1-(acridin-9-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 103002
• Molecular Formular: C17H10N2O2
• Molecular Mass: 274.2735
• Monoisotopic Mass: 274.07422757
• SMILES: O=C1C=CC(=O)N1c1c2ccccc2nc2ccccc12
• Canonical SMILES: O=C1C=CC(=O)N1c1c2ccccc2nc2c1cccc2
• InChI: InChI=1S/C17H10N2O2/c20-15-9-10-16(21)19(15)17-11-5-1-3-7-13(11)18-14-8-4-2-6-12(14)17/h1-10H
• InChIKey: NCFIKBMPEOEIED-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(acridin-9-yl)-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 1-(acridin-9-yl)pyrrole-2,5-dione
• Synonyms: NAM; 9-Maleimidoacridine; N-(9-ACRIDINYL)-MALEIMIDE; 1-(9-Acridinyl)-1H-pyrrole-2,5-dione; N-(9-Acridinyl)maleimide; 9-Maleimidoacridine; 1-acridin-9-yl-3-pyrroline-2,5-quinone; 1-acridin-9-ylpyrrole-2,5-dione; N-(9-Acridinyl)maleimide

Database IDs

• CAS Number: 49759-20-8
• MDL Number: MFCD00042983
• Beilstein Number: 484577
• PubChem SID: 24844903; 162090785
• PubChem CID: 3016496

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.6701527
• LogD (pH = 7.4): 2.7771544
• Log P: 2.7787132
• Molar Refractivity: 78.0252 cm^3
• Polarizability: 32.176437 Å^3
• Polar Surface Area: 50.27 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Yellow Solid
• Melting Point: 188-190°C
• Fluorescence: λex 361 nm; λem 431 nm±5 nm in 0.1 M phosphate pH 7.0, 2-mercaptoethanol

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (HPLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C17H10N2O2

DETAILS

MP Biomedicals - 02150255

Fluorescent thiol reagent.

Sigma Aldrich - 01665

Other Notes
Reagent used for the fluorescent labeling of thiols, sulfides and sulfites for determination by HPLC5,6,7,8
Application
N-(9-Acridinyl)maleimide can be used to determine both the total and total bound sulfite molecules in wine by reacting with sulfite and producing strong fluorescent derivatives, which provide a sensitive fluorometic assay 1,2. Utilized in a simple and highly sensitive fluorometric assay to detect carnitine palmitoyltransferase 3,4.

Toronto Research Chemicals - M125150

Used for fluorometric determination of sulfites in foods and fermentation products.

REFERENCES

• Takahashi, H., et al., Bunseki Kagaku , 30 : 339, (1981).
• Quillardet, P., et al.: Mutat. Res., 297, 235, (1993)
• Purves, D., et al.: Mutagenesis, 10, 297 (1993)
• Bakken, G., et al.: J. Med. Chem., 43, 4534 (1993)