1-Stearoyl-2-arachidonoyl-SN-glycerol

Base Information

• Chemical Name: 1-Stearoyl-2-arachidonoyl-SN-glycerol
• CAS No.: 65914-84-3
• Molecular Formula: C41H72O5
• Molecular Weight: 645.02
• DSSTox Substance ID: DTXSID901286391
• Wikidata: Q27088683
• Metabolomics Workbench ID: 5897
• Mol file: 65914-84-3.mol

Synonyms:1-stearoyl-2-arachidonoyl-sn-glycerol;1-stearoyl-2-arachidonoylglycerol

Chemical Property of 1-Stearoyl-2-arachidonoyl-SN-glycerol

Chemical Property:

• Vapor Pressure: 5.56E-22mmHg at 25°C
• Boiling Point: 689.2°Cat760mmHg
• Flash Point: 190.3°C
• PSA: 72.83000
• Density: 0.942g/cm³
• LogP: 11.84090
• Storage Temp.: −20°C
• Solubility.: chloroform: 20 mg/mL, clear, colorless
• XLogP3: 14.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 36
• Exact Mass: 644.53797539
• Heavy Atom Count: 46
• Complexity: 782

Purity/Quality:

98%min ^*data from raw suppliers

1-Stearoyl-2-arachidonoyl-sn-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCC=CCC=CCC=CCC=CCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
• Uses: 1-Stearoyl-2-arachidonoyl-sn-glycerol activates PKC allosterically. It activates transient receptor potential channels 3 and 6 that regulates the intracellular free calcium levels.

Technology Process of 1-Stearoyl-2-arachidonoyl-SN-glycerol

There total 19 articles about 1-Stearoyl-2-arachidonoyl-SN-glycerol 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: 92.0%

2-O-arachidonoyl-3-O-(4,4-dimethoxytrityl)-1-O-stearoyl-sn-glycerol (496808-61-8) → 1-stearoyl-2-arachidonoyl-sn-glycerol (65914-84-3)

Guidance literature:

With formic acid; acetic acid; In water; at 20 ℃; for 4h;

DOI:10.1039/d0sc06219g

Reference yield: 90.0%

2-O-arachidonoyl-1-O-stearoyl-3-O-triethylsilyl-sn-glycerol (1228359-78-1) → 1-stearoyl-2-arachidonoyl-sn-glycerol (65914-84-3)

Guidance literature:

With methanol; iron(III) chloride; In dichloromethane; at 20 ℃; for 8.91667h;

DOI:10.1021/jo100393c

Reference yield: 46.0%

C57H90O5Si (1037195-83-7) → 1-stearoyl-2-arachidonoyl-sn-glycerol (65914-84-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; acetic acid; at 0 ℃; for 1h;

DOI:10.1016/j.tetlet.2008.04.036

upstream raw materials:

(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (R)-1-octadecanoyloxymethyl-2-(9-phenyl-9H-xanthen-9-yloxy)-ethyl ester

(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (S)-1-octadecanoyloxymethyl-2-(9-phenyl-9H-xanthen-9-yloxy)-ethyl ester

2-O-arachidonoyl-3-O-(4,4-dimethoxytrityl)-1-O-stearoyl-sn-glycerol

(R)-2,3-dihydroxypropyl stearate

Downstream raw materials:

C₅₁H₈₁NO₁₁

2-arachidonoyl glycerol

all cis 5,8,11,14-eicosatetraenoic acid