17685-05-1

Basic information

• Product Name: PHENYL-BETA-D-GLUCURONIDE
• Synonyms: PH-BETA-D-GLCA MONOHYDRATE;PHENYL-BETA-D-GLUCOPYRANOSIDURONIC ACID;PHENYL-BETA-D-GLUCURONIC ACID MONOHYDRATE;PHENYL-BETA-D-GLUCURONIDE;PHENYL-BETA-D-GLUCURONIDE HYDRATE;PHENYL-BETA-D-GLUCURONIDE MONOHYDRATE;PHENYL B-D-GLUCURONIDE;phenyl-β-d-glucopyranosiduronic acid
• CAS NO: 17685-05-1
• Molecular Formula: C₁₂H₁₄O₇
• Molecular Weight: 270.24
• EINECS: 241-666-4
• Product Categories: Carbohydrates & Derivatives;Glucuronides;Metabolites & Impurities
• Mol File: 17685-05-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 158-160°C
• Boiling Point: 542°Cat760mmHg
• Flash Point: 212.3°C
• Appearance: /
• Density: 1.587g/cm³
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Sparingly, Sonicated)
• Stability: Hygroscopic
• BRN: 89117
• CAS DataBase Reference: PHENYL-BETA-D-GLUCURONIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL-BETA-D-GLUCURONIDE(17685-05-1)
• EPA Substance Registry System: PHENYL-BETA-D-GLUCURONIDE(17685-05-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 17685-05-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 17685-05-1 differently. You can refer to the following data:
1. A metabolite of Phenol.
2. 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.

Definition

ChEBI: A beta-D-glucosiduronic acid that is the glucuronide conjugate of phenol.

General Description

Phenyl-β-D-glucuronide is majorly used as a reference standard in chromatographic and mass spectrophotometry studies for quantifying glucuroconjugate metabolites in plasma and urine samples.

Upstream product

• 55811-42-2 methyl phenyl-β-D-glucuronate 
• 4630-61-9 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 108-95-2 phenol 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 5432-32-6 methyl 1,2,3,4-tetraacetyl-α-D-glucopyranuronate 
• 100-67-4 potassium phenolate 
• 1464-44-4 phenyl-β-D-glucopyranoside 

Downstream Products

• 55811-42-2 methyl phenyl-β-D-glucuronate 
• 4630-61-9 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester 
• 98438-73-4 O²,O³,O⁴-triacetyl-O¹-phenyl-β-D-glucopyranuronic acid amide 
• 89435-63-2 4-Bromophenol glucuronide 

Relevant articles and documents

Experimental and kinetic studies of the Escherichia coli glucuronylsynthase: An engineered enzyme for the synthesis of glucuronide conjugates

The detection and study of glucuronide metabolites is essential in many fields including pharmaceutical development, sports drug testing, and the detection of agricultural residues. Therefore, the development of improved methods for the synthesis of glucuronide conjugates is an important aim. The glycosynthase derived from E. coli β-glucuronidase provides an efficient, scalable, single-step synthesis of β-glucuronides under mild conditions. In this article we report on experimental and kinetic studies of the E. coli glucuronylsynthase, including the influence of acceptor substrate, pH, temperature, cosolvents, and detergents, leading to optimized conditions for glucuronide synthesis. Enzyme kinetics also reveals that both substrate and product inhibition may occur in glucuronylsynthase reactions but that these effects can be ameliorated through the judicious choice of acceptor and donor substrate concentrations. An investigation of temporary polar substituents was conducted leading to improved aqueous solubility of hydrophobic steroidal acceptors. In this way the synthesis of the steroidal metabolite dehydroepiandrosterone 3-β-d-glucuronide was achieved in three steps and 86% overall yield from dehydroepiandrosterone.