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: 2024-11-04 20:04:50
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. |
Computed Descriptors for D-ERYTHRO-SPHINGOSINE
InChIKey | WWUZIQQURGPMPG-KRWOKUGFSA-N |
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