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N-Stearoyl-phytosphingosine

SIGMA/SMB00578 - ≥98% (GC)

Synonym: N-(stearoyl)-phytoceramide; N-C18:0 Phytoceramide; N-Octadecanoyl-phytosphingosine; N-octadecanoyl 4-hydroxysphinganine

CAS Number: 34354-88-6
Empirical Formula (Hill Notation): C36H73NO4
Molecular Weight: 583.97
MDL Number: MFCD02259296
Linear Formula: C36H73NO4
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SMB00578-5MG 5 mg
 $672.00
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assay ≥98% (GC)
form powder
functional group amide
  hydroxyl
InChI 1S/C36H73NO4/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-35(40)37-33(32-38)36(41)34(39)30-28-26-24-22-20-16-14-12-10-8-6-4-2/h33-34,36,38-39,41H,3-32H2,1-2H3,(H,37,40)/t33-,34+,36-/m0/s1
InChI key IEZRNEGTKRQRFV-LFBNJJMOSA-N
Quality Level 200 
SMILES string O[C@]([H])(CCCCCCCCCCCCCC)[C@](O)([H])[C@@]([H])(NC(CCCCCCCCCCCCCCCCC)=O)CO
storage temp. −20°C
Biochem/physiol Actions: N-Stearoyl phytosphingosine is an intercellular lipid that has been found to inhibit the expression of the allergic cytokines, IL-4 and TNF-alpha.
Biochem/physiol Actions: Stratum corneum (SC), the uppermost layer of the epidermis, is composed of seven different types of cermaides. They are present in the continuous lipid phase between SC cells, which also includes cholesterol and free fatty acids. It is thought that the varying type of ceramide constitution in skin determines the physiological function of SC. They also determine the lipid barrier structuring of the skin, where ceramide 3 forms a nearly water-impermeable lipid film.
General description: N-Stearoyl-phytosphingosine is also known as ceramide 3. All ceramides contain sphingosine or phytosphingosine as their building block which is linked with nonhydroxy-, ω-hydroxy-, or ω-hydroxyacids with amide bonds. Phytosphingosine type of ceramide is divided into ceramide 3 and 7. Ceramide 3 contains phytosphingosine backbone linked with fatty acid of chain length between 18 and 24 carbons, in an acyl linkage. Ceramide 3 class contains the members- ceramide 3 and ceramide 3b. Ceramide 3 contains stearic acid as the side chain.
Packaging: 5 mg in glass bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (GC)
Storage Temp. −20°C
UNSPSC 12352200

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