15416-77-0

Basic information

• Product Name: 4-(2-Carboxyvinyl)-1,2-benzoquinone
• Synonyms: 3-(3,4-Dioxo-1,5-cyclohexadien-1-yl)propenoic acid;3,4-Dioxo-1,5-cyclohexadiene-1-acrylic acid;4-(2-Carboxyvinyl)-1,2-benzoquinone;Caffeoquinone
• CAS NO: 15416-77-0
• Molecular Formula: C₉H₆O₄
• Molecular Weight: 178.14
• Mol File: 15416-77-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 350.2±42.0 °C(Predicted)
• Appearance: /
• Density: 1.555±0.06 g/cm3(Predicted)
• PKA: 4.40±0.10(Predicted)
• CAS DataBase Reference: 4-(2-Carboxyvinyl)-1,2-benzoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-Carboxyvinyl)-1,2-benzoquinone(15416-77-0)
• EPA Substance Registry System: 4-(2-Carboxyvinyl)-1,2-benzoquinone(15416-77-0)

Safety Data

• Hazardous Substances Data: 15416-77-0(Hazardous Substances Data)

Upstream product

• 331-39-5 caffeic acid 
• 331-39-5 caffeic acid 

Downstream Products

• 331-39-5 caffeic acid 

Relevant articles and documents

CHARACTERIZATION OF COMPOUNDS OBTAINED BY CHEMICAL OXIDATION OF CAFFEIC ACID IN ACIDIC CONDITIONS

Sodium periodate oxidation of caffeic acid was investigated in aqueous solutions with pH ranging from 2 to 7.Products formed from quinone evolution were monitored by HPLC.It was found that they were affected both qualitatively and quantitatively by the conditions of the reaction.The rate and yield of the reaction increased with the pH.In particular, two products obtained at pH values lower than 4.6 approximately, were analysed by reverse phase HPLC.By using 1H and 13C NMR and mass spectrometries, these compounds were shown to be two stereoisomers of 2,5-(3',4'-dihydroxyphenyl)tetrahydrofuran 3,4-dicarboxylic acid.

Effects of lipoic acid, caffeic acid and a synthesized lipoyl-caffeic conjugate on human hepatoma cell lines

Hepatocellular carcinoma (HCC) is among the most aggressive and fatal cancers. Its treatment with conventional chemotherapeutic agents is inefficient, due to several side effects linked to impaired organ function typical of liver diseases. Consequently, there exists a decisive requirement to explore possible alternative chemopreventive and therapeutic strategies. The use of dietary antioxidants and micronutrients has been proposed for HCC successful management. The aim of this work was to test in vitro the effects of lipoic acid, caffeic acid and a new synthesized lipoylcaffeic conjugate on human hepatoma cell lines in order to assess their effect on tumor cell growth. The results of cytotoxicity assays at different times showed that the cell viability was directly proportional to the molecule concentrations and incubation times. Moreover, to evaluate the pro- or anti-inflammatory effects of these molecules, the cytokine concentrations were evaluated in treated and untreated cellular supernatants. The obtained cytokine pattern showed that, at the increasing of three molecules concentrations, three pro-inflammatory cytokines such as IL-1α, IL-8 and TNF-α decreased whereas the antiinflammatory cytokine such as IL-10 increased.

Action of tyrosinase on caffeic acid and its n-nonyl ester. Catalysis and suicide inactivation

Different mechanisms for inhibiting tyrosinase can be designed to avoid postharvest quality losses of fruits and vegetables. The action of tyrosinase on caffeic acid and its n-nonyl ester (n-nonyl caffeate) was characterized kinetically in this work. The

Polyphenol oxidase from yacon roots (Smallanthus sonchifolius)

Polyphenol oxidase (E.C. 1.14.18.1) (PPO) extracted from yacon roots (Smallanthus sonchifolius) was partially purified by ammonium sulfate fractionation and separation on Sephadex G-100. The enzyme had a molecular weight of 45 490 ± 3500 Da and Km/s