What Is Hydantoin?
Hydantoin, also known as glycolylurea, is a compound synthesized by condensing glycolic acid and urea. It naturally occurs in molasses and appears as an odorless, colorless crystal under standard temperature and pressure. Hydantoin can be produced through Yurek’s hydantoin synthesis, involving amino acids, potassium cyanate, and hydrochloric acid. It serves as the foundational structure for various chemicals, including allantoin, phenytoin, and dantrolene.
Uses of Hydantoin
Hydantoin and its derivatives have diverse applications:
1. Antiepileptic Drugs
Phenytoin, a derivative of hydantoin, is a widely used antiepileptic drug. It suppresses nerve cell excitability, reducing seizure occurrences.
2. Cosmetics and Skin Moisturizers
DialkylHydantoin derivatives, used in cosmetics and skincare, effectively retain skin moisture, alleviating dryness and irritation.
3. Ultraviolet Absorber
Hydantoin derivatives also act as UV absorbers in sunscreens and hair products, minimizing UV ray damage to skin and hair.
Additionally, these derivatives are crucial for producing agricultural chemicals and as intermediates in organic synthesis. PhenylHydantoin, derived from hydantoin, aids in amino acid identification due to its crystallinity. Heating hydantoin with barium hydroxide yields PhenylHydantoin, which can also be synthesized from various amino acids and phenyl isocyanate. Hydrolyzing hydantoin produces glycine, a basic amino acid, and substituting carbon at position 5 allows for the synthesis of various amino acids.
Properties of Hydantoin
Hydantoin (C3H4N2O2, molecular weight 100.09 g/mol) is a heterocyclic compound, known as imidazolidine-2,4-dione. Its structure results from the cyclic condensation of glycolic acid and urea. As a colorless crystalline solid, hydantoin is naturally found in molasses and has a melting point of 215-220°C. It is insoluble in water and slightly soluble in organic solvents like alcohol and ether.
Exhibiting cyclic amide properties, hydantoin can be reduced to amino acids and acts as the backbone for drugs such as phenytoin and sodium valproate, suppressing epileptic seizures by affecting the central nervous system. Its derivatives, formed through the condensation of urea and glyoxal, are used in skin moisturizers.
Structure of Hydantoin
Hydantoin features a five-membered cyclic structure with two nitrogen atoms and two carbonyl groups alternately attached to the ring. The nitrogen atoms are positioned at the 1st and 3rd positions, bonded to carbon atoms that have carbonyl groups at the 2nd and 4th positions.
This structure, exhibiting amide bond properties, is reactive under various conditions. Various hydantoin derivatives are produced by attaching different substituents, like phenyl groups in phenytoin, to the 5th carbon atom of the hydantoin ring, serving as antiepileptic drugs and skin moisturizers.
Other Information about Hydantoin
Method for Producing Hydantoin
Hydantoin synthesis includes:
1. Yurek’s Hydantoin Synthesis
This method synthesizes hydantoin derivatives from amino acids and potassium cyanate, where amino acids react with potassium cyanate under heat.
2. Bucherer-Berx Reaction
This method produces 5,5-disubstituted hydantoin derivatives from cyanohydrin and ammonium carbonate through carbamates and aldoximes reactions.