Laurylsphingosine

Base Information

• Chemical Name: Laurylsphingosine
• CAS No.: 74713-60-3
• Molecular Formula: C₃₀H₅₉NO₃
• Molecular Weight: 481.803
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID401304172
• Nikkaji Number: J2.497.694G
• Wikidata: Q27140211
• Metabolomics Workbench ID: 30563
• Mol file: 74713-60-3.mol

Synonyms:dodecyl sphingosine;laurylsphingosine;N-lauroylsphingosine

Chemical Property of Laurylsphingosine

Chemical Property:

• Refractive Index: 1.6310 (estimate)
• Boiling Point: 579.38°C (rough estimate)
• PSA: 69.56000
• Density: 0.9777 (rough estimate)
• LogP: 8.39350
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Heated, Sonicat
• XLogP3: 10.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 26
• Exact Mass: 481.44949474
• Heavy Atom Count: 34
• Complexity: 452

Purity/Quality:

98%,99%, ^*data from raw suppliers

C12Ceramide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(CO)NC(=O)CCCCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCCCCCCCC)O
• Uses: Ceramide is one of the simplest sphingolipids, consisting of a sphingosine base N-linked to a fatty acid, and is a membrane mediator for cell-signaling events. N-Acyl chain length of membrane ceramides can influence bidimensional transitions, condensed domain morphology, and interfacial thickness. C12 Ceramide (d18:1/12:0) or N-lauroyl-D-erythro-sphingosine has been used:as a lipid standard in the optimization of the liquid chromatography-mass spectrometry (LC-MS) method conditionsas an internal standard for lipid extraction in U87MG (human glioma cell line)as an internal standard for the quantification of ceramide using liquid chromatography-mass spectrometry (LC-MS) in rat tissues

Technology Process of Laurylsphingosine

There total 2 articles about Laurylsphingosine 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:

n-dodecanoyl chloride (112-16-3) + (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → N-lauroylceramide (74713-60-3)

Guidance literature:

With pyridine; N,N-dimethyl-formamide; Die konfigurative Einheitlichkeit von E₁ ist ungewiss;

DOI:10.1021/ja01550a061

Reference yield:

(2S,3R,E)-2-aminooctadec-4-ene-1,3-diol hydrochloride (2673-72-5) + C20H29N2O5Pol → N-lauroylceramide (74713-60-3)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 10h;

DOI:10.1002/chir.23179

upstream raw materials:

n-dodecanoyl chloride

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

(2S,3R,E)-2-aminooctadec-4-ene-1,3-diol hydrochloride

Refernces

• 1、 Park, Jin,Li, Qian,Chang, Young-Tae,Kim, Tae Sung. "Inhibitory activity of a ceramide library on interleukin-4 production from activated T cells". . p. 2589 - 2595. Retrieved 2007/10/03.