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126268

Sigma-Aldrich

2,4-Dihydroxypyrimidine-5-carboxylic acid

95%

Synonym(s):

Isoorotic acid, Uracil-5-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C5H4N2O4
CAS Number:
23945-44-0
Molecular Weight:
156.10
EC Number:
245-947-2
MDL number:
MFCD00006023
UNSPSC Code:
12352100
PubChem Substance ID:
24847711
NACRES:
NA.22

Quality Level

100

assay

95%

form

powder

mp

283 °C (dec.) (lit.)

SMILES string

OC(=O)C1=CNC(=O)NC1=O

InChI

1S/C5H4N2O4/c8-3-2(4(9)10)1-6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)

InChI key

ZXYAAVBXHKCJJB-UHFFFAOYSA-N

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General description

2,4-Dihydroxypyrimidine-5-carboxylic acid (Uracil-5-carboxylic acid) has been obtained from 5-formyluracil by the action of enzyme, thymine 7-hydroxylase. It has been used to synthesize N1-alkylated uracil derivatives.

Application

2,4-Dihydroxypyrimidine-5-carboxylic acid (Uracil-5-carboxylic acid) has been used for the visual sensing of melamine (at parts-per-billion (ppb) level) by a highly sensitive analytical method based on Au nanoparticles.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Thymine ≥99%

Sigma-Aldrich

T0376

Thymine

Uracil ≥99.0%

Sigma-Aldrich

U0750

Uracil

P M Shaffer et al.
Journal of bacteriology, 121(2), 648-655 (1975-02-01)
The experiments in this report involve the following series of reactions which were previously demonstrated with purified enzyme preparations from Neurospora crassa: thymidine a yields thymine ribonucleoside b yields thymine c yields 5-hydroxymethyluracil d yields 5-formyluracil e yields uracil-5-carboxylic acid
Raj Kumar Bera et al.
The Analyst, 136(8), 1644-1648 (2011-02-25)
A highly sensitive analytical method based on Au nanoparticles rationally tailored with recognition elements uracil-5-carboxylic acid (UCA) and 2,4,6-trinitrobenzenesulfonic acid (TNBS) for the visual sensing of melamine at the parts-per-billion (ppb) level is described. The tailored Au nanoparticles function as
Alessandro Accetta et al.
Journal of medicinal chemistry, 52(1), 87-94 (2008-12-17)
The synthesis of C5 linked uracil dimers was carried out according to a model developed in order to bind adenine in DNA. N1-Alkylated uracil derivatives were synthesized from isoorotic acid (uracil-5-carboxylic acid) or thymine. The carboxylic acid derivatives were condensed

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