Uracil

Uracil
Ball-and-stick 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
CAS Number	66-22-8 ;
3D model (JSmol)	lactam form: Interactive image; lactim form: Interactive image;
3DMet	B00026;
Beilstein Reference	606623
ChEBI	CHEBI:17568 ;
ChEMBL	ChEMBL566 ;
ChemSpider	1141 ;
DrugBank	DB03419;
ECHA InfoCard	100.000.565
EC Number	200-621-9;
Gmelin Reference	2896
IUPHAR/BPS	4560;
KEGG	C00106;
PubChem CID	1174;
RTECS number	YQ8650000;
UNII	56HH86ZVCT ;
CompTox Dashboard (EPA)	DTXSID4021424 ;
	InChI InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) Key: ISAKRJDGNUQOIC-UHFFFAOYSA-N ;
	SMILES lactam form: O=C1C=CNC(=O)N1; lactim form: Oc1nccc(O)n1;
Properties
Chemical formula	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
Solubility in water	Soluble
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	carcinogen and teratogen with chronic exposure
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H361
Precautionary statements	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). verify (what is ?) Infobox references

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.

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]

^ 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.
^ Garrett RH, Grisham CM (1997). Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning.
^ 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’.]
^ 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.
^ Cite error: The named reference brown1 was invoked but never defined (see the help page).
^ Cite error: The named reference Horton1 was invoked but never defined (see the help page).
^ Cite error: The named reference Murch_base was invoked but never defined (see the help page).
^ Cite error: The named reference Oba 2023 was invoked but never defined (see the help page).
^ Cite error: The named reference Clark 2012 was invoked but never defined (see the help page).
^ Cite error: The named reference Nuevo 2009 was invoked but never defined (see the help page).

[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.

[Garrett1-2] 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.

[brown1-5] Cite error: The named reference brown1 was invoked but never defined (see the help page).

[Horton1-6] Cite error: The named reference Horton1 was invoked but never defined (see the help page).

[Murch_base-7] Cite error: The named reference Murch_base was invoked but never defined (see the help page).

[Oba_2023-8] Cite error: The named reference Oba 2023 was invoked but never defined (see the help page).

[Clark_2012-9] Cite error: The named reference Clark 2012 was invoked but never defined (see the help page).

[Nuevo_2009-10] Cite error: The named reference Nuevo 2009 was invoked but never defined (see the help page).

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