2304-81-6

Basic information

• Product Name: C18 CERAMIDE
• Synonyms: D-ERYTHRO-SPHINGOSINE, N-STEAROYL-;D-ERYTHRO-SPHINGOSINE, N-STEAROYLDIHYDRO;C18 CERAMIDE;C18-D-ERYTHRO-CERAMIDE;C18 DIHYDROCERAMIDE;C18 DIHYDROSPHINGOSINE;18:0 CERAMIDE;(2S, 3R)-2-STEAROYLAMINOOCTADECANE-1,3-DIOL
• CAS NO: 2304-81-6
• Molecular Formula: C₃₆H₇₁NO₃
• Molecular Weight: 565.95
• Product Categories: Mixed Fatty Acids;Activators;Fatty Acid Derivatives & Lipids;Glycerols;Protein Kinase Inhibitors and Activators
• Mol File: 2304-81-6.mol
• Article Data: 20

Chemical Properties

• Melting Point: 99-101 °C
• Boiling Point: 630.97°C (rough estimate)
• Flash Point: 373.8 °C
• Appearance: off white powder
• Density: 0.9512 (rough estimate)
• Vapor Pressure: 2.59E-22mmHg at 25°C
• Refractive Index: 1.6630 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly, Heated, Sonicated), Methanol (Sparingly)
• Stability: Stable, but may be heat sensitive - store below 4 C. Incompatible with strong oxidizing agents.
• BRN: 1717539
• CAS DataBase Reference: C18 CERAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: C18 CERAMIDE(2304-81-6)
• EPA Substance Registry System: C18 CERAMIDE(2304-81-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 2304-81-6(Hazardous Substances Data)

Usage

Description

C18 CERAMIDE, also known as the sphingolipid ceramide, is a type of lipid molecule that plays a crucial role in cellular processes. It is an essential component of the cell membrane and is involved in various cellular functions, including cell signaling, growth, and differentiation. C18 CERAMIDE is characterized by its off-white powder appearance and is a potent inhibitor of the mitochondrial permeability transition pore.

Uses

Used in Pharmaceutical Industry:
C18 CERAMIDE is used as a therapeutic agent for its potential role in treating various diseases. It is particularly being studied for its effects on cancer cells, as it can modulate several oncological signaling pathways and exert inhibitory effects on tumor growth and progression.
Used in Cosmetic Industry:
C18 CERAMIDE is used as an ingredient in skincare products for its ability to help maintain the skin's natural barrier and retain moisture. It is also known to support skin elasticity and reduce the appearance of fine lines and wrinkles.
Used in Research Applications:
C18 CERAMIDE is used as a research tool in the study of cellular processes and the development of new drugs. Its role in cell signaling and the mitochondrial permeability transition pore makes it a valuable compound for understanding the underlying mechanisms of various diseases and conditions.
Used in Drug Delivery Systems:
C18 CERAMIDE can be employed in the development of novel drug delivery systems to enhance the efficacy and bioavailability of therapeutic agents. Its incorporation into carriers such as organic and metallic nanoparticles can improve the delivery of drugs to target cells and tissues, leading to better therapeutic outcomes.

InChI:InChI=1/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)/b31-29+

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 
• 58909-84-5 sphingomyelin 
• 103931-09-5 S_P-D-erythro-2-N-stearoylsphingosyl-1-thiophosphocholine 
• 103931-09-5 R_P-D-erythro-2-N-stearoylsphigosyl-1-thiophosphocholine 
• 104826-35-9 <2(S),3(R),4E>-1,3-O-isopropylidene-2-octadecanamido-4-octadecene-1,3-diol 
• 147910-00-7 (2S,3R,4E)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene 
• 57-11-4 stearic acid 
• 14617-86-8 4-nitrophenyl stearate 
• 56776-02-4 N-hydroxysuccinimide ester of stearic acid 
• 638-08-4 stearic anhydride 
• 112-76-5 Stearoyl chloride 
• 103348-49-8 2-azido-sphingosine 

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.

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 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.