Hydantoin

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ImageFile=Hydantoin.pngImageSize=
IUPACName=imidazolidine-2,4-dione
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Section1= Chembox Identifiers
CASNo=461-72-3
PubChem=10006
SMILES=C1C(=O)NC(=O)N1
Section2= Chembox Properties
Formula=C₃H₄N₂O₂
MolarMass=100.076
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Density=
MeltingPt=220°C
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Solubility=39.7 g/L (100°C)
Section3= Chembox Hazards
MainHazards=
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Hydantoin, which is also known as glycolylurea, is a heterocyclic organic compound that can be thought of as a cyclic "double-condensation reaction" product of glycolic acid and urea. Its chemical structure, shown in the Table of Properties at right, is similar to that of imidazolidine except that the molecule of hydantoin has carbonyl groups in the number 2 and 4 positions in the ring. Imidazolidine is the hydrogen-saturated of imidazole. Imidazole is a heterocyclic aromatic organic compound.

In a more general sense, hydantoins can refer to chemical compounds that have substituent groups bonded to a hydantoin ring "skeletal structure". For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule. ["The Chemistry of the Hydantoins."Elinor Ware Chem. Rev.; 1950; 46(3) pp 403 - 470; DOI|10.1021/cr60145a001]

ynthesis

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 [Urech, Ann., 165, 99 (1873).] synthesized the derivative 5-methylhydantoin from alanine sulfate and potassium cyanate in what is now known as the Urech hydantoin synthesis:

The 5,5-dimethyl compound can also be obtained from acetone cyanohydrin (also discovered by Urech: see cyanohydrin reaction) and ammonium carbonate. [Organic Syntheses, Coll. Vol. 3, p.323 (1955); Vol. 20, p.42 (1940) [http://www.orgsynth.org/orgsyn/pdfs/CV3P0323.pdf Link] .] . This reaction type is called the Bucherer-Bergs reaction. [Bucherer and Steiner, J. prakt. Chem., 140, 291 (1934).] [Bergs, Ger. pat. 566,094 (1929) [C. A., 27, 1001 (1933)] .]

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 hydrochloric acid, glycine is one of the products.

Medicine

Derivatives

Dantrolene is used in malignant hyperthermia, neuroleptic malignant syndrome, spasticity, and Ecstasy intoxication.

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

Pharmaceutical Industry

Hydantoin is used to synthesize the following anticonvulsants:
* ethotoin
* phenytoin
* mephenytoin
* fosphenytoin

=DNA Da

A high proportion of cytosine and thymine bases in 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 [Hofreiter M., Serre D., Poinar H.N., Kuch M., and Paabo S. "Nature Reviews Genetics" (2001) 2:353. ] .

External links

* [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10006 PubChem Compound Summary: Hydantoin]
* [http://www.iephb.nw.ru/~spirov/hazard/hydantoin.html Hazard DB: Hydantoin]
* [http://chem.sis.nlm.nih.gov/chemidplus/direct.jsp?name=hydantoin NIH ChemIDPlus: Hydantoin]
* [http://www.chemexper.com/chemicals/supplier/cas/461-72-3.html Hydantoin - CAS 461-72-3 - Catalog of Chemical Suppliers] ChemExper.com.

References