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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Pyrimidine-2-carboxylic acid 97%

Sigma-Aldrich

754315

Pyrimidine-2-carboxylic acid

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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