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

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

Uses

Used in Pharmaceutical Research:
(2S,3R,4E)-N-TETRACOSANOYL SPHINGOSINE is used as a research compound for investigating its role in cell signaling, apoptosis, and cell adhesion processes. Its unique structure and function in the lipid bilayer of cell membranes make it a valuable molecule for exploring its potential therapeutic applications in various diseases and conditions.
Used in Biochemical Studies:
In the field of biochemistry, (2S,3R,4E)-N-TETRACOSANOYL SPHINGOSINE is utilized as a model compound to study the properties and behavior of ceramides in biological systems. Its long fatty acid chain provides insights into the structural and functional aspects of lipid bilayers, which are crucial for understanding membrane dynamics and interactions with other cellular components.
Used in Drug Development:
(2S,3R,4E)-N-TETRACOSANOYL SPHINGOSINE is employed as a lead compound in the development of new drugs targeting cell membrane-related diseases. Its potential involvement in various cellular processes and biological functions suggests that it may have therapeutic benefits in treating conditions associated with membrane dysfunction or alterations in lipid metabolism.
Used in Cosmetics Industry:
In the cosmetics industry, (2S,3R,4E)-N-TETRACOSANOYL SPHINGOSINE is used as an ingredient in skincare products for its potential moisturizing and skin barrier-strengthening properties. Its role in maintaining the integrity of the lipid bilayer may contribute to improved skin hydration and protection against environmental stressors.
Used in Food Industry:
(2S,3R,4E)-N-TETRACOSANOYL SPHINGOSINE may be utilized in the food industry as a functional ingredient to enhance the stability and quality of food products. Its role in forming lipid bilayers could potentially improve the texture, shelf life, and nutritional value of certain food items by maintaining the integrity of cellular structures and protecting against oxidation.

Upstream product

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

• 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 
• 114716-67-5 3-O-benzoyl-2-N-tetracosanoyl-1-O-trityl-4-E-D-erythro-sphingenine 
• 107034-41-3 3-O-benzoyl-2-N-tetracosanoyl-4-E-D-erythro-sphingenine 
• 109582-79-8 2-N-tetracosanoyl-1-O-trityl-4-E-D-erythro-sphingenine 
• 75196-33-7 Cer (d18:0/24:0) 

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

Structure-activity relationship of α-galactosylceramides against b16- bearing mice

Agelasphin-9b, (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-16-methyl-2-[N- ((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(α- D-galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

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.

A HIGHLY STEREOSELECTIVE SYNTHESIS OF 2(S),3(R),4E- AND 2(S),3(R),4Z-N-TETRACOSANOYLSPHINGENINE FROM D-GLUCOSE

The synthesis of 4-E- and 4-Z-D-erythro-ceramide was achieved in 10 steps in ca. 20-30percent overall yield, starting from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose.E- and Z-5-Deoxy-1,2-O-isopropylidene-5-C-tetradecylidene-α-D-xylofuranose were used a