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Encyclopedia > Hydantoin
Hydantoin
General
Systematic name imidazolidine-2,4-dione
Other names glycolylurea, 2,4(3H,5H)-Imidazoledione
Molecular formula C3H4N2O2
SMILES C1C(=O)NC(=O)N1
InChI InChI=1/C3H4N2O2/c6-2-1-4-3(7)5-2
/h1H2,(H2,4,5,6,7)/f/h4-5H
Molar mass 100.076 g/mol
Appearance White crystalline powder
CAS number [461-72-3]
Properties
Density and phase  ? g/cm3, solid
Solubility in water 39.7 g/L (100°C)
Other solvents  ?
Melting point 220°C (493 K)
Boiling point  ?°C (? K)
Structure
Molecular shape Planar
Dipole moment  ? D
Hazards
MSDS External MSDS
Main hazards  ?
NFPA 704  ?
Flash point  ?°C
R/S statement R: ?
S: 24/25[1]
RTECS number MT8210000
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
 ?
Spectral data UV, IR, NMR, MS
Related compounds
Related
heterocyclic compounds
imidazolidine (see imidazole),
cyanuric acid
Related compounds  ?
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 heterocyclic organic compound which 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 imidazolidine except that the molecule has carbonyl groups in the number 2 and 4 positions in the ring. Imidazolidine is the hydrogen-saturated analogue of imidazole. Imidazole is a heterocyclic aromatic organic compound. Image File history File links Hydantoin. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... Italic textLink titleLink titlelink titlelink titleBold text General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... InChI is the IUPACs International Chemical Identifier. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid. ... four sp³ orbitals three sp² orbitals In chemistry, hybridisation is the mixing of atomic orbitals belonging to a same electron shell to form new orbitals suitable for the qualitative description of atomic bonding properties. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Worker safety and health is the prevention and reduction of the number of occupational safety and health hazards at the places of employment, providing safe and healthful working conditions. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... The flash point of a fuel is the lowest temperature at which it can form an ignitable mix with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index of a material is the factor by which the phase velocity of electromagnetic radiation is slowed relative to vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Mass spectrometry is an analytical technique to measure the mass-to-charge ratio (m/q) of ions. ... Pyridine a simple heterocyclic compound Heterocyclic compounds are organic compounds which contain a ring structure containing atoms in addition to carbon, such as sulfur, oxygen or nitrogen, as part of the ring. ... Imidazole is a heterocyclic aromatic organic compound. ... Cyanuric acid or 1,3,5-triazine-2,4,6-triol is an organic chemical compound with the chemical formula C3H3N3O3. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Heterocyclic compounds are substances which contain a ring structure as found in benzene and the aromatic compounds, or aromatic hydrocarbons, but in which other atoms than carbon, such as sulfur, oxygen or nitrogen are found as part of the ring. ... An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and gases containing carbon. ... A condensation reaction (also known as a dehydration reaction or dehydration synthesis when water is lost) is a chemical reaction in which two molecules or moieties react and become covalently bonded to one another by the concurrent loss of a small molecule, often water, methanol, or a type of hydrogen... Glycolic acid (or hydroxyacetic acid) is the smallest α-hydroxy acid (AHA). ... Urea is an organic compound of carbon, nitrogen, oxygen and hydrogen, with the formula CON2H4 or (NH2)2CO. Urea is also known as carbamide, especially in the recommended International Non-proprietary Names (rINN) in use in Europe. ... Chemical structure is the arrangement of atoms within a molecule, usually linked by covalent bonds. ... In general, a molecule is the smallest particle of a pure chemical substance that still retains its composition and chemical properties. ... In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ... Italic textLink titleLink titlelink titlelink titleBold text General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... Imidazole is a heterocyclic aromatic organic compound. ... Heterocyclic compounds are substances which contain a ring structure as found in benzene and the aromatic compounds, or aromatic hydrocarbons, but in which other atoms than carbon, such as sulfur, oxygen or nitrogen are found as part of the ring. ... In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and gases containing carbon. ...


In a more general sense, hydantoins can refer to chemical compounds which 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. A chemical compound is a chemical substance formed from two or more elements, with a fixed ratio determining the composition. ... In organic chemistry functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... Phenytoin sodium (marketed as Dilantin® in the USA and as Epanutin® in the UK, by Parke-Davis, now part of Pfizer) is a commonly used antiepileptic. ... In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 Picture where the six carbon atoms are arranged in a cyclic manner. ...

