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N-Octanoyl-D-erythro-dihydrosphingosine

CATALOG # 1854

Specifications

  • Catalog #:1854
  • Scientific Name:N-Octanoyl-D-erythro-dihydrosphingosine
  • Common Name:N-C8:0-D-erythro-Dihydroceramide; N-Octanoyl-D-erythro-sphinganine
  • Empirical Formula:C26H53NO3
  • CAS#:145774-33-0
  • SDS:View Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:428
  • Unit:5 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, HPLC, identity confirmed by MS
  • Solubility:ethanol, DMSO, chloroform
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No

Description

Application Notes:

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.

References:
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
Price $79.00

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