102917-80-6

Basic information

• Product Name: (2S,3R,4E)-N-TETRACOSANOYL SPHINGOSINE
• Synonyms: N-LIGNOCEROYL-D-ERYTHRO-SPHINGOSINE;24:0 CERAMIDE;(2S,3R,4E)-N-TETRACOSANOYL SPHINGOSINE;C24 CERAMIDE;N-TETRACOSANOYL-D-SPINGOSINE;[R-(R*,S*)]-N-[2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-tetracosanamide;C24 Ceramide (d18:1/24:0)
• CAS NO: 102917-80-6
• Molecular Formula: C₄₂H₈₃NO₃
• Molecular Weight: 650.11
• Mol File: 102917-80-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 750.0±60.0 °C(Predicted)
• Appearance: /
• Density: 0.906±0.06 g/cm3(Predicted)
• PKA: 13.82±0.20(Predicted)
• CAS DataBase Reference: (2S,3R,4E)-N-TETRACOSANOYL SPHINGOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-N-TETRACOSANOYL SPHINGOSINE(102917-80-6)
• EPA Substance Registry System: (2S,3R,4E)-N-TETRACOSANOYL SPHINGOSINE(102917-80-6)

Safety Data

• Hazardous Substances Data: 102917-80-6(Hazardous Substances Data)

Usage

General Description

"(2S,3R,4E)-N-tetracosanoyl sphingosine" is a chemical compound that belongs to the sphingolipid family. It is a long-chain ceramide with a tetracosanoyl (24:0) fatty acid connected to the amino group of sphingosine. Ceramides are important components of cell membranes and play crucial roles in cell signaling, apoptosis, and cell adhesion. This particular ceramide, with its long fatty acid chain, is likely involved in forming the lipid bilayer of cell membranes, contributing to membrane stability and function. Additionally, it may have implications in various cellular processes and biological functions, making it an important molecule for further research and understanding its potential physiological relevance.

Upstream product

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 112-71-0 1-Bromotetradecane 
• 104826-33-7 <2(S),3(R),4E>-2-amino-1,3-O-isopropylidene-4-octadecene-1,3-diol 
• 104826-27-9 <2(R),3(R),4E>-1,3-O-isopropylidene-4-octadecene-1,2,3-triol 
• 104826-31-5 <2(S),3(R),4E>-2-azido-1,3-O-isopropylidene-4-octadecene-1,3-diol 
• 104826-29-1 (2R,3R,4E)-1,3-O-isopropylidene-2-O-(methylsulfonyl)octadec-4-en-1,2,3-triol 
• 113785-46-9 Trifluoro-methanesulfonic acid (4R,5R)-2,2-dimethyl-4-((E)-pentadec-1-enyl)-[1,3]dioxan-5-yl ester 
• 557-59-5 n-tetracosanoic acid 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 97818-16-1 1,3-bis(1-ethoxyethoxy)-2-tetracosanamido-4-E-D-erythro-octadec-4-ene 
• 104846-28-8 <2(S),3(R),4E>-1,3-O-isopropylidene-2-tetracosanamido-4-octadecene-1,3-diol 

Downstream Products

• 75196-33-7 Cer (d18:0/24:0) 
• 148289-55-8 (2S,3R,4E)-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)-4-octadecene-1,3-diol 
• 107034-41-3 3-O-benzoyl-2-N-tetracosanoyl-4-E-D-erythro-sphingenine 
• 114716-67-5 3-O-benzoyl-2-N-tetracosanoyl-1-O-trityl-4-E-D-erythro-sphingenine 
• 109582-79-8 2-N-tetracosanoyl-1-O-trityl-4-E-D-erythro-sphingenine 

Relevant articles and documents

Total synthesis of sulfated glycosphingolipid SM1a, a kind of human epithelial carcinoma antigen

A highly efficient and practical total synthesis of the sulfated ganglioside SM1a, a kind of human epithelial carcinoma antigen identified in mammalian kidney, has been accomplished for the first time. The characteristic sequence of SM1a, β-D-Galp-(1→3)-β

A NOVEL ROUTE TO D-erythro-SPHINGOSINE AND RELATED COMPOUNDS FROM MONO-O-ISOPROPYLIDENE-D-XYLOSE OR -D-GALACTOSE

An efficient synthesis of D-erythro-sphingosine and -ceramide from D-xylose or D-galactose is described.A mixture of 2,4-O-isopropylidene-D-threose and its formate, which is available in one step from 3,5-O-isopropylidene-D-xylofuranose or 4,6-O-isopropylidene-D-galactopyranose, was subjected to the Wittig alkenation with triphenylphosphonio-tetra- and -hexa-decylid.The resulting 1,3-O-isopropylidenated C18 and C20 alkenes were each transformed, by introduction of an azido group at C-2, and selective reduction of the azide, into the corresponding 1,3-O-protected sphingosines that have the 2(S),3(R)-D-erythro configuration, from which a variety of ceramides were prepared by the sequence of N-acylation with the stearoyl or lignoceroyl group, and hydrolytic removal of the isopropylidene group.Some ceramides were also obtained by direct N-acylations of the corresponding sphingosines.