Contents


Synthesis

According to the 1911 Encyclopedia Britannica, hydantoin can be synthesized either by heating allantoin with hydroiodic acid or by "heating bromacetyl urea with alcoholic ammonia." (Redirected from 1911 Encyclopedia Britannica) The Eleventh Edition of the Encyclopædia Britannica (1911) in many ways represents the sum of knowledge at the beginning of the 20th century. ... Allantoin is a botanical extract of the comfrey plant and is used for its healing, soothing, and anti-irritating properties. ... Hydroiodic acid (sometimes also spelled hydriodic acid) is a highly acidic aqueous solution of hydrogen iodide (HI) (Concentrated solution is usually 48 - 57% HI). ...


Uses

Medicine

Derivatives

Dantrolene is used in malignant hyperthermia, neuroleptic malignant syndrome, spasticity, and Ecstasy intoxication. Dantrolene sodium is a muscle relaxant that is currently the only specific and effective treatment for malignant hyperthermia. ... Malignant hyperthermia (MH or MHS for malignant hyperthermia syndrome) is a life-threatening condition resulting from a genetic sensitivity of skeletal muscles to volatile anaesthetics and depolarizing neuromuscular blocking drugs that occurs during or after anaesthesia. ... Neuroleptic malignant syndrome (NMS) is a life-threatening, neurological disorder most often caused by an adverse reaction to neuroleptic or antipsychotic drugs. ... Spasticity is a disorder of the bodys motor system in which certain muscles are continuously contracted. ... MDMA (3,4-methylenedioxymethamphetamine), most commonly known today by the street name ecstasy, is a synthetic entactogen of the phenethylamine family whose primary effect is to stimulate the secretion of and inhibit the re-uptake of large amounts of serotonin as well as dopamine and noradrenaline in the brain, causing...


Halogenated analogues of hydantoin are used as chlorinating or brominating agents in disinfectant/sanitizer or biocide products. Disinfection The destruction of pathogenic and other kinds of microorganisms by physical or chemical means Disinfectants are chemical substances used to kill viruses and microbes (germs), such as bacteria and fungi. ... A biocide is a chemical substance, such as pesticides, which can be fungicides, herbicides, insecticides, miticides, or rodenticides, etc. ...


Pharmaceutical Industry

Hydantoin is used to synthesize the following anticonvulsants:

Ethotoin (marketed as Peganone® by Ovation) is an anticonvulsant drug used in the treatment of epilepsy. ... Phenytoin sodium (marketed as Dilantin® in the USA and as Epanutin® in the UK, by Parke-Davis, now part of Pfizer) is a commonly used antiepileptic. ... Mephenytoin (marketed as Mesantoin® by Novartis) is a hydantoin, used as an anticonvulsant. ... Fosphenytoin (Cerebyx®, Parke-Davis) is a water-soluble phenytoin prodrug used in only in hospitals for the treatment of epileptic seizures. ...

References and end notes

  • PubChem Compound Summary: Hydantoin
  • Hazard DB: Hydantoin
  • ChemIDPlus: Hydantoin
  1. ^  Hydantoin - CAS 461-72-3 - Catalog of Chemical Suppliers ChemExper.com.

This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain. Encyclopædia Britannica, the 11th edition The Encyclopædia Britannica Eleventh Edition (1910–1911) is perhaps the most famous edition of the Encyclopædia Britannica. ... The public domain comprises the body of all creative works and other knowledge—writing, artwork, music, science, inventions, and others—in which no person or organization has any proprietary interest. ...


  Results from FactBites:
 
Hydantoin diglycidyl compounds - Patent 4071477 (2330 words)
Hydantoin diglycidyl compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, alkyl containing 1 to 8 carbon atoms or cycloalkyl containing 5 to 6 carbon atoms; and R.sub.2 is alkyl containing 5 to 8 carbon atoms or cycloalkyl containing 5 to 6 carbon atoms, are prepared.
The hydantoin diglycidyl resins of this patent, however, when used as a room temperature cured casting or laminating resin, for example, in the electrical, building and decorative areas, have the disadvantage of being crystalline solids or being highly viscous and the "lower alkyl" examples display poor resistance to water.
More specifically, the diglycidyl hydantoin resins of this invention when combined with the appropriate curing agents may be used as insulating compositions for electrical parts, as compositions to prepare printed circuit boards and can coatings, and further, as compositions for the preparation of structural laminates and flooring.
CIGNA - Fetal Hydantoin Syndrome (1410 words)
The child with Fetal Hydantoin Syndrome may be small at birth, with increased hair on the body and face, and with poorly developed fingernails and toenails.
Fetal Hydantoin Syndrome is a rare disorder that is caused by exposure of a fetus to phenytoin (Dilantin) which is an anticonvulsant drug prescribed for epilepsy.
Biochemical and molecular teratology of fetal hydantoin syndrome.
  More results at FactBites »

 
 

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