54336-64-0

Basic information

• Product Name: Octadecanamide, N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-
• CAS NO: 54336-64-0
• Molecular Formula: C36H71NO3
• Molecular Weight: 565.965
• Mol File: 54336-64-0.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: Octadecanamide, N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Octadecanamide, N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-(54336-64-0)
• EPA Substance Registry System: Octadecanamide, N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-(54336-64-0)

Safety Data

• Hazardous Substances Data: 54336-64-0(Hazardous Substances Data)

Upstream product

• 14464-32-5 stearic acid N-hydroxysuccinimide ester 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 116467-63-1 N-tert-butyloxycarbonylsphingosine 
• 147910-00-7 (2S,3R,4E)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene 
• 57-11-4 stearic acid 
• 14617-86-8 4-nitrophenyl stearate 
• 56776-02-4 N-hydroxysuccinimide ester of stearic acid 
• 58909-84-5 sphingomyelin 
• 2673-72-5 (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol hydrochloride 
• 1215008-40-4 (2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-1,3-diol 
• 221455-36-3 tert-butyl ((2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-octadec-4-en-2-yl)carbamate 
• 103931-03-9 (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol 
• 115523-49-4 Toluene-4-sulfonate(2-{[(E)-(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyloxy]-methoxy-phosphoryloxy}-ethyl)-trimethyl-ammonium; 
• 115523-47-2 Toluene-4-sulfonate(2-{[(E)-(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyloxy]-methoxy-phosphanyloxy}-ethyl)-trimethyl-ammonium; 

Downstream Products

• 114656-44-9 N-stearoyl-1-O-trityl-D-erythro-sphingosine 
• 1310805-62-9 C₆₂H₁₀₇NO₁₂SSi 
• 1046791-73-4 C₆₁H₉₅NO₁₂ 
• 1046791-71-2 C₆₇H₁₀₁NO₁₂S 
• 1046791-69-8 C₇₃H₁₁₅NO₁₂SSi 
• 36271-49-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(octadecanoylamino)-3-hydroxyoctadec-4-ene 
• 299172-56-8 3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-stearoyl-D-erythro-sphingosine 
• 114656-46-1 3-O-benzoyl-N-stearoyl-1-O-trityl-D-erythro-sphingosine 
• 41106-92-7 (2S,3R,4E)-3-O-benzoyl-2-octadecanamido-4-octadecene-1,3-diol 
• 103931-03-9 (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol 
• 164988-80-1 Octadecanoic acid [(E)-(1S,2R)-2-hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-3-enyl]-amide 

Relevant articles and documents

Total synthesis of ceramides and β-O-glucosylceramides via intramolecular fatty acyl group migration

Acyl migration of alkyl and aromatic acyl groups from an alcohol to another alcohol or amine is a phenomenon that occurs in nature and can be a bane to some synthetic strategies. An acyl migration-dependent method was developed for the synthesis of ceramide and glucosyl ceramide derivatives, in which the desired fatty acyl moiety acts both as protecting and migrating group. Removal of the tetrachlorophthalimido (TCP) group with ethylenediamine as a mild base at room temperature resulted in subsequent intramolecular fatty acyl group migration from -O to -N, on sphingosine or per acetylated glucosyl sphingosine to yield the desired N-acylated products. Deacetylation reaction afforded the desired β-O-glucosylceramide derivatives. Thus, choice of the appropriate blocking group turns acyl migration into a tool for synthesis, rather than an impediment.

Ceramide compound and application

The invention relates to a ceramide compound; in the structural general formula, m=2-12; n=0-20. The ceramide compound has significant pseudo neural growth factor activity, and is the small molecule compound capable of passing through blood-brain barrier. The structural general formula is shown as Figure.

Design and synthesis of caged ceramide: UV-responsive ceramide releasing system based on UV-induced amide bond cleavage followed by O-N acyl transfer

Sphingolipids, recognized as membrane constructs and as key signaling molecules, have been studied to examine intracellular function. Some caged sphingolipids that release parent sphingolipids after exposure to UV-irradiation have been previously developed, but caged ceramide has yet to be reported. In this study, we report the design and synthesis of a caged ceramide. Photo-irradiation experiment clarified that the caged ceramide can be successfully converted to the parent ceramide by UV-irradiation. Introduction of an alkyne-handle moiety for further modification of the caged ceramide is also reported.