585-05-7

Basic information

• Product Name: 3-OXALURIC ACID
• Synonyms: oxaluricacid;3-OXALURIC ACID;Carbamoyloxamic acid;N-Oxarourea;Oxalic monoureide;Ureidooxoacetic acid;2-(aminocarbonylamino)-2-oxo-ethanoic acid;2-(carbamoylamino)-2-oxoacetic acid
• CAS NO: 585-05-7
• Molecular Formula: C₃H₄N₂O₄
• Molecular Weight: 132.07
• Mol File: 585-05-7.mol

Chemical Properties

• Appearance: /
• Density: 1.663g/cm³
• Refractive Index: 1.534
• PKA: 1.22±0.20(Predicted)
• CAS DataBase Reference: 3-OXALURIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-OXALURIC ACID(585-05-7)
• EPA Substance Registry System: 3-OXALURIC ACID(585-05-7)

Safety Data

• Hazardous Substances Data: 585-05-7(Hazardous Substances Data)

Usage

Definition

ChEBI: A 2-oxo monocarboxylic acid that is amino(oxo)acetic acid substituted by a carbamoylamino group at the nitrogen atom.

InChI:InChI=1/C3H4N2O4/c4-3(9)5-1(6)2(7)8/h(H,7,8)(H3,4,5,6,9)

Upstream product

• 66-22-8 uracil 
• 7732-18-5 water 
• 65-86-1 orotic acid 
• 69-93-2 uric Acid 
• 64-19-7 acetic acid 
• 626-48-2 6-Methyluracil 
• 16632-21-6 5-nitro-6-methyluracil 
• 15018-56-1 5-bromo-6-methyluracil 
• 1074-84-6 1-ethyl-6-methyl-1H-pyrimidine-2,4-dione 
• 861542-63-4 5,5,6-trihydroxy-6-methyldihydropyrimidine-2,4(1H,3H)-dione 
• 5676-27-7 Oxalyldiurea 
• 944-73-0 1,3-dimethyluric acid 
• 33443-58-2 1-benzyl-6-methylpyrimidine-2,4(1H,3H)-dione 
• 487-63-8 (2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-urea 

Downstream Products

• 120-89-8 parabanic acid 
• 2207-75-2 monopotassium 1,2,3,4-tetrahydro-2,4-dioxo-1,3,5-triazine-6-carboxylate 
• 144-62-7 oxalic acid 
• 57-13-6 urea 
• 6009-70-7 ammonium oxalate monohydrate 
• 631-62-9 urea-oxalic acid co-crystal 2:1 
• 530084-26-5 oxalic acid methyl ester ureide 

Relevant articles and documents

(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid

Previously, we identified that parabanic acid (PA) and its hydrolysate, oxaluric acid (OUA), are the singlet oxygen-specific oxidation products of uric acid (UA). In this study, we investigated the PA formation mechanism by using HPLC and a time-of-flight mass spectrometry technique and identified unknown intermediates as (2,5-dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic acid (DIAA), dehydroallantoin, and 4-hydroxyallantoin (4-HAL). DIAA is the key to PA production, and its formation pathway was characterized using 18O2 and H218O. Two oxygen atoms were confirmed to be incorporated into DIAA: the 5-oxo- oxygen from singlet oxygen and the carboxylic oxygen from water. Isolated DIAA and 4-HAL gave PA stoichiometrically. A plausible reaction scheme in which two pathways branch out from DIAA is presented, and the potential for PA as an endogenous probe for biological formation of singlet oxygen is discussed.

The sonolysis of uracil

The sonolysis of uracil (1) has been studied at 630 kHz in the presence of air, oxygen, nitrogen and argon.The degradation products were identified by gc-ms analysis.Under aerated conditions the following products were found: uracil glycols (7), isobarbituric acid (8), N-formyl-N'-glyoxylurea (6), 5-hydroxyhydantoin (9), dialuric acid (10), alloxan monohydrate (12), parabanic acid (13), and oxaluric acid (14).In deaerated solutions 6, 13, and 14 were not observed but either 6-hydroxy-5,6-dihydrouracil (17) or its isomer (18) were detected in addition to 7, 8, 9, 10, and 12.The observed products have been used to develop a possible mechanism for the sonolytic degradation and the results are similar to those obtained in radiolysis.The sonolytic degradation of 5-bromouracil (19) is also reported: the products observed were 5-bromobarbituric acid (20), 12, 13, 14, and 9 and these can be rationalized by a similar mechanism scheme.