Glyceryl palmitate

Base Information

• Chemical Name: Glyceryl palmitate
• CAS No.: 542-44-9
• Deprecated CAS: 10161-77-0,19670-51-0,19670-51-0
• Molecular Formula: C₁₉H₃₈O₄
• Molecular Weight: 330.508
• European Community (EC) Number: 268-083-8,243-218-3,251-283-4,208-812-9,247-887-2
• NSC Number: 404240
• UNII: U9H9OM3S75
• DSSTox Substance ID: DTXSID00891470
• Nikkaji Number: J6.399A
• Wikidata: Q27887716
• NCI Thesaurus Code: C77468
• RXCUI: 1426928
• Metabolomics Workbench ID: 75086
• ChEMBL ID: CHEMBL1078140
• Mol file: 542-44-9.mol

Synonyms:1-glyceryl hexadecanoate;1-monohexadecanoyl-rac-glycerol;1-monohexadecanoylglycerol;1-monopalmitin;palmitoyl glycerol;palmitoyl glycerol, (+,-)-isomer;palmitoyl glycerol, hexadecanoic-1-(14)C-labeled cpd, (R)-isomer;rac-1(3)-palmitoyl glycerol

Chemical Property of Glyceryl palmitate

Chemical Property:

• Melting Point: 75oC
• Boiling Point: 451.3°Cat760mmHg
• PKA: 13.16±0.20(Predicted)
• Flash Point: 146.7°C
• PSA: 66.76000
• Density: 0.969g/cm³
• LogP: 4.36410
• Storage Temp.: −20°C
• Solubility.: soluble in Methanol
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 18
• Exact Mass: 330.27700969
• Heavy Atom Count: 23
• Complexity: 256

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: UVCB,Other Uses -> Biochemical Research
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(CO)O
• Description: 1-Palmitoyl-rac-glycerol is a monoacylglycerol that contains palmitic acid at the sn-1 position. It is an emulsifying agent and has been used to increase the viscoelasticity of processed cheese.

Technology Process of Glyceryl palmitate

There total 21 articles about Glyceryl palmitate 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: 93.0%

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) + n-hexadecanoyl chloride (112-67-4) → (R)-2,3-dihydroxypropyl n-hexadecanoate (19670-51-0,32899-41-5,542-44-9,5309-46-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 22 ℃; for 3h;

DOI:10.1021/cg101654c

Reference yield: 93.0%

(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-hexadecanoate (119617-61-7) → (S)-2,3-dihydroxypropyl hexadecanoic acid ester (542-44-9,5309-46-6,19670-51-0,32899-41-5)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; water; at 20 ℃; for 0.5h;

DOI:10.1039/c9ob02302j

Reference yield: 92.5%

(R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-hexadecanoate (57416-03-2) → (R)-2,3-dihydroxypropyl n-hexadecanoate (19670-51-0,32899-41-5,542-44-9,5309-46-6)

Guidance literature:

With boric acid; In 2-methoxy-ethanol; for 2h; Heating;

DOI:10.1002/1522-2675(20001004)83:10<2756::AID-HLCA2756>3.0.CO;2-I

upstream raw materials:

(R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-hexadecanoate

1-O-trityl-3-O-palmitoyl-sn-glycerol

1-hexadecylcarboxylic acid

n-hexadecanoyl chloride

Downstream raw materials:

(S)-2,3-di[(E)-2-methyl-2-butenoyloxy]propyl n-hexadecanoate

(R)-2,3-di[(E)-2-methyl-2-butenoyloxy]propyl n-hexadecanoate

C₃₉H₅₂F₆O₈

sn-1,2-dioleoyl-3-palmitoylglycerol

Refernces

• 1、 Gudmundsson, Haraldur G.,Linderborg, Kaisa M.,Kallio, Heikki,Yang, Baoru,Haraldsson, Gudmundur G.. "Synthesis of enantiopure ABC-type triacylglycerols". . . Retrieved 2019/12/26.
• 2、 Ni, Guanghui,Li, Zhiyuan,Liang, Kangjiang,Wu, Ting,De Libero, Gennaro,Xia, Chengfeng. "Synthesis and evaluation of immunostimulant plasmalogen lysophosphatidylethanolamine and analogues for natural killer T cells". . p. 2966 - 2973. Retrieved 2014/05/20.