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D,L-C16-Dihydrosphingosine (mixed isomers)

CATALOG # 1326

Specifications

  • Catalog #:1326
  • Scientific Name:D,L-C16-Dihydrosphingosine (mixed isomers)
  • Common Name:D,L-Sphinganine,C16 chain
  • Empirical Formula:C16H35NO2
  • CAS#:50731-08-3
  • SDS:View Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:273
  • Unit:10 mg
  • Solvent:none
  • Source:synthetic
  • Purity:erythro 90%, threo 10%
  • Analytical Methods:TLC, GC
  • Solubility:chloroform, methanol, ethanol, DMSO
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No

Description

Application Notes:

This dihydrosphingosine standard is a mixture of D and L isomers and contains approximately 90% erythro and 10% threo isomers. It is a 16 carbon chain, two carbons shorter than the most prevalent dihydrosphingosine in most animals. However, some animals, such as Drosophila melanogaster, have the shorter C16 dihydrosphingosine base.1 Dihydrosphingosine (Sphinganine) 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 sphinganine can induce cell death in a number of types of malignant cells and is being tested for its pharmacological properties.2 Inhibition of dihydroceramide synthesis by some fungal toxins that have a similar structure causes an increase in sphinganine and sphinganine-1-phosphate and a decrease in other sphingolipids leading to a number of diseases including oesophageal cancer.3 Sphinganine has been found to mediate fumonisin (a toxic sphinganine analog) induced hypotension.4

References:
1. H. Fyrst et al. “Characterization of free endogenous C14 and C16 sphingoid bases from Drosophila melanogaster” Journal of Lipid Research, vol. 45 pp. 54-62, 2004
2. W. Zheng “Fenretinide increases dihydroceramide and dihydrosphingolipids due to inhibition of dihydroceramide desaturase” Georgia Institute of Technology, 2006
3. L. van der Westhuizen et al. “Sphingoid base levels in humans consuming fumonisin-contaminated maize in rural areas of the former Transkei, South Africa: a cross-sectional study” Food Additives and Contaminants, Vol. 25(11), pages 1385 – 1391, 2008
4. Shih-Hsuan Hsiao et al. “Effects of Exogenous Sphinganine, Sphingosine, and Sphingosine-1-Phosphate on Relaxation and Contraction of Porcine Thoracic Aortic and Pulmonary Arterial Rings” Toxicological Sciences, Vol. 86(1) Pp. 194-199, 2005
Price $157.00

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