D-ERYTHRO-SPHINGOSINE

Synonym(s):Sphingosine;D-erythro-sphingosine;Sphingosine 2S, 3R; D-erythro-Sphingosine; (2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol; (2S,3R,4E)-2-amino-1,3-octadec-4-enediol;(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol;trans-D-erythro-2-Amino-4-octadecene-1,3-diol

CAS NO.：123-78-4
Empirical Formula: C18H37NO2
Molecular Weight: 299.49
MDL number: MFCD00036751
EINECS: 204-651-3
SAFETY DATA SHEET (SDS)
Update Date: 2026-01-20 14:53:06

What is D-ERYTHRO-SPHINGOSINE?

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

The Uses of D-ERYTHRO-SPHINGOSINE

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

The Uses of D-ERYTHRO-SPHINGOSINE

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

The Uses of D-ERYTHRO-SPHINGOSINE

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

What are the applications of Application

D-erythro-Sphingosine is a potent, highly selective PKC inhibitor

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

Properties of D-ERYTHRO-SPHINGOSINE

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.
CAS DataBase Reference	123-78-4

Safety information for D-ERYTHRO-SPHINGOSINE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection.