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Cas Database

111466-75-2

111466-75-2

Identification

  • Product Name:1,2-dioctanoylthiophosphatidylcholine

  • CAS Number: 111466-75-2

  • EINECS:

  • Molecular Weight:0

  • Molecular Formula:

  • HS Code:

  • Mol File:111466-75-2.mol

Synonyms:1,2-dioctanoylthiophosphatidylcholine;3,5,9-Trioxa-4-phosphaheptadecan-1-aminium, 4-hydroxy-N,N,N-trimethyl-10-oxo-7-((1-oxooctyl)oxy)-, hydroxide, inner salt, 4-oxide, (+-)-;3-S-Phosphocholine-1,2-o-dioctanoyl-3-mercapto-1,2-propanediol;4-Hydroxy-N,N,N-trimethyl-10-oxo-7-((1-oxooctyl)oxy)-3,5,9-trioxa-4-phosphaheptadecan-1-aminium hydroxide, inner salt, 4-oxide, (+-)-;Dic8-S-pc;Doct-S-pc

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Relevant articles and documentsAll total 2 Articles be found

Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water

Fernández-García, Christian,Powner, Matthew W.

, p. 78 - 83 (2017)

A convenient selective synthesis of 2′,3′-di-O-acetyl-nucleotide-5′-phosphates, 2′,3′-di-O-acetyl-nucleotide-5′-triphosphates and 2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their incorporation into protometabolism.

Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism

Taniguchi, Tohru,Manai, Daisuke,Shibata, Masataka,Itabashi, Yutaka,Monde, Kenji

supporting information, p. 12191 - 12194 (2015/10/12)

The stereochemistry of glycerophospholipids (GPLs) has been of interest for its roles in the evolution of life and in their biological activity. However, because of their structural complexity, no convenient method to determine their configuration has been reported. In this work, through the first systematic application of vibrational circular dichroism (VCD) spectroscopy to various diacylated GPLs, we have revealed that their chirality can be assigned by the sign of a VCD exciton couplet generated by the interaction of two carbonyl groups. This paper also presents spectroscopic evidence for the stereochemistry of GPLs isolated from bacteria, eukaryotes, and mitochondria.

Process route upstream and downstream products

Process route

N-octanoyl-imidazole
17450-31-6

N-octanoyl-imidazole

glycerolcholine phosphate
34688-34-1,563-24-6

glycerolcholine phosphate

dicapryloyl phosphatidylcholine
41017-85-0,111466-75-2

dicapryloyl phosphatidylcholine

Conditions
Conditions Yield
In water-d2; acetonitrile; for 4h; pH=7 - 7.5;
67%
1,2-dioctanoyl-sn-glycerol
60514-48-9

1,2-dioctanoyl-sn-glycerol

choline tosylate
55357-38-5

choline tosylate

Dioctanoylphosphatidylcholine
19191-91-4,111466-75-2

Dioctanoylphosphatidylcholine

Conditions
Conditions Yield
1,2-dioctanoyl-sn-glycerol; trichlorophosphate; With triethylamine; In dichloromethane; at 0 ℃; for 1.5h;
choline tosylate; With pyridine; In dichloromethane; water; at 20 ℃; for 1h;
37%
Dioctanoylphosphatidylcholine
19191-91-4,111466-75-2

Dioctanoylphosphatidylcholine

Conditions
Conditions Yield
With ethanol; platinum;
choline tosylate
55357-38-5

choline tosylate

sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin
36475-14-6,111466-75-2

2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin

Conditions
Conditions Yield
sn-2,3-dioctanoylglycerol; trichlorophosphate; With triethylamine; In dichloromethane; at 0 ℃; for 1.5h;
choline tosylate; With pyridine; In dichloromethane; water; at 20 ℃; for 1h;
C<sub>27</sub>H<sub>44</sub>O<sub>6</sub>

C27H44O6

Dioctanoylphosphatidylcholine
19191-91-4,111466-75-2

Dioctanoylphosphatidylcholine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 20 °C
2.1: triethylamine / dichloromethane / 1.5 h / 0 °C
2.2: 1 h / 20 °C
With triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
Octanoic acid (R)-2-(4-methoxy-benzyloxy)-1-octanoyloxymethyl-ethyl ester
214068-80-1

Octanoic acid (R)-2-(4-methoxy-benzyloxy)-1-octanoyloxymethyl-ethyl ester

2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin
36475-14-6,111466-75-2

2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 20 °C
2.1: triethylamine / dichloromethane / 1.5 h / 0 °C
2.2: 1 h / 20 °C
With triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin
36475-14-6,111466-75-2

2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: pyridine / 4 h / 20 °C
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 20 °C
3.1: triethylamine / dichloromethane / 1.5 h / 0 °C
3.2: 1 h / 20 °C
With pyridine; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
dicapryloyl phosphatidylcholine
41017-85-0,111466-75-2

dicapryloyl phosphatidylcholine

Conditions
Conditions Yield
Entspr. Phosphorsaeure-Verb./Cholin-tosylat, Trichlor-acetonitril;
2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin
36475-14-6,111466-75-2

2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin

Conditions
Conditions Yield
Aus rac.-1,2-Dioctanoylglycero-3-phosphorylcholin, Phospholipase A2 (aus Schlan-gengift);
Dioctanoylphosphatidylcholine
19191-91-4,111466-75-2

Dioctanoylphosphatidylcholine

1-octanoyl-sn-glycero-3-phosphocholine
45287-18-1

1-octanoyl-sn-glycero-3-phosphocholine

Conditions
Conditions Yield
With water; In various solvent(s); at 37 ℃; pH=8.5; Enzyme kinetics;

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