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MilliporeSigma

U0750

Sigma-Aldrich

Uracil

≥99.0%, synthetic (organic), powder

Synonym(s):

2,4(1H,3H)-Pyrimidinedione, 2,4-Dihydroxypyrimidine, 2,4-Pyrimidinediol

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About This Item

Empirical Formula (Hill Notation):
C4H4N2O2
CAS Number:
66-22-8
Molecular Weight:
112.09
Beilstein/REAXYS Number:
507828
EC Number:
200-621-9
MDL number:
MFCD00006016
UNSPSC Code:
41106305
PubChem Substance ID:
24900618
NACRES:
NA.51

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Product Name

Uracil, ≥99.0%

biological source

synthetic (organic)

Quality Level

300

assay

≥99.0%

form

powder

mp

>300 °C (lit.)

solubility

1 M NaOH: 50 mg/mL, clear to hazy, colorless to faint yellow or tan

SMILES string

O=C1NC=CC(=O)N1

InChI

1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)

InChI key

ISAKRJDGNUQOIC-UHFFFAOYSA-N

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General description

Uracil belongs to the pyrimidine nucleobase family. It is naturally occurring and is an important and active part of RNA.

Application

Uracil has been used as:
  • a nucleotide standard to determine DNA methylation by high-performance liquid chromatography
  • a component of synthetic define medium for culturing Saccharomyces cerevisiae and its strain
  • a component of the amino acid supplement to culture Bacillus sp

Biochem/physiol Actions

Uracil and its derivatives play an integral part in medicinal chemistry for the synthesis of cancer, viral infections, autosomal recessive disorder, thyroid, and diabetic drugs.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6705V
WXBD5496V
WXBD6092V
WXBD5758V
WXBD4893V

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Sandra M Carvalho et al.
PloS one, 8(3), e58492-e58492 (2013-03-19)
Links between carbohydrate metabolism and virulence in Streptococcus pneumoniae have been recurrently established. To investigate these links further we developed a chemically defined medium (CDM) and standardized growth conditions that allowed for high growth yields of the related pneumococcal strains
William B White et al.
The New England journal of medicine, 369(14), 1327-1335 (2013-09-03)
To assess potentially elevated cardiovascular risk related to new antihyperglycemic drugs in patients with type 2 diabetes, regulatory agencies require a comprehensive evaluation of the cardiovascular safety profile of new antidiabetic therapies. We assessed cardiovascular outcomes with alogliptin, a new
Daisuke Katagiri et al.
Journal of the American Society of Nephrology : JASN, 24(12), 2034-2043 (2013-10-05)
Accumulating evidence of the beyond-glucose lowering effects of a gut-released hormone, glucagon-like peptide-1 (GLP-1), has been reported in the context of remote organ connections of the cardiovascular system. Specifically, GLP-1 appears to prevent apoptosis, and inhibition of dipeptidyl peptidase-4 (DPP-4)
Jaunius Urbonavicius et al.
Methods in enzymology, 425, 103-119 (2007-08-04)
Formation of 5-methyluridine (ribothymidine) at position 54 of the T-psi loop of tRNA is catalyzed by site-specific tRNA methyltransferases (tRNA[uracil-54,C5]-MTases). In eukaryotes and many bacteria, the methyl donor for this reaction is generally S-adenosyl-L-methionine (S-AdoMet). However, in other bacteria, like
Mirta M L Sousa et al.
Molecular aspects of medicine, 28(3-4), 276-306 (2007-06-26)
Uracil is usually an inappropriate base in DNA, but it is also a normal intermediate during somatic hypermutation (SHM) and class switch recombination (CSR) in adaptive immunity. In addition, uracil is introduced into retroviral DNA by the host as part
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