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F5013

Sigma-Aldrich

5-Fluoroorotic acid hydrate

≥98%

Synonym(s):

2,6-Dihydroxy-5-fluoropyrimidine-4-carboxylic acid, 5-Fluorouracil-4-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C5H3FN2O4 · xH2O
CAS Number:
207291-81-4
Molecular Weight:
174.09 (anhydrous basis)
EC Number:
211-876-0
MDL number:
MFCD00150658
UNSPSC Code:
12352204
PubChem Substance ID:
24894877
NACRES:
NA.32

biological source

synthetic

Quality Level

200

assay

≥98%

form

powder

technique(s)

cell culture | plant: suitable

mp

278 °C (dec.) (lit.)

solubility

4 M NH4OH: 50 mg/mL, clear, colorless to light yellow

storage temp.

−20°C

SMILES string

OC(C(NC(N1)=O)=C(F)C1=O)=O.[H]O[H]

InChI

1S/C5H3FN2O4.H2O/c6-1-2(4(10)11)7-5(12)8-3(1)9;/h(H,10,11)(H2,7,8,9,12);1H2

InChI key

LODRRYMGPWQCTR-UHFFFAOYSA-N

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Application

5-Fluoroorotic acid hydrate has also been used as a counter-selection agent to screen L. lactis (multi) peptidase knockout mutants and C. albicans. It has been used in synthesis of 5-fluoroorotidine 5′-monophosphate (FOMP).
Useful in the selection of orotidine-5′-phosphate decarboxylase mutants of Saccharomyces cerevisiae.

Biochem/physiol Actions

5-Fluoroorotic acid is a selective inhibitor of rRNA synthesis in mammals.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Inhibition of ribosomal ribonucleic acid maturation in rat liver by 5-fluoroorotic acid resulting in the selective labeling of cytoplasmic messenger ribonucleic acid
Wilkinson D S, et al.
The Journal of Biological Chemistry, 246(21), 6418-6427 (1971)
Mechanism of the orotidine 5?-monophosphate decarboxylase-catalyzed reaction: Effect of solvent viscosity on kinetic constants
Wood B M, et al.
Biochemistry, 48(24), 5510-5517 (2009)
Lakshmi Sreekumar et al.
Genetics, 212(4), 1121-1132 (2019-05-31)
The diploid budding yeast Candida albicans harbors unique CENPA-rich 3- to 5-kb regions that form the centromere (CEN) core on each of its eight chromosomes. The epigenetic nature of these CENs does not permit the stabilization of a functional kinetochore
Jiaxin Gao et al.
Nature communications, 9(1), 4495-4495 (2018-10-31)
Fungal infections by drug-resistant Candida albicans pose a global public health threat. However, the pathogen's diploid genome greatly hinders genome-wide investigations of resistance mechanisms. Here, we develop an efficient piggyBac transposon-mediated mutagenesis system using stable haploid C. albicans to conduct

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