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5,5-Dimethylhydantoin
DMH · 5,5-Dimethylimidazolidine-2,4-dione · DIMETHYLHYDANTOIN · T10 · DM Hydantoin · dantoindmh · 5,5-DIMETHYL-2,4-IMIDAZOLIDINEDIONE · ADPRC1
Identifikatoren & physikalische Daten
| CAS No. | 77-71-4 |
|---|---|
| Summenformel | C5H8N2O2 |
| Durchschnittliche Molmasse | 128,13 g/mol |
| Monoisotopische Masse | 128,0585775 g/mol |
| SMILES | CC1(C)NC(=O)NC1=O |
| InChIKey | YIROYDNZEPTFOL-UHFFFAOYSA-N |
| PubChem CID | 6491 |
| ChEMBL | CHEMBL3181806 |
| ChEBI | CHEBI:183672 |
| EC No. | 201-051-3 |
| DTXSID | DTXSID5021754 |
| Lokaler Name | 5,5-Dimethylhydantoin |
Chemische & physikalische Eigenschaften
| XLogP | -0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 58,2 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 174 |
| Stoffklassen | Nitrogen Compounds -> Other Nitrogen Compounds |
| Kosmetika | Cosmetic ingredients (DM Hydantoin) -> CIR (Cosmetic Ingredient Review)Hair conditioningViscosity controlling |
| LogP (Verteilungskoeffizient) | log Kow = -0.48 |
| Color/Form | White, crystalline solidPrisms from dilute alcohol |
| Löslichkeit | Very soluble in ethanol, ether, acetone, benzene, chloroformsoluble in DMSOH2O: 0.1 g/mL hot, clear |
| Siedepunkt | Sublimes237.54°C (rough estimate) |
| Schmelzpunkt | 178 °C174-177 °C (lit.) |
| Dampfdruck | 0.0000028 [mmHg] |
| Food Contact Substances | FCS -> FDA Cumulative Estimated Daily Intake (CEDI)FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications |
| Physical Description | Large CrystalsLiquidWhite solid[Hawley] White odorless crystalline powder[Alfa Aesar MSDS] |
| Dissociation Constants | pKa = 9.19 |
| Dichte | 1.2864 (rough estimate) |
| Brechungsindex | 1.4730 (estimate) |
| Flammpunkt | 193°C |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| pKa (Säurekonstante) | pKa 8.1 (Uncertain) |
| Aggregatzustand | Crystalline Powder or Crystals |
| Farbe | White to off-white |
| BRN | 2827 |
| Henry-Konstante | 3.5×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR CONDITIONINGVISCOSITY CONTROLLING |
| InChI | 1S/C5H8N2O2/c1-5(2)3(8)6-4(9)7-5/h1-2H3,(H2,6,7,8,9) |
| InChIKey | YIROYDNZEPTFOL-UHFFFAOYSA-N |
| SMILES | CC1(C)NC(=O)NC1=O |
| LogP (Verteilungskoeffizient) | -0.480 |
| CAS Datenbank | 77-71-4(CAS DataBase Reference) |
| NIST chemische Informationen | 2,4-Imidazolidinedione, 5,5-dimethyl-(77-71-4) |
| EPA chemische Informationen | 5,5-Dimethylhydantoin (77-71-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 91% (252 of 277) of all reports.Not ClassifiedAggregated GHS information provided per 277 reports by companies from 4 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 2,4-Imidazolidinedione, 5,5-dimethyl-2,4-Imidazolidinedione, 5,5-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,4-Imidazolidinedione, 5,5-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 08-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/131555,5-Dimethylhydantoin: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | No compound related effects observed in 13-week dermal study of ratsIncreased adrenal weight (with corresponding adrenal cortical hypertrophy) was observed in a one year feeding study of dogs, but no other significant adverse effects observed in long term studies of mice, rats, or dogsNo evidence of developmental toxicityTwo generation gavage study of rats produced decreased pup weights in both generations and decreased mean live litter sizes in the second generationNo evidence of mutagenicity[HSDB] Decreased testicular and epididymides weights (without corresponding histopathology) observed in 4-week oral (capsule) study of dogs at highest tested dose (2,000 mg/kg/day)90-day gavage studies of rats produced histopathological changes to kidneys (renal pelvic urolithiasis and chronic interstitial nephritis) and increased kidney weights in mid and high dose animals (5,000 and 10,000 mg/kg/day)No significant adverse effects observed in several other animal studies including a 90-day gavage study of rats (doses up to 2,000 mg/kg/day), 13-week dermal study of rats, 24-month feeding study of rats (doses up to 1,000 mg/kg/day), and 1-year feeding (capsules) study of dogs (up to 1,000 mg/kg/day)No evidence of carcinogenicity in rats or miceNo evidence of adverse effects on reproduction or reproductive tissue in two generational feeding study of rats (doses up to 20,000 ppm)Limited evidence or teratogenicity[EPA HPVIS] May cause irritation[Alfa Aesar MSDS] See DMDM hydantoin. |
| Hazard Classes and Categories | Not Classified |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Wechselwirkungen | A case of allergic contact dermititis secondary to photographic print coating liquid is described ... . Patch test reactions to the mixture were positive, but negative to the individual components which included dimethylhydantoin formaldehyde resin, the logical allergen. ... In this patient, the combination of components was necessary to yield a sensitivity reaction. ... Dermatitis secondary to this product has not been previously reported. |
