Dodecyl beta-D-glucopyranoside

Base Information

• Chemical Name: Dodecyl beta-D-glucopyranoside
• CAS No.: 59122-55-3
• Molecular Formula: C18H36 O6
• Molecular Weight: 348.48
• Hs Code.: 29389090
• European Community (EC) Number: 261-614-4
• UNII: 76LN7P7UCU
• DSSTox Substance ID: DTXSID40891954
• Nikkaji Number: J278.594C
• Wikipedia: Lauryl_glucoside
• Wikidata: Q2614811
• RXCUI: 1364382
• ChEMBL ID: CHEMBL4068837
• Mol file: 59122-55-3.mol

Synonyms:dodecyl glucopyranoside;dodecyl glucoside;dodecyl-beta-D-glucopyranoside

Chemical Property of Dodecyl beta-D-glucopyranoside

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.05E-12mmHg at 25°C
• Melting Point: Boiling point:
• Refractive Index: 1.4450 (estimate)
• Boiling Point: 513.8oC at 760 mmHg
• PKA: 12.95±0.70(Predicted)
• Flash Point: 264.5oC
• PSA: 99.38000
• Density: 1.0573 (rough estimate)
• LogP: 1.72380
• Storage Temp.: −20°C
• Solubility.: Soluble in methanol at 50mg/ml
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 348.25118886
• Heavy Atom Count: 24
• Complexity: 301

Purity/Quality:

98%, ^*data from raw suppliers

Dodecyl b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCOC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CCCCCCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Uses: n-Dodecyl-beta-D-glucopyranoside is a non-ionic detergent.

Technology Process of Dodecyl beta-D-glucopyranoside

There total 43 articles about Dodecyl 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%

1-n-dodecyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (66854-07-7) → n-dodecyl-b-D-glucopyranoside (59122-55-3)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1016/j.jfluchem.2007.02.013

Reference yield: 15.0%

D-Glucose (2280-44-6) + 1-dodecyl alcohol (112-53-8) → n-dodecyl α-D-glucopyranoside (29980-16-3) + n-dodecyl-b-D-glucopyranoside (59122-55-3)

Guidance literature:

With sulfuric acid; In 1,4-dioxane;

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

Reference yield:

1-dodecyl alcohol (112-53-8) → n-dodecyl-b-D-glucopyranoside (59122-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / BF₃*Et₂O / 1,2-dichloro-ethane

2: 100 percent / NaOMe; MeOH

With methanol; boron trifluoride diethyl etherate; sodium methylate; In 1,2-dichloro-ethane;

DOI:10.1016/j.jfluchem.2007.02.013

upstream raw materials:

1-n-dodecyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

D-Glucose

1-dodecyl alcohol

lauryl maltoside

Downstream raw materials:

dodecyl 4,6-O-benzylidene-2,3-bis-O-[cyanomethyl]-β-D-glucopyranoside

dodecyl 4,6-O-benzylidene-2,3-bis-(2-aminoethyl)-β-D-glucopyranoside

dodecyl 4,6-O-benzylidene-2,3-bis-[2-(2-chloroacetamido)ethyl]-β-D-glucopyranoside

dodecyl 4,6-O-benzylidene-2,3-[15-cr-5]thiadiamido-β-D-glucopyranoside

Refernces

• 1、 Sabah, Karem J.,Zahid, N. Idayu,Hashim, Rauzah. "Synthesis of new chiral macrocycles-based glycolipids and its application in asymmetric Michael addition". . p. 2653 - 2667. Retrieved 2021/03/19.
• 2、 Ramdani, Wahiba Ghezali,Karam, Ayman,De Oliveira Vigier, Karine,Rio, Sébastien,Ponchel, Anne,Jér?me, Fran?ois. "Catalytic glycosylation of glucose with alkyl alcohols over sulfonated mesoporous carbons". . p. 125 - 129. Retrieved 2019/03/06.