2,3-Dihydroxypropyl decanoate

Base Information

• Chemical Name: 2,3-Dihydroxypropyl decanoate
• CAS No.: 2277-23-8
• Deprecated CAS: 1322-59-4,27214-36-4
• Molecular Formula: C13H26O4
• Molecular Weight: 246.347
• Hs Code.: 2915900090
• European Community (EC) Number: 247-667-6,614-915-3,886-775-3
• UNII: 197M6VFC1W
• DSSTox Substance ID: DTXSID40891378
• Nikkaji Number: J102.875H
• Wikidata: Q27105050
• NCI Thesaurus Code: C66185
• RXCUI: 1366664
• ChEMBL ID: CHEMBL1595008
• Mol file: 2277-23-8.mol

Synonyms:1-monocaprin;glycerol 1-monocaprinate;monocaprin;rac-glycerol 1-monodecanoate

Chemical Property of 2,3-Dihydroxypropyl decanoate

Chemical Property:

• Melting Point: 51.4 °C
• Refractive Index: 1.4280 (estimate)
• Boiling Point: 369.1 °C at 760 mmHg
• PKA: 13.16±0.20(Predicted)
• Flash Point: 129.6 °C
• PSA: 66.76000
• Density: 1.017 g/cm³
• LogP: 2.02350
• Storage Temp.: −20°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 246.18310931
• Heavy Atom Count: 17
• Complexity: 182

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Decanoyl-rac-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC(=O)OCC(CO)O
• Uses: 1-Decanoyl-rac-glycerol is a monoacylglyecrol with antibacterial activity. Studies show that 1-Decanoyl-rac-glycerol maybe potential apoptotic agents in T-cells. 1-Decanoyl-rac-glycerol may be used as an analytical standard in determining the purity of the analyte synthesized from camphor tree seed kernel oil and glycerol using the lipase from porcine pancreas as a catalyst by gas chromatography technique.

Technology Process of 2,3-Dihydroxypropyl decanoate

There total 6 articles about 2,3-Dihydroxypropyl decanoate 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: 79.0%

Methyl decanoate (110-42-9) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 3-decanoyloxy-propane-1,2-diol (2277-23-8) + 1,2-didecanoyl glycerol (17863-69-3,82950-64-9) + 1, 3-dicaprin (17598-93-5)

Guidance literature:

at 160 ℃; for 16h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c3gc36907b

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) → capric acid triglyceride (621-71-6) + 3-decanoyloxy-propane-1,2-diol (2277-23-8) + 1,2-didecanoyl glycerol (17863-69-3,82950-64-9) + 1, 3-dicaprin (17598-93-5)

Guidance literature:

With lipozyme; at 35 ℃; for 12h; under 3 Torr;

DOI:10.1007/s11746-999-0074-7

upstream raw materials:

1-decanoic acid

glycerol

decanoic acid ethyl ester

Methyl decanoate

Downstream raw materials:

glycerol 1-O-decylether

2-decyloxy-propane-1,3-diol

Refernces

• 1、 Sanchez, Daniel Alberto,Tonetto, Gabriela Marta,Ferreira, Maria Lujan. "Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in an organic solvent system". . p. 7 - 18. Retrieved 2014/01/06.
• 2、 Rosu, Roxana,Yasui, Mamoru,Iwasaki, Yugo,Yamane, Tsuneo. "Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system". . p. 839 - 843. Retrieved 2007/10/03.