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569371 Sigma-Aldrich

SREBP Processing Inhibitor, Betulin - CAS 473-98-3 - Calbiochem

The SREBP Processing Inhibitor, Betulin, also referenced under CAS 473-98-3, controls the biological activity of SCAP (SREBP cleavage activating protein). This small molecule/inhibitor is primarily used for Cell Signaling applications.

Synonym: Lup-20(29)-ene-3β,28-diol, Sterol Regulatory Element Binding Protein Processing Inhibitor, Betulin, SREBP Processing Inhibitor, Betulin - CAS 473-98-3 - Calbiochem

  • CAS Number 473-98-3

  • Empirical Formula (Hill Notation) C30H50O2

  • Molecular Weight 442.72

  •  MDL number MFCD00016802

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Properties

Quality Level   100
assay   ≥95% (NMR)
form   powder
mfr. no.   Calbiochem®
storage condition   OK to freeze
storage conditions   +2C to +8C
color   off-white
solubility   DMSO: 3.5 mg/mL
shipped in   wet ice
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

Description

General description

A cell-permeable pentacyclic triterpenoid from birch bark extract that interacts with SCAP (SREBP cleavage activating protein) and prevents SREBP (sterol regulatory element-binding protein) Golgi proteolytic activation (1 to 13.55 µM in Rat hepatocytes CRL-1601) via a similar mechanism as oxysterols by inducing the association of SCAP with Insig-1 (insulin-induced gene-1), thereby causing SCAP-SREBPs complex ER retention. Unlike oxysterols, Betulin does not activate LXR to induce concomitant HMGCR (HMG-CoA reductase) degradation and SREBP-1 up-regulation. While both Betulin and HMGCR inhibitor Lovastatin (Cat. No. 438185) inhibit cellular cholesterol synthesis (by ~70% in CRL-1601 cultures with respective compound at 13.55 and 1 µM concentration), only Betulin suppresses cellular fatty acid synthesis (by ~55% at 13.55 µM in CRL-1601). Betulin is shown to exhibit comparable in vivo efficacy as Lovastatin (both dosed at 30 mg/kg/day with chow) in ameliorate high fat/cholesterol diet-induced obesity (% fat/lean tissue ratio increase from non-fat diet mice = 167, 44, and 33 in mice consuming fat diet alone, with Lovastatin, with Betulin, respectively). However, only Betulin is demonstrated to lower fasting blood glucose and insulin levels and reduce fat cell size in white adipose tissue in high fat diet mice. Fatostatin (Cat. No. 341329) in comparison does not target SCAP via sterol-binding site, nor does it induce SCAP binding to Insig-1.

A cell-permeable pentacyclic triterpenoid from birch bark extract that interacts with SCAP (SREBP cleavage activating protein) and prevents SREBP (sterol regulatory element-binding protein) Golgi proteolytic activation (1 to 13.55 µM in Rat hepatocytes CRL-1601) via a similar mechanism as oxysterols by inducing the association of SCAP with Insig-1 (insulin-induced gene-1), thereby causing SCAP-SREBPs complex ER retention. Unlike oxysterols, Betulin does not activate LXR to induce concomitant HMGCR (HMG-CoA reductase) degradation and SREBP-1 up-regulation. While both Betulin and HMGCR inhibitor Lovastatin (Cat. No. 438185) inhibit cellular cholesterol synthesis (by ~70% in CRL-1601 cultures with respective compound at 13.55 and 1 µM concentration), only Betulin suppresses cellular fatty acid synthesis (by ~55% at 13.55 µM in CRL-1601). Betulin is shown to exhibit comparable in vivo efficacy as Lovastatin (both dosed at 30 mg/kg/day with chow) in ameliorating high fat/cholesterol diet-induced obesity (% fat/lean tissue ratio increase from non-fat diet mice = 167, 44, and 33 in mice consuming fat diet alone, with Lovastatin, with Betulin, respectively). However, only Betulin is demonstrated to lower fasting blood glucose and insulin levels and reduce fat cell size in white adipose tissue in high fat diet mice. Fatostatin (Cat. No. 341329) in comparison does not target SCAP via sterol-binding site, nor does it induce SCAP binding to Insig-1.

Packaging

250 mg in Glass bottle

Warning

Toxicity: Toxic (F)

Other Notes

Tang, J.J., et al. 2011. Cell Metab.13, 44.

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CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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