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N-C8:0-D-erythro-Dihydroceramide; N-Octanoyl-D-erythro-sphinganine

This high purity and well-defined product is ideal as a standard and for biological studies.1 Dihydroceramide is a critical intermediate in the synthesis of many complex sphingoid bases. Inhibition of dihydroceramide synthesis by some fungal toxins (such as fumonisin B1) 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. Dihydroceramide, synthesized by the acylation of sphinganine, is subsequently converted into ceramide via a desaturase enzyme or into phytosphingosine via the C4-hydrozylase enzyme2. N-(4-Hydroxyphenyl) retinamide (4-HPR) has been tested as an anticancer 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
1854 5 mg £58.65

Additional Information

Property Value or Rating
Product Size 5 mg
Manufacturer Matreya, LLC
Empirical Formula C26H53NO3
CAS# 145774-33-0
Formula Weight 427.7
Solvent none
Source synthetic
Purity 98+%
Analytical Methods TLC, GC, identity confirmed by MS
Natural Source Synthetic
Solubility ethanol, DMSO, chloroform
Physical Appearance A neat solid
Storage -20°C

1. Z. Zakeri et al. “Stereospecific Induction of Apoptosis in U937 Cells by N-Octanoyl-Sphingosine Stereoisomers and N-Octyl-Sphingosine” European Journal of Biochemistry, vol. 236 pp. 729-737, 1996 
2. Y. Mizutani, A. Kihara, and Y. Igarashi “Identifcation of the human sphingolipid C4-hydroxylase, hDES2, and its up-regulation during keratinocyte differentiation” FEBS Letters, vol. 563 pp. 93-97, 2004 
3. W. Zheng “Fenretinide increases dihydroceramide and dihydrosphingolipids due to inhibition of dihydroceramide desaturase” Georgia Institute of Technology, 2006

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