1,2-Dimyristoyl-rac-glycerol

Base Information

• Chemical Name: 1,2-Dimyristoyl-rac-glycerol
• CAS No.: 20255-94-1
• Molecular Formula: C31H60 O5
• Molecular Weight: 512.814
• Hs Code.: 2915900090
• European Community (EC) Number: 243-643-4
• UNII: G0ZI9U6LC3
• DSSTox Substance ID: DTXSID00942375
• Nikkaji Number: J21.204K
• Wikidata: Q27156751
• Mol file: 20255-94-1.mol

Synonyms:1,2-dimyristoylglycerol;dimyristoyl diglyceride

Chemical Property of 1,2-Dimyristoyl-rac-glycerol

Chemical Property:

• Vapor Pressure: 1E-15mmHg at 25°C
• Melting Point: 59℃
• Boiling Point: 577.2°Cat760mmHg
• Flash Point: 166.8°C
• PSA: 114.43000
• Density: 0.94g/cm³
• LogP: 18.71740
• Storage Temp.: −20°C
• XLogP3: 11.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 30
• Exact Mass: 512.44407501
• Heavy Atom Count: 36
• Complexity: 480

Purity/Quality:

99% ^*data from raw suppliers

1,2-Dimyristoyl-rac-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCC
• Uses: 1,2-Dimyristoyl-rac-glycerol is used to synthesize lipophilic peptides for gene delivery. 1,2-Dimyristoyl-rac-glycerol is used to synthesize?lipophilic peptides for gene delivery.
• Description: DMG (1,2-Dimyristoyl-rac-glycerol) is a carboxylic ester, glycerolipid and diglyceride with an attached myristoyl group, promoting interactions between proteins and lipids. It can be employed as a detergent or reagent. It's functional in cell biology experimentation concerning metabolism and metabolic pathways involving glycerolipids. As a diglyceride, the substance consists of two fatty acid chains covalently bonded to the glycerol molecule in the 1,2- formation. Diglyceride (DAG) research investigates the process of suppressing fat accumulation through DAG consumption.

Technology Process of 1,2-Dimyristoyl-rac-glycerol

There total 12 articles about 1,2-Dimyristoyl-rac-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: 88.0%

3-(benzyloxy)propane-1,2-diyl ditetradecanoate (73083-33-7) → 1,2-dimyristoyl-rac-glycerol (20255-94-1,56270-93-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; at 30 ℃; for 12h;

Reference yield: 84.0%

1-(tert-butyl)dimethylsilyl-2,3-dimyristoyl glycerol (56176-80-8) → 1,2-dimyristoyl-rac-glycerol (20255-94-1,56270-93-0)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 5h; Inert atmosphere; Cooling with ice;

Reference yield: 73.0%

tetradecanoic acid 2-oxopropane-1,3-diyl ester (132333-70-1) → 1,2-dimyristoyl-rac-glycerol (20255-94-1,56270-93-0) + glycerol 1,3-dimyristate (7770-09-4)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water; at 0 ℃; for 0.25h; Title compound not separated from byproducts;

DOI:10.1071/CH9902093

upstream raw materials:

2,3-Dibromopropan-1-ol

potassium myristate

3-(1-ethoxy-ethoxy)-propane-1,2-diol

tetradecanoyl chloride

Downstream raw materials:

2,3-dimyristoylglycerol-tosylate

Dimyristoylphosphatidic acid

Tetradecanoic acid 2-{[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxy}-1-tetradecanoyloxymethyl-ethyl ester

3'-deoxy-N⁶,2'-O-bis<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 5'-<(2RS)-2,3-bis(tetradecanoyloxy)-propyl 2-(4-nitrophenyl)ethyl phosphate>

Refernces

• 1、 Chapman. "". . p. 4680,4681. Retrieved 1958.
• 2、 -. "LIPID-LINKED PRODRUGS". . . Retrieved 2017/08/01.