N-hexadecanoylphytosphingosine

Base Information

• Chemical Name: N-hexadecanoylphytosphingosine
• CAS No.: 111149-09-8
• Molecular Formula: C34H69NO4
• Molecular Weight: 555.91600
• DSSTox Substance ID: DTXSID401317527
• Nikkaji Number: J1.478.406C
• Wikidata: Q27133656
• Metabolomics Workbench ID: 30687
• Mol file: 111149-09-8.mol

Synonyms:N-hexadecanoylphytosphingosine;111149-09-8;Cer(t18:0/16:0);N-(palmitoyl)-phytoceramide;N-(hexadecanoyl)-phytoceramide;N-(hexadecanoyl)-4R-hydroxysphinganine;N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]hexadecanamide;C16 Phytoceramide (t18:0/16:0);N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]-hexadecanamide;D-ribo-Phytoceramide;N-hexadecanoyl phytosphingosine;SCHEMBL22911039;CHEBI:65107;IVBULNXGVIHEKN-MVIDNBQJSA-N;DTXSID401317527;LMSP02030001;AKOS040756267;N-hexadecanoyl-(4R)-hydroxysphinganine;Q27133656;N-16:0 Phytosphingosine, N-palmitoyl-phytosphingosine (Saccharomyces Cerevisiae), powder

Chemical Property of N-hexadecanoylphytosphingosine

Chemical Property:

• PSA: 89.79000
• LogP: 9.14870
• XLogP3: 12.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 31
• Exact Mass: 555.52265968
• Heavy Atom Count: 39
• Complexity: 502

Purity/Quality:

99% ^*data from raw suppliers

C16 Phytoceramide (t18:0/16:0) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Sphingolipids
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NC(CO)C(C(CCCCCCCCCCCCCC)O)O
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O
• Description: C16 Phytoceramide (t18:0/16:0) is a phytoceramide, which is a family of sphingolipids found in the intestine, kidney, and extracellular spaces of the stratum corneum of the mammalian epidermis. C16 Phytoceramide (t18:0/16:0) is composed of a phytosphingosine backbone amine-linked to a C16 fatty acid chain. The levels of C16 phytoceramide (t18:0/16:0) increase following heat stress in S. cerevisiae. It has been used with other ceramides to create stratum corneum substitutes to study percutaneous penetration and psoriasis in vitro. [Matreya, LLC. Catalog No. 2035]

Technology Process of N-hexadecanoylphytosphingosine

There total 16 articles about N-hexadecanoylphytosphingosine 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: 88.6%

D-ribo-phytosphingosine (554-62-1) + hexadecanoic acid ethyl ester (628-97-7) → N-palmitoyl-D-ribo-phytosphingosine (111149-09-8)

Guidance literature:

With sodium methylate; In methanol; at 55 ℃;

Reference yield: 85.0%

4-(methoxymethyl)-N-palmitoyl-D-ribo-phytosphingosine (309946-76-7) → N-palmitoyl-D-ribo-phytosphingosine (111149-09-8)

Guidance literature:

With hydrogenchloride; methanol; In chloroform; at 20 ℃;

DOI:10.1021/jo001225v

Reference yield: 82.9%

D-ribo-phytosphingosine (554-62-1) + palmitic acid isopropyl ester (142-91-6) → N-palmitoyl-D-ribo-phytosphingosine (111149-09-8)

Guidance literature:

With potassium hydroxide; In ethanol; at 55 ℃;

upstream raw materials:

n-hexadecanoyl chloride

4-(methoxymethyl)-N-palmitoyl-D-ribo-phytosphingosine

D-ribo-phytosphingosine

1-hexadecylcarboxylic acid

Downstream raw materials:

Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-hexadecanoylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester

Refernces

• 1、 Stankeviciute, Gabriele,Tang, Peijun,Ashley, Ben,Chamberlain, Joshua D.,Hansen, Matthew E. B.,Coleman, Aimiyah,D’Emilia, Rachel,Fu, Larina,Mohan, Eric C.,Nguyen, Hung,Guan, Ziqiang,Campopiano, Dominic J.,Klein, Eric A.. "Convergent evolution of bacterial ceramide synthesis". . p. 305 - 312. Retrieved 2022/01/06.
• 2、 Goff, Randal D.,Gao, Ying,Mattner, Jochen,Zhou, Dapeng,Yin, Ning,Cantu III, Carlos,Teyton, Luc,Bendelac, Albert,Savage, Paul B.. "Effects of lipid chain lengths in α-galactosylceramides on cytokine release by natural killer T cells". . p. 13602 - 13603. Retrieved 2007/10/03.