Allantoin

ALL · Allatoin · ALANTOIN · GLYOXYLDIUREIDE · 5-UREIDOHYDANTOIN · Egopsoryl · GLYOXYLIDIUREIDE · N-(2,5-Dioxo-4-imidazolidinyl)urea

https://huagongshe.com/de/chemical/204

Identifikatoren & physikalische Daten

CAS No.	97-59-6
Summenformel	C4H6N4O3
Durchschnittliche Molmasse	158,12 g/mol
Monoisotopische Masse	158,04399005 g/mol
SMILES	NC(=O)NC1NC(=O)NC1=O
InChIKey	POJWUDADGALRAB-UHFFFAOYSA-N
PubChem CID	204
ChEMBL	CHEMBL593429
ChEBI	CHEBI:15676
EC No.	202-592-8
DTXSID	DTXSID3020043
Lokaler Name	Allantoin

Chemische & physikalische Eigenschaften

XLogP	-2,2
Polarare Oberfläche (TPSA)	113
H-Brücken-Donoren	4
H-Brücken-Akzeptoren	3
Frei drehbare Bindungen	1
Schwere Atome	11
Formalladung	0
Komplexität	225
Stoffklassen	Biological Agents -> Plant Oils and Extracts
Arzneimittel	Pharmaceuticals
Kosmetika	Cosmetic ingredients (Allantoin) -> CIR (Cosmetic Ingredient Review)Soothing
pH	pH = 4.5 - 6 (5% in water, 20 °C)
Geruch	OdorlessPleasant smelling
Geschmack	Tasteless
Color/Form	Crystals from aqueous methanolWhite to colorless powder or crystalsMonoclinic plates
Löslichkeit	Soluble in alcohol, methanol, pyridineSoluble in ethanol, sodium hydroxideinsoluble in ethyl ether, methanolWater: 0.57% (25 °C)ethanol (96%): 0.04% (25 °C)eth/water (1/1): 0.35% (25 °C)propylene glycol/water (1/1): 0.40% (25 °C)glycerol/water (1/1): 0.60% (25 °C)In water, 5.26X10+3 mg/L at 25 °C5.26 mg/mLH2O: soluble0.1g/10 mL, clear, colorlessSlightly soluble in water. Freely soluble in alkalis
Schmelzpunkt	239 °C /Racemic form/MP: 230 °C (decomposes)230 °C (dec.) (lit.)
Physical Description	Dry PowderColorless to white odorless solid[Hawley] White powder[MSDSonline]
Collision Cross Section	125.5 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]145.61 Å² [M+Na]+ [CCS Type: DTMethod: stepped-field]134.17 Å² [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]143.3 Å² [M+Na]+
Other Experimental Properties	Stable at pH 4-9. Hydrolytic decomposition with strong acids and bases
Siedepunkt	283.17°C (rough estimate)
Dichte	1.6031 (rough estimate)
Brechungsindex	1.8500 (estimate)
Flammpunkt	230-234°C
Lagerbedingungen	2-8°C
Aggregatzustand	Powder
pKa (Säurekonstante)	8.96(at 25℃)
Farbe	White
Geruch	odorless, tasteless
Decomposition	230-234 ºC
Merck	14,258
BRN	102364
Henry-Konstante	2.9×1012 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität	Stable. Incompatible with strong oxidizing agents.
Kosmetik-Inhaltsstoffe Funktionen	SOOTHINGSKIN PROTECTINGSKIN CONDITIONING
InChI	1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)
InChIKey	POJWUDADGALRAB-UHFFFAOYSA-N
SMILES	NC(=O)NC1NC(=O)NC1=O
LogP (Verteilungskoeffizient)	-2.26 at 20℃
CAS Datenbank	97-59-6(CAS DataBase Reference)
NIST chemische Informationen	Urea, (2,5-dioxo-4-imidazolidinyl)-(97-59-6)
EPA chemische Informationen	Allantoin (97-59-6)

