N-hexanoylsphingosine

Base Information

• Chemical Name: N-hexanoylsphingosine
• CAS No.: 124753-97-5
• Molecular Formula: C₂₄H₄₇NO₃
• Molecular Weight: 397.642
• Hs Code.: 29241990
• UNII: 038753E78J
• DSSTox Substance ID: DTXSID90924923
• Nikkaji Number: J2.399.509C,J635.470J
• Wikidata: Q27132875
• RXCUI: 1603859
• Metabolomics Workbench ID: 63014
• ChEMBL ID: CHEMBL224877
• Mol file: 124753-97-5.mol

Synonyms:C(6)-ceramide;C6-ceramide;N-caproylsphingosine;N-hexanoylsphingosine

Chemical Property of N-hexanoylsphingosine

Chemical Property:

• Vapor Pressure: 1.34E-15mmHg at 25°C
• Melting Point: 76-77℃
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 574.7°C at 760 mmHg
• PKA: 13.53±0.20(Predicted)
• Flash Point: 301.4°C
• PSA: 69.56000
• Density: 0.946g/cm³
• LogP: 6.05290
• Storage Temp.: −20°C
• Solubility.: Soluble in 100% ethanol at 25mg/ml and also in DMSO at 50mg/ml.
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 20
• Exact Mass: 397.35559436
• Heavy Atom Count: 28
• Complexity: 371

Purity/Quality:

99% ^*data from raw suppliers

C6 Ceramide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(CO)NC(=O)CCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCC)O
• Description: C6 ceramide is a cell-permeable analog of naturally occurring ceramides. With a longer carbon chain than C2 ceramide, it is somewhat more hydrophobic, and may more closely mimic the effects of natural ceramides. C6 ceramide mediates many diverse biological activities including apoptosis, activation of protein phosphatase 2A, and inhibition of the mitochondrial respiratory chain. It also enhances the expression of COX-2 in rat granulosa cells and stimulates the growth of bovine aortic smooth muscle cells. C6 ceramide acts in neuronal axons to inhibit neurite growth.
• Uses: A biologically active, cell permeable, but nonphysiologic ceramide analog. It stimulates protein phosphatase 2A at concentrations as low as 10 nM and activiates MAP kinase. It induces apoptosis and inhibits glycoproptein traffic by the secretory pathway. C6 Ceramide (d18:1/6:0) has been used as a chemotherapeutic agent to test its anti-tumor effect in breast cancer cells and ovarian cancer cell lines. It has also been used to test chemo-sensitization effects in cancer cells.

Technology Process of N-hexanoylsphingosine

There total 5 articles about N-hexanoylsphingosine 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: 68.0%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + Hexanoyl chloride (142-61-0) → N-hexanoyl-D-sphingosine (189894-79-9,124753-97-5,189894-80-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1016/j.bmcl.2010.05.042

Reference yield: 57.0%

Hexanoyl chloride (142-61-0) + sphingosine 1-phosphate → C6-ceramide (189894-79-9,124753-97-5,189894-80-2)

Guidance literature:

Hexanoyl chloride; sphingosine 1-phosphate; With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.166667h;

With sodium hydrogencarbonate; In dichloromethane; water;

Reference yield:

(2R,3R,4E)-2-amino-octadec-4-ene-1,3-diol (6036-85-7) + Hexanoyl chloride (142-61-0) → Hexanoic acid ((E)-(1R,2R)-2-hydroxy-1-hydroxymethyl-heptadec-3-enyl)-amide (124753-97-5,189894-80-2)

Guidance literature:

Hexanoyl chloride; With pyridine; 1-methyl-pyrrolidin-2-one; p-OH-m-NO₂-C₆H₃-C(O)-resin; at 20 ℃;

(2R,3R,4E)-2-amino-octadec-4-ene-1,3-diol; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmc.2005.01.027

upstream raw materials:

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

Hexanoyl chloride

(2S,3S,4E)-L-threo sphingosine

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

Refernces

• 1、 -. "SPHINGOSINE COMPOUND, METHOD FOR PRODUCING THE SAME, AND SPHINGOMYELINASE INHIBITOR". Page/Page column 14. . Retrieved 2009/12/27.
• 2、 Chang, Young-Tae,Choi, Jaehwa,Ding, Sheng,Prieschl, Eva E.,Baumruker, Thomas,Lee, Jae-Mok,Chung, Sung-Kee,Schultz, Peter G.. "The synthesis and biological characterization of a ceramide library". . p. 1856 - 1857. Retrieved 2007/10/03.