, 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
. 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
. Imidazole is a heterocyclic aromatic
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.
Hydantoin was first isolated in 1861 by Adolf von Baeyer
in the course of his study of uric acid
. He obtained it by hydrogenation
, hence the name. Urech in 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.. This reaction type is called the Bucherer-Bergs reaction.
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".
When hydantoin reacts with hot, dilute hydrochloric acid
is one of the products.
is used in malignant hyperthermia
, neuroleptic malignant syndrome
, and Ecstasy
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).
Hydantoin is used to synthesize the following anticonvulsants
A high proportion of cytosine
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 .