Uracil

For research use only. Not for therapeutic Use.

  • CAT Number: A000678
  • CAS Number: 66-22-8
  • Molecular Formula: C4H4N2O2
  • Molecular Weight: 112.09
  • Purity: ≥95%
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Uracil(Cat No.:A000678)is one of the four nucleobases found in RNA, where it pairs with adenine through two hydrogen bonds. As a pyrimidine derivative, it replaces thymine (found in DNA) and plays a key role in RNA’s structure and function. Uracil is involved in several biological processes, including enzymatic reactions and regulation of gene expression. It is also a precursor in the synthesis of cofactors like UDP-glucose and vitamins such as thiamine. Due to its simplicity, uracil is studied in prebiotic chemistry as a potential building block of early life.


CAS Number 66-22-8
Synonyms

66-22-8; 2,4-Dihydroxypyrimidine; 2,4(1H,3H)-Pyrimidinedione; Pyrimidine-2,4(1H,3H)-dione; 2,4-Pyrimidinediol

Molecular Formula C4H4N2O2
Purity ≥95%
Storage -20°C
IUPAC Name 1H-pyrimidine-2,4-dione
InChI InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
InChIKey ISAKRJDGNUQOIC-UHFFFAOYSA-N
SMILES C1=CNC(=O)NC1=O
Reference

1: Bag SS, Yashmeen A. Uracil-amino acid as a scaffold for β-sheet
peptidomimetics: Study of photophysics and interaction with BSA protein. Bioorg
Med Chem Lett. 2017 Nov 10. pii: S0960-894X(17)31104-6. doi:
10.1016/j.bmcl.2017.11.017. [Epub ahead of print] PubMed PMID: 29153423.
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2: Ilyina MG, Khamitov EM, Mustafin AG, Khursan SL. Controlled stabilization of
anionic forms of the uracil derivatives: A DFT study. J Mol Graph Model. 2017 Nov
11;79:65-71. doi: 10.1016/j.jmgm.2017.11.007. [Epub ahead of print] PubMed PMID:
29145035.
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3: Wang Y, Liu D, Deng J, Wang Y, Xu J, Ye C. Loop-mediated isothermal
amplification using self-avoiding molecular recognition systems and antarctic
thermal sensitive uracil-DNA-glycosylase for detection of nucleic acid with
prevention of carryover contamination. Anal Chim Acta. 2017 Dec 15;996:74-87.
doi: 10.1016/j.aca.2017.10.022. Epub 2017 Oct 27. PubMed PMID: 29137710.

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4: Yan Y, Qing Y, Pink JJ, Gerson SL. Loss of Uracil DNA Glycosylase Selectively
Re-sensitizes p53 Mutant and Deficient Cells to 5-FdU. Mol Cancer Res. 2017 Nov
8. pii: molcanres.0215.2017. doi: 10.1158/1541-7786.MCR-17-0215. [Epub ahead of
print] PubMed PMID: 29117941.
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5: Anithaa VS, Vijayakumar S, Sudha M, Shankar R. Theoretical investigation on
hydrogen bond interaction of diketo/keto-enol form uracil and thymine tautomers
with intercalators. J Mol Model. 2017 Nov 6;23(12):333. doi:
10.1007/s00894-017-3476-8. PubMed PMID: 29105034.
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6: Wu RR, Hamlow LA, He CC, Nei YW, Berden G, Oomens J, Rodgers MT. The intrinsic
basicity of the phosphate backbone exceeds that of uracil and thymine residues:
protonation of the phosphate moiety is preferred over the nucleobase for pdThd
and pUrd. Phys Chem Chem Phys. 2017 Nov 3. doi: 10.1039/c7cp05521h. [Epub ahead
of print] PubMed PMID: 29099122.

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7: Deng X, Han L, Zhou J, Zhang H, Li Q. Discovery of triazole-based uracil
derivatives bearing amide moieties as novel dipeptidyl peptidase-IV inhibitors.
Bioorg Chem. 2017 Dec;75:357-367. doi: 10.1016/j.bioorg.2017.10.010. Epub 2017
Oct 23. PubMed PMID: 29096096.
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8: Yang L, Yang L, Yu H, Liu L, Zhao X, Huang X. Conformational transitions of
uracil transporter UraA from Escherichia coli: a molecular simulation study. J
Biomol Struct Dyn. 2017 Oct 26:1-13. doi: 10.1080/07391102.2017.1388288. [Epub
ahead of print] PubMed PMID: 29072107.

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9: Fennimore MA, Matsika S. Correction: Core-excited and shape resonances of
uracil. Phys Chem Chem Phys. 2017 Nov 1;19(42):29005-29006. doi:
10.1039/c7cp90241g. PubMed PMID: 29057412.
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10: Kuznetsova AA, Iakovlev DA, Misovets IV, Ishchenko AA, Saparbaev MK,
Kuznetsov NA, Fedorova OS. Pre-steady-state kinetic analysis of damage
recognition by human single-strand selective monofunctional uracil-DNA
glycosylase SMUG1. Mol Biosyst. 2017 Oct 20. doi: 10.1039/c7mb00457e. [Epub ahead
of print] PubMed PMID: 29051947.

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