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O2750

Sigma-Aldrich

Orotic acid

≥98% (titration), anhydrous

Synonym(s):

2,6-Dihydroxypyrimidine-4-carboxylic acid, 6-Carboxy-2,4-dihydroxypyrimidine, 6-Carboxyuracil, Uracil-6-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C5H4N2O4
CAS Number:
65-86-1
Molecular Weight:
156.10
Beilstein/REAXYS Number:
383901
EC Number:
200-619-8
MDL number:
MFCD00006027
UNSPSC Code:
41106305
PubChem Substance ID:
24897967
NACRES:
NA.51

grade

anhydrous

Quality Level

200

assay

≥98% (titration)

mp

≥300 °C

SMILES string

OC(=O)C1=CC(=O)NC(=O)N1

InChI

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

InChI key

PXQPEWDEAKTCGB-UHFFFAOYSA-N

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Application

Orotic acid (OA) is an intermediate in de novo pyrimidine biosynthesis that may be used to study the specificity and kinetics of orotate phosphoribosyltransferase (OPRT) which catalyzes the reversible phosphoribosyl transfer from 5′-phospho-α-d-ribose 1′-diphosphate (PRPP) to orotic acid (OA), forming pyrophosphate and orotidine 5′-monophosphate (OMP). Orotic acid is used as a starting material for the potential commercial bioproduction of uridine 5′-monophosphate (UMP) by microbes such as Corynebacterium ammoniagenes (ATCC 6872) or Saccharomyces cerevisiae. OA may be used to study the AMPK/SREBP-1 dependent cell signaling pathway and transcription regulation mechanisms that induce hepatic lipogenesis.

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

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Mattias Carlsson et al.
PloS one, 8(10), e52094-e52094 (2013-10-15)
5-Fluorouracil (5-FU) is an anticancer drug and pyrimidine analogue. A problem in 5-FU therapy is acquired resistance to the drug. To find out more about the mechanisms of resistance, we screened a plasmid library in yeast for genes that confer
Juliana Cheleski et al.
European journal of medicinal chemistry, 45(12), 5899-5909 (2010-10-23)
The enzyme dihydroorotate dehydrogenase (DHODH) has been suggested as a promising target for the design of trypanocidal agents. We report here the discovery of novel inhibitors of Trypanosoma cruzi DHODH identified by a combination of virtual screening and ITC methods.
Thomas D Loan et al.
New biotechnology, 49, 104-111 (2018-10-23)
Nucleoside triphosphates (NTPs) are important synthetic targets with diverse applications in therapeutics and diagnostics. Enzymatic routes to NTPs from simple building blocks are attractive, however the cost and complexity of assembling the requisite mixtures of multiple enzymes hinders application. Here
David Pérez-Pascual et al.
Frontiers in microbiology, 8, 2168-2168 (2017-11-23)
A fascinating characteristic of most members of the genus
Izumi Miyabe et al.
PLoS genetics, 7(12), e1002407-e1002407 (2011-12-07)
Coordinated replication of eukaryotic genomes is intrinsically asymmetric, with continuous leading strand synthesis preceding discontinuous lagging strand synthesis. Here we provide two types of evidence indicating that, in fission yeast, these two biosynthetic tasks are performed by two different replicases.
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