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 
• 14617-86-8 4-nitrophenyl stearate 
• 432038-16-9 6-benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyran 
• 331456-62-3 2,3,4-Tris-O-(tert-butyldimethylsilyl)-β-D-xylopyranosyl phenyl sulfone 
• 331456-61-2 Phenyl 2,3,4-tris-O-(tert-butyldimethylsilyl)-1-thio-β-D-xylopyranoside 
• 331456-63-4 1,5-Anhydro-3,4-bis-O-(tert-butyldimethylsilyl)-2-deoxy-1-phenylsulfonyl-D-threo-pent-1-enitol 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 103348-49-8 2-azido-sphingosine 
• 112-76-5 Stearoyl chloride 
• 638-08-4 stearic anhydride 
• 56776-02-4 N-hydroxysuccinimide ester of stearic acid 

Downstream Products

• 41106-92-7 (2S,3R,4E)-3-O-benzoyl-2-octadecanamido-4-octadecene-1,3-diol 
• 114656-46-1 3-O-benzoyl-N-stearoyl-1-O-trityl-D-erythro-sphingosine 
• 299172-56-8 3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-stearoyl-D-erythro-sphingosine 
• 1310805-62-9 C₆₂H₁₀₇NO₁₂SSi 
• 1046791-73-4 C₆₁H₉₅NO₁₂ 
• 1046791-71-2 C₆₇H₁₀₁NO₁₂S 
• 1046791-69-8 C₇₃H₁₁₅NO₁₂SSi 
• 103931-03-9 (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol 
• 114656-44-9 N-stearoyl-1-O-trityl-D-erythro-sphingosine 
• 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 
• 36271-49-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(octadecanoylamino)-3-hydroxyoctadec-4-ene 

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 sphingomyelin-cholesterol conjugates and their formation of ordered membranes

A lipid raft is a cholesterol (Chol)-rich microdomain floating in a sea of lipid bilayers. Although Chol is thought to interact preferentially with sphingolipids such as sphingomyelin (SM), rather than with glycerophospholipids, the origin of the specific interaction has remained unresolved, primarily because of the high mobility of lipid molecules and weak intermolecular interactions. In this study, we synthesized SM-Chol conjugates with functionally designed linker portions to restrain Chol mobility and examined their formation of ordered membranes by a detergent insolubility assay, fluorescence anisotropy experiments, and fluorescence-quenching assay. In all of the tests, membranes prepared from the conjugates showed properties of ordered domains comparable to a SM-Chol (1:1) membrane. To gain insight into the structure of bilayers composed from the conjugates, we performed molecular dynamics simulations with 64 molecules of the conjugates, which suggested that the conjugates form a stable bilayer structure by bending at the linker portion and, mostly, reproduce the hydrogen bonds between the SM and Chol portions. These results imply that the molecular recognition between SM and Chol in an ordered domain is essentially reproduced by the conjugated molecules and, thus, demonstrates that these conjugate molecules could potentially serve as molecular probes for understanding molecular recognition in lipid rafts.