3-Indolyl-b-D-galactopyranoside

Base Information

• Chemical Name: 3-Indolyl-b-D-galactopyranoside
• CAS No.: 126787-65-3
• Molecular Formula: C14H17 N O6
• Molecular Weight: 295.292
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50370003
• Nikkaji Number: J1.948.685K
• Wikidata: Q72483213
• Mol file: 126787-65-3.mol

Synonyms:126787-65-3;3-Indolyl-b-D-galactopyranoside;3-Indoxyl-beta-D-galactopyranoside;Indoxyl-beta-D-galactopyranoside;(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol;beta-D-Galactopyranoside, 1H-indol-3-yl;1H-Indol-3-yl beta-D-galactopyranoside;Indoxyl beta-D-galactopyranoside;MFCD00083389;Indoxyl--D-galactopyranoside;SCHEMBL153372;Indol-3-yl--D-galactopyranoside;DTXSID50370003;Indoxyl beta -D-galactopyranoside;3-indolyl beta-d-galactopyranoside;1H-Indole-3-yl beta-D-galactopyranoside;A889367;(2S,3R,4S,5R,6R)-2-(1H-indol-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of 3-Indolyl-b-D-galactopyranoside

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 1.43E-15mmHg at 25°C
• Boiling Point: 606.7 °C at 760 mmHg
• Flash Point: 320.7 °C
• PSA: 115.17000
• Density: 1.562 g/cm³
• LogP: -0.65340
• Storage Temp.: 2-8°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 295.10558726
• Heavy Atom Count: 21
• Complexity: 356

Purity/Quality:

98%, ^*data from raw suppliers

3-Indolyl b-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Statements: 67
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)O
• Uses: 3-Indolyl-β-D-galactopyranoside is used in microbiology culture media to identify lac+ organisms (e.g. general coliforms.) It is also used in histochemistry and in biochemistry. Indoxyl β-D-Galactopyranoside is a chromogenic substrate for Beta-galactosidase.

Technology Process of 3-Indolyl-b-D-galactopyranoside

There total 4 articles about 3-Indolyl-b-D-galactopyranoside 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: 98.0%

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((1-acetyl-1H-indol-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate → (2S,3R,4S,5R,6R)-2-((1H-indol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (126787-65-3)

Guidance literature:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((1-acetyl-1H-indol-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate; With sodium methylate; In methanol; at 20 ℃; for 16h; Inert atmosphere;

Inert atmosphere;

DOI:10.2174/1570178615666180212152030

Reference yield:

D-galactose pentaacetate (25878-60-8) → (2S,3R,4S,5R,6R)-2-((1H-indol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (126787-65-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen bromide; acetic acid / 2.5 h / 20 °C / Inert atmosphere

2.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / dichloromethane; water / 20 °C / Inert atmosphere

3.1: potassium carbonate; silver(I) acetate; sodium acetate / 1 h / 125 °C / Inert atmosphere

4.1: sodium methylate / methanol / 16 h / 20 °C / Inert atmosphere

4.2: Amberlite IR-120 (H⁺) resin / Inert atmosphere

With hydrogen bromide; sodium methylate; silver(I) acetate; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; acetic acid; In methanol; dichloromethane; water;

DOI:10.2174/1570178615666180212152030

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → (2S,3R,4S,5R,6R)-2-((1H-indol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (126787-65-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / dichloromethane; water / 20 °C / Inert atmosphere

2.1: potassium carbonate; silver(I) acetate; sodium acetate / 1 h / 125 °C / Inert atmosphere

3.1: sodium methylate / methanol / 16 h / 20 °C / Inert atmosphere

3.2: Amberlite IR-120 (H⁺) resin / Inert atmosphere

With sodium methylate; silver(I) acetate; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In methanol; dichloromethane; water;

DOI:10.2174/1570178615666180212152030

upstream raw materials:

D-galactose pentaacetate

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Downstream raw materials:

(1-acetyl-indol-3-yl)-(tetra-O-acetyl-β-D-glucopyranoside)

indoxyl

indigo

1-phenyl-1H-indol-3-yl-beta-D-galactopyranoside

Refernces