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ProductsBack/(S)-3-Hydroxybutyric acid [6168-83-8]
Chemical Structure
Chemical Structure
Chemical Structure

(S)-3-Hydroxybutyric acid [6168-83-8]

Research Use Only
AG-CR1-3617
AdipoGen Life Sciences
CAS Number6168-83-8
DownloadMSDS
Product group Chemicals
Estimated Purity>98%
Molecular Weight104.1
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    (S)-3-Hydroxybutyric acid [6168-83-8]
  • Delivery Days Customer
    10
  • CAS Number
    6168-83-8
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Hazard Information
    Warning
  • Molecular Formula
    C4H8O3
  • Molecular Weight
    104.1
  • Scientific Description
    Chemical. CAS: 6168-83-8. Formula: C4H8O3. MW: 104.1. Physiologically insignificant stereoisomer of (R)-3-Hydroxybutyric acid, a key metabolite of the ketolytic pathway. Anticonvulsant. Endogenous inhibitor of histone deacetylases (HDACs) 1, 3 and 4. Ligand of free fatty acid receptor 3 (FFAR3; GPR41) and hydroxycarboxylic acid receptor 2 (HCAR2; GPR109B). NLRP3 inflammasome inhibitor. Prevents K+-efflux and reduces ASC oligomerization and speck formation. - Physiologically insignificant stereoisomer of (R)-3-Hydroxybutyric acid, a key metabolite of the ketolytic pathway. Anticonvulsant. Endogenous inhibitor of histone deacetylases (HDACs) 1, 3 and 4. Ligand of free fatty acid receptor 3 (FFAR3; GPR41) and hydroxycarboxylic acid receptor 2 (HCAR2; GPR109B). NLRP3 inflammasome inhibitor. Prevents K+-efflux and reduces ASC oligomerization and speck formation.
  • SMILES
    C[C@H](O)CC(O)=O
  • Storage Instruction
    2°C to 8°C,RT
  • UNSPSC
    12352200

References

  • Effects of beta-hydroxy butyric acid on insulin binding to its receptor and on autophosphorylation of the receptor: H. Ohtusaka, et al.; Endocrinol. Jpn. 37, 915 (1990)
  • Acetoacetate, acetone, and dibenzylamine (a contaminant in L-(+)-beta-hydroxybutyrate) exhibit direct anticonvulsant actions in vivo: J.M. Rho, et al.; Epilepsia 43, 358 (2002)
  • The direct measurement of 3-beta-hydroxy butyrate enhances the management of diabetic ketoacidosis in children and reduces time and costs of treatment: M. Vanelli, et al.; Diabetes Nutr. Metab. 16, 312 (2003)
  • Detection of cerebral {beta}-hydroxy butyrate, acetoacetate, and lactate on proton MR spectroscopy in children with diabetic ketoacidosis: S.L. Wootton-Gorges, et al.; AJNR 26, 1286 (2005)
  • beta-Hydroxybutyrate activates the NF-kappaB signaling pathway to promote the expression of pro-inflammatory factors in calf hepatocytes: X. Shi, et al.; Cell. Physiol. Biochem. 33, 920 (2014)
  • beta-hydroxybutyrate: Much more than a metabolite: J. C. Newman & E. Verdin; Diab. Res. Clin. Pract. 106, 173 (2014) (Review)
  • BHBA suppresses LPS-induced inflammation in BV-2 cells by inhibiting NF-kappaB activation: S.P. Fu, et al.; Med. Inflamm. 2014, ID983401 (2014)
  • Anti-inflammatory effects of BHBA in both in vivo and in vitro Parkinson's disease models are mediated by GPR109A-dependent mechanisms: S.P. Fu, et al.; J. Neuroinflamm. 12, ID9 (2015)
  • The ketone metabolite beta-hydroxybutyrate blocks NLRP3 inflammasome-mediated inflammatory disease: Y.H. Youm, et al.; Nat. Med. 21, 263 (2015)
  • Taming the inflammasome: M. Levy, et al.; Nat. Med. 21, 213 (2015)