M6885
1-Methyluric acid
Synonym(s):
1-Methyl-2,6,8-trihydroxypurine, 1-U, 1MUA
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About This Item
Empirical Formula (Hill Notation):
C6H6N4O3
CAS Number:
Molecular Weight:
182.14
UNSPSC Code:
41106305
NACRES:
NA.51
PubChem Substance ID:
EC Number:
211-905-7
Beilstein/REAXYS Number:
195190
MDL number:
InChI key
QFDRTQONISXGJA-UHFFFAOYSA-N
InChI
1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)
SMILES string
CN1C(=O)NC2=C(NC(=O)N2)C1=O
assay
≥98% (HPLC)
form
powder
solubility
1 M NaOH: 20 mg/mL, clear to slightly hazy
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Application
1-Methyluric acid has been used:
- for the determination of uric acid in stool samples by liquid chromatography and tandem mass spectrometry
- in turbidimetric assay of synthetic urine samples
- as a substrate for CYP1A2(cytochrome P450 family 1 subfamily A member 2) assay
Biochem/physiol Actions
1-Methyluric acid (1-U) is a major metabolite of caffeine and theophylline with antioxidant activity that protects molecules such as low density lipoproteins (LDL) from oxidative modifications. 1-Methyluric acid may be used in studies aimed at differentiating the activities of caffeine and theophylline metabolites.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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C Lee
Clinica chimica acta; international journal of clinical chemistry, 295(1-2), 141-154 (2000-04-18)
Although caffeine has been suggested as an antioxidant at millimolar concentrations, little information is available about the antioxidant activity of caffeine and its metabolites at physiological concentrations. Antioxidant activity was measured by oxygen-radical absorbing capacity (ORAC) using 2, 2'-azobis(2-amidinopropane) dihydrochloride
Effects of peppermint tea consumption on the activities of CYP1A2, CYP2A6, Xanthine Oxidase, N-acetyltranferase-2 and UDP-glucuronosyltransferases-1A1/1A6 in healthy volunteers
Begas E, et al.
Food And Chemical Toxicology, 100, 80-89 (2017)
Early-onset metabolic syndrome in mice lacking the intestinal uric acid transporter SLC2A9
DeBosch BJ, et al.
Nature Communications, 5, 4642-4642 (2014)
José Angel Gómez-Ruiz et al.
Journal of agricultural and food chemistry, 55(17), 6962-6969 (2007-07-28)
In this paper we report the antioxidant activity of different compounds which are present in coffee or are produced as a result of the metabolism of this beverage. In vitro methods such as the ABTS*+ [ABTS = 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)] decolorization
Theophano A Psarra et al.
Fundamental & clinical pharmacology, 22(5), 537-547 (2008-10-11)
The present study, aimed to clarify whether the gastrointestinal adverse effects following administration of the bronchodilator theophylline are owing to the action of the drug itself or its metabolites, investigates the pharmacodymanic effects of theophylline's metabolites on the spontaneous contractility
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