Phenyl beta-D-glucopyranosiduronic acid

Base Information

• Chemical Name: Phenyl beta-D-glucopyranosiduronic acid
• CAS No.: 17685-05-1
• Molecular Formula: C12H14 O7
• Molecular Weight: 270.239
• Hs Code.: 29329990
• European Community (EC) Number: 241-666-4
• DSSTox Substance ID: DTXSID601034474
• Nikkaji Number: J246.103J
• Wikidata: Q27133372
• Metabolomics Workbench ID: 63456
• Mol file: 17685-05-1.mol

Synonyms:17685-05-1;phenyl glucuronide;Phenyl-beta-D-glucuronide;Phenyl beta-D-glucopyranosiduronic acid;phenol O-(beta-D-glucuronide);phenyl beta-glucuronide;phenyl beta-D-glucuronide;phenol glucuronide;phenyl beta-D-glucosiduronic acid;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-phenoxyoxane-2-carboxylic acid;(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-phenoxytetrahydro-2H-pyran-2-carboxylic acid;EINECS 241-666-4;.beta.-D-Glucopyranosiduronic acid, phenyl;Phenyl .beta.-D-glucuronide;Phenyl- beta -D-glucuronide;SCHEMBL2540920;CHEBI:64681;DTXSID601034474;Phenyl-beta-D-glucopyranosiduronic acid;beta-D-Glucopyranosiduronic acid, phenyl;Phenyl-beta-D-glucuronide, >=99.0% (HPLC);Q27133372;(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-phenoxytetrahydro-2H-pyran-2-carboxylicacid

Chemical Property of Phenyl beta-D-glucopyranosiduronic acid

Chemical Property:

• Melting Point: 158-160°C
• Boiling Point: 542°Cat760mmHg
• Flash Point: 212.3°C
• PSA: 116.45000
• Density: 1.587g/cm³
• LogP: -1.04240
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Sparingly, Sonicated)
• XLogP3: 0
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 270.07395278
• Heavy Atom Count: 19
• Complexity: 315

Purity/Quality:

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

Phenyl b-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2C(C(C(C(O2)C(=O)O)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O
• Uses: A metabolite of Phenol. Phenyl-β-D-glucuronide has been used as a nonpeptide chromogen for testing biuret reagent and as a reference standard for phenol analysis in urine samples.

Technology Process of Phenyl beta-D-glucopyranosiduronic acid

There total 13 articles about Phenyl beta-D-glucopyranosiduronic acid 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: 28.4%

1-deoxy-1-fluoro-α-D-glucopyranuronic acid ammonium salt + phenol (108-95-2,27073-41-2) → phenyl β-D-glucuronide (17685-05-1)

Guidance literature:

With Escherichia coli glucuronylsynthase mutant E₅₀₄G; at 20 ℃; for 96h; pH=7.5; aq. phosphate buffer;

DOI:10.1021/ol8002767

Reference yield:

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → phenyl β-D-glucuronide (17685-05-1)

Guidance literature:

Multi-step reaction with 3 steps

1: mercury (II)-cyanide

2: sodium methylate; methanol

3: barium hydroxide; water

With methanol; barium dihydroxide; water; sodium methylate; mercury(II) cyanide;

Reference yield:

2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester (4630-61-9) → phenyl β-D-glucuronide (17685-05-1)

Guidance literature:

With barium dihydroxide; water;

upstream raw materials:

phenyl-β-D-glucopyranoside

methyl phenyl-β-D-glucuronate

2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

Downstream raw materials:

methyl phenyl-β-D-glucuronate

2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester

O²,O³,O⁴-triacetyl-O¹-phenyl-β-D-glucopyranuronic acid amide

4-Bromophenol glucuronide

Refernces

• 1、 Wilkinson, Shane M.,Liew, Chu W.,Mackay, Joel P.,Salleh, Hamzah M.,Withers, Stephen G.,McLeod, Malcolm D.. "Escherichia coli glucuronylsynthase: An engineered enzyme for the synthesis of β-glucuronides". supporting information; experimental part. p. 1585 - 1588. Retrieved 2009/04/10.