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O2875

Sigma-Aldrich

Orotic acid potassium salt

≥98%

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Synonym(s):
6-Carboxy-2,4-dihydroxypyrimidine, Uracil-6-carboxylic acid
Linear Formula:
C5H3N2O4K
CAS Number:
Molecular Weight:
194.19
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.51

Quality Level

assay

≥98%

form

powder

solubility

1 M NaOH: 25 mg/mL, clear to slightly hazy, colorless to faintly yellow

SMILES string

[K+].[O-]C(=O)C1=CC(=O)NC(=O)N1

InChI

1S/C5H4N2O4.K/c8-3-1-2(4(9)10)6-5(11)7-3;/h1H,(H,9,10)(H2,6,7,8,11);/q;+1/p-1

InChI key

DHBUISJCVRMTAZ-UHFFFAOYSA-M

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Yong Chen et al.
Applied microbiology and biotechnology, 86(1), 75-81 (2009-10-15)
A whole cell biocatalytic process for uridine 5'-monophosphate (UMP) production from orotic acid by Saccharomyces cerevisiae was developed. The concentration of UMP was increased by 23% when 1 g l(-1) sodium citrate was fed into the broth. Effects of citrate
Enhanced uridine 5'-monophosphate production by whole cell of Saccharomyces cerevisiae through rational redistribution of metabolic flux.
Liu D, Chen Y, Li A, Xie J, Xiong J, et al.
Bioprocess and Biosystems Engineering (2011)
Xing Wang et al.
Applied microbiology and biotechnology, 76(2), 321-328 (2007-05-24)
Attempts were made with success to develop a two-step biocatalytic process for uridine 5'-monophosphate (UMP) production from orotic acid by Corynebacterium ammoniagenes ATCC 6872: the strain was first cultivated in a high salt mineral medium, and then cells were harvested
Ardala Breda et al.
Molecular bioSystems, 8(2), 572-586 (2011-11-15)
Tuberculosis (TB) is a chronic infectious disease caused mainly by Mycobacterium tuberculosis. The worldwide emergence of drug-resistant strains, the increasing number of infected patients among immune compromised populations, and the large number of latent infected individuals that are reservoir to
Eun-Jeong Jung et al.
Journal of lipid research, 52(9), 1617-1625 (2011-07-16)
Orotic acid (OA), an intermediate in pyrimidine metabolism, has been used for a variety of purposes, such as dietary supplements. Although it is well documented that OA induces fatty liver in a species-specific manner, the precise molecular mechanisms remain unclear.

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