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Hydantoin

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Hydantoin

Hydantoin
Skeletal formula of hydantoin
Ball-and-stick model of hydantoin
Names
IUPAC name
Imidazolidine-2,4-dione
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
KEGG  Y
PubChem
Properties
C3H4N2O2
Molar mass 100.08 g·mol−1
Melting point 220 °C (428 °F; 493 K)
39.7 g/L (100 °C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Hydantoin, or glycolylurea, is a glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sense, hydantoins can refer to a groups and a class of compounds with the same ring structure as the parent. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.[1]

Contents

  • Synthesis 1
  • Uses and occurrence 2
    • Pharmaceuticals 2.1
    • Pesticides 2.2
    • Synthesis of amino acids 2.3
    • Halogenation 2.4
    • DNA Oxidation to hydantoins after cell death 2.5
  • References 3
  • External links 4

Synthesis

Hydantoin was first isolated in 1861 by Adolf von Baeyer in the course of his study of uric acid. He obtained it by hydrogenation of allantoin, hence the name.

Urech in 1873 synthesized 5-methylhydantoin from alanine sulfate and potassium cyanate in what is now known as the Urech hydantoin synthesis[2] The method is very similar to the modern route using alkyl and arylcyanates. The 5,5-dimethyl compound can also be obtained from acetone cyanohydrin (also discovered by Urech: see cyanohydrin reaction) and ammonium carbonate.[3] This reaction type is called the Bucherer–Bergs reaction.[4][5]

According to the 1911 Encyclopædia Britannica, hydantoin can also be synthesized either by heating allantoin with hydroiodic acid or by "heating bromacetyl urea with alcoholic ammonia". The cyclic structure of hydantoins was confirmed by Dorothy Hahn 1913.[6]

Of practical importance, hydantoins are obtained by condensation of a cyanohydrin with ammonium carbonate. Another useful route involves the condensation of amino acids with cyanates:

Uses and occurrence

Pharmaceuticals

Hydantoin group can be found in several medicinally important compounds. In pharmaceuticals, 'hydantoins' most often refer to anticonvulsants; phenytoin and fosphenytoin both contain hydantoin moieties and are both used as anticonvulsants in the treatment of seizure disorders. The hydantoin derivative dantrolene is used as a muscle relaxant to treat malignant hyperthermia, neuroleptic malignant syndrome, spasticity, and ecstasy intoxication.

Pesticides

The hydantoin derivative Imiprothrin is a pyrethroid insecticide. Iprodione is a popular fungicide containing the hydantoin group.[7]

Synthesis of amino acids

Hydrolysis of hydantoins affords amino acids:

RCHC(O)NHC(O)NH + H2O → RCHC(NH2)CO2H + NH3

Hydantoin itself reacts with hot, dilute hydrochloric acid to give glycine. Methionine is produced industrially via the hydantoin obtained from methional.[7]

Halogenation

Some N-halogenated derivatives of hydantoin are used as chlorinating or brominating agents in disinfectant/sanitizer or biocide products. The three major N-halogenated derivatives are dichlorodimethylhydantoin (DCDMH), bromochlorodimethylhydantoin (BCDMH), and dibromodimethylhydantoin (DBDMH).

Iprodione is a popular fungicide containing the hydantoin group.

DNA Oxidation to hydantoins after cell death

A high proportion of PCR from working. Such damage is a problem when dealing with ancient DNA samples.[8]

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. ^ Oakes, Elizabeth H. (2007). Encyclopedia of World Scientists. Facts on File, Incorporated. p. 298.  
  7. ^ a b Karlheinz Drauz, Ian Grayson, Axel Kleemann, Hans-Peter Krimmer, Wolfgang Leuchtenberger, Christoph Weckbecker (2005), "Amino Acids",  
  8. ^ Hofreiter M., Serre D., Poinar H.N., Kuch M., and Paabo S. Nature Reviews Genetics (2001) 2:353.

External links

  • CID 10006 from PubChem
  • Hazard DB: Hydantoin
  • Hydantoin in the ChemIDplus database
  • [2] English Translation of 1926 German review article on the Preparation of hydantoins by Heinrich Biltz and Karl Slotta

 

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