(2S)-3-hydroxypropane-1,2-diyl didecanoate

Base Information

• Chemical Name: (2S)-3-hydroxypropane-1,2-diyl didecanoate
• CAS No.: 60514-49-0
• Molecular Formula: C23H44 O5
• Molecular Weight: 400.599
• Hs Code.: 2915900090
• DSSTox Substance ID: DTXSID70209260
• Nikkaji Number: J161.395B
• Wikidata: Q27102856
• NCI Thesaurus Code: C29869
• Metabolomics Workbench ID: 51173
• Mol file: 60514-49-0.mol

Synonyms:1,2-dicaprin;1,2-didecanoyl-sn-glycerol;1,2-didecanoylglycerol;1,2-didecanoylglycerol, (+-)-isomer;1,2-didecanoylglycerol, (S)-isomer

Chemical Property of (2S)-3-hydroxypropane-1,2-diyl didecanoate

Chemical Property:

• Vapor Pressure: 2.62E-11mmHg at 25°C
• Boiling Point: 481.9°C at 760 mmHg
• Flash Point: 148°C
• PSA: 72.83000
• Density: 0.969g/cm³
• LogP: 5.71510
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 22
• Exact Mass: 400.31887450
• Heavy Atom Count: 28
• Complexity: 370

Purity/Quality:

99% ^*data from raw suppliers

1,2-Didecanoyl-sn-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCC
• Isomeric SMILES: CCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCCCC
• Description: 1,2-Didecanoyl-sn-glycerol is an analog of the PKC-activating second messenger DAG. Although the biological activities of 1,2-didecanoyl-sn-glycerol have not been well characterized, it is expected to behave similarly to 1,2-dioctanoyl-sn-glycerol .
• Uses: 1,2-Didecanoyl-sn-glycerol increases ornithine decarboxylase activity associated with tumor promotion in mouse skin. It can also function as a bioregulator of protein kinase C in human platelets.

Technology Process of (2S)-3-hydroxypropane-1,2-diyl didecanoate

There total 7 articles about (2S)-3-hydroxypropane-1,2-diyl didecanoate 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: 94.0%

1,2-di-O-decanoyl-3-O-benzyl-sn-glycerol (103160-49-2) → (S)-1,2-O-didecanoyl-sn-glycerol (60514-49-0,82950-64-9)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In ethanol; ethyl acetate; for 18h; under 2068.59 Torr;

DOI:10.1016/j.tet.2006.04.071

Reference yield:

1-decanoic acid (334-48-5) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → (S)-1,2-O-didecanoyl-sn-glycerol (60514-49-0,82950-64-9) + capric acid triglyceride (621-71-6) + 3-decanoyloxy-propane-1,2-diol (2277-23-8) + 1, 3-dicaprin (17598-93-5) + (R)-2,3-O-didecanoyl-sn-glycerol (172588-12-4,82950-64-9)

Guidance literature:

With Rhizomucor miehei 1,3-specific lipase immobilized by adsorption on anion exchange phenolic resin Duolite A-568; silica gel; In n-heptane; at 50 ℃; for 6h; Concentration; Temperature; Enzymatic reaction;

DOI:10.1016/j.molcatb.2013.11.010

Reference yield:

1-decanoic acid (334-48-5) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → (S)-1,2-O-didecanoyl-sn-glycerol (60514-49-0,82950-64-9) + 3-decanoyloxy-propane-1,2-diol (2277-23-8) + 1, 3-dicaprin (17598-93-5) + (R)-2,3-O-didecanoyl-sn-glycerol (172588-12-4,82950-64-9)

Guidance literature:

With Rhizomucor miehei 1,3-specific lipase immobilized by adsorption on anion exchange phenolic resin Duolite A-568; silica gel; In n-heptane; at 40 ℃; for 6h; Enzymatic reaction;

DOI:10.1016/j.molcatb.2013.11.010

upstream raw materials:

1,2-di-O-decanoyl-3-O-benzyl-sn-glycerol

n-decanoyl chloride

1-decanoic acid

1,2-didecanoyl-sn-glycero-3-phosphocholine

Downstream raw materials:

2-O-benzyl-1,3-bis[(1,2-di-O-decanoyl-sn-glycero-3)-phosphoryl]glycerol di(2-cyanoethyl) ester