Uracil
Chemical compound of RNA / From Wikipedia, the free encyclopedia
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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.
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Names | |||
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Preferred IUPAC name
Pyrimidine-2,4(1H,3H)-dione | |||
Other names
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Identifiers | |||
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3D model (JSmol) |
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3DMet | |||
606623 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider |
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DrugBank | |||
ECHA InfoCard | 100.000.565 | ||
EC Number |
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2896 | |||
KEGG | |||
PubChem CID |
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RTECS number |
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UNII | |||
CompTox Dashboard (EPA) |
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Properties | |||
C4H4N2O2 | |||
Molar mass | 112.08676 g/mol | ||
Appearance | Solid | ||
Density | 1.32 g/cm3 | ||
Melting point | 335 °C (635 °F; 608 K)[1] | ||
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) | |||
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).
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Uracil is a common and naturally occurring pyrimidine derivative.[2] The name "uracil" was coined in 1885 by the German chemist Robert Behrend, who was attempting to synthesize derivatives of uric acid.[3] Originally discovered in 1900 by Alberto Ascoli, it was isolated by hydrolysis of yeast nuclein;[4] it was also found in bovine thymus and spleen, herring sperm, and wheat germ.[5] It is a planar, unsaturated compound that has the ability to absorb light.[6]
Uracil that was formed extraterrestrially has been detected in the Murchison meteorite,[7] in a near-Earth asteroid,[8] and possibly on the surface of the moon Titan.[9] It has been synthesized under cold laboratory conditions similar to outer space, from pyrimidine embedded in water ice and exposed to ultraviolet light.[10]