Octyl beta-D-glucopyranoside

Base Information

• Chemical Name: Octyl beta-D-glucopyranoside
• CAS No.: 29836-26-8
• Deprecated CAS: 1044708-52-2,65309-84-4
• Molecular Formula: C14H28O6
• Molecular Weight: 292.373
• Hs Code.: 29400090
• European Community (EC) Number: 255-367-1,249-887-8
• UNII: V109WUT6RL
• DSSTox Substance ID: DTXSID6042234
• Nikkaji Number: J236.172H
• Wikipedia: Octyl_glucoside
• Wikidata: Q7077127
• RXCUI: 1307766
• ChEMBL ID: CHEMBL446037
• Mol file: 29836-26-8.mol

Synonyms:1-O-n-octyl-beta-D-glucopyranoside;beta-octyl-D-glucoside;beta-octylglucopyranoside;N-octyl-beta-D-glucopyranoside;octyl glucoside;octyl-alpha-D-glucoside;octyl-beta-D-glucoside;octyl-D-glucoside, (alpha)-isomer;octylglucopyranoside;octylglucoside

Chemical Property of Octyl beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 3.72E-10mmHg at 25°C
• Melting Point: 105 °C
• Refractive Index: -27 ° (C=1, MeOH)
• Boiling Point: 454.1 °C at 760 mmHg
• PKA: 12.95±0.70(Predicted)
• Flash Point: 228.4 °C
• PSA: 99.38000
• Density: 1.18 g/cm³
• LogP: 0.16340
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: DMSO (Slightly), Water (Slightly)
• Water Solubility.: 3 g/10 mL
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 292.18858861
• Heavy Atom Count: 20
• Complexity: 250

Purity/Quality:

98%, ^*data from raw suppliers

Octyl β-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: CCCCCCCCOC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Uses: A nonionic detergent for the solubilization of membrane bound protein. Unlike many other detergents, octyl glucoside is a pure, single compound of defined structure. Very effective for insulin binding and solubilization studies of membran Detergent and surfactant for biological systems.

Technology Process of Octyl beta-D-glucopyranoside

There total 61 articles about Octyl beta-D-glucopyranoside 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: 100.0%

octyl (2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside (38954-67-5,128299-96-7) → n-octyl β-D-glucopyranoside (29836-26-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2008.01.015

Reference yield: 40.0%

β-D-glucose (492-61-5) + octanol (111-87-5) → n-octyl β-D-glucopyranoside (29836-26-8)

Guidance literature:

With citrate buffer; Aerosol-OT; β-glucosidase; In octane; at 20 ℃; for 120h; pH=5.5;

DOI:10.1023/A:1012936702457

Reference yield: 30.0%

D-Glucose (2280-44-6) + octanol (111-87-5) → octyl alpha-D-glucopyranoside (29781-80-4) + n-octyl β-D-glucopyranoside (29836-26-8)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; Yields of byproduct given;

DOI:10.1016/S0008-6215(98)00302-4

upstream raw materials:

D-Glucose

octanol

phenyl-β-D-glucopyranoside

n-octyl α-D-glucopyranosyl-(1->4)-β-D-glucopyranoside

Downstream raw materials:

octyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside

Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-4-(tert-butyl-dimethyl-silanyloxy)-6-octyloxy-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

Refernces

• 1、 Kouptsova,Klyachko,Levashov. "Synthesis of Alkyl Glycosides Catalyzed by β-Glycosidases in a System of Reverse Micelles". . p. 380 - 384. Retrieved 2001.
• 2、 Wang, Feng,Ma, Yong,Liu, Yan-Hua,Zhang, Xuan,Zhang, Fuming,Linhardt, Robert J.. "Improved octyl glucoside synthesis using immobilized β-glucosidase on PA-M with reduced glucose surplus inhibition". . p. 349 - 362. Retrieved 2017.
• 3、 Matin, Mohammed M.,Bhattacharjee, Sreebash C.,Chakraborty, Priyanka,Alam, Muhammad S.. "Synthesis, PASS predication, in vitro antimicrobial evaluation and pharmacokinetic study of novel n-octyl glucopyranoside esters". supporting information. . Retrieved 2019/10/10.
• 4、 Arthornthurasuk, Siriphan,Jenkhetkan, Wantha,Suwan, Eukote,Chokchaichamnankit, Daranee,Srisomsap, Chantragan,Wattana-Amorn, Pakorn,Svasti, Jisnuson,Kongsaeree, Prachumporn T.. "Molecular Characterization and Potential Synthetic Applications of GH1 β-Glucosidase from Higher Termite Microcerotermes annandalei". . p. 877 - 894. Retrieved 2018/05/25.