[(E,2S,3R)-2-Azaniumyl-3-hydroxyoctadec-4-enyl] hydrogen phosphate

Base Information

• Chemical Name: [(E,2S,3R)-2-Azaniumyl-3-hydroxyoctadec-4-enyl] hydrogen phosphate
• CAS No.: 26993-30-6
• Molecular Formula: C18H38NO5P
• Molecular Weight: 379.477
• Hs Code.: 29225090
• Pharos Ligand ID: 1AHT2MA4KC9V
• Mol file: 26993-30-6.mol

Synonyms:[(E,2S,3R)-2-Azaniumyl-3-hydroxyoctadec-4-enyl] hydrogen phosphate;C18H38NO5P;C18-H38-N-O5-P;SCHEMBL15050308;SCHEMBL15050314;Sphingosine-1-Phosphate (d18:1), D-erythro-sphingosine-1-phosphate, powder

Chemical Property of [(E,2S,3R)-2-Azaniumyl-3-hydroxyoctadec-4-enyl] hydrogen phosphate

Chemical Property:

• Appearance/Colour: Off-white to grey powder
• Vapor Pressure: 2.49E-14mmHg at 25°C
• Melting Point: 190 ºC
• Refractive Index: 1.501
• Boiling Point: 548.8 °C at 760 mmHg
• PKA: 1.76±0.10(Predicted)
• Flash Point: 285.7 °C
• PSA: 122.82000
• Density: 1.094 g/cm³
• LogP: 4.74150
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Solubility.: methanol: THF: water (6:3:1): >0.5 mg/mL
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 17
• Exact Mass: 379.24876031
• Heavy Atom Count: 25
• Complexity: 370

Purity/Quality:

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

Sphingosine 1-phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(COP(=O)(O)[O-])[NH3+])O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)[O-])[NH3+])O
• Description: Sphingosine-1-phosphate (S1P) is the product of phosphorylation of sphingosine by sphingosine kinase that is secreted from cells and acts as an agonist at S1P receptors. It increases intracellular calcium levels in TAg-Jurkat cells expressing S1P1 and Gqi5, which allows for phospholipase C stimulation by Gi proteins, when used at a concentration of 200 nM, as well as in TAg-Jurkat cells expressing S1P2 and S1P3 receptors (EC50s = 8 and 11 nM, respectively). Intra- and extracellular levels of S1P vary spatially allowing it to function as an autocrine or paracrine factor, respectively, and dysregulation of S1P levels are associated with various disease states, such as inflammation and autoimmunity. S1P has a wide variety of effects, including an involvement in cell growth, angiogenesis, immunity, and neuroprotection.
• Uses: A putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cel l metastasis and inflammatory processes; mobilizes intracellular calcium stores; decreases cellular cAMP; activates phospholipase D; does not inhibitprotein kinase C. A ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12. A putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes. It mobilizes intracellular calcium stores, decreases cellular cAMP, activates phospholipase D and does not inhibitprotein kinase C. D-erythro-Dihydrosphingosine-1-phosphate is a saturated analog of D-erythro-Sphingosine-1-phosphate a putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes.

Technology Process of [(E,2S,3R)-2-Azaniumyl-3-hydroxyoctadec-4-enyl] hydrogen phosphate

There total 20 articles about [(E,2S,3R)-2-Azaniumyl-3-hydroxyoctadec-4-enyl] hydrogen phosphate 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: 83.0%

tert-butyl ((2S,3R,E)-1-((dimethoxyphosphoryl)oxy)-3-hydroxyoctadec-4-en-2-yl)carbamate (312933-38-3) → Sphingosine-1-phosphate (26993-30-6,26993-39-5)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at 0 - 20 ℃; for 6h;

Reference yield: 75.0%

<(2S,3R,4E)-2-amino-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-yl> dihydrogen phosphate (149035-79-0) → Sphingosine-1-phosphate (26993-30-6,26993-39-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 45 ℃; for 72h;

DOI:10.1016/S0040-4039(00)60772-4

Reference yield: 73.0%

Phosphoric acid (E)-(2S,3R)-2-amino-3-hydroxy-octadec-4-enyl ester dimethyl ester; hydrochloride → Sphingosine-1-phosphate (26993-30-6,26993-39-5)

Guidance literature:

Phosphoric acid (E)-(2S,3R)-2-amino-3-hydroxy-octadec-4-enyl ester dimethyl ester; hydrochloride; With trimethylsilyl bromide; In dichloromethane; at 0 - 20 ℃; for 1h;

With water;

DOI:10.1016/S0040-4039(00)01361-7

upstream raw materials:

<(2S,3R,4E)-2-amino-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-yl> dihydrogen phosphate

Phosphoric acid (E)-(2S,3R)-2-amino-3-hydroxy-octadec-4-enyl ester bis-[1-(2-nitro-phenyl)-ethyl] ester

tert-butyl ((2S,3R,E)-1-((dimethoxyphosphoryl)oxy)-3-hydroxyoctadec-4-en-2-yl)carbamate

N-tert-butyloxycarbonylsphingosine

Downstream raw materials:

N-[(1S,2R,3E)-2-hydroxy-1-[(phosphonooxy)methyl]-3-heptadecen-1-yl]-5-[(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-pentanamide

N-[(1S,2R,3E)-2-hydroxy-1-[(phosphonooxy)methyl]-3-heptadecen-1-yl]-propanamide

N-[(1S,2R,3E)-2-hydroxy-1-[(phosphonooxy)methyl]-3-heptadecen-1-yl]-(15Z)-tetracosenamide

N-[(1S,2R,3E)-2-hydroxy-1-[(phosphonooxy)methyl]-3-heptadecen-1-yl]-octadecanamide

Refernces

• 1、 -. "4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO". Page/Page column 309-310. . Retrieved 2021/07/10.
• 2、 -. "NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO". Page/Page column 67; 68. . Retrieved 2017/07/14.