3-Oxo-3H-phenoxazin-7-yl beta-D-glucopyranoside

Base Information

• Chemical Name: 3-Oxo-3H-phenoxazin-7-yl beta-D-glucopyranoside
• CAS No.: 101490-85-1
• Molecular Formula: C18H17NO8
• Molecular Weight: 375.335
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID40543840
• Nikkaji Number: J362.271A
• Wikidata: Q72506552
• Mol file: 101490-85-1.mol

Synonyms:101490-85-1;Resorufin beta-D-glucopyranoside;3-Oxo-3H-phenoxazin-7-yl beta-D-glucopyranoside;3-Phenoxazone 7-(beta-D-glucopyranoside);resorufin-beta-D-glucopyranoside;7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxazin-3-one;Resorufin |A-D-glucopyranoside;3H-Phenoxazin-3-one,7-(b-D-glucopyranosyloxy)-;Resorufin -D-Glucopyranoside;Resorufin-?-D-glucopyranoside;SCHEMBL16069671;BDBM18429;DTXSID40543840;Resorufin beta -D-glucopyranoside;Resorufin-I(2)-D-glucopyranoside;Resorufin beta-D-glucopyranoside, >=90%;M03666;3H-Phenoxazin-3-one, 7-(beta-D-glucopyranosyloxy)-;Resorufin beta-D-glucopyranoside, for fluorescence, >=95% (HPLC);7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3H-phenoxazin-3-one;7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H-phenoxazin-3-one

Chemical Property of 3-Oxo-3H-phenoxazin-7-yl beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 7.25E-18mmHg at 25°C
• Melting Point: 218-220℃ (decomposition)
• Refractive Index: 1.723
• Boiling Point: 651.6 °C at 760 mmHg
• PKA: 12.72±0.70(Predicted)
• Flash Point: 347.9 °C
• PSA: 142.48000
• Density: 1.71 g/cm³
• LogP: -0.52850
• Storage Temp.: −20°C
• Solubility.: DMF: soluble
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 375.09541650
• Heavy Atom Count: 27
• Complexity: 689

Purity/Quality:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1OC3C(C(C(C(O3)CO)O)O)O)OC4=CC(=O)C=CC4=N2
• Isomeric SMILES: C1=CC2=C(C=C1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC4=CC(=O)C=CC4=N2
• Uses: Resorufin β-D-Glucopyranoside is a fluorogenic galactosidase substrate that generates a red fluorescent product upon interaction with the enzyme.

Technology Process of 3-Oxo-3H-phenoxazin-7-yl beta-D-glucopyranoside

There total 3 articles about 3-Oxo-3H-phenoxazin-7-yl 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: 90.0%

resorufinyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (101490-84-0) → resorufin β-D-glucopyranoside (101490-85-1,136565-96-3,1175532-13-4)

Guidance literature:

With methanol; potassium carbonate;

DOI:10.1248/cpb.38.3466

Reference yield:

7-hydroxy-3H-phenoxazin-3-one sodium salt (34994-50-8) → resorufin β-D-glucopyranoside (101490-85-1,136565-96-3,1175532-13-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / Ag₂O / acetonitrile / 40 °C

2: 90 percent / K₂CO₃, MeOH

With methanol; potassium carbonate; silver(l) oxide; In acetonitrile;

DOI:10.1248/cpb.38.3466

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → resorufin β-D-glucopyranoside (101490-85-1,136565-96-3,1175532-13-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / Ag₂O / acetonitrile / 40 °C

2: 90 percent / K₂CO₃, MeOH

With methanol; potassium carbonate; silver(l) oxide; In acetonitrile;

DOI:10.1248/cpb.38.3466

upstream raw materials:

resorufinyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

7-hydroxy-3H-phenoxazin-3-one sodium salt

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

Downstream raw materials:

β-D-glucose

resorufin

Refernces