17680-99-8

Basic information

• Product Name: P-TOLYL-BETA-D-GLUCURONIDE
• Synonyms: p-Tolyl-β-D-glucuronic acid;p-Tolyl-β-D-glucuronide;p-Cresol Glucuronide
• CAS NO: 17680-99-8
• Molecular Formula: C₁₃H₁₆O₇
• Molecular Weight: 284.26
• Product Categories: Aromatics, Glucuronides, Metabolites & Impurities
• Mol File: 17680-99-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 549.7 °C at 760 mmHg
• Flash Point: 211.6 °C
• Appearance: /white powder
• Density: 1.524 g/cm³
• Vapor Pressure: 6.42E-13mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: −20°C
• Solubility: H2O: 50 mg/mL, soluble
• CAS DataBase Reference: P-TOLYL-BETA-D-GLUCURONIDE(CAS DataBase Reference)
• NIST Chemistry Reference: P-TOLYL-BETA-D-GLUCURONIDE(17680-99-8)
• EPA Substance Registry System: P-TOLYL-BETA-D-GLUCURONIDE(17680-99-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 17680-99-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 17680-99-8 differently. You can refer to the following data:
1. P-TOLYL-BETA-D-GLUCURONIDE is a metabolite of o-Cresol (C781910), which is a compound used as a disinfectant and have also been used as antiseptic in surgery.
2. p-Cresol Glucuronide, is a metabolite of o-Cresol (C781910), which is a compound used as a disinfectant and have also been used as antiseptic in surgery.

Definition

P-TOLYL-BETA-D-GLUCURONIDE is a glucosiduronic acid that is beta-D-glucuronic acid in which the anomeric hydroxyl hydrogen is replaced by a p-tolyl group.

InChI:InChI=1/C13H16O7/c1-6-2-4-7(5-3-6)19-13-10(16)8(14)9(15)11(20-13)12(17)18/h2-5,8-11,13-16H,1H3,(H,17,18)/t8-,9-,10+,11-,13+/m0/s1

Upstream product

• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 92420-85-4 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate 
• 106-44-5 p-cresol 
• 2616-64-0 UDP-glucuronic acid 
• 55325-14-9 O¹-p-tolyl-β-D-glucopyranuronic acid methyl ester 

Relevant articles and documents

Urinary metabolomics in Fxr-null mice reveals activated adaptive metabolic pathways upon bile acid challenge

Farnesoid X receptor (FXR) is a nuclear receptor that regulates genes involved in synthesis, metabolism, and transport of bile acids and thus plays a major role in maintaining bile acid homeostasis. In this study, metabolomic responses were investigated in urine of wild-type and Fxr-null mice fed cholic acid, an FXR ligand, using ultra-performance liquid chromatography (UPLC) coupled with electrospray time-of-flight mass spectrometry (TOFMS). Multivariate data analysis between wild-type and Fxr-null mice on a cholic acid diet revealed that the most increased ions were metabolites of p-cresol (4-methylphenol), corticosterone, and cholic acid in Fxr-null mice. The structural identities of the above metabolites were confirmed by chemical synthesis and by comparing retention time (RT) and/or tandem mass fragmentation patterns of the urinary metabolites with the authentic standards. Tauro-3α,6,7α,12α-tetrol (3α,6,7α,12α- tetrahydroxy-5β-cholestan-26-oyltaurine), one of the most increased metabolites in Fxr-null mice on a CA diet, is a marker for efficient hydroxylation of toxic bile acids possibly through induction of Cyp3a11. A cholestatic model induced by lithocholic acid revealed that enhanced expression of Cyp3a11 is the major defense mechanism to detoxify cholestatic bile acids in Fxr-null mice. These results will be useful for identification of biomarkers for cholestasis and for determination of adaptive molecular mechanisms in cholestasis.