C17 Sphingosine

Base Information

• Chemical Name: C17 Sphingosine
• CAS No.: 6918-48-5
• Molecular Formula: C17H35NO2
• Molecular Weight: 285.47
• Hs Code.: 2922199090
• DSSTox Substance ID: DTXSID701025448
• Nikkaji Number: J247.780G
• Wikidata: Q27144531
• Metabolomics Workbench ID: 30481
• Mol file: 6918-48-5.mol

Synonyms:C17 Sphingosine;6918-48-5;heptadecasphing-4-enine;Sphingosine (d17:1);(2S,3R,E)-2-Amino-4-heptadecene-1,3-diol;C17-Sphingosine;(E,2S,3R)-2-aminoheptadec-4-ene-1,3-diol;D-erythro-Sphingosine-C17;(2S,3R,4E)-2-aminoheptadec-4-ene-1,3-diol;heptadecasphingosine;LMSP01040002;C17 sphing-4-enine;Sphingosine (C17 base);SPHINGOSINE D17:1;SCHEMBL12694552;CHEBI:74220;RBEJCQPPFCKTRZ-LHMZYYNSSA-N;DTXSID701025448;AS-83209;HY-141579;CS-0181727;F82940;(2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol;Q27144531;Sphingosine (d17:1), D-erythro-sphingosine (C17 base), powder

Chemical Property of C17 Sphingosine

Chemical Property:

• PSA: 66.48000
• LogP: 4.23440
• Storage Temp.: -20°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 285.266779359
• Heavy Atom Count: 20
• Complexity: 219

Purity/Quality:

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

D-erythro-Sphingosine-C17 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCC=CC(C(CO)N)O
• Isomeric SMILES: CCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
• Description: Sphingosine is an amino alcohol most commonly characterized by an 18-carbon unsaturated hydrocarbon chain sphingosine (d18:1) . However, the hydrocarbon chain length of sphingosine, and the related dihydrosphingosine, can vary from 12-26 carbons in mammalian tissues. Sphingosine (d17:1) is a naturally-occurring but uncommon form of sphingosine, accounting for approximately 13% of the sphingosine in human skin. It can be phosphorylated by sphingosine kinases to produce C-17 sphingosine-1-phosphate. More commonly, sphingosine C-17 is used as an internal standard in the analysis of sphingoid compounds by chromatographic or spectrometric methods.
• Uses: Sphingosine (d17:1) has been used as a lipid standard in the analysis of sphingolipids by liquid chromatography-mass spectrometry (LC-MS) and tandem mass spectrometry. D-erythro-Sphingosine-C17 is a substrate for sphingosine kinase.

Technology Process of C17 Sphingosine

There total 16 articles about C17 Sphingosine 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:

(+/-)-erythro-2-nitro-heptadec-4-yne-1,3-diol (93478-78-5) → (+/-)-erythro-2-amino-heptadec-4t-ene-1,3-diol (6918-48-5,29707-25-3)

Guidance literature:

With tetrahydrofuran; lithium aluminium tetrahydride;

DOI:10.1002/hlca.19590420202

Reference yield:

pentadec-2-ynal (101106-59-6) → (+/-)-erythro-2-amino-heptadec-4t-ene-1,3-diol (6918-48-5,29707-25-3)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; potassium carbonate

2: lithium alanate; THF

With tetrahydrofuran; methanol; lithium aluminium tetrahydride; potassium carbonate;

DOI:10.1002/hlca.19590420202

Reference yield:

pentadec-2-ynal-diethylacetal (103598-24-9) → (+/-)-erythro-2-amino-heptadec-4t-ene-1,3-diol (6918-48-5,29707-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1: aqueous hydrochloric acid; dioxane

2: methanol; potassium carbonate

3: lithium alanate; THF

With tetrahydrofuran; 1,4-dioxane; hydrogenchloride; methanol; lithium aluminium tetrahydride; potassium carbonate;

DOI:10.1002/hlca.19590420202

upstream raw materials:

(+/-)-threo-2-amino-heptadec-4-yne-1,3-diol

pentadec-2-ynal

pentadec-2-ynal-diethylacetal

(+/-)-threo-2-nitro-heptadec-4-yne-1,3-diol

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