Basic information Safety Supplier Related

D-ERYTHRO-SPHINGOSINE

Basic information Safety Supplier Related

D-ERYTHRO-SPHINGOSINE Basic information

Product Name:
D-ERYTHRO-SPHINGOSINE
Synonyms:
  • SPHINGOSINE
  • SPHINGOSINE, C18 CHAIN
  • SPHINGOSINE, D-ERYTHRO
  • TRANS D-THREO-SPHINGOSINE
  • TRANS D-ERYTHRO-SPHINGOSINE
  • TRANS-D-ERYTHRO-2-AMINO-4-OCTADECENE-1,3-DIOL
  • BRAIN SPHINGOSINE
  • BRAIN, BOVINE
CAS:
123-78-4
MF:
C18H37NO2
MW:
299.49
EINECS:
204-651-3
Product Categories:
  • Amines
  • Protein Kinase
  • Mixed Fatty Acids
  • Fatty Acid Derivatives & Lipids
  • Glycerols
  • Inhibitors
  • Protein Kinase Inhibitors and Activators
Mol File:
123-78-4.mol
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D-ERYTHRO-SPHINGOSINE Chemical Properties

Melting point:
74.2-78.1 °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
Merck 
14,8747
BRN 
1727294
Stability:
Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
InChIKey
WWUZIQQURGPMPG-KRWOKUGFSA-N
CAS DataBase Reference
123-78-4
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Safety Information

Safety Statements 
22-24/25
WGK Germany 
3
1-8-10
HS Code 
29221985

MSDS

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D-ERYTHRO-SPHINGOSINE Usage And Synthesis

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

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

Uses

D-erythro-Sphingosine is used to inhibits protein kinase C and calmodulin-dependent enzymes, induces apoptosis. And also used to constituent of cell membranes.

Uses

Sphingosine (d18:1) has been used:

  • for sphingosine inhalations studies in mice to evaluate its therapeutic potential in respiratory epithelial cells
  • to investigate its effect on Pseudomonas aeruginosa strains
  • as a standard in liquid chromatography tandem mass spectrophotometry for the quantification of epidermal ceramides

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.

Biological Activity

Inhibitor of protein kinase C and calmodulin-dependent enzymes, but may stimulate mast cells by activation of protein kinase C.

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.

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

D-ERYTHRO-SPHINGOSINESupplier

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