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N-Stearoyl-phytosphingosine

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N-Stearoyl-phytosphingosine Basic information

Product Name:
N-Stearoyl-phytosphingosine
Synonyms:
  • YEAST N-18:0 PHYTOSPHINGOSINE
  • N-STEAROYL-PHYTOSPHINGOSINE
  • N-STEAROYL-PHYTOSPHINGOSINE (SACCHAROMYCES CEREVISIAE)
  • C18-PHYTOCERAMIDE
  • (2S, 3S, 4R)-2-STEAROYLIMINO-1,3,4-OCTADECANETRIOL-1-PHOSPHOCHOLINE (SACCHAROMYCES CEREVISIAE)
  • 2S,3S,4R-2-StearoylaMide-1,3,4-octadecanetriol
  • C18 3-Hydroxy DihydroceraMide
  • D-ribo-1,3,4-Trihydroxy-2-octadecanoylaMidooctadecane
CAS:
34354-88-6
MF:
C36H73NO4
MW:
583.97
EINECS:
812-962-6
Product Categories:
  • Amines
  • Fatty Acid Derivatives & Lipids
  • Glycerols
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
Mol File
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N-Stearoyl-phytosphingosine Chemical Properties

Melting point:
122-124°C
Boiling point:
718℃ at 10hPa
Density 
0.994-1.014 at 20℃
vapor pressure 
0Pa at 25℃
storage temp. 
Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility 
Chloroform : Methanol = 3 : 1 (Slightly), Pyridine (Slightly, Heated, Sonicated)
form 
Solid
color 
White to Off-White
InChIKey
IEZRNEGTKRQRFV-LFBNJJMOSA-N
SMILES
C(N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)(=O)CCCCCCCCCCCCCCCCC
LogP
12.01 at 25℃ and pH7
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N-Stearoyl-phytosphingosine Usage And Synthesis

Description

N-Stearoyl-phytosphingosine (SPS), sphingolipids frequently found in mammalian skin, plants, and yeast, have been used in cosmetics. In mice, treatment with SPS inhibited histamine-induced scratching behavior and vascular permeability. This agent inhibited the expression of the allergic cytokines IL-4 and TNF-a and the activation of the transcription factors NF-jB and c-jun in histamine-stimulated skin tissues[1].

Uses

An intercellular lipid that benefits skin hydration and protects against SLS irritation.

Definition

ChEBI: N-octadecanoyl-4-hydroxysphinganine is a phytoceramide in which the ceramide N-acyl group is specified as octadecanoyl (stearoyl). It is a N-acylphytosphingosine and a N-stearoyl-sphingoid base.

References

[1] Kwon-Ryeol Ryu. “Anti-scratching Behavioral Effects of N-Stearoyl-phytosphingosine and 4-Hydroxysphinganine in Mice.” Lipids 45 7 (2010): 613–618.

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