Bio-Connect
Chemical Structure
Chemical Structure
Chemical Structure

OCH [383187-82-4]

Research Use Only
AG-CR1-3593
AdipoGen Life Sciences
CAS Number383187-82-4
Product group Chemicals
Estimated Purity>95%
Molecular Weight704
Price on request
Packing Size
Large volume orders?
Order with a bulk request

Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    OCH [383187-82-4]
  • Delivery Days Customer
    10
  • CAS Number
    383187-82-4
  • Certification
    Research Use Only
  • Estimated Purity
    >95%
  • Hazard Information
    Non-hazardous
  • Molecular Formula
    C39H77NO9
  • Molecular Weight
    704
  • Scientific Description
    Chemical. CAS: 383187-82-4. Formula: C39H77NO9. MW: 704. Truncated analog of alpha-GalCer. iNKT cell glycolipid agonist. Immunosuppressive. Th2 polarizing. Stimulation of NKT with OCH results in release of primarily Th2 cytokine compared to stimulation with alpha-GalCer, which results in release of a mixture of Th1 and Th2 cytokines. Induces stronger interleukin-4 (IL-4) secretion and weaker interferon-gamma (IFN-gamma) secretion than alpha-GalCer both in vitro and in vivo. Inducer of interleukin-10 (IL-10) and suppressor of diabetes. Shown to prevent experimental autoimmune encephalomyelitis (EAE) in mice, an animal model of multiple sclerosis. Has beneficial effects on type I diabetes in NOD mice. Suppressor of collagen-induced arthritis. Might be useful for immunotherapy of transplant rejection. - Truncated analog of alpha-GalCer. iNKT cell glycolipid agonist. Immunosuppressive. Th2 polarizing. Stimulation of NKT with OCH results in release of primarily Th2 cytokine compared to stimulation with alpha-GalCer, which results in release of a mixture of Th1 and Th2 cytokines. Induces stronger interleukin-4 (IL-4) secretion and weaker interferon-gamma (IFN-gamma) secretion than alpha-GalCer both in vitro and in vivo. Inducer of interleukin-10 (IL-10) and suppressor of diabetes. Shown to prevent experimental autoimmune encephalomyelitis (EAE) in mice, an animal model of multiple sclerosis. Has beneficial effects on type I diabetes in NOD mice. Suppressor of collagen-induced arthritis. Might be useful for immunotherapy of transplant rejection.
  • SMILES
    CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COC1OC(CO)C(O)C(O)C1O)C(O)[C@H](O)CCCCC
  • Storage Instruction
    2°C to 8°C,-20°C
  • UNSPSC
    12352200

References

  • A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing TH2 bias of natural killer T cells: K. Miyamoto, et al.; Nature 413, 531 (2001)
  • Synthetic glycolipid OCH prevents insulitis and diabetes in NOD mice: M. Mizuno, et al.; J. Autoimmun. 23, 293 (2004)
  • The clinical implication and molecular mechanism of preferential IL-4 production by modified glycolipid-stimulated NKT cells: S. Oki, et al.; J. Clin. Invest. 113, 1631 (2004)
  • Suppression of collagen-induced arthritis by natural killer T cell activation with OCH, a sphingosine-truncated analog of alpha-galactosylceramide: A. Chiba, et al.; Arthritis Rheum. 50, 305 (2004)
  • Total synthesis of an immunosuppressive glycolipid, (2S,3S,4R)-1-O- (alpha-d-galactosyl)-2- tetracosanoylamino-1,3,4-nonanetriol: K. Murata, et al.; J. Org. Chem. 70, 2398 (2005)
  • Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH: R.M. Ndonye, et al.; J. Org. Chem. 70, 10260 (2005)
  • IFN-gamma–mediated negative feedback regulation of NKT-cell function by CD94/NKG2: T. Ota, et al.; Blood 106, 184 (2005)
  • Modulation of CD1d-restricted NKT cell responses by using N-acyl variants of alpha-galactosylceramides: Y. KO, et al.; PNAS 102, 3383 (2005)
  • alpha-Galactosylceramide therapy for autoimmune diseases: prospects and obstacles: L. Van Kaer; Nat. Rev. Immunol. 5, 31 (2005)
  • Glycolipids for natural killer T cells: P.B. Savage, et al.; Chem. Soc. Rev. 351, 771 (2006)