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

Description

C16 Ceramide, also known as N-hexadecanoylsphingosine, is a type of ceramide lipid molecule that plays a crucial role in cellular processes. It is a predominant, rather hydrophobic natural ceramide with a white crystalline solid appearance. C16 Ceramide is involved in various cellular functions, including the regulation of apoptosis and stress signaling, as well as activating specific protein kinases and phosphatases.

Uses

Used in Pharmaceutical Industry:
C16 Ceramide is used as a therapeutic agent for its potential role in treating various diseases. Its ability to regulate apoptosis and stress signaling pathways makes it a promising candidate for the development of drugs targeting cancer and other conditions related to cell death and stress response.
Used in Cosmetics Industry:
C16 Ceramide is used as an ingredient in skincare products for its hydrophobic properties, which help maintain the skin's natural barrier and retain moisture. It is also known to improve skin elasticity and reduce the appearance of fine lines and wrinkles.
Used in Research Applications:
C16 Ceramide is used as a research tool in cell biology and molecular biology to study the role of ceramides in cellular processes, such as cell signaling, apoptosis, and stress response. It can be employed in various experimental setups, including cell culture, gene expression analysis, and protein-protein interaction studies.
Used in Drug Delivery Systems:
C16 Ceramide can be used in the development of drug delivery systems, particularly for targeted therapies. Its hydrophobic nature allows for the formulation of liposomal or nanoparticle-based drug carriers, which can improve the bioavailability and targeted delivery of therapeutic agents.

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 
• 116447-99-5 (2S,3R,4E)-1,3-benzylidene-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 309916-44-7 (2R,3R)-2-palmitoylamido-4-hydroxyoctadecyn-1,3-diol 
• 112-67-4 n-hexadecanoyl chloride 
• 143517-08-2 1-OTBDPS ceramide 
• 917604-77-4 N-[1,(3R)-dihydroxy-4-penten-(2S)-yl]hexadecanamide 
• 13360-61-7 1-pentadecene 
• 905266-75-3 1-(tert-butyldimethylsilyloxy)-(2S)-(N-tert-butyloxycarbonyl)amino-3-oxo-4-pentene 
• 134210-26-7 (2S,3R)-2-amino-1-(tert-butyldimethylsiloxy)-N-<(tert-butyloxy)carbonyl>-3-hydroxy-4-pentene 
• 117603-66-4 tert-butyl ((2S,3R)-1,3-dihydroxypent-4-en-2-yl)carbamate 
• 761407-89-0 (1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine 
• 761407-86-7 [(2S,3R)-2-Azido-3-(4-methoxy-benzyloxy)-pent-4-enyloxy]-tert-butyl-diphenyl-silane 
• 761407-90-3 [1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 

Downstream Products

• 143517-08-2 1-OTBDPS ceramide 
• 94198-71-7 (2S,3R,4E)-1-(triphenylmethyl)-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 4201-55-2 (2S,3R,4E)-3-benzoyl-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 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 
• 886213-24-7 D-erythro-2-N-hexadecanoyl-14-bromo-sphingosine 
• 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 

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.