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85618-26-4 , Octyl 2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside, CAS:85618-26-4

85618-26-4,Octyl 2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside,
CAS:85618-26-4
C22H36O9S / 476.58
MFCD04039659

Octyl 2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside

正辛基-2,3,4,6-O-四乙酰基-beta-D-1-硫代吡喃葡萄糖苷,

Octyl 2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside (OTG) is a nonionic detergent that is commonly used in biochemistry and molecular biology experiments. It is a glycoside-based surfactant that is synthesized from thioethyl glucopyranoside and octanol. OTG is often used for the solubilization and purification of membrane proteins and other hydrophobic biomolecules.

Synthesis and Characterization

OTG can be synthesized by several methods, including the reaction of thioethyl glucopyranoside with octanol in the presence of an acid catalyst, the reaction of thioethyl glucopyranoside with octyl bromide, and the reaction of thioethyl glucopyranoside with octanal followed by hydrogenation.

OTG can be characterized by various methods, including NMR spectroscopy, mass spectrometry, and HPLC.

Analytical Methods

OTG can be quantified by HPLC, UV-Vis spectrophotometry, and capillary electrophoresis. The critical micelle concentration (CMC) of OTG can be determined by surface tension measurements or fluorescence spectroscopy.

Biological Properties

OTG has low toxicity and is considered safe for most biological applications. It has been shown to have little effect on the integrity and function of membrane proteins, and it is often used in the solubilization and reconstitution of such proteins.

Toxicity and Safety in Scientific Experiments

OTG is generally considered safe for use in scientific experiments, but caution should be taken when handling it in concentrated form. It can cause skin and eye irritation, and inhalation of its dust or vapor may cause respiratory irritation.

Applications in Scientific Experiments

OTG is commonly used in a variety of biochemical and molecular biology experiments, including the solubilization and purification of membrane proteins, the characterization of membrane properties, and the study of lipid-protein interactions. It is also used in the preparation of liposomes and other lipid-based nanoparticles.

Current State of Research

There is extensive research on the properties and applications of OTG in scientific experiments. Recent studies have focused on the optimization of its use for different types of membrane proteins and the development of new analytical methods for its quantification.

Potential Implications in Various Fields of Research and Industry

OTG has potential implications in various fields of research and industry, including pharmaceuticals, biotechnology, and nanotechnology. Its use in the solubilization and purification of membrane proteins could lead to the development of new drugs targeting membrane-bound receptors, and its use in the preparation of lipid-based nanoparticles could lead to the development of new drug delivery systems.

Limitations and Future Directions

Despite its many applications, OTG has some limitations, such as stability issues in the presence of salt and the potential for interference with certain assays. Future research should focus on the development of more stable variants of OTG and the optimization of its use in different experimental conditions. Other future directions could include the exploration of novel applications of OTG in areas such as the study of lipid-protein interactions in disease states.

Abbreviations and acronyms should be used sparingly, and only if they are widely used and easily recognizable by the scientific community.

CAS Number85618-26-4
Product NameOctyl 2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside
IUPAC Name[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-octylsulfanyloxan-2-yl]methyl acetate
Molecular FormulaC22H36O9S
Molecular Weight476.58 g/mol
InChIInChI=1S/C22H36O9S/c1-6-7-8-9-10-11-12-32-22-21(30-17(5)26)20(29-16(4)25)19(28-15(3)24)18(31-22)13-27-14(2)23/h18-22H,6-13H2,1-5H3/t18-,19-,20+,21-,22+/m1/s1
InChI KeyXIROMIKWUKFPAA-BDHVOXNPSA-N
SMILESCCCCCCCCSC1C(C(C(C(O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
SynonymsOctyl 1-Thio-β-D-glucopyranoside Tetraacetate;
Canonical SMILESCCCCCCCCSC1C(C(C(C(O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Isomeric SMILESCCCCCCCCS[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
CAS No: 85618-26-4 Synonyms: Octyl 1-thio-b-D-glucopyranoside tetraacetate MDL No: MFCD04039659 Chemical Formula: C22H36O9S Molecular Weight: 476.58


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