85618-19-5

Usage

Uses

Used in Biochemistry and Molecular Biology:
Hexylb-D-thioglucopyranoside is used as a solubilizing agent for the extraction and purification of membrane proteins from Escherichia coli. Its non-ionic nature and high critical micelle concentration contribute to the stabilization of these proteins, facilitating their study and analysis.
Used in Pharmaceutical Industry:
Hexylb-D-thioglucopyranoside is utilized as a reconstitution agent to reintroduce solubilized membrane proteins into a lipid environment, mimicking their natural cellular context. This is crucial for the functional characterization of these proteins and for the development of drugs targeting membrane protein-related diseases.
Used in Nanotechnology and Drug Delivery Systems:
Due to its solubility and electroneutral properties, Hexylb-D-thioglucopyranoside can be employed in the development of novel drug delivery systems, particularly for hydrophobic drugs or those requiring specific targeting to cellular membranes. Its ability to form micelles can enhance the bioavailability and therapeutic efficacy of various pharmaceutical agents.

InChI:InChI=1/C12H24O5S/c1-2-3-4-5-6-18-12-11(16)10(15)9(14)8(7-13)17-12/h8-16H,2-7H2,1H3/t8?,9-,10+,11?,12+/m1/s1

Upstream product

• 111-31-9 Hexanethiol 
• 85618-25-3 hexyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-68-2 α-D-glucopyranose peracetylate 
• 604-69-3 β-D-glucose pentaacetate 
• 111-25-1 1-bromo-hexane 
• 85618-25-3 n-hexyl 2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 

Relevant academic research and scientific papers

Synthesis and surface properties of alkyl β?D?thioglucopyranoside

Alkyl thioglycosides are a class of nonionic sugar-based sulfur-containing surfactants and bioreagents. The surfactants 1,2?trans alkyl β?D?thioglucopyranosides with different alkyl chain length (n = 6–12) were stereoselectively prepared by the Helferich method. Their properties including HLB number, logP value, water solubility, foam property, emulsifying property, surface property and thermotropic liquid crystal property were mainly investigated. The results showed that their HLB numbers and water-solubility decreased as the related logP values increased with increasing the alkyl chain length. Alkyl β?D?thioglucosides were already insoluble in water with n ≥ 10. Both β?D?thioglucopyranosides (n = 8, 9) reduced the surface tension of the related aqueous solution to nearly 29 mN·m?1 at the critical micelle concentration (CMC), they also had excellent foaming ability and foam stability. Nonyl β?D?thioglucopyranoside had good emulsifying properties for both n?octane/water system and toluene/water system. Alkyl β?D?thioglucopyranosides (n = 6–12) were observed to have the thermotropic liquid crystal properties.

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.

Synthesis, purification and liquid-crystalline behaviour of several alkyl 1-thio-D-glycopyranosides

This paper describes the synthesis, purification, and liquid- crystalline behaviour of a series of alkyl 1-thioglycopyranosides. The synthesis of these derivatives was carried out via a Lewis acid mediated coupling of the fully acetylated monosaccharide with an alkanethiol. The choice of the Lewis acid depends on the configuration of AcO-2. The carbohydrate-derived surfactants exhibit thermotropic liquid-crystalline behaviour. The alkyl 1-thioglycopyranosides form the expected smectic A phases upon heating. The clearing temperatures vary with alkyl chain length which is in accordance with the accepted model for the S(A) phase of amphiphilic carbohydrate mesogens. For the alkyl 1-thiotalopyranosides, the clearing points are much lower than expected, presumably due to the formation of an intramolecular hydrogen bond in the talose moiety.

Non-amphiphilic carbohydrate liquid crystals containing an intact monosaccharide moiety

A chiral rigid moiety which forms the basis of a new class of non-amphiphilic carbohydrate liquid crystals has been developed. This moiety contains a fully intact glucopyranose ring embedded in a trans-decalin structure. The original carbohydrate is substituted so that only two hydroxyl groups are left, resulting in derivatives with reduced hydrophilicity. The substituents R and X-R′ on the 4,6-O-ylidene β-D-glucopyranoside are in the equatorial position and can be varied extensively, using straightforward synthetic procedures. Investigations as to the requirements for R and X-R′ for inducing liquid-crystalline behavior have shown that at least one of the substituents should contain a large, polarizable aromatic moiety. An aromatic Schiff base fulfils this requirement.

Ampiphilic Carbohydrate-Based Mesogens, VI: Synthesis of a Series of Alkyl 1-Thio-D-glucopyranosides and Their Regioselective Reductions to 1-Alkylthio-1-deoxy-D-glucitols

Alkyl 1-thio-α,β-D-glucopyranosides (hexyl to decyl, 1a-e) are prepared by reaction of penta-O-acetyl-β-D-glucopyranose with the respective thiols in the presence of diethylether-trifluoroborane, followed by deacetylation. 1a-e are converted into their tetra-O-diethylboryl derivatives 2a-e and reduced with ethyldiboranes(6) in the presence of the catalyst 9-methylsulfonyloxy-9-borabicyclononane (9-BBN-mesylate, MSBBN) to give the mesogenic 1-alkylthio-1-deoxy-D-glucitols 3a-e after deboronation.

Synthesis of Alkyl-β-D-thioglucopyranosides, a Series of New Nonionic Detergents

As a part of our search for new types of detergent useful for biological applications, a series of alkyl-β-D-thioglucopyranosides was synthesized in several steps from glucose.The overall yield was about 80percent.Critical micelle concentrations of n-hexyl-, n-heptyl-, n-octyl-, and n-nonyl-β-D-thioglucopyranoside were determined.Because of their electroneutrality, high solubility in water and high critical micelle concentration, n-heptyl- and n-octyl-β-D-thioglucopyranoside seem to be potentially useful detergents for applications in biological systems.