4201-58-5

Basic information

• Product Name: N-palmitoylsphingosine
• Synonyms: N-hexadecanoylsphingosine
• CAS NO: 4201-58-5
• Molecular Formula: C₃₄H₆₇NO₃
• Molecular Weight: 0
• Mol File: 4201-58-5.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 675.4°Cat760mmHg
• Flash Point: 362.3°C
• Appearance: /
• Density: 0.919g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.48
• CAS DataBase Reference: N-palmitoylsphingosine(CAS DataBase Reference)
• NIST Chemistry Reference: N-palmitoylsphingosine(4201-58-5)
• EPA Substance Registry System: N-palmitoylsphingosine(4201-58-5)

Safety Data

• Hazardous Substances Data: 4201-58-5(Hazardous Substances Data)

Usage

Definition

ChEBI: A N-acylsphingosine in which the ceramide N-acyl group is specified as hexadecanoyl (palmitoyl).

InChI:InChI=1/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+

Upstream product

• 116467-63-1 N-tert-butyloxycarbonylsphingosine 
• 112-67-4 n-hexadecanoyl chloride 
• 2673-72-5 (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol hydrochloride 
• 123-78-4 erythro-(E)-2-amino-4-octadecene-1,3-diol 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 1492-30-4 4-nitrophenyl palmitate 
• 109770-63-0 erythro-2,2-dimethyl-5-nitro-4-<(E)-pentadec-1-enyl>-1,3-dioxane 
• 109770-63-0 threo-2,2-dimethyl-5-nitro-4-<(E)-pentadec-1-enyl>-1,3-dioxane 
• 109770-63-0 2,2-dimethyl-5-nitro-4-<(E)-pentadec-1-enyl>-1,3-dioxane 
• 94306-60-2 2-nitro-octadec-4(E)-ene-1,3-diol 
• 104826-33-7 erythro-5-amino-2,2-dimethyl-4-<(E)-pentadec-1-enyl>-1,3-dioxane 
• 109770-65-2 2,2-dimethyl-5-palmitamido-4-<(E)-pentadec-1-enyl>-1,3-dioxane 
• 4201-55-2 D-erythro-3-O-Benzoyl-N-palmitoyl-sphingosin 
• 506-46-7 1-hexacosanoic acid 

Downstream Products

• 94198-71-7 (2S,3R,4E)-1-(triphenylmethyl)-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 34324-89-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene 
• 94069-99-5 (2S,3R)-N-palmitoyl-3-O-benzoyl-1-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-sphingosine 
• 124338-03-0 Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester 
• 94069-99-5 Benzoic acid (E)-(R)-1-[(S)-1-hexadecanoylamino-2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 536-14-1 N-palmitoyl-D-erythro-sphingomyelin 
• 4201-63-2 (2S,3R,4E)-[4'-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 886213-24-7 D-erythro-2-N-hexadecanoyl-14-bromo-sphingosine 
• 74365-77-8 glucosylceramide 
• 94069-99-5 Benzoic acid (E)-(R)-1-[(S)-1-hexadecanoylamino-2-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 143517-09-3 Benzoic acid (E)-(R)-1-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester 
• 4201-55-2 (2S,3R,4E)-3-benzoyl-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 143517-08-2 1-OTBDPS ceramide 

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.

NOVEL SYNTHESIS INTERMEDIATES FOR OBTAINING DERIVATIVES OF SPHINGOSINES, CERAMIDES AND SPHINGOMYELINS WITH GOOD YIELDS

The subject matter of the present invention is the novel molecules of formulae E, E′ and F. These molecules prove to be synthesis intermediates that are very advantageous for the manufacture of derivatives of sphingosine or of ceramides functionalized in position 1, with good yields, in which R1 and R2 are fatty chains, R3 is an alkyl group and R4 is a protective group for alcohol functions. Another subject of the invention is the use of the intermediates of type F for converting same into intermediates of type G, by means of reduction in the presence of lithium borohydride. The G molecules are precursors that are known to make it possible to obtain sphingolipids or sphingomyelin.