| Ökotoxizitätswerte | LC50 Saltwater mysid (Mysidopsis bahia) 921.7 mg/L/96 (nominal concentration)static, saltwater.LC50 Grass shrimp (Palaemonetes pugio) 1300 mg/L/96 hr (nominal concentration)LC50 American oyster (Crassostrea virginica) 13300 mg/L/96 hr (nominal concentration)LC50 Water flea (Daphnia magna) 6200 mg/L/48 hr (nominal concentration)static, freshwater.For more Ecotoxicity Values (Complete) data for 5,5-DIMETHYLHYDANTOIN (12 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 13(SRC), determined from a log Kow of -0.48(2) and a regression-derived equation(3), indicates that 5,5-dimethylhydantoin is expected to have very high mobility in soil(SRC). Volatilization of 5,5-dimethylhydantoin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 5,5-Dimethylhydantoin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-6 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation half-lives range from 194 days using static tests and sewage inoculum to 5 days using a SCAS test and activated sludge(6)these diverse test conditions and results indicate that biodegradation may be a slow environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 13(SRC), determined from a log Kow of -0.48(2) and a regression-derived equation(3), indicates that 5,5-dimethylhydantoin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.8X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation half-lives range from 194 days using static tests and sewage inoculum to 5 days using a SCAS test and activated sludge(7)these diverse test conditions and results indicate that biodegradation may be a slow environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 5,5-dimethylhydantoin, which has an estimated vapor pressure of 2.8X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 5,5-dimethylhydantoin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 5 days(SRC), calculated from its rate constant of 3.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 5,5-dimethylhydantoin may be removed from the air by wet or dry deposition(SRC). 5,5-Dimethylhydantoin does not absorb light at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ In a chronic Flow through test of Pimephales promelas (fathead minnow) with nominal concentrations (ppm): 0, 7.5, 15, 30, 60 and 120 ppm and measured concentrations (ppm): 0, 6.8, 14, 29, 55 and 116 ppm. There were no treatment-related effects upon mean hatching success or on the survival of fathead minnow larvae during the 28-day post hatch exposure period at any concentration of 5,5-dimethylhydantoin (DMH) tested. Based upon the hatching success and survival data, the NOEC was 116 ppm and the LOEC was >116 ppm. The mean length of the fish in the 0, 6.8, 14, 29, 55 and 116 ppm groups at study termination were 18.3, 17.8, 18.7, 17.8, 17.6 and 17.9 cm, respectively. The mean wet weight of the fish in the 0, 6.8, 14, 29, 55 and 116 ppm groups at study termination were 66.5, 67.8, 72.4, 65.2, 62.0 and 65.5 mg, respectively, and the mean dry weight of the fish in the 0, 6.8, 14, 29, 55 and 116 ppm groups at study termination were 14.1, 14.2, 14.2, 12.5, 11.4 and 11.8 mg, respectively. There were no statistically significant differences in the mean total length or mean wet weight of fish exposed to any concentration of DMH. However, fish dry weights were significantly decreased in the 29, 55 and 116 ppm treatment groups when compared to the control group. This reduction appeared to be treatment related. Conclusions: Based on measurements of length, wet weight and dry weight of fathead minnows, the NOEC and LOEC of DMH were 14 and 29 ppm, respectively./AQUATIC SPECIES/ In a 21-day study of Daphnia magna using fresh water in a flow-through system, at nominal concentrations (ppm): 0, 15.6, 25.9, 43.2, 72.0 and 120 ppm and measured concentrations (ppm): 0, 15.7, 25.3, 42.2, 70.9 and 116 ppm, Mortality of the daphnids in the control group was 9% (2 of 22). Mortality of the daphnids in the 15.7, 25.3, 42.2 and 70.9 ppm groups ranged from 5 to 14% (1 to 3 of 22) and was considered similar to that of the control group. Mortality of the daphnids in the 116 ppm group was 55% (12 of 22) and was statistically different from the control group. Based on survival and clinical observations data, the NOEC for DMH was 70.9 ppm and the LOEC for DMH was 116 ppm. Mean neonatal production in the 0, 15.7, 25.3, 42.2, 70.9 and 116 ppm groups was 69, 104, 80, 85, 94 and 58 neonates per daphnid, respectively. Although the number of neonates per daphnid in the 116 ppm group was lower than any other treated group, it was not statistically different from the control group and therefore was not considered to be treatment-related. When compared to the control group, there were no significant decreases in the length or dry weight of daphnids at any of the concentrations of DMH tested. Conclusions: Based on neonate production and measurements of length and dry weight the NOEC for DMH was 116 ppm and the LOEC for DMH was >116 ppm. |
