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

569371
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₃₀H₅₀O₂ 473-98-3

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      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 Image
          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

          SDS

          Title

          Safety Data Sheet (SDS) 

          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 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.