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Hydantoin information


Hydantoin
Skeletal formula of hydantoin
Ball-and-stick model of hydantoin
Names
Preferred IUPAC name
Imidazolidine-2,4-dione
Identifiers
CAS Number
  • 461-72-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:27612 checkY
ChEMBL
  • ChEMBL122334 checkY
ChemSpider
  • 9612 checkY
ECHA InfoCard 100.006.650 Edit this at Wikidata
KEGG
  • C05146 checkY
PubChem CID
  • 10006
UNII
  • I6208298TA
CompTox Dashboard (EPA)
  • DTXSID1052111 Edit this at Wikidata
InChI
  • InChI=1S/C3H4N2O2/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7) checkY
    Key: WJRBRSLFGCUECM-UHFFFAOYSA-N checkY
  • InChI=1/C3H4N2O2/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7)
    Key: WJRBRSLFGCUECM-UHFFFAOYAD
SMILES
  • O=C1NC(=O)NC1
Properties
Chemical formula
C3H4N2O2
Molar mass 100.077 g·mol−1
Melting point 220 °C (428 °F; 493 K)
Solubility in water
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).
checkY verify (what is checkY☒N ?)
Infobox references

Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sense, hydantoins can refer to groups or a class of compounds with the same ring structure as the parent compound. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.[1]

  1. ^ Konnert, Laure; Lamaty, Frédéric; Martinez, Jean; Colacino, Evelina (2017). "Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold" (PDF). Chemical Reviews. 117 (23): 13757–13809. doi:10.1021/acs.chemrev.7b00067. PMID 28644621. S2CID 23653941.

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Hydantoin

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Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction...

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DMDM hydantoin

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DMDM hydantoin is an antimicrobial formaldehyde releaser preservative with the trade name Glydant. DMDM hydantoin is an organic compound belonging to a...

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Fetal hydantoin syndrome

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Fetal hydantoin syndrome, also called fetal dilantin syndrome, is a group of defects caused to the developing fetus by exposure to teratogenic effects...

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Hydantoin racemase

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Hydantoin racemase (EC 5.1.99.5, 5'-monosubstituted-hydantoin racemase, HyuA, HyuE) is an enzyme with systematic name D-5-monosubstituted-hydantoin racemase...

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Dantrolene

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concentration. Chemically it is a hydantoin derivative, but does not exhibit antiepileptic activity like other hydantoin derivates such as phenytoin. The...

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Phenacemide

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ring-opened analogue of phenytoin (a hydantoin), and is structurally related to the barbiturates and to other hydantoins. Phenacemide was introduced in 1949...

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Urech hydantoin synthesis

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The Urech hydantoin synthesis is the chemical reaction of amino acids with potassium cyanate and hydrochloric acid to give hydantoins. Bucherer–Bergs...

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Formaldehyde

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ketones includes several complexes of formaldehyde. 1,3-Dioxetane DMDM hydantoin Sawdust | Health impacts of sawdust Sulphobes Wood glue Wood preservative...

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Mannich base

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acidic compound (any enolizable carbonyl compound, amide, carbamate, hydantoin or urea) to the imine gives the Mannich base. With primary or secondary...

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Acne

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medicamentosa form of acne. Examples of such medications include lithium, hydantoin, isoniazid, glucocorticoids, iodides, bromides, and testosterone. When...

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Urea

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or other groups. Examples include carbamide peroxide, allantoin, and hydantoin. Ureas are closely related to biurets and related in structure to amides...

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Potassium cyanide

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particularly in the von Richter reaction. It also finds use for the synthesis of hydantoins, which can be useful synthetic intermediates, when reacted with a carbonyl...

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Anticonvulsant

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analgesic, anticonvulsant, and anxiolytic effects. The following are hydantoins: Ethotoin (1957). Phenytoin (1938). Mephenytoin. Fosphenytoin (1996)....

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Phenytoin

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dosing calculations. Pregnancy: Pregnancy category D due to risk of fetal hydantoin syndrome and fetal bleeding. However, optimal seizure control is very...

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Iprodione

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Iprodione is a hydantoin fungicide and nematicide. Iprodione is used on crops affected by Botrytis bunch rot, Brown rot, Sclerotinia and other fungal...

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Formaldehyde releaser

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in the EU since 2017 and a bill is under consideration in the US. DMDM hydantoin (ethylenedioxy)dimethanol (EDDM) (Benzyloxy)methanol (BHF, benzylhemiformal)...

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Fetal alcohol spectrum disorder

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syndrome Dubowitz syndrome Brachman-DeLange syndrome Toluene syndrome Fetal hydantoin syndrome Fetal valproate syndrome Maternal PKU fetal effects Other disorders...

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Webbed toes

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Cornelia de Lange syndrome Edwards syndrome Jackson–Weiss syndrome Fetal hydantoin syndrome Miller syndrome Pfeiffer syndrome Smith–Lemli–Opitz syndrome...

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Mephenytoin

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Mephenytoin (marketed as Mesantoin by Novartis) is a hydantoin, used as an anticonvulsant. It was introduced approximately 10 years after phenytoin, in...

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Methionine

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synthesis combines acrolein, methanethiol, and cyanide, which affords the hydantoin. Racemic methionine can also be synthesized from diethyl sodium phthalimidomalonate...

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Microcephaly

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varicella syndrome Zika virus (see Zika fever#Microcephaly) Drugs Fetal hydantoin syndrome Fetal alcohol syndrome Other Radiation exposure to mother Maternal...

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Ethotoin

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is an anticonvulsant drug used in the treatment of epilepsy. It is a hydantoin, similar to phenytoin. It is not available in the United States. The mechanism...

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List of syndromes

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Felty's syndrome Femur fibula ulna syndrome Fetal alcohol syndrome Fetal hydantoin syndrome Fetal trimethadione syndrome Fetal valproate syndrome Fetal warfarin...

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Air freshener

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methylisothiazoline and benzisothiazolinone formaldehyde releasers such as DMDM hydantoin These are substances that help other ingredients mix together, either...

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Thymine

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in actively dividing cells. Thymine bases are frequently oxidized to hydantoins over time after the death of an organism. During growth of bacteriophage...

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Acheiria

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syndrome, particularly if unilateral Cornelia de Lange syndrome Fetal hydantoin syndrome Incontinentia pigmenti Weerakkody, Dr Yuranga; et al. "Acheiria"...

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Generalized lymphadenopathy

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erythematosus Felty's syndrome Still's disease Drug hypersensitivity as Hydantoin, Hydralazine, Allopurinol Misc. : Sarcoidosis Amyloidosis Lipid storage...

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