Octadecanoic acid, 3-hydroxy-2-methoxypropyl ester

Base Information

• Chemical Name: Octadecanoic acid, 3-hydroxy-2-methoxypropyl ester
• CAS No.: 100156-48-7
• Molecular Formula: C22H44O4
• Molecular Weight: 0
• DSSTox Substance ID: DTXSID70905230
• Mol file: 100156-48-7.mol

Synonyms:1-O-octadecyl-2-O-methylglycerol;1-O-octadecyl-2-O-methylglycerol, (+-)-isomer

Chemical Property of Octadecanoic acid, 3-hydroxy-2-methoxypropyl ester

Chemical Property:

• Vapor Pressure: 1.8E-10mmHg at 25°C
• Boiling Point: 461.9°Cat760mmHg
• Flash Point: 142.6°C
• PSA: 55.76000
• Density: 0.932g/cm³
• LogP: 5.79840
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 21
• Exact Mass: 372.32395988
• Heavy Atom Count: 26
• Complexity: 294

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC

Technology Process of Octadecanoic acid, 3-hydroxy-2-methoxypropyl ester

There total 6 articles about Octadecanoic acid, 3-hydroxy-2-methoxypropyl ester 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:

C28H58O4Si (1232676-42-4) → rac.-1-Stearoyl-glycerin-methylaether-2 (18679-04-4,100156-48-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1039/b9nj00704k

Reference yield:

1-stearoyI-3-(tert-butyldimethylsilyl)-sn-glycerol (132679-65-3) → rac.-1-Stearoyl-glycerin-methylaether-2 (18679-04-4,100156-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrafluoroboric acid / hexane; dichloromethane / 2.5 h / 0 - 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With tetrafluoroboric acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/b9nj00704k

Reference yield:

stearic acid (57-11-4) → rac.-1-Stearoyl-glycerin-methylaether-2 (18679-04-4,100156-48-7)

Guidance literature:

Multi-step reaction with 4 steps

1: tributyl-amine / 5 h / 85 °C

2: dmap; triethylamine / dichloromethane / 17 h / 20 °C

3: tetrafluoroboric acid / hexane; dichloromethane / 2.5 h / 0 - 20 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With dmap; tetrafluoroboric acid; tributyl-amine; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/b9nj00704k

upstream raw materials:

2-methylglycerol

Stearoyl chloride

1-stearoyI-3-(tert-butyldimethylsilyl)-sn-glycerol

C₂₈H₅₈O₄Si

Refernces

• 1、 Gendaszewska-Darmach, Edyta,Laska, Edyta,Rytczak, Przemys?aw,Okruszek, Andrzej. "The chemical synthesis of metabolically stabilized 2-OMe-LPA analogues and preliminary studies of their inhibitory activity toward autotaxin". . p. 2698 - 2700. Retrieved 2012.
• 2、 Rytczak, Przemyslaw,Koziolkiewicz, Maria,Okruszek, Andrzej. "The chemical synthesis of phosphorothioate and phosphorodithioate analogues of lysophosphatidic acid (LPA) and cyclic phosphatidic acid (CPA)". . p. 1008 - 1017. Retrieved 2010/08/05.