85618-21-9

Basic information

• Product Name: Octyl thioglucoside
• Synonyms: N-OCTYL-1-THIO-BETA-D-GLC;octyl-beta-D-1-thioglycopyranoside;Octyl β-D-thioglucopyranoside, Octyl thioglucoside;n-Octyl-β-D-thio-glucopyranosid;1-(Octylthio)-1-deoxy-β-D-glucopyranose;Octyl-1-thio-β-D-glucopyranoside;1-S-Octyl-beta-D-thioglucopyranoside,98%;n-octyl b-D-thioglueoside
• CAS NO: 85618-21-9
• Molecular Formula: C₁₄H₂₈O₅S
• Molecular Weight: 308.43
• EINECS: 1308068-626-2
• Product Categories: Carbohydrates;Sulfur & Selenium Compounds;detergent;Pharm intermediate;Carbohydrates & Derivatives;Detergents
• Mol File: 85618-21-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 125-131 °C
• Boiling Point: 418.82°C (rough estimate)
• Flash Point: 250 °C
• Appearance: White/crystalline
• Density: 1.1831 (rough estimate)
• Vapor Pressure: 1.21E-11mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: −20°C
• Solubility: ethanol: soluble50mg/mL, clear, colorless
• PKA: 13.02±0.70(Predicted)
• Water Solubility: soluble
• BRN: 4182783
• CAS DataBase Reference: Octyl thioglucoside(CAS DataBase Reference)
• NIST Chemistry Reference: Octyl thioglucoside(85618-21-9)
• EPA Substance Registry System: Octyl thioglucoside(85618-21-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 85618-21-9(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Waxy Semi-Solid

Uses

Different sources of media describe the Uses of 85618-21-9 differently. You can refer to the following data:
1. A non-ionic detergent for solubilization and reconstitution of membrane proteins of Escherichia coli
2. resistant to b-glucosidases and has a wider pH stability range
3. A non-ionic detergent for solubilization and reconstitution of membrane proteins of Escherichia coli.

InChI:InChI=1/C14H28O5S/c1-2-3-4-5-6-7-8-20-14-13(18)12(17)11(16)10(9-15)19-14/h10-18H,2-9H2,1H3/t10-,11-,12?,13-,14+/m1/s1

Upstream product

• 111-88-6 Octanethiol 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 85618-26-4 β-thiooctylperacetyl D-glucoside 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 111-83-1 1-bromo-octane 

Downstream Products

• 1194234-41-7 2-hexyl-1-octyl 6-O-(2,3,6-tri-O-benzyl-4-O-isobutyryl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1194234-40-6 2-hexyl-1-octyl 6-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1194234-39-3 C₆₈H₈₄O₁₁ 
• 1194234-34-8 2-hexyl-1-octyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1194234-33-7 2-hexyl-1-octyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 1194234-32-6 octyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-1-thioglucopyranoside 
• 1194234-31-5 octyl 4,6-O-benzylidene-β-D-thioglucopyranoside 

Relevant articles and documents

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.

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.

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.