Uracil

Uracil (/ˈjʊərəsɪl/) (symbol U or Ura) is one of the four nucleobases in the nucleic acid RNA. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine (T). Uracil is a demethylated form of thymine.

Not to be confused with uridine.
Uracil
Names
Preferred IUPAC name
Pyrimidine-2,4(1H,3H)-dione
Other names
  • 2-Oxy-4-oxypyrimidine
  • 2,4(1H,3H)-Pyrimidinedione
  • 2,4-Dihydroxypyrimidine
  • 2,4-Pyrimidinediol
Identifiers
3D model (JSmol)
3DMet
606623
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.565
EC Number
  • 200-621-9
2896
KEGG
RTECS number
  • YQ8650000
UNII
  • InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) N
    Key: ISAKRJDGNUQOIC-UHFFFAOYSA-N N
Properties
C4H4N2O2
Molar mass 112.08676 g/mol
Appearance Solid
Density 1.32 g/cm3
Melting point 335 °C (635 °F; 608 K)
Boiling point N/A – decomposes
Soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 carcinogen and teratogen with chronic exposure
GHS labelling:
Warning
H315, H319, H335, H361
P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
1
1
Flash point Non-flammable
Related compounds
Related compounds
 Thymine
Cytosine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Uracil is a common and naturally occurring pyrimidine derivative. The name "uracil" was coined in 1885 by the German chemist Robert Behrend, who was attempting to synthesize derivatives of uric acid. Originally discovered in 1900 by Alberto Ascoli, it was isolated by hydrolysis of yeast nuclein; it was also found in bovine thymus and spleen, herring sperm, and wheat germ. It is a planar, unsaturated compound that has the ability to absorb light.

Uracil that was formed extraterrestrially has been detected in the Murchison meteorite, in a near-Earth asteroid, and possibly on the surface of the moon Titan. It has been synthesized under cold laboratory conditions similar to outer space, from pyrimidine embedded in water ice and exposed to ultraviolet light.

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