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

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

1-8-10

HS Code 

29221985

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

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

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