(2,5-dioxoimidazolidin-4-yl)urea

• ChemBase ID: 102155
• Molecular Formular: C4H6N4O3
• Molecular Mass: 158.11544
• Monoisotopic Mass: 158.04399007
• SMILES: NC(=O)NC1NC(=O)NC1=O
• Canonical SMILES: NC(=O)NC1NC(=O)NC1=O
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2,5-dioxoimidazolidin-4-yl)urea
• IUPAC Traditional name: (2,5-dioxoimidazolidin-4-yl)urea; allantoin
• Synonyms: Ureidohydantoin; Glyoxyldiureide; 1-(2,5-dioxoimidazolidin-4-yl)urea; Allantoin; NSC 7606; (2,5-dioxo-4-imidazolidinyl)urea; 5-Ureido-2,4-imidazolidinedione; Dermalex; Cordianin; Actinac; Alphosyl; (2,5-Dioxo-4-imidazolidinyl)urea; Allantol; Cordianine; Glyoxyldiureid; Glyoxylic Diureide; Psoralon; Sebical; Septalan; 5-Ureidohydantoin; Glyoxylic(acid) diureide; ALLANTOIN; 5-脲尿囊素; 尿基间二-氮茂烷-2,4-二酮; 尿囊素

Database IDs

• CAS Number: 97-59-6
• EC Number: 202-592-8
• MDL Number: MFCD00005260
• Beilstein Number: 102364
• Merck Index: 14258
• PubChem SID: 24845863; 162089975
• PubChem CID: 204
• CHEBI ID: 15676
• CHEMBL: 593429
• Chemspider ID: 199
• KEGG ID: D00121
• Unique Ingredient Identifier: 344S277G0Z
• Wikipedia Title: Allantoin

CALCULATED PROPERTIES

• Acid pKa: 7.9488487
• H Acceptors: 3
• H Donor: 4
• LogD (pH = 5.5): -2.3620656
• LogD (pH = 7.4): -2.4672303
• Log P: -2.3605409
• Molar Refractivity: 32.0225 cm^3
• Polarizability: 12.4722 Å^3
• Polar Surface Area: 113.32 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.5% at 25 °C in water; DMSO; H2O: soluble0.1 g/10 mL, clear, colorless
• Apperance: colourless crystalline powder; Powder; White SolidWhite Solid
• Melting Point: 222-224°C (dec.); 230 °C (dec.)(lit.); 230°C; ca 230°C dec.
• Density: 1.45g/cm3

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: YT1600000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22
• Safety Statements: 22
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Cell proliferation promoter.

Product Information

• Purity: ≥98%; ≥98.0% (HPLC); ≥98.0% (N); 97%; 98%
• Grade: analytical standard
• Ignition Residue: ≤0.2%
• Biological Source: Occurs in allantoic fluid. A product of purine metabolism. V. widely distributed in biol. systems, isol. from numerous plants. Formed in animals, except primates, by enzymic oxidn. of Uric acid
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Healing, antiinflammatory, moisturizing, soothing, anti-irritating, keratolytic, non-toxic agent useful in dermatological, cosmetic and veterinary preparation.
• Empirical Formula (Hill Notation): C4H6N4O3

DETAILS

MP Biomedicals - 05206440

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02100379

Crystalline

Sigma Aldrich - A7878

Biochem/physiol Actions
通过尿酸途径的嘌呤代谢物。尿酸也可与自由基反应生成尿囊素，因此尿囊素可作为氧化应激反应的有效生物标记。

Sigma Aldrich - 05670

Biochem/physiol Actions
Purine metabolite via the uric acid pathway. Uric acid also reacts with free radicals to produce allantoin, thus allantoin may be a useful biomarker for oxidative stress.
Application
Reactant for: Synthesis of Mannich bases for use as antibacterial agents1 Synthesis of sulofenur analogs for use as antitumor agents2

Sigma Aldrich - 93791

Biochem/physiol Actions
Purine metabolite via the uric acid pathway. Uric acid also reacts with free radicals to produce allantoin, thus allantoin may be a useful biomarker for oxidative stress.

Toronto Research Chemicals - A540500

Vulnerary; debriding agent. Purine metabolite via the uric acid pathway.

REFERENCES

• Vissers, S., et al.: Eur. J. Biochem., 181, 357 (1989)
• Baars, J., et al.: Microbiology 140, 1161 (1989)
• Skinner, K., et al.: J. Biol. Chem., 273, 24491 (1989)
• Moriwaki, Y., et al., Histol. Histopathol., 14, 1321(1999).
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 1316C, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 809A, (ir)
• Biltz, H., Ber., 1911, 44, 282, (derivs)
• Org. Synth., 1933, 13, 1, (synth, bibl)
• Fosse, R. et al., C. R. Hebd. Seances Acad. Sci., 1934, 98, 689; 1374; 1953, (isol, resoln)
• Greenbaum, F.R., Am. J. Pharm., 1940, 112, 205, (rev)
• U.S. Pat., 1956, 2 761 867; CA, 51, 3668i, (synth, Al compds)
• U.S. Pat., 1967, 3 305 557; CA, 66, 85787x, (synth)
• Gravenmade, E.J. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1969, 88, 929, (resoln)
• Abblard, J. et al., Bull. Soc. Chim. Fr., 1971, 942, (struct)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 2569, (occur)
• Mecca, S.B., Soap, Perfum. Cosmet., 1976, 49, 434, (rev)
• Coxon, B. et al., J.O.C., 1977, 42, 3132, (cmr)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 184
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 754; 755