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

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

• 58909-84-5 sphingomyelin 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 14617-86-8 4-nitrophenyl stearate 
• 56776-02-4 N-hydroxysuccinimide ester of stearic acid 
• 185681-40-7 (2R,3R,4E)-1,3-Di-O-benzyl-2-O-methylsulfonyloctadec-4-ene-1,2,3-triol 
• 137410-26-5 (2S,3R,4E)-2-azido-1,3-dibenzyloxyoctadeca-4-ene 
• 115464-01-2 (4S,1'R)-4-(1'-Hydroxy-2'-hexadecinyl)-2,2-dimethyl-3-oxazolidincarbonsaeure-tert-butylester 
• 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 
• 78715-85-2 erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline 

Downstream Products

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

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.

Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthase

Enantiomers or diastereomers of chiral bioactive compounds often exhibit different biological and toxicological properties. Here, we report the efficient synthesis of four stereoisomers of sphingosine and derivatization of unique chiral ceramides through a combinatorial chemistry by solid-phase activated resin ester. In addition, to test the effectivity of stereochemistry of ceramide, we demonstrated a cell-based assay of sphingomyelin synthase inhibition in the presence ofchiral unique ceramides, which suggested that libraries of this sort will be a rich source of biologically active synthetic molecules.

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.

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.

Highly efficient and stereoselective synthesis of β-glycolipids

β-Galactosylceramide and glycolipid analogues were prepared in high yield and with complete chemo and stereoselectivity by reaction of α-iodo glycosides with stannyl ceramides, formed in situ. TBAI was used to activate both the iodogalactose and the stannyl ether. The Royal Society of Chemistry 2008.

ONE-POT SYNTHESIS OF ALPHA/BETA-O-GLYCOLIPIDS

The present invention provides a one-pot method of preparing an unprotected α-O-glycolipid. The first step involves contacting a protected α-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected α- O-glycolipid. The second step involves deprotecting the protected α-O-glycolipid under conditions sufficient to prepare the unprotected α-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected β-O-glycolipid following the steps for the preparation of the unprotected α-O-glycolipid.

Efficient, one-pot syntheses of biologically active α-linked glycolipids

Per-O-silylated galactosyl iodides undergo α-glycosidation with fully functionalized glycolipids producing biologically relevant conjugates. The Royal Society of Chemistry.

Ganglioside GM3 derivatives with truncated ceramide moiety: Facial synthesis and inhibitory activity against KB cell growth

An expeditious sialylation reaction with phenylthioglycoside 4 as a sialyl donor and MeSOTf as a promoter was developed. These conditions are very useful for synthesizing ganglioside GM 3 (1), its C8-ceramide analog 2, and 3-deoxy analog 3 of 2 in an efficient manner. The GM 3 analog 2, whose hydrophilicity is increased by shortening the ceramide moiety, exhibits increased growth inhibiton of KB cells. The 3-hydoxy group of ceramide does not influence its activity against KB cells. Copyright Taylor & Francis Group, LLC.

Sphingomyelin analogues as inhibitors of sphingomyelinase

To search for neutral sphingomyelinase inhibitors we designed and synthesized hydrolytically stable analogues of sphingomyelin. The novel compounds 8 and 9 which were replaced the phosphodiester moiety of sphingomyelin with the carbamate moiety showed inhibitory activity with an IC50 value of μM on neutral sphingomyelinase in rat brain microsomes. Compound 8i showed a selective neutral sphingomyelinase inhibitory activity.