N-(S)-alpha-Hydroxytetracosanoyl-phytosphingosine

CATALOG # 2095
Amount 1 mg
Price $275.00
Qty
 
N-(S)-alpha-Hydroxytetracosanoyl-phytosphingosine
  • Catalog #:2095
  • Scientific Name:N-(S)-alpha-Hydroxytetracosanoyl-phytosphingosine
  • Common Name:N-(S)-alpha-Hydroxy-C24:0-phytoceramide;
    N-(S)-Cerebronoyl-phytoceramide
  • Empirical Formula:C42H85NO5
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:684
  • Unit:1 mg
  • Solvent:none
  • Source:semisynthetic
  • Purity:98+%
  • Analytical Methods:TLC; HPLC; identity confirmed by MS
  • Natural Source:yeast (Pichia ciferri)
  • Solubility:chloroform/methanol 4:1, warm ethanol
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    Phytosphingosine is a long-chain sphingoid base having important cellular functions such as signaling, skin barrier function, cytoskeletal structure, celluar cycle, and heat stress response. It is found largely in mammals, plants, and yeast. Phytosphingosine has seen much use in cosmetics due to its effects on the skin such as reducing inflammation by inhibiting the expression of the allergic cytokines IL-4 and TNF-α and the activation of the transcription factors NF-jB and c-jun in histamine-stimulated skin tissues.1 Phytosphingosine can lead to apoptosis via two distinct pathways and has been investigated as a possible cancer therapeutic treatment.2 Phytoceramides are distributed at the microvillous membrane of the epithelial cells of the small intestine. Crypt cells and the adjacent epithelial cells produce phytosphingoglycolipids in much greater quantities than more differentiated epithelial cells.3 The kidney and skin also contain phytosphingoglycolipids although in much lower concentrations than in the small intestine. Skin cells contain significant amounts of long chain ceramides, such as alpha-hydroxyphytoceramides, that are vital for maintaining skin barrier functions.4

    Selected References:
    1. K. Ryu et al. “Anti-scratching Behavioral Effects of N-Stearoylphytosphingosine and 4-Hydroxysphinganine in Mice” Lipids, Vol. 45 pp. 615-618, 2010
    2. M. Park et al. “Suppression of Extracellular Signal-related Kinase and Activation of p38 MAPK Are Two Critical Events Leading to Caspase-8- and Mitochondria-mediated Cell Death in Phytosphingosine-treated Human Cancer Cells” Journal of Biological Chemistry, Vol. 278, pp. 50624-50634, 2003
    3. F. Omae et al. “DES2 protein is responsible for phytoceramide biosynthesis in the mouse small intestine” Journal of Biochemistry, vol. 379 pp. 687-695, 2004
    4. S. Grond et al., "PNPLA1 Deficiency in Mice and Humans Leads to a Defect in the Synthesis of Omega-O-Acylceramides" J Invest Dermatol. Vol. 137(2) pp. 394-402, 2017