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569371 SREBP Processing Inhibitor, Betulin - CAS 473-98-3 - Calbiochem

Overview

Replacement Information

Key Specifications Table

Empirical FormulaCAS #
C₃₀H₅₀O₂ 473-98-3

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569371-250MG
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      Glass bottle 250 mg
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      Description
      OverviewA 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.
      Catalogue Number569371
      Brand Family Calbiochem®
      SynonymsLup-20(29)-ene-3β,28-diol, Sterol Regulatory Element Binding Protein Processing Inhibitor, Betulin
      References
      ReferencesTang, J.J., et al. 2011. Cell Metab. 13, 44.
      Product Information
      CAS number473-98-3
      FormOff-white powder
      Hill FormulaC₃₀H₅₀O₂
      Chemical formulaC₃₀H₅₀O₂
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Purity≥95% by NMR
      Physicochemical Information
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      Safety Information
      R PhraseR: 20/21/22

      Harmful by inhalation, in contact with skin and if swallowed.
      S PhraseS: 22-26-36

      Do not breathe dust.
      In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
      Wear suitable protective clothing.
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Shipped at Ambient Temperature or with Blue Ice or with Dry Ice
      Toxicity Toxic
      Storage +2°C to +8°C
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
      Packaging Information
      Transport Information
      Supplemental Information
      Specifications

      Documentation

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

      Title

      Safety Data Sheet (SDS) 

      SREBP Processing Inhibitor, Betulin - CAS 473-98-3 - Calbiochem Certificates of Analysis

      TitleLot Number
      569371

      References

      Reference overview
      Tang, J.J., et al. 2011. Cell Metab. 13, 44.
      Data Sheet

      Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

      Revision03-October-2011 RFH
      SynonymsLup-20(29)-ene-3β,28-diol, Sterol Regulatory Element Binding Protein Processing Inhibitor, Betulin
      DescriptionA 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.
      FormOff-white powder
      CAS number473-98-3
      Chemical formulaC₃₀H₅₀O₂
      Structure formulaStructure formula
      Purity≥95% by NMR
      SolubilityDMSO (3.5 mg/ml)
      Storage +2°C to +8°C
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
      Toxicity Toxic
      ReferencesTang, J.J., et al. 2011. Cell Metab. 13, 44.