Phytosphingosine

Base Information

• Chemical Name: Phytosphingosine
• CAS No.: 554-62-1
• Molecular Formula: C18H39NO3
• Molecular Weight: 317.513
• Hs Code.: 29221990
• European Community (EC) Number: 439-210-6
• UNII: GIN46U9Q2Q
• DSSTox Substance ID: DTXSID80203951
• Nikkaji Number: J13.584D
• Wikipedia: Phytosphingosine
• Wikidata: Q3746193
• RXCUI: 1363444
• Metabolomics Workbench ID: 30478
• ChEMBL ID: CHEMBL236036
• Mol file: 554-62-1.mol

Synonyms:4-D-hydroxysphinganine;8-(Z-E)-C18-phytosphingenine;phytosphingosine

Chemical Property of Phytosphingosine

Chemical Property:

• Vapor Pressure: 2.18E-11mmHg at 25°C
• Melting Point: 102 °C
• Refractive Index: 9 ° (C=1, Pyridine)
• Boiling Point: 483.733 °C at 760 mmHg
• PKA: 11.91±0.45(Predicted)
• Flash Point: 246.353 °C
• PSA: 86.71000
• Density: 0.983 g/cm³
• LogP: 3.81930
• Storage Temp.: −20°C
• Solubility.: Soluble in Ethanol (up to 2 mg/ml).
• Water Solubility.: 2.6mg/L at 20℃
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 16
• Exact Mass: 317.29299411
• Heavy Atom Count: 22
• Complexity: 226

Purity/Quality:

99%, ^*data from raw suppliers

Phytosphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCC(C(C(CO)N)O)O
• Isomeric SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)N)O)O
• Description: Phytosphingosine is a sphingolipid with a hydroxyl group at the C4 position that is found mainly in fungi and plants but also in animals, including humans. It is metabolized to odd-numbered fatty acids with 2-hydroxy palmitic acid as an intermediate. Phytosphingosine dose-dependently induces cell death of CHO cells and inhibits carbachol-induced activation of phospholipase D (PLD) in CHO cells transfected with C. elegans muscarinic acetylcholine receptors. It is essential in the heat stress response in S. cerevisiae. [Matreya, LLC. Catalog No. 1330]
• Uses: phytosphingosine is a sphingolipid that can improve the overall condition of skin and hair. Some sources site anti-microbial and anti-inflammatory properties. Research indicates similar activity to retinoic acid, in which case it may be particularly beneficial for aging and photo-aging skin.

Technology Process of Phytosphingosine

There total 207 articles about Phytosphingosine 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: 95.0%

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol (117168-59-9) → D-ribo-phytosphingosine (554-62-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; 1.) 30 min, RT; 2.) 1 h, reflux;

DOI:10.1016/0008-6215(88)85090-0

Reference yield: 95.0%

(S)-tert-butyl 4-[(1S,2R)-1,2-dihydroxyhexadecyl]-2,2-dimethyloxazolidine-3-carboxylate (124127-36-2) → D-ribo-phytosphingosine (554-62-1)

Guidance literature:

With water; trifluoroacetic acid; for 0.25h;

DOI:10.1021/jo00292a013

Reference yield: 93.0%

(2S,3S,4R)-2-azidooctadec-6-yne-1,3,4-triol → D-ribo-phytosphingosine (554-62-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; Ambient temperature;

upstream raw materials:

(2S,3S,4R)-2-(phthalimido)-octadecane-1,3,4-triol

(+)-2-Cyclohexanoylamino-1,3,4-trihydroxy-octadecan

(2S,3S,4R)-2-(benzylamino)octadecane-1,3,4-triol

(S)-tert-butyl 4-[(1S,2R)-1,2-dihydroxyhexadecyl]-2,2-dimethyloxazolidine-3-carboxylate

Downstream raw materials:

(2S,3R,4R)-2-(N-benzoyl)amino-octadecane-1,3,4-triol

tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

N-palmitoyl-D-ribo-phytosphingosine

Refernces

RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: Their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines

10.1016/j.bmc.2008.08.060

The research centers on the synthesis and assessment of sulfonamide analogs of KRN7000, which are known for activating natural killer (NK) T cells. The goal was to create compounds that could selectively stimulate the production of Th2-biased cytokines to potentially alleviate autoimmune diseases and enhance transplantation tolerance. The study involved synthesizing a range of sulfonamide analogs, including both aromatic and aliphatic types, using phytosphingosine as the starting material and employing various chemical reactions such as protection and deprotection of hydroxyl groups, glycosidation, and sulfonamide formation. The synthesized analogs were then tested for their bioactivity using mouse spleen cells in vitro to evaluate the production of Th1 and Th2 cytokines. The analysis was performed using a cytometric bead array (CBA) to quantify IFN-?, IL-4, and IL-13 levels, allowing the researchers to assess the cytokine profile induced by each analog. The findings indicated that most of the analogs were effective in promoting Th2-biased cytokine production, with certain analogs showing particularly high IL-4/IFN-? ratios, suggesting their potential in modulating immune responses towards a Th2 phenotype.