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857858

Sigma-Aldrich

5-Iodouracil

98%

Synonym(s):

2,4-Dihydroxy-5-iodopyrimidine

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About This Item

Empirical Formula (Hill Notation):
C4H3IN2O2
CAS Number:
696-07-1
Molecular Weight:
237.98
EC Number:
211-788-2
MDL number:
MFCD00006020
UNSPSC Code:
12352100
PubChem Substance ID:
24888454
NACRES:
NA.22

Quality Level

100

Assay

98%

form

powder

mp

274-276 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

IC1=CNC(=O)NC1=O

InChI

1S/C4H3IN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)

InChI key

KSNXJLQDQOIRIP-UHFFFAOYSA-N

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Related Categories

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Doreen Dobritzsch et al.
The Journal of biological chemistry, 277(15), 13155-13166 (2002-01-18)
Dihydroprymidine dehydrogenase catalyzes the first and rate-limiting step in pyrimidine degradation by converting pyrimidines to the corresponding 5,6- dihydro compounds. The three-dimensional structures of a binary complex with the inhibitor 5-iodouracil and two ternary complexes with NADPH and the inhibitors
Yan Xu et al.
Journal of the American Chemical Society, 126(20), 6274-6279 (2004-05-20)
To explore the structure-dependent hydrogen abstraction in antiparallel and parallel G-quartet DNA structures, the photochemical reactivity of 5-iodouracil ((I)U)-containing human telomeric DNA 22-mers was investigated under the 302 nm UV irradiation conditions. We discovered that only antiparallel ODN 4, in
M C Willis et al.
Science (New York, N.Y.), 262(5137), 1255-1257 (1993-11-19)
5-Iodouracil-substituted RNA and DNA were crosslinked regiospecifically to associated proteins in yields of 70 to 94% of bound nucleic acid. Irradiation of the iodouracil chromophore with monochromatic, long-wavelength ultraviolet radiation (325 nanometers) eliminates excitation of other nucleic acid and protein
D L Wong et al.
Nucleic acids research, 26(2), 645-649 (1998-02-28)
We describe a novel strategy combining photocrosslinking and HPLC-based electrospray ionization mass spectrometry to identify UV crosslinked DNA-protein complexes. Eco RI DNA methyltransferase modifies the second adenine within the recognition sequence GAATTC. Substitution of 5-iodouracil for the thymine adjacent to
Supaluk Prachayasittikul et al.
Molecules (Basel, Switzerland), 14(8), 2768-2779 (2009-08-25)
This study reports the synthesis of some substituted 5-iodouracils and their bioactivities. Alkylation of 5-iodouracils gave predominately N1-substituted-(R)-5-iodouracil compounds 7a-d (R = n-C(4)H(9), s-C(4)H(9), CH(2)C(6)H(11), CH(2)C(6)H(5)) together with N1,N3-disubstituted (R) analogs 8a-b (R = n-C(4)H(9), CH(2)C(6)H(11)). Their antimicrobial activity was
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