2-(2,5-dioxoimidazolidin-4-yl)acetic acid

• ChemBase ID: 34842
• Molecular Formular: C5H6N2O4
• Molecular Mass: 158.11214
• Monoisotopic Mass: 158.03275668
• SMILES: N1C(=O)NC(C1=O)CC(=O)O
• Canonical SMILES: OC(=O)CC1NC(=O)NC1=O
• InChI: InChI=1S/C5H6N2O4/c8-3(9)1-2-4(10)7-5(11)6-2/h2H,1H2,(H,8,9)(H2,6,7,10,11)
• InChIKey: DQQLZADYSWBCOX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,5-dioxoimidazolidin-4-yl)acetic acid
• IUPAC Traditional name: (2,5-dioxoimidazolidin-4-yl)acetic acid
• Synonyms: (2,5-Dioxoimidazolidin-4-yl)acetic acid; 5-Hydantoinacetic acid; HYDANTOIN-5-ACETIC ACID; 2,4-Dioxoimidazolidine-5-acetic acid; DL-5-(Carboxymethyl)hydantoin; Hydantoin-5-acetic acid; 2,4-Imidazolidinedione-5-acetic acid; 2-(2,5-dioxoimidazolidin-4-yl)acetic acid; 5-海因乙酸; 乙内酰脲-5-乙酸

Database IDs

• CAS Number: 5427-26-9
• EC Number: 226-574-4
• MDL Number: MFCD00005267
• Beilstein Number: 83035
• PubChem SID: 160998149; 24888300
• PubChem CID: 95492

CALCULATED PROPERTIES

• Acid pKa: 3.7386549
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.2847433
• LogD (pH = 7.4): -4.8140016
• Log P: -1.5232681
• Molar Refractivity: 31.5754 cm^3
• Polarizability: 12.478441 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 214-215 °C (dec.)(lit.); ca 217°C dec.

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C5H6N2O4

DETAILS

MP Biomedicals - 02101989

Crystalline

Sigma Aldrich - 850624

Packaging
5 g in glass bottle
Application
Reactant for synthesis of:
• Nonfolate compounds as antiparasitic agents inhibiting pteridine reductase1
• 2,4-Azolidinedione-acetic acid derivatives as anticancer agents2
• Anti-inflammatory and analgesic drugs3,4
• Amides via polystyrene-supported N-hydroxybenxotriazole resin5