(R)-3-(Hexadecyloxy)propane-1,2-diol

Base Information

• Chemical Name: (R)-3-(Hexadecyloxy)propane-1,2-diol
• CAS No.: 10550-58-0
• Molecular Formula: C19H40O3
• Molecular Weight: 316.525
• European Community (EC) Number: 234-133-2
• DSSTox Substance ID: DTXSID101286642
• Nikkaji Number: J71.845I
• Mol file: 10550-58-0.mol

Synonyms:3-o-hexadecyl-sn-glycerol;10550-58-0;(R)-3-(Hexadecyloxy)propane-1,2-diol;(2R)-3-hexadecoxypropane-1,2-diol;C19H40O3;(R)-3-(hexadecyloxy)-1,2-propanediol;3-hexadecyl-sn-glycerol;1,2-Propanediol, 3-(hexadecyloxy)-, (2R)-;SCHEMBL1086330;OOWQBDFWEXAXPB-LJQANCHMSA-N;DTXSID101286642;CCG-35274;HY-W127328;(R)-3-[hexadecyloxy)-1.2-propanediol;(2R)-3-(Hexadecyloxy)-1,2-propanediol;1,2-Propanediol,3-(hexadecyloxy)-,(2R)-;CS-0185569;NS00085563

Chemical Property of (R)-3-(Hexadecyloxy)propane-1,2-diol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 63-64 °C
• Refractive Index: 1.464
• Boiling Point: 445.177 °C at 760 mmHg
• PKA: 13.68±0.20(Predicted)
• Flash Point: 223.035 °C
• PSA: 49.69000
• Density: 0.92 g/cm³
• LogP: 4.83750
• Storage Temp.: -15°C
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 18
• Exact Mass: 316.29774513
• Heavy Atom Count: 22
• Complexity: 197

Purity/Quality:

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

3-O-Hexadecyl-sn-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCOCC(CO)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCOC[C@@H](CO)O
• Uses: 3-O-Hexadecyl-sn-glycerol is used to prepare phosphatidylcholine analogs as phospholipase A2 inhibitors. It is also used to prepare oxidized phospholipids for prevention and treatment of atherosclerosis and other disorders.

Technology Process of (R)-3-(Hexadecyloxy)propane-1,2-diol

There total 18 articles about (R)-3-(Hexadecyloxy)propane-1,2-diol 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: 100.0%

3-O-hexadecyl-1,2-O-isopropylidene-sn-glycerol (57959-37-2) → (R)-3-(hexadecyloxy)-1,2-propanediol (10550-58-0)

Guidance literature:

With hydrogenchloride; In methanol; for 1h; Heating;

DOI:10.1016/0040-4039(93)85070-D

Reference yield: 98.0%

3-O-hexadecyl-1-O-(tert-butyldiphenylsilyl)-sn-glycerol (119879-84-4) → (R)-3-(hexadecyloxy)-1,2-propanediol (10550-58-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00280a034

Reference yield: 86.0%

1-hexadecyl-2,3-dibenzylglycerol (174289-76-0) → (R)-3-(hexadecyloxy)-1,2-propanediol (10550-58-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; chloroform; for 12h; Ambient temperature;

DOI:10.1016/S0957-4166(97)00341-8

upstream raw materials:

3-O-hexadecyl-1,2-O-isopropylidene-sn-glycerol

3-O-hexadecyl-1-O-(tert-butyldiphenylsilyl)-sn-glycerol

methanesulfonic acid hexadecyl ester

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

Downstream raw materials:

(S)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-ol

2-azido-2-deoxy-1-O-hexadecyl-sn-glycerol

2-azido-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-1-O-hexadecyl-sn-glycerol

3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-1-O-hexadecyl-2-hexanamido-sn-glycerol

Refernces

• 1、 Magnusson, Carlos D.,Haraldsson, Gudmundur G.. "Activation of n-3 polyunsaturated fatty acids as oxime esters: A novel approach for their exclusive incorporation into the primary alcoholic positions of the glycerol moiety by lipase". . p. 712 - 720. Retrieved 2012.
• 2、 Stamatov, Stephan D.,Stawinski, Jacek. "Stereospecific and regioselective opening of an oxirane system. A new efficient entry to 1- or 3-monoacyl- and 1- or 3-monoalkyl-sn-glycerols". . p. 1601 - 1605. Retrieved 2005.
• 3、 -. "Method for preventing cancer metastasis". . . Retrieved 2015/11/10.
• 4、 Li, Liang,Wang, Chang-Yun,Shao, Chang-Lun,Guo, Yue-Wei,Li, Guo-Qiang,Sun, Xue-Ping,Han, Lei,Huang, Hui,Guan, Hua-Shi. "Sarcoglycosides A-C, new O-glycosylglycerol derivatives from the South China sea soft coral Sarcophyton infundibuliforme". experimental part. p. 1495 - 1502. Retrieved 2009/10/17.