| Identification | Back Directory | [Name]
D-ERYTHRO-SPHINGOSINE | [CAS]
123-78-4 | [Synonyms]
CERAMIDE
SPHINGOSINE
CEREBROSIDE
Sphingenine
BRAIN, BOVINE
D-SPHINGOSINE
4-SPHINGENINE
EGG SPHINGOSINE
C18-Sphingosine
BRAIN SPHINGOSINE
Erythrosphingosine
trans-4-Sphingenine
Sphingosine (d18:1)
erythro-4-Sphingenine
D-ERYTHRO-SPINGHOSINE
D-ERYTHRO-SPHINGOSINE
D-SPHINGOSINE (BOVINE)
SPHINGOSINE, C18 CHAIN
SPHINGOSINE, D-ERYTHRO
TRANS D-THREO-SPHINGOSINE
D-erythro-Sphingosine(DES)
D-erythro-Sphingosine C-18
D-erythro-Sphingosine, 99+%
TRANS D-ERYTHRO-SPHINGOSINE
D-ERYTHRO-SPHINGASINE (EGG)
D-ERYTHRO-SPHINGOSINE, BOVINE
2-AMINO-4-OCTADECENE-1,3-DIOL
2-aminooctadec-4-ene-1,3-diol
D-ERYTHRO-SPHINGOSINE (BRAIN)
D-erythro-Sphingosine (synthetic)
D-erythro-Sphingosine, synthetical
D-ERYTHRO-SPHINGOSINE, BOVINE BRAIN
(2S,3R,E)-2-Amino-4-octadecene-1,3-diol
(2S,3R,E)-2-aMinooctadec-4-ene-1,3-diol
(E,2S,3R)-2-Aminooctadec-4-Ene-1,3-Diol
D-erythro-Sphingosine, synthetical, 99+%
D-ERYTHRO-SPHINGOSINE, 99+%, SYNTHETICAL
(2S,3R,4E)-2-amino-4-Octadecene-1,3-diol
D-SPHINGOSINE FROM BOVINE BRAIN &
D-ERYTHRO-SPHINGOSINE (1,2-13C2, 1,1-D2)
D-SPHINGOSINE FROM BOVINE BRAIN*CEREBROS IDES
TRANS-D-ERYTHRO-2-AMINO-4-OCTADECENE-1,3-DIOL
D-SPHINGOSINE FROM BOVINE BRAIN SPHINGOMYELIN*
D-Sphingosine (from bovine brain sphinogomyelin)
4-Sphingenine, trans-D-erythro-2-Amino-4-octadecene-1,3-diol
D-Sphingosine: trans-D-erythro-2-Amino-4-octadecene-1,3-diol | [EINECS(EC#)]
204-651-3 | [Molecular Formula]
C18H37NO2 | [MDL Number]
MFCD00036751 | [MOL File]
123-78-4.mol | [Molecular Weight]
299.49 |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
81-82 °C
| [Boiling point ]
440.8°C (rough estimate) | [density ]
0.9758 (rough estimate) | [refractive index ]
1.5000 (estimate) | [storage temp. ]
−20°C
| [solubility ]
chloroform: 20 mg/mL, clear, colorless to very faintly yellow
| [form ]
Powder or Waxy Solid | [pka]
11.80±0.45(Predicted) | [color ]
White to cream | [Stability:]
Stable. Incompatible with strong acids, strong bases, strong oxidizing agents. | [biological source]
synthetic | [Merck ]
14,8747 | [BRN ]
1727294 | [InChIKey]
WWUZIQQURGPMPG-KRWOKUGFSA-N | [CAS DataBase Reference]
123-78-4 |
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Uses]
Selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes; natural isomer of sphingosine | [Biological Activity]
Inhibitor of protein kinase C and calmodulin-dependent enzymes, but may stimulate mast cells by activation of protein kinase C. | [Description]
Sphingosine (123-78-4) is an inhibitor of protein kinase C (IC50 = 1-3 μM).1 It is abundant in cell membranes and is an important mediator in various biochemical pathways.2-4 | [Definition]
cerebroside: Any one of a class ofglycolipids in which a single sugarunit is bound to a sphingolipid. The most commoncerebrosides are galactocerebrosides,containing the sugar group galactose;they are found in the plasma membranesof neural tissue and are abundantin the myelin sheaths ofneurones. | [General Description]
Sphingosine (d18:1) is a spingoid base present in plant and animals. It has 2-amino-1,3-diol functionality and its extraction from animal tissue is laborious. Sphingosine (d18:1) synthesis is performed by chirospecific method using D-galactose. | [Biochem/physiol Actions]
A constituent of cell membranes. Precursor of ceramide. Selective inhibitor of protein kinase C, but does not inhibit protein kinase?A or myosin light chain kinase. Inhibitor of calmodulin-dependent enzymes. | [storage]
Store at -20°C | [Purification Methods]
D-Sphingosine is purified by recrystallisation from EtOAc, Et2O or pet ether (60-80o). It is insoluble in H2O but is soluble in Me2CO, EtOH and MeOH. It has IR bands at 1590 and 875 cm-1, and is characterised as the tribenzoate m 122-123o (from 95% EtOH). [Tipton Biochemical Preparations 9 127 1962.] | [References]
1) Merrill et al., (1989) Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds; Biochemistry, 28 3138
2) Ohanian and Ohanian (2001) Sphingolipids in mammalian cell signaling; Cell. Mol. Life Science, 58 2053
3) Ruvolo (2003) Intracellular signal transduction pathways activated by ceramide and its metabolites; Pharm. Res., 47 383
4) Olivier (2002) Sphingosine in apoptosis signaling; Biochim. Biophys. Acta, 1585 153 |
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