70351-51-8

Basic information

• Product Name: 1,3-Dihydro-1-methyl-3-(2-oxopropylidene)-2H-Indol-2-one
• Synonyms: 1,3-Dihydro-1-methyl-3-(2-oxopropylidene)-2H-Indol-2-one;Supercinnamaldehyde
• CAS NO: 70351-51-8
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.22
• Mol File: 70351-51-8.mol
• Article Data: 8

Chemical Properties

• Appearance: faint red to very dark red/
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble10mg/mL, clear
• CAS DataBase Reference: 1,3-Dihydro-1-methyl-3-(2-oxopropylidene)-2H-Indol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydro-1-methyl-3-(2-oxopropylidene)-2H-Indol-2-one(70351-51-8)
• EPA Substance Registry System: 1,3-Dihydro-1-methyl-3-(2-oxopropylidene)-2H-Indol-2-one(70351-51-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-52/53
• Safety Statements: 26-36/37-61
• WGK Germany: 3
• Hazardous Substances Data: 70351-51-8(Hazardous Substances Data)

Usage

Uses

Supercinnamaldehyde may be used in transient receptor potential ankyrin 1 (TRPA 1)-mediated cell signaling studies.

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.

Upstream product

• 76325-64-9 3-hydroxy-1-methyl-3-(2'-oxopropyl)indolin-2-one 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 91-56-5 indole-2,3-dione 
• 67-64-1 acetone 
• 2236-01-3 acetonyltriphenylphosphonium bromide 

Relevant articles and documents

Dynamic Kinetic Asymmetric Transformation of Racemic Diastereomers: Diastereo- and Enantioconvergent Michael–Henry Reactions to Afford Spirooxindoles Bearing Furan-Fused Rings

Dynamic kinetic asymmetric transformation (DYKAT) reactions of racemic diastereomer mixtures that afford the products as essentially single diastereomers with high enantioselectivities are described. We demonstrated the DYKAT in the diastereo- and enantio

Base-catalyzed controllable reaction of 3-ylideneoxindoles with O-Boc hydroxycarbamates for the synthesis of amidoacrylates and spiroaziridine oxindoles

A base-catalyzed divergent reaction of 3-ylideneoxindoles with O-Boc hydroxycarbamates has been developed to provide efficient access to various amidoacrylates and spiroaziridine oxindoles with generally high yields, which should be potentially useful in drug discovery.

Design and synthesis of marine natural product-based 1H-indole-2,3-dione scaffold as a new antifouling/antibacterial agent against fouling bacteria

Marine organisms such as seaweeds, sponges and corals protect their own surfaces from fouling by their high anesthetic, repellant, and settlement inhibition properties. Within the marine ecosystem, evolution has allowed for the development of certain antifouling properties. Isatin is a biologically active chemical produced by an Alteromonas sp. strain inhibiting the surface of embryos of the cardiean shrimp Palaemon macrodectylus, which protect them from the pathogenic fungus Lagenidium callinectes. In present study, an antibacterial activity of isatin and its synthetic analogues were evaluated against different fouling bacteria in order to explore the structure activity relationships for the first time. The synthesized compounds along with parent isatin were tested against different ecologically relevant marine microorganisms by using the Kirby-Bauer disc diffusion method. Few synthetically modified isatin exhibited potent inhibitory activity at concentration of 2 μg/disc against Planococcus donghaensis, Erythrobacter litoralis, Alivibrio salmonicida, Vibrio furnisii. Overall, the modified analogues showed stronger activity than the parent marine natural product (isatin) and hence 1H-indole-2,3-dione scaffold has immense potential as future antibacterial/antifouling candidate.