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L-erythro-Sphinganine, C18 chain

This product is a high purity, well-defined, L-erythro-dihydrosphingosine which demonstrates unique properties as compared with the natural D-erythro isomer and is therefore ideal for use in studies of dihydrosphingosine. Natural D-erythrodihydrosphingosine is the precursor of dihydroceramide which is then desaturated to form ceramide. It is a critical intermediate in the synthesis of many complex sphingoid bases and ceramide analogs. It has been found that dihydrosphingosine can induce cell death in a number of types of malignant cells and it is being tested for its pharmacological properties.1 Whereas both D-threo and L-threo-C2-dihydroceramide induced apoptosis in cells neither Derythro nor L-erythro-C2-dihydroceramide showed activity.2 One report has concluded that all four of the enantiomers of dihydrosphingsoine act as substrates for sphingosine kinase with only the natural D-erythro-dihydrosphingosine being metabolized by sphinganine-1-phosphate lyase.3 However, another report concludes that only the erythro isomers of dihydrosphingosine act as substrates for this enzyme with both of the threo isomers inhibiting its activity.4
Cat# Size Price Qty Buy
1846 1 mg £145.31

Additional Information

Property Value or Rating
Product Size 1 mg
Manufacturer Matreya, LLC
Empirical Formula C18H39NO2
CAS# 6036-76-6
Formula Weight 301.5
Solvent none
Source synthetic
Purity 98+%
Analytical Methods TLC, GC
Natural Source Synthetic
Solubility chloroform, methanol, ethanol, DMSO
Physical Appearance A neat solid
Storage -20°C

1. W. Zheng “Fenretinide increases dihydroceramide and dihydrosphingolipids due to inhibition of dihydroceramide desaturase” Georgia Institute of Technology, 2006 
2. A. Bielawska “Selectivity of Ceramide-Mediated Biology Lack of Activity of erythro-Dihydroceramide” Journal of Biological Chemistry, vol. 268 pp. 26226-26232, 1993 
3. W. Stoffel and K. Bister “Stereospecificities in the metabolic reactions of the four isomeric sphinganines (dihydrosphingosines) in rat liver” Hoppe Seylers Z Physiol Chem, vol. 354 pp. 169-181, 1973 
4. B. Buehrer and R. Bell “Inhibition of Sphingosine Kinase in Vitro and in Platelets Implications for Signal Transduction Pathways” Journal of Biological Chemistry, vol. 267 pp. 3154-3159, 1992

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