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191213

Sigma-Aldrich

5-Aminoorotic acid

99%

Synonym(s):

5-Amino-2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid, 5-Amino-6-carboxy-2,4-dihydroxypyrimidine

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About This Item

Empirical Formula (Hill Notation):
C5H5N3O4
CAS Number:
7164-43-4
Molecular Weight:
171.11
EC Number:
230-514-2
MDL number:
MFCD00010563
UNSPSC Code:
12352100
PubChem Substance ID:
24851474
NACRES:
NA.22

Quality Level

100

assay

99%

form

solid

mp

>300 °C (lit.)

functional group

carboxylic acid

SMILES string

NC1=C(NC(=O)NC1=O)C(O)=O

InChI

1S/C5H5N3O4/c6-1-2(4(10)11)7-5(12)8-3(1)9/h6H2,(H,10,11)(H2,7,8,9,12)

InChI key

HWCXJKLFOSBVLH-UHFFFAOYSA-N

General description

5-Aminoorotic acid forms complexes with cerium (III), lanthanum (III) and neodymium (III). It reacts with dianhydride of ethylenedinitrilotetraacetic acid in dry DMF or DMSO to yield functionalized dicarboxamide derivatives.

Application

5-Aminoorotic acid was used as an internal standard during the electrochemical determination of orotic acid.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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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Certificates of Analysis (COA)

Lot/Batch Number
MKBB8933
05409HG
11224CN
06626TB
02226TB

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Irena Kostova et al.
Medicinal chemistry (Shariqah (United Arab Emirates)), 4(4), 371-378 (2008-08-05)
The cerium (III), lanthanum (III) and neodymium (III) complexes of 5-aminoorotic acid were synthesized and their structures were determined by means of theoretical study, spectral and physicochemical analysis. Significant differences in the spectra of the complexes were observed as compared
Synthesis and characterisation of chelating polycarboxylate ligands capable of forming intermolecular, complementary triple hydrogen bonds.
Georgopoulou AS, et al.
J. Chem. Soc., Dalton Trans., 11, 1869-1878 (1998)
Tommaso R I Cataldi et al.
Journal of chromatography. A, 1107(1-2), 130-138 (2006-01-13)
The application of activated pulsed amperometric detection (APAD) for the determination of orotic acid (OrA) in real samples at a gold working electrode in alkaline solutions, in combination with anion-exchange chromatography, is reported. Such an activated potential waveform was designed
Rony Panarsky et al.
Cancer & metabolism, 8, 7-7 (2020-08-11)
The loss-of-function mutation of fumarate hydratase (FH) is a driver of hereditary leiomyomatosis and renal cell carcinoma (HLRCC). Fumarate accumulation results in activation of stress-related mechanisms leading to upregulation of cell survival-related genes. To better understand how cells compensate for

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