Chimyl alcohol

Base Information

• Chemical Name: Chimyl alcohol
• CAS No.: 6145-69-3
• Molecular Formula: C19H40 O3
• Molecular Weight: 316.525
• Hs Code.: 2909499000
• European Community (EC) Number: 228-149-9
• NSC Number: 59269
• UNII: P9FNL3D0MN
• DSSTox Substance ID: DTXSID80862067
• Nikkaji Number: J6.228F
• Wikidata: Q27887159
• Metabolomics Workbench ID: 173914
• ChEMBL ID: CHEMBL142186
• Mol file: 6145-69-3.mol

Synonyms:1-O-hexadecylglycerol;alpha-hexadecylglyceryl ether;chimyl alcohol;chimyl alcohol, (+)-isomer;chimyl alcohol, (+-)-isomer;glyceryl-1-palmityl ether;testriol

Chemical Property of Chimyl alcohol

Chemical Property:

• Melting Point: 60-65 °C
• Boiling Point: 445.2±25.0 °C(Predicted)
• PKA: 13.68±0.20(Predicted)
• PSA: 49.69000
• Density: 0.920±0.06 g/cm3(Predicted)
• LogP: 4.83750
• Storage Temp.: −20°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% ^*data from raw suppliers

1-O-Hexadecyl-rac-glycerol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: CCCCCCCCCCCCCCCCOCC(CO)O
• Uses: 1-O-Hexadecyl-rac-glycerol is used in the synthesis of N-linked and diglycosylated glucosamine-based glycerolipids as antitumor agents.

Technology Process of Chimyl alcohol

There total 24 articles about Chimyl alcohol 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%

4-(n-hexadecyloxymethyl)-2,2-dimethyl-1,3-dioxolane (89496-73-1) → 3-(hexadecyloxy)-1,2-propanediol (6145-69-3)

Guidance literature:

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

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

Reference yield: 79.0%

hexadecanyl bromide (112-82-3) + 1,2-O-isopropylidene-D-glycerol (14347-78-5,36543-79-0) → 3-(hexadecyloxy)-1,2-propanediol (6145-69-3)

Guidance literature:

hexadecanyl bromide; 1,2-O-isopropylidene-D-glycerol; With potassium hydroxide; In benzene; at 20 ℃; Reflux;

With hydrogenchloride; water; In methanol; for 2h; Reflux;

Reference yield: 76.0%

hexadecanyl bromide (112-82-3) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0) → 3-(hexadecyloxy)-1,2-propanediol (6145-69-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1021/jo00057a015

upstream raw materials:

allyl-1-hexadecyl ether

methanesulfonic acid hexadecyl ester

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol

tosylate de n-hexadecyle

Downstream raw materials:

rac-1-O-hexadecyl-3-O-benzylglycerol

4-Benzyloxy-3-hexadecyloxymethyl-butyric acid ethyl ester

Trifluoro-methanesulfonic acid 2-benzyloxy-1-hexadecyloxymethyl-ethyl ester

2-(2-Benzyloxy-1-hexadecyloxymethyl-ethyl)-malonic acid diethyl ester

Refernces

• 1、 Fyles, Thomas M.,Tong, Christine C.. "Long-lived and highly conducting ion channels formed by lipophilic ethylenediamine palladium(ii) complexes". . p. 655 - 661. Retrieved 2007.
• 2、 Nascimento, Thiana Santiago,Braga, Esther Faria,Casaes Gomes, Giselle Cristina,Batista, William Rom?o,Mazzei Albert, André Luís,Capella Lopes, Rosangela Sabbatini,Lopes, Claudio Cerqueira. "Synthesis of natural 1- O -alkylglycerols: A study on the chemoselective opening of the epoxide ring by onium quaternary salts (N and P) and ionic liquids". . p. 1050 - 1054. Retrieved 2020/01/23.
• 3、 Pinault, Michelle,Guimaraes, Cyrille,Couthon, Hélène,Thibonnet, Jér?me,Fontaine, Delphine,Chant?me, Aurélie,Chevalier, Stephan,Besson, Pierre,Jaffrès, Paul-Alain,Vandier, Christophe. "Synthesis of alkyl-glycerolipids standards for gas chromatography analysis: Application for chimera and shark liver oils". . . Retrieved 2018/04/16.