N-tetracosanoylsphingosine

Base Information

• Chemical Name: N-tetracosanoylsphingosine
• CAS No.: 34435-05-7
• Molecular Formula: C₄₂H₈₃NO₃
• Molecular Weight: 650.126
• Nikkaji Number: J2.113.999H,J904.085D
• Wikidata: Q27140218
• Metabolomics Workbench ID: 30572
• Mol file: 34435-05-7.mol

Synonyms:C24 Ceramide;34435-05-7;Lignoceric Ceramide;N-tetracosanoylsphingosine;Cer(d18:1/24:0);C24-Ceramide;C24 Cer;N-Lignoceroylsphingosine;N-lignoceroyl-sphingosine;N-(tetracosanoyl)-ceramide;N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]tetracosanamide;N-(tetracosanoyl)-sphing-4-enine;N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tetracosanamide;C24 Ceramide (d18:1/24:0);Ceramide d42:1;LMSP02010012;C24:0-Ceramide;N-(tetracosanoyl)ceramide;N-Lignoceroyl-4-sphingenine;sphing-4-enine-24-ceramide;N-tetracosanoylsphing-4-enine;N-tetracosanoyl-sphing-4-enine;Ceramide (d18:1/24:0);CHEBI:72965;N-(tetracosanoyl)sphing-4-enine;ceramide N(24:0)S(18:1);BP-28823;HY-134508;CS-0143703;J-019603;N-[1.3-dihydroxyoctadec-4-en-2-yl]tetracosanamide;Q27140218;C24 Ceramide (d18:1/24:0), N-lignoceroyl-D-erythro-sphingosine, powder;N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-tetracosanamide

Chemical Property of N-tetracosanoylsphingosine

Chemical Property:

• Vapor Pressure: 5.84E-26mmHg at 25°C
• Melting Point: 94-96
• Boiling Point: 750°C at 760 mmHg
• PKA: 13.54±0.20(Predicted)
• Flash Point: 407.4°C
• PSA: 69.56000
• Density: 0.906g/cm³
• LogP: 13.07470
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Sparingly)
• XLogP3: 17.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 38
• Exact Mass: 649.63729551
• Heavy Atom Count: 46
• Complexity: 622

Purity/Quality:

98%Min ^*data from raw suppliers

C14 Ceramide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Sphingolipids
• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(CO)C(C=CCCCCCCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O
• Description: Production of ceramide occurs upon hydrolysis of sphingomyelin by a specific isoform of PLC, appropriately named sphingomyelinase. C24 Ceramide (d18:1/24:0) is one of the most abundant naturally occurring ceramides. Ceramides mediate many diverse biological activities, as has been demonstrated in studies utilizing cell-permeable ceramide analogs. A few of the processes regulated by ceramides include apoptosis, cell differentiation, proliferation of smooth muscle cells, and inhibition of the mitochondrial respiratory chain.
• Uses: Production of ceramide occurs upon hydrolysis of sphingomyelin by a specific isoform of phospholipase C, appropriately named sphingomyelinase Production of ceramide occurs upon hydrolysis of sphingomyelin by a specific isoform of phospholipase C, appropriately named sphingomyelinase.

Technology Process of N-tetracosanoylsphingosine

There total 12 articles about N-tetracosanoylsphingosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

1,3-bis(1-ethoxyethoxy)-2-tetracosanamido-4-E-D-erythro-octadec-4-ene (97818-16-1) → N-tetracosanoyl-D-erythro-sphingosine (17673-74-4,26549-48-4,73354-07-1,75171-91-4,98103-17-4,102917-80-6,105089-23-4,121468-19-7,121470-52-8,121470-53-9,130607-51-1,130608-87-6,34435-05-7)

Guidance literature:

With Amberlyst 15 resin; In methanol; dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/0008-6215(86)84010-1

Reference yield: 71.0%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + n-tetracosanoic acid (557-59-5) → N-tetracosanoyl-D-erythro-sphingosine (17673-74-4,26549-48-4,73354-07-1,75171-91-4,98103-17-4,102917-80-6,105089-23-4,121468-19-7,121470-52-8,121470-53-9,130607-51-1,130608-87-6,34435-05-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 5h; Inert atmosphere;

DOI:10.1002/ejoc.201403296

Reference yield: 45.0%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + p-nitrophenyl tetracosanoate → N-tetracosanoyl-D-erythro-sphingosine (17673-74-4,26549-48-4,73354-07-1,75171-91-4,98103-17-4,102917-80-6,105089-23-4,121468-19-7,121470-52-8,121470-53-9,130607-51-1,130608-87-6,34435-05-7)

Guidance literature:

With dmap; In tetrahydrofuran; at 40 ℃; for 12h;

DOI:10.1021/jm00012a018

upstream raw materials:

<2(S),3(R),4E>-1,3-O-isopropylidene-2-tetracosanamido-4-octadecene-1,3-diol

1,3-bis(1-ethoxyethoxy)-2-tetracosanamido-4-E-D-erythro-octadec-4-ene

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

1-Bromotetradecane

Downstream raw materials:

(2S,3R,4E)-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-tetracosanoylamino)-4-octadecene-1,3-diol

3-O-benzoyl-2-N-tetracosanoyl-1-O-trityl-4-E-D-erythro-sphingenine

3-O-benzoyl-2-N-tetracosanoyl-4-E-D-erythro-sphingenine

2-N-tetracosanoyl-1-O-trityl-4-E-D-erythro-sphingenine

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