Uracil

Names

IUPAC name

Pyrimidine-2,4(1H,3H)-dione

Other names

2-oxy-4-oxy pyrimidine,
2,4(1H,3H)-pyrimidinedione,
2,4-dihydroxypyrimidine,
2,4-pyrimidinediol

Identifiers

CAS Number

66-22-8^Y

3D model (Jmol)

CHEBI:17568^N

ChEMBL566^N

1141^N

YQ8650000

56HH86ZVCT^N

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
InChI=1/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)

Key: ISAKRJDGNUQOIC-UHFFFAOYAV

SMILES

O=C1NC=CC(=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

Main hazards

carcinogen and teratogen with chronic exposure

NFPA 704

Flash point

Non-flammable

Related compounds

Thymine
Cytosine

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

Uracil /ˈjʊərəsɪl/ (U) is one of the four nucleobases in the nucleic acid of RNA that are represented by the letters A, G, C and U. 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. Uracil is a demethylated form of thymine.

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.

Based on ¹²C/¹³C isotopic ratios of organic compounds found in the Murchison meteorite, it is believed that uracil, xanthine and related molecules can also be formed extraterrestrially.

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Wikipedia