2-Stearoylglycerol

Base Information

• Chemical Name: 2-Stearoylglycerol
• CAS No.: 621-61-4
• Deprecated CAS: 75656-13-2
• Molecular Formula: C₂₁H₄₂O₄
• Molecular Weight: 358.562
• UNII: QCK4W723ZX
• DSSTox Substance ID: DTXSID70873440
• Nikkaji Number: J25.098H
• Wikidata: Q27145324
• Mol file: 621-61-4.mol

Synonyms:2-stearoylglycerol

Chemical Property of 2-Stearoylglycerol

Chemical Property:

• Melting Point: 74-75 °C
• Boiling Point: 485.7±25.0 °C(Predicted)
• PKA: 13.54±0.10(Predicted)
• PSA: 66.76000
• Density: 0.958±0.06 g/cm3(Predicted)
• LogP: 5.49190
• Storage Temp.: ?70°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 20
• Exact Mass: 358.30830982
• Heavy Atom Count: 25
• Complexity: 277

Purity/Quality:

99% ^*data from raw suppliers

2-Stearoyl-rac-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO
• Description: 2-Stearoyl-rac-glycerol is a monoacylglycerol containing stearic acid at the sn-2 position. 2-Stearoyl-rac-glycerol levels are increased in mouse plasma following exposure to low-dose ionizing radiation, as well as in rat kidney in a model of ischemia-reperfusion injury.
• Uses: 2-Stearoyl-rac-glycerol is a biomarker of metabolic responses to hepatotoxicants and carcinogens.

Technology Process of 2-Stearoylglycerol

There total 11 articles about 2-Stearoylglycerol 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: 74.0%

(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-octadecanoate (111425-86-6) → glycerol monostearate (621-61-4,75656-13-2) + (S)-2,3-dihydroxypropyl n-octadecanoate (22610-61-3,342394-34-7)

Guidance literature:

With triethyl borate; 2,2,2-trifluoroethanol; trifluoroacetic acid; for 5.5h; Ambient temperature;

DOI:10.1016/S0040-4039(97)00395-X

Reference yield:

Methyl stearate (112-61-8) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → octadecanoic acid 2,3-dihydroxypropyl ester (22610-63-5,342394-34-7) + DL-α,β-distearin (51063-97-9) + glycerol monostearate (621-61-4,75656-13-2) + 1,3-distearoylglycerol (504-40-5)

Guidance literature:

HMS-TBD; In dimethyl sulfoxide; at 110 ℃; for 4h;

DOI:10.1039/b418509a

Reference yield:

glycerol tristearate (555-43-1) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → octadecanoic acid 2,3-dihydroxypropyl ester (22610-63-5,342394-34-7) + DL-α,β-distearin (51063-97-9) + glycerol monostearate (621-61-4,75656-13-2) + 1,3-distearoylglycerol (504-40-5)

Guidance literature:

With sodium methylate; at 115 ℃; for 4h;

DOI:10.1021/jf021085l

upstream raw materials:

(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-octadecanoate

Methyl stearate

glycerol

glycerol tristearate

Downstream raw materials:

(R)-N-(tert-butoxycarbonyl)-4-hydroxyphenylglycine methyl ester

stearic acid

glycerol