Sicherheit & Vorschriften

GHS-Einstufung	This chemical does not meet GHS hazard criteria for 86.9% (319 of 367) of all reports.WarningH302 (13.1%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 367 reports by companies from 4 notifications to the ECHA C&L Inventory.
Regulatorische Informationen	Chemical: Urea, (2,5-dioxo-4-imidazolidinyl)-Urea, N-(2,5-dioxo-4-imidazolidinyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Urea, N-(2,5-dioxo-4-imidazolidinyl)- 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: 30-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13641Allantoin: Does not have an individual approval but may be used under an appropriate group standard
Weitere Sicherheitsinformationen	Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Gefahrenübersicht	May cause irritation[MSDSonline] No increased congenital anomalies found in children of 51 women treated with allantoin during the first trimester of pregnancy[REPROTOX]
FDA-Anforderungen	Skin protectant active ingredients. The active ingredients of the products consist of any of the following, within the concentration specified for each ingredient. Allantoin, 0.5 to 2 percent.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: allantoin is included in dandruff/seborrheic dermatitis/psoriasis drug products.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: allantoin (wound healing claims only) is included in skin protectant drug products.Drug products containing active ingredients offered over-the-counter (OTC) for human use as oral wound healing agents. Allantoin ... /has/ been present in oral mucosal injury drug products for use as oral wound healing agents. Oral wound healing agents have been marketed as aids in the healing of minor oral wounds by means other than cleansing and irrigating, or by serving as a protectant. Allantoin, carbamide peroxide in anhydrous glycerin, water soluble chlorophyllins, and hydrogen peroxide in aqueous solution are safe for use as oral wound healing agents, but there are inadequate data to establish general recognition of the effectiveness of these ingredients as oral wound healing agents.
FIFRA-Anforderungen	As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Allantoin is found on List C. Case No: 3015Pesticide type: insecticideCase Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effectsActive ingredient (AI): allantoinAI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled."
Hazard Classes and Categories	Acute Tox. 4 (13.1%)
Entsorgungsverfahren	SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Wechselwirkungen	Feed containing 0.2% allantoin ... with or without 0.2% sodium nitrite, was given ad lib. to groups of 20 or 24 male and 20 or 24 female F344 rats for 106 wk. ... Control rats were given untreated feed ... and nitrite-treated controls were given sodium nitrite at a concentration of 0.2% in feed or drinking-water. At the end of the treatment period the rats were given untreated feed ...and observed until death. There was little or no life-shortening effect in any treatment group. /Allantoin / administered alone /and in combination with sodium nitrite did not induce/ an increase in the incidence of any tumor in comparison with the untreated control groups ...
Umweltverhalten	TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that allantoin is expected to have very high mobility in soil(SRC). Volatilization of allantoin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.4X10-18 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Allantoin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.3X10-9 mm Hg(SRC), determined from a fragment constant method(4). Allantoin was biodegraded 6, 10, and 88% in 5, 15, and 30 days, respectively(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that allantoin 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 3.4X10-18 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 an estimated log Kow of -3.14(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Allantoin was biodegraded 6, 10, and 88% in 5, 15, and 30 days, respectively(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), allantoin, which has an estimated vapor pressure of 4.3X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase allantoin may be removed from the air by wet or dry deposition(SRC).
Toxizitätsübersicht	Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Soil Adsorption/Mobility	Using a structure estimation method based on molecular connectivity indices(1), the Koc of allantoin can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that allantoin is expected to have very high mobility in soil(SRC).
Natural Pollution Sources	The end product of purine metabolism in mammals other than humans and other primatesit results from the oxidation of uric acid... present in tobacco seeds, sugar beets, white sprouts
