34435-05-7

Usage

Uses

Used in Pharmaceutical Industry:
C14 CERAMIDE is used as a pharmaceutical agent for its potential role in regulating various biological processes. Its ability to mediate apoptosis, cell differentiation, and proliferation of smooth muscle cells makes it a promising candidate for the development of drugs targeting various diseases.
Used in Cosmetic Industry:
C14 CERAMIDE is used as an ingredient in cosmetic products for its potential skin benefits. It is believed to help maintain the skin's natural barrier function, improve skin hydration, and reduce the appearance of fine lines and wrinkles.
Used in Research:
C14 CERAMIDE is used as a research tool in cell biology and biochemistry studies. It is utilized to investigate the role of ceramides in various cellular processes and to develop a better understanding of their mechanisms of action.

InChI:InChI=1/C42H83NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-42(46)43-40(39-44)41(45)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,40-41,44-45H,3-34,36,38-39H2,1-2H3,(H,43,46)/b37-35+

Upstream product

• 104846-28-8 <2(S),3(R),4E>-1,3-O-isopropylidene-2-tetracosanamido-4-octadecene-1,3-diol 
• 97818-16-1 1,3-bis(1-ethoxyethoxy)-2-tetracosanamido-4-E-D-erythro-octadec-4-ene 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 112-71-0 1-Bromotetradecane 
• 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 

Downstream Products

• 75196-33-7 Cer (d18:0/24:0) 
• 109582-79-8 2-N-tetracosanoyl-1-O-trityl-4-E-D-erythro-sphingenine 
• 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 

Relevant academic research and scientific papers

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