Octylthioglucoside

Base Information

• Chemical Name: Octylthioglucoside
• CAS No.: 85618-21-9
• Molecular Formula: C14H28O5S
• Molecular Weight: 308.43
• Hs Code.: 29329990
• Mol file: 85618-21-9.mol

Synonyms:Glc-S-C7-Me;n-octyl-beta-D-thioglucopyranoside;n-octyl-beta-D-thioglucoside;octyl beta-D-thioglucoside;octyl-thioglucoside;octylthioglucoside

Chemical Property of Octylthioglucoside

Chemical Property:

• Appearance/Colour: colourless waxy semi-solid
• Vapor Pressure: 1.21E-11mmHg at 25°C
• Melting Point: 125-131 °C
• Refractive Index: 1.547
• Boiling Point: 489.7 °C at 760 mmHg
• PKA: 13.02±0.70(Predicted)
• Flash Point: 250 °C
• PSA: 115.45000
• Density: 1.21 g/cm³
• LogP: 0.88000
• Storage Temp.: −20°C
• Solubility.: ethanol: soluble50mg/mL, clear, colorless
• Water Solubility.: soluble
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 308.16574516
• Heavy Atom Count: 20
• Complexity: 254

Purity/Quality:

98%min ^*data from raw suppliers

Octyl b-D-Thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCSC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CCCCCCCCS[C@H]1[C@@H](C([C@@H]([C@H](O1)CO)O)O)O
• Uses: A non-ionic detergent for solubilization and reconstitution of membrane proteins of Escherichia coli resistant to b-glucosidases and has a wider pH stability range A non-ionic detergent for solubilization and reconstitution of membrane proteins of Escherichia coli.

Technology Process of Octylthioglucoside

There total 6 articles about Octylthioglucoside 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:

β-thiooctylperacetyl D-glucoside (85618-26-4) → octyl-beta-D-thioglucopyranoside (85618-21-9)

Guidance literature:

With sodium hydroxide; In methanol; Ambient temperature;

Reference yield:

Octanethiol (111-88-6) + β-D-glucose pentaacetate (604-69-3) → octyl-beta-D-thioglucopyranoside (85618-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: indium(III) bromide / chloroform / Reflux

2.1: sodium methylate / methanol / 16 h / pH 9

2.2: dowex^? resin (H⁺ form)

With indium(III) bromide; sodium methylate; In methanol; chloroform;

DOI:10.1016/j.carres.2015.12.008

Reference yield:

1-bromo-octane (111-83-1) → octyl-beta-D-thioglucopyranoside (85618-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / K₂CO₃, NaHSO₃ / acetone; H₂O / Ambient temperature

2: NaOH / methanol / Ambient temperature

With sodium hydroxide; potassium carbonate; sodium hydrogensulfite; In methanol; water; acetone;

upstream raw materials:

β-thiooctylperacetyl D-glucoside

1-bromo-octane

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

octyl 4,6-O-benzylidene-β-D-thioglucopyranoside

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

2-hexyl-1-octyl 6-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

C₆₈H₈₄O₁₁

Refernces

• 1、 Szabó, Lajos Z.,Hanrahan, Dillon J.,Jones, Evan M.,Martin, Erin,Pemberton, Jeanne E.,Polt, Robin. "Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis". . p. 1 - 4. Retrieved 2016/02/03.
• 2、 Smits,Engberts,Kelogg,Van Doren. "Non-amphiphilic carbohydrate liquid crystals containing an intact monosaccharide moiety". . p. 185 - 199. Retrieved 2007/10/02.