betulin potentially offers cognitive protection against STZ-induced diabetes in rats through the HO-1/Nrf-2/NF-κB pathway.
• In Vitro:
  Betulin (BE) is recognized for its extensive biological and pharmacological benefits, notably its anticancer and chemopreventive capabilities, which have garnered substantial interest. Research indicates that BE impedes the growth of cancer cells across various cancer types, showing a range of antiproliferative effects—from minimal in human erythroleukaemia cells (K562) to pronounced in human neuroblastoma cells (SK-N-AS). Additionally, BE demonstrates marked cytotoxicity towards primary cancer cell cultures from ovarian, cervical carcinoma, and glioblastoma, with IC50 values between 2.8 to 3.4 μM, notably lower than those in established cell lines. Comparative studies of crude birch bark extract, alongside purified betulin and betulinic acid, reveal significant efficacy against human gastric carcinoma (EPG85-257) and human pancreatic carcinoma (EPP85-181), including drug-sensitive and drug-resistant types, indicating their potential as promising therapeutic agents for cancer treatment.
• Cell Research:
  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.

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Trochol, SREBP( K562 cell), Fatty Acid Synthase (FASN), Fatty Acid Synthase, FattyAcidSynthase, EndogenousMetabolite, Endogenous Metabolite, Betulin, betuline, betulinic alcohol, betulinol, Betulol, Apoptosis

Compound Identifiers

PubChem CID

72326