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Betulin

Item № 11041
CAS № 473-98-3
Purity ≥98%
product image
                (CAS 473-98-3)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     250 mg $25.00 0.00
     500 mg $48.00 0.00
     1 g $90.00 0.00
     5 g $398.00 0.00

Pricing updated 2019-07-23. Prices are subject to change without notice.

Description
Synonyms
  • NSC 4644
  • Trochol

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.1,2 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.3 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.4 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.4 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.4 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.5

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Technical Information
Formal Name
lup-20(29)-ene-3β,28-diol
CAS Number
473-98-3
Synonyms
  • NSC 4644
  • Trochol
Molecular Formula
C30H50O2
Formula Weight
442.7
Purity
≥98%
Formulation
A crystalline solid
SMILES
O[C@H]1CC[C@@]2(C)[C@](CC[C@]3(C)[C@]2([H])CC[C@@]4([H])[C@]3(CC[C@]5(CO)[C@]4([H])[C@H](C(C)=C)CC5)C)([H])C1(C)C
InChI Code
InChI=1S/C28H46O2/c1-18(2)21-10-13-28(17-29)15-14-26(4)22(24(21)28)6-7-23-25(3)11-9-20(30)16-19(25)8-12-27(23,26)5/h19-24,29-30H,1,6-17H2,2-5H3/t19-,20-,21-,22+,23+,24+,25-,26+,27+,28+/m0/s1
InChI Key
XQHSXWXRLYHKSF-VFXNRHIGSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Sakai, J., Nohturfft, A., Goldstein, J.L., et al. Cleavage of sterol regulatory element-binding proteins (SREBPs) at site-1 requires interaction with SREBP cleavage-activating protein. Evidence from in vivo competition studies The Journal of Biological Chemisty 273(10), 5785-5793 (1998).

2. Brown, M.S., and Goldstein, J.L. The SREBP pathway: Regulation of cholesterol metabolism by proteolysis of a membrane-bound transcription factor Cell 89, 331-340 (1997).

3. Smith, L.H., Petrie, M.S., Morrow, J.D., et al. The sterol response element binding protein regulates cyclooxygenase-2 gene expression in endothelial cells Journal of Lipid Research 46, 862-871 (2005).

4. Tang, J.J., Li, J.G., Qi, W., et al. Inhibition of SREBP by a small molecule, betulin, improves hyperlipidemia and insulin resistance and reduces atherosclerotic plaques Cell Metabolism 13(1), 44-56 (2011).

5. Mullauer, F.B., Kessler, J.H., and Medema, J.P. Betulin is a potent anti-tumor agent that is enhanced by cholesterol PLoS One 4(4), (2009).

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