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| D-ERYTHRO-SPHINGOSINE Basic information |
| 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 |
| 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-SPHINGOSINE Preparation Products And Raw materials |
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