Hydantoin



Hydantoin
IUPAC name imidazolidine-2,4-dione
Identifiers
CAS number 461-72-3
PubChem 10006
SMILES C1C(=O)NC(=O)N1
Properties
Molecular formula C3H4N2O2
Molar mass 100.076
Melting point

220°C

Solubility in water 39.7 g/L (100°C)
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Hydantoin, which is also known as glycolylurea, is a aromatic organic compound.

In a more general sense, hydantoins can refer to phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.[1]


Synthesis

Hydantoin was first isolated in 1881 by Urech hydantoin synthesis:


The 5,5-dimethyl compound can also be obtained from ammonium carbonate.[3]. This reaction type is called the Bucherer-Bergs reaction.[4][5]

According to the 1911 Encyclopedia Britannica, hydantoin can also be synthesized either by heating allantoin with hydroiodic acid or by "heating bromacetyl urea with alcoholic ammonia".

Uses

Chemical

When hydantoin reacts with hot, dilute glycine is one of the products.

Medicine

Derivatives

Ecstasy intoxication.

Halogenated analogues of hydantoin are used as chlorinating or brominating agents in DBDMH).

Pharmaceutical Industry

Hydantoin is used to synthesize the following anticonvulsants:

DNA Damage

A high proportion of DNA are oxidized to hydantoins over time after the death of an organism. Such modifications block DNA polymerases and thus prevents PCR from working. Such damage is a problem with dealing with ancient DNA samples [6].


References

  1. ^ The Chemistry of the Hydantoins.Elinor Ware Chem. Rev.; 1950; 46(3) pp 403 - 470; doi:10.1021/cr60145a001
  2. ^ Urech, Ann., 165, 99 (1873).
  3. ^ Organic Syntheses, Coll. Vol. 3, p.323 (1955); Vol. 20, p.42 (1940) Link.
  4. ^ Bucherer and Steiner, J. prakt. Chem., 140, 291 (1934).
  5. ^ Bergs, Ger. pat. 566,094 (1929) [C. A., 27, 1001 (1933)].
  6. ^ Hofreiter M., Serre D., Poinar H.N., Kuch M., and Paabo S. Nature Reviews Genetics (2001) 2:353.


This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.

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