Sphingosine

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Structural formula
Structural formula of sphingosine
General
Surname Sphingosine
other names
  • D - erythro -2-aminooctadec-4-en-1,3-diol
  • 2-amino-1,3-dihydroxy-4- trans octadecene
Molecular formula C 18 H 37 NO 2
Brief description

white solid

External identifiers / databases
CAS number 123-78-4
EC number 204-651-3
ECHA InfoCard 100.004.230
PubChem 5280335
DrugBank DB03203
Wikidata Q46298
properties
Molar mass 299.49 g mol −1
Physical state

firmly

solubility

poor in chloroform (20 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sphingosine is a monounsaturated amino alcohol whose molecules consist of 18 carbon atoms , one amino group and two hydroxyl groups . Sphingosine forms the backbone of sphingolipids , a class of membrane lipids in which the amino group of sphingosine is bound to a fatty acid with an amide bond .

General structural formula of the sphingolipids

Sphingolipids are divided into ceramides , sphingomyelins , cerebrosides , gangliosides and sulfatides . They are found in nerve tissue , they play an important role in signal transmission and the interaction of individual cells .

synthesis

Sphingosine is synthesized in the body from palmitoyl-CoA and serine .

First, palmitoyl-CoA and serine are condensed to 3-dehydrosphinganine . This is then reduced to dihydrosphingosine (sphinganine) with the help of NADPH , and then further oxidized to sphingosine with the help of FAD .

Web links

Wikibooks: Biochemistry and Pathobiochemistry: Sphingolipid Metabolism  - Learning and Teaching Materials

Individual evidence

  1. ↑ a b c data sheet D-Sphingosine from bovine brain from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).