1-methyl-3-(2-oxopropylidene)-2,3-dihydro-1H-indol-2-one

• ChemBase ID: 153857
• Molecular Formular: C12H11NO2
• Molecular Mass: 201.22124
• Monoisotopic Mass: 201.0789786
• SMILES: CC(=O)/C=C\1/c2ccccc2N(C1=O)C
• Canonical SMILES: CC(=O)/C=C\1/c2ccccc2N(C1=O)C
• InChI: InChI=1S/C12H11NO2/c1-8(14)7-10-9-5-3-4-6-11(9)13(2)12(10)15/h3-7H,1-2H3
• InChIKey: CZKBLHCEDVWPRN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-3-(2-oxopropylidene)-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: 1-methyl-3-(2-oxopropylidene)indol-2-one
• Synonyms: 1,3-Dihydro-1-methyl-3-(2-oxopropylidene)-2H-Indol-2-one; Supercinnamaldehyde

Database IDs

• CAS Number: 70351-51-8
• MDL Number: MFCD08530327
• PubChem SID: 162247996
• PubChem CID: 12480412

CALCULATED PROPERTIES

• Acid pKa: 19.19348
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.2819211
• LogD (pH = 7.4): 1.2819211
• Log P: 1.2819211
• Molar Refractivity: 57.9454 cm^3
• Polarizability: 21.738081 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL; H2O: insoluble <2 mg/mL
• Apperance: red solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38-52/53
• Safety Statements: 26-36/37-61
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H11NO2

DETAILS

Sigma Aldrich - S3322

Caution
Air-sensitive
Biochem/physiol Actions
Supercinnamaldehyde is a transient receptor potential ankyrin 1 (TRPA1) activator; EC50 = 0.8 μM; derivative of cinnamaldehyde; covalently binds to and activates TRPA1 receptor (expressed in nociceptive neurons) by modifying its cysteine residues. Covalent modification of reactive cysteines within TRPA1 can cause channel activation, rapidly signaling potential tissue damage through the pain pathway.