| Effluent Concentrations | 5,5-Dimethylhydantoin was detected at a concentration of 456 mg/L in wastewater from a coal gasification plant in North Dakota, processing Indian Head lignite(1). Levels in four samples of coal-gasification condensate waters at this plant were 660, 150, 230, and 40 mg/L collected in June 1998, June 1981, September 1981, and April 1982, respectively, and immediately acidified to pH 2(2). The concentrations in samples where the pH was not adjusted and were allowed to stand for 30 days actually increased to 1,720, 300, 400, and 165 mg/L, respectively(2). |
| Soil Adsorption/Mobility | The Koc of 5,5-dimethylhydantoin is estimated as 13(SRC), using a log Kow of -0.48(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 5,5-dimethylhydantoin is expected to have very high mobility in soil. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Central nervous system depressant |
| Artificial Pollution Sources | 5,5-Dimethylhydantoin's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC). Its use as an inert ingredient in some pesticide formulations(2) will result in its direct release to the environment(SRC). |
| Environmental Biodegradation | AEROBIC: 5,5-Dimethylhydantoin, present at 25 ppm 14-C, was 94% degraded in 19 days using an activated sludge inoculum acclimated for 14 days, incubated in fermenters, corresponding to a half-life of 5 days(1). The compound was 100% degraded when added to a 24-hr SCAS system acclimated for 16 days, in accordance with OECD test method 302Afrom test day 18 through test day 42, the average daily removal was noted at >95%, corresponding to a half-life of 6 days(1). However, the compound was not readily biodegraded when subjected to a standard DOC test (TSCA guideline 40CFR796.3240) using a sewage inoculum and test compound concentration of 20 mg C/Lpercent degradation was 7.3, 4.5, 10.1, and 9.5 on day 7, 14, 21, 27,and 28, respectively, corresponding to a half-life of 194 days(1). |
| Environmental Bioconcentration | An estimated BCF of 3 was calculated in fish for 5,5-dimethylhydantoin(SRC), using a log Kow of -0.48(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 5,5-dimethylhydantoin is estimated as 2.8X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 5,5-dimethylhydantoin is expected to be essentially nonvolatile from water surfaces(2). 5,5-Dimethylhydantoin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-6 mm Hg(SRC), determined from a fragment constant method(3). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Ten young adult rats (five males and five females) were administered /5,5-dimethylhydantoin, purity not stated/ via gavage at a dose level of 5,000 mg/kg. Males and females weighed 151 to 159 g and 131 to 146 g, respectively, and were fasted for approximately 16 hours prior to dosing. Rats were observed for signs of toxicity and mortality at frequent intervals during the day of dosing, and twice daily thereafter for a total of 14 days. Body weights were taken on days 0, 7 and 14. At the end of the 14-day observation period, surviving rats were sacrificed and gross necropsies were performed. No signs of toxicity were observed in any of the males throughout the study. On the day of dosing, two females were observed to be slightly to moderately lethargic and slight lacrimation was noted, which subsided by day 1. The females were observed to be normal throughout the remainder of the study. The acute oral LD50 was determined to be greater than 5,000 mg/kg./LABORATORY ANIMALS: Acute Exposure/ Eight albino rabbits (four males and four females) were administered /5,5-dimethylhydantoin, purity not stated/ dermally at a dose level of 3000 mg/kg. Rabbits were 10 to 13 weeks old and weighed 2.75 to 3.35 kg. Twenty-four hours prior to the application of the test substance the hair was clipped from the back and flanks of each rabbit. The exposure sites of two rabbits (one male and one female) were lightly abraded. The exposure area was occluded. The rabbits were exposed to the test substance for 24 hours. All rabbits were observed for systemic toxicity and skin irritation for 14 days following the 24-hour exposure period. Body weights were recorded for each rabbit before dosing and at 7 and 14 days post dose. At the end of the 14-day observation period, all rabbits were killed and gross necropsies were performed. Slight erythema