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化工社化工社 化学情報印刷レポート · 研究参考用
HCID 204作成日：2026年10月27日

アラントイン

アラントイン · 5-ウレイドヒダントイン · アラントイン (JAN) · ALL · Allatoin · ALANTOIN · GLYOXYLDIUREIDE · 5-UREIDOHYDANTOIN

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

アラントイン の分子構造式

識別子と物理属性

CAS No.97-59-6
分子式C4H6N4O3
平均分子量158.12 g/mol
単同位体質量158.04399005 g/mol
SMILESNC(=O)NC1NC(=O)NC1=O
InChIKeyPOJWUDADGALRAB-UHFFFAOYSA-N
PubChem CID204
ChEMBLCHEMBL593429
ChEBICHEBI:15676
EC No.202-592-8
DTXSIDDTXSID3020043
現地名アラントイン

化学・物理的性質

XLogP-2.2
極性表面積113
水素結合供与体数4
水素結合受容体数3
回転可能結合数1
重原子数11
形式電荷0
複雑度225
物質分類Biological Agents -> Plant Oils and Extracts
医薬品Pharmaceuticals
化粧品Cosmetic ingredients (Allantoin) -> CIR (Cosmetic Ingredient Review)Soothing
pHpH = 4.5 - 6 (5% in water, 20 °C)
臭いOdorlessPleasant smelling無臭、無味
味Tasteless
Color/FormCrystals from aqueous methanolWhite to colorless powder or crystalsMonoclinic plates
溶解度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: 可溶0.1g/10mL 無色透明水にわずかに溶ける。アルカリに易溶
融点239 °C /Racemic form/MP: 230 °C (decomposes)230 °C (dec.) (lit.)
Physical DescriptionDry PowderColorless to white odorless solid[Hawley] White powder[MSDSonline]
Collision Cross Section125.5 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]145.61 Ų [M+Na]+ [CCS Type: DTMethod: stepped-field]134.17 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]143.3 Ų [M+Na]+
Other Experimental PropertiesStable at pH 4-9. Hydrolytic decomposition with strong acids and bases
沸点283.17°C (rough estimate)
密度1.6031 (rough estimate)
屈折率1.8500 (estimate)
引火点230-234°C
貯蔵条件2-8°C
外観・状態粉
pKa（酸解離定数）8.96(at 25℃)
色白い
Decomposition230-234 ºC
Merck14,258
BRN102364
ヘンリー定数2.9×1012 mol/(m3Pa) at 25℃, HSDB (2015)
安定性安定。強力な酸化剤とは相容れない。
化粧品成分の機能鎮静作用肌を保護するスキンコンディショニング
InChI1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)
InChIKeyPOJWUDADGALRAB-UHFFFAOYSA-N
SMILESNC(=O)NC1NC(=O)NC1=O
LogP（分配係数）-2.26 at 20℃
CAS データベース97-59-6(CAS DataBase Reference)
NISTの化学物質情報Urea, (2,5-dioxo-4-imidazolidinyl)-(97-59-6)
EPAの化学物質情報Allantoin (97-59-6)

化学的特性

White Solid

安全性と法規制

GHS 分類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.
規制情報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
その他の安全情報Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
有害性の概要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 要件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.

用途

解説

(2,5-dioxo-4-imidazolidinyl)urea．C4H6N4O3(158.12)．アラントインは，プリンが代謝されてできる化合物．プリン代謝でできた尿酸が，多くの哺乳類ではさらに尿酸オキシダーゼによって代謝されて，水に溶けやすいアラントインとなり排泄される．動物の尿中に多くあり，植物界からも多く見いだされている．プリンの代謝産物．尿酸を過マンガン酸カリウムで酸化するか，グリオキサール酸またはジクロロ酢酸を尿素と加熱して合成される．ラセミ体は融点238 ℃(分解)．冷水，冷エタノールに微溶．外傷の治癒促進に用いられる．[CAS 97-59-6] 森北出版「化学辞典（第2版）

用途

薬理研究用(生長促進作用)。

説明

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.

使用

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.

一般的な説明

Allantoin, the final catabolic product of purines in mammals, is a highly polar and amphoteric substance. Allantoin is mainly used for skin protection as the drug promotes cell proliferation and wound healing.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

製法・合成法

純化方法

It crystallises from water or EtOH [Hartman et al. Org Synth Coll Vol II 21 1943]. [Beilstein 25 III/IV 4071.]

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 要件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 CategoriesAcute Tox. 4 (13.1%)
処分方法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.
相互作用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 ...
環境中動態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).
毒性の概要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/MobilityUsing 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 SourcesThe 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 SourcesAllantoin's production and use as a topical medication(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationAEROBIC: Allantoin was biodegraded 6, 10, and 88% in 5, 15, and 30 days, respectively in closed bottle tests at 20 °C(1).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental BioconcentrationAn 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/SoilThe 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 DegradationThe 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).
水環境危害等級（WGK）1
TSCA 収載状態TSCA listed
RTECS 番号YT1600000
税関コード29332100
危険文句（R）22-36/37/38
化審法(9)-199
危険表示Xn,Xi
安全措置（S）22-24/25-36-26
貯蔵分類11 - Combustible Solids
有害物質データ97-59-6(Hazardous Substances Data)