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Uracil

Chemical Properties and Reactions: – Uracil base-pairs with adenine in RNA and replaces thymine in DNA transcription. – Methylation of uracil produces thymine. – Uracil […]

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Chemical Properties and Reactions:
– Uracil base-pairs with adenine in RNA and replaces thymine in DNA transcription.
– Methylation of uracil produces thymine.
– Uracil undergoes amide-imidic acid tautomeric shifts and can recycle itself to form nucleotides.
– Reactions include oxidation, nitration, alkylation, and with elemental halogens.
– Different pH levels affect uracil’s reactivity in various reactions.

Synthesis and Uses:
– Organisms synthesize uracil from orotidine 5-monophosphate.
– Uracil is involved in the synthesis of enzymes, acts as a regulator and coenzyme, and aids in polysaccharide biosynthesis.
– Uracil is used in drug delivery, pharmaceuticals, and has industrial applications.
– Laboratory and prebiotic methods for uracil synthesis have been achieved.
– Uracil has potential in detoxification, affecting DNA production, and in the synthesis of various molecules.

Biological and Medical Applications:
– Uracil is rarely found in DNA but can be excised by Uracil-DNA glycosylase.
– Uracil derivatives have antiviral, anti-tubercular, and anti-leishmanial activity.
– Uracil reacts with fluorine to produce 5-fluorouracil, an anticancer drug.
– Uracil shows promise as an HIV viral capsid inhibitor.
– Uracil levels in DNA increase with folate deficiency in cultured human lymphocytes.

Astronomical and Astrobiological Significance:
– Uracil has been found in carbonaceous asteroids and meteorites.
– NASA has reproduced uracil in laboratory settings.
– Studies show the photochemistry of pyrimidine in astrophysical ices can lead to the production of nucleobases.
– Uracil’s acidity and biological implications have been studied in gas phase experiments.
– Extraterrestrial nucleobases containing uracil have been discovered in meteorites.

Research and Studies:
– Publications and studies related to uracil, including its role as an index in various studies.
– Research on human hepatic and extrahepatic UDP-glucuronosyltransferase enzymes.
– Novel methods and compounds related to uracil derivatives in various treatments.
– Studies on uracil-induced down-regulation of yeast uracil permease and its significance in biochemistry.
– Articles on caffeine synthesis from uracil, glucuronidation by UDP-glucuronosyltransferases, and combating HIV and hepatitis viruses with uracil derivatives.

Uracil (Wikipedia)

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
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)
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).
☒N verify (what is checkY☒N ?)

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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