was noted in one female rabbit for the first two days following the exposure period. No other irritation was noted throughout the study. During the first two or three days of the observation period, most of the rabbits exhibited a creamy nasal discharge, these signs reappeared intermittently throughout the remainder of the observation period. Watery eye discharge was noted daily in one female rabbit. A gross necropsy revealed no significant gross pathological findings in any of the rabbits. The acute dermal LD50 was determined to be greater than 3000 mg/kg./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of mice (five males and five females) were administered /5,5-dimethylhydantoin, purity not stated/ in the diet at concentrations of 1000, 5000, 10000 and 50000 ppm for a period of four weeks. A concurrent control group was administered the basal diet alone. Mice were approximately 43 days old at study initiation. All mice were observed twice daily for mortality and signs of overt toxicity. Detailed physical examinations, individual body weights and food consumption were recorded weekly. The following clinical pathology parameters were evaluated for all mice after 28 consecutive days of test substance administration: hematology (including differential white blood cell count, platelet estimate, red blood cell morphology, white cell estimate and hemoglobin estimate) and serum chemistry (including urea nitrogen, creatinine, total bilirubin, aspartate aminotransferase, alanine aminotransferase and serum alkaline phosphatase). Clinical necropsy examinations were performed at the scheduled sacrifice and the following organs were weighed: brain, kidneys, liver, ovaries and testes. A microscopic examination was conducted on the following tissues from mice in the control and 50,000 ppm groups: adrenals, bone with marrow, brain, duodenum, gallbladder, heart, kidneys, liver, lungs, ovaries with oviducts, peripheral sciatic nerve, pituitary, spinal cord, spleen, stomach, testes with epididymides, thyroid and all gross lesions. Evaluation of tissues for the 1000, 5000 and 10,000 ppm groups was limited to kidneys and liver. All animals survived to the scheduled sacrifice. No compound related effect was apparent at any dose level on survival, clinical observations, body weight data, food consumption, hematology parameters, macroscopic or microscopic necropsy findings, or organ weight data. In the serum chemistry parameters, mean serum alkaline phosphatase was statistically significantly increased in the 50,000 ppm group females. However, based on the apparent wide range of biological variability in serum alkaline phosphatase values exhibited in the control group, and the limited sample size in this study, this increase may not be toxicologically meaningful. Systemic toxicity was not apparent at any dose level. The only potential effect ... was increased serum alkaline phosphatase in the female mice at 50,000 ppm./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of /COBS CD/ rats (20 males and 20 females) were administered ... /5,5-dimethylhydantoin, purity 99%,/ via oral gavage at concentrations of 250, 500, 1000 and 2000 mg/kg/day for a period of at least 90 days. A concurrent vehicle control group, also composed of 20 male and 20 female rats, received 1.0% aqueous methylcellulose on a comparable regimen at 20 mL/kg/day. The animals were observed twice daily for signs of overt toxicity. No deaths occurred during the study period. The incidence and duration of hair loss on the forepaws and forelegs was increased in the 2000 mg/kg/day group males and slightly increased in the 500 and 1000 mg/kg/day group males. Hair loss in females from all treated groups was comparable to that observed in females from the control group. No treatment-related effects in body weights, food consumption, clinical laboratory parameters, ophthalmoscopic, macroscopic or microscopic examinations, or organ weights were apparent in any treated groups. The differences noted in this study were considered to occur spontaneously in rats of this strain and age and could not be attributed to treatment with the test substance. NOEL = 2000 mg/kg/dayFor more Non-Human Toxicity Excerpts (Complete) data for 5,5-DIMETHYLHYDANTOIN (36 total), please visit the HSDB record page. |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29332100 |
| RTECS-Nr. | MU0977000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 oral in rabbit: 12660mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 22-24/25-36/37-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 77-71-4(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
5,5-Dimethylhydantoin is part of a group of hydantoin compounds that are being evaluated for their anticonvulsant and central nervous system antitumour properties.