Uracil

Not to be confused with uridine.
Uracil
Structural formula of uracil
Ball-and-stick model of uracil
Ball-and-stick model of uracil
Space-filling model of uracil
Space-filling model of 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 Edit this at Wikidata
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)[1]
Boiling point N/A – decomposes
Soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 carcinogen and teratogen with chronic exposure
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability (yellow): no hazard codeSpecial hazards (white): no code
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).
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Uracil (/ˈjʊərəsɪl/) (symbol U or Ura) is one of the four nucleotide bases 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.

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]

  1. ^ Myers RL (2007). "Chapter 29: Cytosine Thymine and Uracil". The 100 most important chemical compounds : a reference guide. Westport, Conn.: Greenwood Press. pp. 92–93. ISBN 978-0-313-33758-1.
  2. ^ Garrett RH, Grisham CM (1997). Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning.
  3. ^ Behrend R (1885). "Versuche zur Synthese von Körpern der Harnsäurereihe" [Experiments on the synthesis of substances in the uric acid series]. Annalen der Chemie. 229 (1–2): 1–44. doi:10.1002/jlac.18852290102. Dasselbe stellt sich sonach als Methylderivat der Verbindung: welche ich willkürlich mit dem Namen Uracil belege, dar. [The same compound is therefore represented as the methyl derivative of the compound, which I will arbitrarily endow with the name ‘uracil’.]
  4. ^ Ascoli A (1900). "Über ein neues Spaltungsprodukt des Hefenucleins" [On a new cleavage product of nucleic acid from yeast]. Zeitschrift für Physiologische Chemie. 31 (1–2): 161–164. doi:10.1515/bchm2.1901.31.1-2.161. Archived from the original on 12 May 2018.
  5. ^ Cite error: The named reference brown1 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Horton1 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Murch_base was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Oba 2023 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Clark 2012 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference Nuevo 2009 was invoked but never defined (see the help page).