Sphingosine (2-amino-4-trans-octadecene-1,3-diol) is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids, a class of cell membrane lipids that include sphingomyelin, an important phospholipid.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||299.499 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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There is no direct route of synthesis from sphinganine to sphingosine; it has to be acylated first to dihydroceramide, which is then dehydrogenated to ceramide. Sphingosine is formed via degradation of sphingolipid in the lysosome.
- Radin N (2003). "Killing tumours by ceramide-induced apoptosis: a critique of available drugs". Biochem J. 371 (Pt 2): 243–56. doi:10.1042/BJ20021878. PMC 1223313. PMID 12558497. article
- Carter, H. E., F. J. Glick, W. P. Norris, and G. E. Phillips. 1947. Biochemistry of the sphingolipides. III. Structure of sphingosine. J. Biol. Chem. 170: 285–295
General structures of sphingolipids