Betulin , Analysis standard , 473-98-3

Synonym(s):
Trochol;Betulinol;Betulol;Lup-20(29)-ene-3β,28-diol;Lup-20(29)-ene-3β,28-diol, Sterol Regulatory Element Binding Protein Processing Inhibitor, Betulin

CAS NO.：473-98-3

Empirical Formula: C30H50O2

Molecular Weight: 442.72

MDL number: MFCD00016802

EINECS: 207-475-5

PRODUCT Properties

• Melting point: 256-257 °C(lit.)
• Boiling point: 493.26°C (rough estimate)
• alpha: D15 +20° (c = 2 in pyridine)
• Density: 0.9882 (rough estimate)
• refractive index: 1.5045 (estimate)
• storage temp.: 2-8°C
• solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• form: Off-white powder
• pka: 15.10±0.10(Predicted)
• color: Pale Brown to Beige
• optical activity: +2015 (c 6, pyridine)
• Merck: 14,1189
• Stability: Hygroscopic
• InChIKey: FVWJYYTZTCVBKE-ROUWMTJPSA-N
• LogP: 8.607 (est)

Description and Uses

Sterol regulatory element binding protein 2 (SREBP-2) regulates cholesterol synthesis by activating the transcription of genes for HMG-CoA reductase and other enzymes of the cholesterol synthetic pathway. When cellular sterol levels are high, SREBP is bound by SCAP and Insig to ER membranes as a glycosylated precursor protein. Upon cholesterol depletion, the protein is cleaved to its active form and translocated into the nucleus to stimulate transcription of genes involved in the uptake and synthesis of cholesterol. Betulin, the precursor of betulinic acid, is a pentacyclic triterpene found in the bark of birch trees. Betulin inhibits the SREBP-driven pathway of cholesterol and fatty acid biosynthesis by promoting SCAP–Insig binding which prevents the activation and release of SREBP-2 from the ER. At 15-30 mg/kg/day, betulin has been shown to decrease lipid levels and increase insulin sensitivity in mice fed a western-type diet. In an atherosclerosis disease model, 30 mg/kg/day betulin can reduce the size and improve the stability of atherosclerotic plaques in LDLR-knockout mice. At 2.5-5 μg/ml betulin, in combination with cholesterol, demonstrates anticancer effects by inducing apoptosis in Jurkat cells, A549 lung carcinoma cells, and HeLa cervical carcinoma cells.

birch bark extract is described as having anti-irritant and antiseptic properties, and effective in acne treatment. It is used to make sunburn products, soothing lotions, and aftershaves. The oil is astringent and is mainly used for its curative effects, especially in cases of acne and eczema. In folkloric medicine, birch bark extract was considered good for bathing skin eruptions. Destructive distillation of the bark’s white epidermis yields an empyreumatic oil known as oil of birch tar, Oleum rusci, or dagget. This is a thick, bituminous, brownish-black liquid with a pungent, balsamic odor. It contains a high percentage of methylsalicilate, creosol, and guaiacol and is almost identical to wintergreen oil.

Safety

• Symbol(GHS): GHS08
• Signal word: Warning
• Hazard statements: H371
• Precautionary statements: P260-P264-P270-P308+P311-P405-P501
• Hazard Codes: Xn,Xi
• Risk Statements: 36/37/38-20/21/22-68/20/21/22-68
• Safety Statements: 36/37-36-26
• WGK Germany: 3
• RTECS: OK5755000
• HS Code: 29181985