Cer(d18:1/24:1(15Z))

Base Information

• Chemical Name: Cer(d18:1/24:1(15Z))
• CAS No.: 54164-50-0
• Molecular Formula: C42H81NO3
• Molecular Weight: 648.1
• Hs Code.: 2922199090
• DSSTox Substance ID: DTXSID60415272
• Nikkaji Number: J525.583J
• Wikidata: Q27144679
• Metabolomics Workbench ID: 30569
• Mol file: 54164-50-0.mol

Synonyms:Nervonic Ceramide;54164-50-0;C24:1 Ceramide;Cer(d18:1/24:1(15Z));C24:1 Cer;C24:1-Ceramide;N-Nervonoyl-D-sphingosine;N-nervonyl-sphingosine;N-nervonoyl-D-erythro-sphingosine;N-(15Z-tetracosenoyl)-sphing-4-enine;(Z)-N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]tetracos-15-enamide;N-(15Z-tetracosenoyl)-ceramide;N-(15Z)-tetracosenoylsphingosine;C24:1 Ceramide (d18:1/24:1(15Z));Ceramide (d18:1/24:1(15Z));15-Tetracosenamide;N-nervonylsphingosine;Ceramide d42:2;LMSP02010009;N-Nervonoylsphingosine;N-nervonoyl sphingosine;N-Tetracosenoyl-4-sphingenine;N-(15Z-tetracosenoyl)ceramide;SCHEMBL22855979;CHEBI:74450;DTXSID60415272;VJSBNBBOSZJDKB-KPEYJIHVSA-N;HMS3649E09;N-(15-cis)-tetracosenoylsphingosine;N-(15Z-tetracosenoyl)sphing-4-enine;AS-82929;BP-28825;HY-134575;CS-0145570;SR-01000947055;SR-01000947055-1;Q27144679;N-[1.3-dihydroxyoctadec-4-en-2-yl]tetracos-15-enamide;C24:1 Ceramide (d18:1/24:1(15Z)), N-nervonoyl-D-erythro-sphingosine, powder;N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-15Z-tetracosenamide;15-Tetracosenamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-, (15Z)-

Chemical Property of Cer(d18:1/24:1(15Z))

Chemical Property:

• PSA: 69.56000
• LogP: 12.85070
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 16.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 37
• Exact Mass: 647.62164545
• Heavy Atom Count: 46
• Complexity: 661

Purity/Quality:

98%Min ^*data from raw suppliers

Nervonyl-D-sphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Sphingolipids
• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(CO)NC(=O)CCCCCCCCCCCCCC=CCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCCCCCCCCCC/C=C\CCCCCCCC)O
• Uses: N-Nervonoyl-D-sphingosine is a sphingolipid. Sphingolipids (SLs) act as signaling molecules and as structural components in both neuronal cells and myelin.

Technology Process of Cer(d18:1/24:1(15Z))

There total 2 articles about Cer(d18:1/24:1(15Z)) 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: 91.0%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + nervonic acid N-hydroxysuccinimide ester (191354-88-8) → N-(15Z-tetracosenoyl)-sphing-4-enine (54164-50-0)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0009-3084(97)00042-X

Reference yield:

Nervonic acid (506-37-6) → N-(15Z-tetracosenoyl)-sphing-4-enine (54164-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / dicyclohexylcarbodiimide / ethyl acetate

2: 91 percent / tetrahydrofuran

With dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/S0009-3084(97)00042-X

Reference yield: 72.0%

trityl chloride (76-83-5) + N-(15Z-tetracosenoyl)-sphing-4-enine (54164-50-0) → 1-O-triphenylmethyl-24:1-Cer (124751-47-9)

Guidance literature:

With dmap; In toluene; for 16h; Heating;

DOI:10.1016/S0009-3084(97)00042-X

upstream raw materials:

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

nervonic acid N-hydroxysuccinimide ester

Nervonic acid

Downstream raw materials:

1-O-triphenylmethyl-24:1-Cer

Refernces