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N-C2:0-D-erythro-Dihydroceramide; N-Acetyl-D-erythro-sphinganine

N-Acetyl-D-erythro-dihydrosphingosine is a non-natural analog of the ceramide precursor dihydroceramide. This acetyl dihydroceramide has properties and functions that are different from natural dihydroceramide and is therefore a useful tool for studying dihydroceramides and ceramides. Whereas short chain ceramides potently induce apoptosis in cells neither short nor long-chain dihydroceramides are able to do so.1 N-Acetyl-dihydroceramide has been shown to be incorporated into mitochondria membranes at the same rate as N-acetyl-ceramide and at a greater rate than N-palmitoyl-ceramide. This demonstrates that both dihydroceramide and ceramide insert into the mitochondrial membrane at the same rate indicating that the inability of dihydroceramide to induce apoptosis is not due to a lack of its insertion into the membrane.2 The presence of the 4–5 trans double bond is essential for ceramide-channel formation. Dihydroceramides are unable to form these ceramidechannels due to their lack of a 4-5 double bond and it is suggested that this is the reason for its lack of apoptotic activity.3 Natural 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 dihydrosphingosine and dihydrosphingosine-1-phosphate and a decrease in other sphingolipids leading to a number of diseases including oesophageal cancer. 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.4
Cat# Size Price Qty Buy
1834 5 mg £62.90

Additional Information

Property Value or Rating
Product Size 5 mg
Manufacturer Matreya, LLC
Empirical Formula C20H41NO3
CAS# 13031-64-6
Formula Weight 343.5
Solvent none
Source synthetic
Purity 98+%
Analytical Methods TLC, GC
Natural Source Synthetic
Solubility chloroform, ethanol, methanol
Physical Appearance A neat solid
Storage -20°C

1. F. Bi et al. “A Conserved Cysteine Motif Is Critical for Rice Ceramide Kinase Activity and Function” PLoS ONE 6(3): e18079. doi:10.1371/journal.pone.0018079, 2011 
2. L. Siskind et al. “Ceramide forms channels in mitochondrial outer membranes at physiologically relevant concentrations” Mitochondrion, vol. 6 pp. 118- 125, 2006 
3. T. Goldkorn et al. “H2O2 acts on cellular membranes to generate ceramide signaling and initiate apoptosis in tracheobronchial epithelial cells” Journal of Cell Science, vol. 111 pp. 3209-3220, 1998 
4. W. Zheng “Fenretinide increases dihydroceramide and dihydrosphingolipids due to inhibition of dihydroceramide desaturase” Georgia Institute of Technology, 2006

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