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

D-riboPhytosphingosine ^*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:

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

2-phenyl-4-(S)-[(1R,2R)-1,2-dihydroxyhexadecyl]-1,3-oxazoline

Refernces

• 1、 Qu, Yan,Zhang, Hong-Bin,Liu, Ji-Kai. "Isolation and structure of a new ceramide from the basidiomycete Hygrophorus eburnesus". . p. 241 - 244. Retrieved 2004.
• 2、 Gao, Jin-Ming,Zhang, An-Ling,Zhang, Cun-Li,Liu, Ji-Kai. "Paxillamide: A novel phytosphingosine derivative from the fruiting bodies of Paxillus panuoides". . p. 1483 - 1487. Retrieved 2004.
• 3、 Mridha, Moniruzzaman,Ma, Guangning,Palo-Nieto, Carlos,Afewerki, Samson,Cordova, Armando. "Development of an Amino Acid/Hydroxy Oxime Dual Catalyst System for Highly Stereoselective Direct Asymmetric Aldol Reactions in the Presence of Water". . p. 383 - 390. Retrieved 2016/12/24.
• 4、 Haghshenas, Pouyan,Gravel, Michel. "Chemo- and Diastereoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-α-amino Aldehydes". supporting information. p. 4518 - 4521. Retrieved 2016/09/28.