C16-0(Palmitoyl)ceramide

Base Information

• Chemical Name: C16-0(Palmitoyl)ceramide
• CAS No.: 4201-58-5
• Molecular Formula: C₃₄H₆₇NO₃
• Molecular Weight: 537.911
• European Community (EC) Number: 640-541-5
• Nikkaji Number: J2.169.396K
• Metabolomics Workbench ID: 167181
• Mol file: 4201-58-5.mol

Synonyms:C(16)-ceramide;C16-0(palmitoyl)ceramide;C16-ceramide;C16-palmitoylceramide;ceramide-C16;N-palmitoylsphingosine;N-palmitoylsphingosine, (R*,S*-(E))-(+-);N-palmitoylsphingosine, R-(R*,S*-(E));NFA(C16)CER;palmitoylceramide;pCer cpd

Chemical Property of C16-0(Palmitoyl)ceramide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 675.4°Cat760mmHg
• Flash Point: 362.3°C
• PSA: 73.05000
• Density: 0.919g/cm³
• LogP: 10.40330
• XLogP3: 12.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 30
• Exact Mass: 537.51209500
• Heavy Atom Count: 38
• Complexity: 508

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NC(CO)C(C=CCCCCCCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)NC(CO)C(/C=C/CCCCCCCCCCCCC)O

Technology Process of C16-0(Palmitoyl)ceramide

There total 73 articles about C16-0(Palmitoyl)ceramide 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: 99.0%

N-tert-butyloxycarbonylsphingosine (116467-63-1) + n-hexadecanoyl chloride (112-67-4) → (2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol (4201-58-5,4201-59-6,24696-34-2,52019-77-9,74743-19-4,102917-79-3,24696-26-2)

Guidance literature:

N-tert-butyloxycarbonylsphingosine; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

In dichloromethane; water;

n-hexadecanoyl chloride; With potassium carbonate; ammonium chloride; more than 3 stages;

Reference yield: 99.0%

(E)-1-(Benzyloxy)-2-palmitamidooctadec-4-en-3-ol → rac-erythro-N-palmitoylsphingosine (4201-58-5,4201-59-6,24696-26-2,24696-34-2,52019-77-9,74743-19-4,102917-79-3)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; 1.) -78 deg C, 2 h, 2.) -40 deg C, 4 h;

DOI:10.1021/jo00076a042

Reference yield: 91.0%

1,3-bis(1-ethoxyethoxy)-2-hexadecanamido-4-E-D-erythro-octadec-4-ene → (2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol (4201-58-5,4201-59-6,24696-34-2,52019-77-9,74743-19-4,102917-79-3,24696-26-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 20 ℃; for 47h;

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

upstream raw materials:

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

4-nitrophenyl palmitate

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

(2R,3R)-2-palmitoylamido-4-hydroxyoctadecyn-1,3-diol

Downstream raw materials:

(2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene

(2S,3R)-N-palmitoyl-3-O-benzoyl-1-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-sphingosine

Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester

Benzoic acid (E)-(R)-1-[(S)-1-hexadecanoylamino-2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester

Refernces

• 1、 -. "COSMETIC COMPOSITION FOR SKIN IMPROVEMENT COMPRISING GREEN BARLEY EXTRACT". . . Retrieved 2022/02/05.
• 2、 Rudd, Andrew K.,Devaraj, Neal K.. "Traceless synthesis of ceramides in living cells reveals saturation-dependent apoptotic effects". . p. 7485 - 7490. Retrieved 2018/07/25.