Artificial Pollution Sources	Allantoin's production and use as a topical medication(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation	AEROBIC: Allantoin was biodegraded 6, 10, and 88% in 5, 15, and 30 days, respectively in closed bottle tests at 20 °C(1).
Carcinogen Classification	No indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration	An estimated BCF of 3 was calculated in fish for allantoin(SRC), using an estimated log Kow of -3.14(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 allantoin is estimated as 3.4X10-18 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that allantoin is expected to be essentially nonvolatile from water surfaces(2). Allantoin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.3X10-9 mm Hg(SRC), determined from a fragment constant method(3).
Non-Human Toxicity Excerpts	/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Feed containing 0.2% allantoin ... with or without 0.2% sodium nitrite, was given ad lib. to groups of 20 or 24 male and 20 or 24 female F344 rats for 106 wk. ... Control rats were given untreated feed ... and nitrite-treated controls were given sodium nitrite at a concentration of 0.2% in feed or drinking-water. At the end of the treatment period the rats were given untreated feed ...and observed until death. There was little or no life-shortening effect in any treatment group. /Allantoin / administered alone /and in combination with sodium nitrite did not induce/ an increase in the incidence of any tumor in comparison with the untreated control groups .../ALTERNATIVE and IN VITRO TESTS/ Rabbit renal cortical slices were incubated at 25 degrees C, pH 7.4, for 2 hr under 100% O2 in a phosphate-buffered medium. (14-C)allantoin was accumulated to a tissue water/medium ratio of 1.38 +/- 0.03 (mean +/- S.E., n = 22). Under 100% N2, the tissue water/medium ratio fell significantly to 0.90 +/- 0.02 (n = 14, P less than .001). Probenecid (an anion) inhibited the uptake of allantoin at doses which had no effect on the water content of the slices, i.e., did not appear to have a toxic effect on the tissue. Its effect was specific. In contrast, salicylate (another anion) and quinine (a cation) inhibited the uptake of allantoin only at concentrations which simultaneously increased the water content of the slices. These results suggest a toxic effect on cell metabolism. Salicylate (an anion) and quinine (a cation), in dosage which inhibited allantoin uptake, also inhibit the uptake of the para-aminohippuric acid (an anion) and tetraethylammonium bromide (a cation). Net secretion of allantoin was observed in urinary clearance experiments on anesthetized rabbits acutely loaded with allantoin, under mannitol diuresis. At flow rates less than 1 ml/kg/min, fractional excretion of (14-C)allantoin was 0.85 +/- 0.03 (n = 27 clearance periods) indicating significant net reabsorption. When urine flow was increased above 1 ml/kg/min, fractional excretion of (14-C)allantoin reached 1.07 +/- 0.03 (n = 18 clearance periods), i.e., net secretion.
Environmental Abiotic Degradation	The rate constant for the vapor-phase reaction of allantoin with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 20 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).
Wassergefährdungsklasse (WGK)	1
TSCA-Inventar-Status	TSCA listed
Zollcode	29332100
RTECS-Nr.	YT1600000
R-Sätze (R)	22-36/37/38
Gefahrensymbole	Xn,Xi
Sicherheitshinweise (S)	22-24/25-36-26
Lagerklasse	11 - Combustible Solids
Gefahrstoffdaten	97-59-6(Hazardous Substances Data)

Anwendungen & Verwendung

Beschreibung

Allantoin is a product of purine and uric acid metabolism. It is formed through oxidation of uric acid by urate oxidase in most mammals but is formed only through non-enzymatic oxidation by free radicals in humans. Urinary levels of allantoin are increased prior to the onset of Alzheimer’s disease symptoms in mice expressing mutations in amyloid precursor protein and tau (APP/tau) but not during the early/middle stage of the disease, indicating its potential use as a biomarker for predicting Alzheimer’s disease onset. Due to the formation of allantoin by free radicals in humans, increased urinary levels are a potential biomarker for oxidative stress status.

Verwenden

allantoin is a botanical extract said to be healing, calming, and soothing, it can also help protect the skin from harmful external factors (e.g., wind burn). It is considered an excellent temporary anti-irritant and is believed to stimulate new tissue growth, helping heal damaged skin. Allantoin is appropriate for sensitive, irritated, and acne skins. Derived from the comfrey root, it is considered non-allergenic.