24696-26-2

Basic information

• Product Name: C16 CERAMIDE
• Synonyms: D-ERYTHRO-SPHINGOSINE, N-PALMITOYL;CERAMIDE-C16;C16 CERAMIDE;C16-D-ERYTHRO-CERAMIDE;16:0 CERAMIDE;PALMITOYL CERAMIDE;N-PALMITOYL CERAMIDE;N-PALMITOYL-D-ERYTHRO-SPHINGOSINE
• CAS NO: 24696-26-2
• Molecular Formula: C₃₄H₆₇NO₃
• Molecular Weight: 537.9
• Product Categories: Mixed Fatty Acids;Activators;Fatty Acid Derivatives & Lipids;Glycerols;Protein Kinase Inhibitors and Activators
• Mol File: 24696-26-2.mol
• Article Data: 25

Chemical Properties

• Melting Point: 94-95 °C
• Boiling Point: 614.41°C (rough estimate)
• Flash Point: 362.3 °C
• Appearance: White/Crystalline Powder
• Density: 0.9596 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6630 (estimate)
• Storage Temp.: −20°C
• Solubility: Soluble in DMF at 0.15mg/ml
• CAS DataBase Reference: C16 CERAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: C16 CERAMIDE(24696-26-2)
• EPA Substance Registry System: C16 CERAMIDE(24696-26-2)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 24696-26-2(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 24696-26-2 differently. You can refer to the following data:
1. A predominant, rather hydrophobic natural ceramide. Activates a cytosolic serine/threonine protein phosphatase in T9 cells; induces EGF receptor phosphorylation in A-431 cells; stimulates ceramide-activated protein kinase
2. An endogenous ceramide that acts as a lipid second messenger to regulate apoptosis and stress signaling.

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

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 1492-30-4 4-nitrophenyl palmitate 
• 112-71-0 1-Bromotetradecane 
• 112-67-4 n-hexadecanoyl chloride 
• 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 
• 123-78-4 erythro-(E)-2-amino-4-octadecene-1,3-diol 
• 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 
• 2673-72-5 (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol hydrochloride 
• 506-46-7 1-hexacosanoic acid 

Downstream Products

• 143517-09-3 Benzoic acid (E)-(R)-1-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester 
• 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 
• 74365-77-8 glucosylceramide 
• 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 
• 4201-55-2 (2S,3R,4E)-3-benzoyl-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 94198-71-7 (2S,3R,4E)-1-(triphenylmethyl)-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 143517-08-2 1-OTBDPS ceramide 

Relevant articles and documents

COSMETIC COMPOSITION FOR SKIN IMPROVEMENT COMPRISING GREEN BARLEY EXTRACT

Provided is a cosmetic composition for skin improvement including a green barley extract.

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.