N-Hexanoyl-NBD-D-erythro-dihydrospingosineN-Hexanoyl-NBD-D-erythro-dihydrospingosine
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N-Hexanoyl-NBD-D-erythro-dihydrospingosine

N-C6:0-NBD-Dihydroceramide; N-C6:0-NBD-D-erythro-Dihydrosphingosine

This high purity fluorescent product is ideal for the identification of dihydroceramide in samples and biological systems. 7- nitrobenzofurazan (NBD) has been shown to have only a small influence on lipid adsorption into cells and cellular membranes. This fluorescent analog of natural dihydroceramide is comparable to C6:0-dyhidroceramide in many biological functions.1,2 Dihydroceramide is a critical intermediate in the synthesis of many complex sphingoid bases. Inhibition of dihydroceramide synthesis by some fungal toxins that have a similar structure causes an increase in dihydroceramide and dihydroceramide-1-phosphate and a decrease in other sphingolipids leading to a number of diseases including oesophageal cancer. Dihydroceramide, synthesized by the acylation of sphinganine, is subsequently converted into ceramide via a desaturase enzyme. N-(4-Hydroxyphenyl) retinamide (4-HPR) has been tested as an anti-cancer agent. It inhibits the dihydroceramide desaturase enzyme in cells resulting in a high concentration of dihydroceramide and dihydro-sphingolipids and this is thought to be the cause of the anti-cancer effects.3 Dihydrosphingosine induces cell death in a number of types of malignant cells.
Cat# Size Price Qty Buy
1626 100 ug £187.50

Additional Information

Property Value or Rating
Product Size 100 ug
Manufacturer Matreya, LLC
Empirical Formula C30H51N5O6
CAS# 114301-97-2
Formula Weight 577.8
Solvent none
Source synthetic
Purity 98+%
Analytical Methods TLC; identity confirmed by MS
Natural Source Synthetic
Melting Point n/a
Solubility chloroform/methanol,2:1; methanol
Physical Appearance A neat solid
Storage -20°C
References

1. G van Meer et al. “Epithelial sphingolipid sorting allows for extensive variation of the fatty acyl chain and the sphingosine backbone” Journal of Biochemistry, vol. 283 pp. 913-917, 1992 
2. A. Merrill, Jr. et al. “Dihydroceramide Biology STRUCTURE-SPECIFIC METABOLISM AND INTRACELLULAR LOCALIZATION” Journal of Biological Chemistry, vol. 272 pp. 21128-21136, 1997 
3. W. Zheng “Fenretinide increases dihydroceramide and dihydrosphingolipids due to inhibition of dihydroceramide desaturase” Georgia Institute of Technology, 2006

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