Obtaining 4-vinylphenols by decarboxylation of natural 4-hydroxycinnamic acids under microwave irradiation

Bernini, Roberta; Mincione, Enrico; Barontini, Maurizio; Provenzano, Gianfranco; Setti, Leonardo

doi:10.1016/j.tet.2007.07.035

Cited by 73 publications

(49 citation statements)

References 40 publications

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“…Cinnamic acid derivatives, especially those combining the cinnamoyl moiety with hydroxyl groups, present strong free radical scavenging properties. Acids, esters, amides, hydrazides and related derivatives of cinnamic acid with such activities are reported in the literature for their health benefits [14,15]. Especially, p-coumaric acid or 4-hydroxy-trans-cinnamic acid presents antioxidant activity, involving direct scavenger of reactive oxygen species (ROS) by minimizing the oxidation of low-density lipoprotein (LDL) [16].…”

Section: Introductionmentioning

confidence: 99%

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

et al. 2014

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Cinnamic acids have been identified as interesting compounds with antioxidant, anti-inflammatory and cytotoxic properties. In the present study, simple cinnamic acids were synthesized by Knoevenagel condensation reactions and evaluated for the above biological activities. Compound 4ii proved to be the most potent LOX inhibitor. Phenylsubstituted acids showed better inhibitory activity against soybean LOX, and it must be noted that compounds 4i and 3i with higher lipophilicity values resulted less active than compounds 2i and 1i. The compounds have shown very good activity in different antioxidant assays. The antitumor properties of these derivatives have been assessed by their 1/IC 50 inhibitory values in the proliferation of HT-29, A-549, OAW-42, MDA-MB-231, HeLa and MRC-5 normal cell lines. The compounds presented low antitumor activity considering the IC 50 values attained for the cell lines, with the exception of compound 4ii. Molecular docking studies were carried out on cinnamic acid derivative 4ii and were found to be in accordance with our experimental biological results.

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Section: Introductionmentioning

confidence: 99%

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

et al. 2014

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“…It is to be noted that the 4-vinylphenols, obtained by the decarboxylation of 4-hydroxycinnamic acids, are highly valuable chemicals with wide range of applicability. 4-Vinylguaiacol (4a), the decarboxylated product of ferulic acid (3a), is an antioxidant and flavoring agent [23]. The sinapic acid (3b) provided vinylsyringol (canolol) (4b) which is an antimutagenic compound [24].…”

Section: Resultsmentioning

confidence: 99%

Cellulose supported copper nanoparticles as a versatile and efficient catalyst for the protodecarboxylation and oxidative decarboxylation of aromatic acids under microwave heating

Baruah

Konwar

2015

Catalysis Communications

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“…The 1 H-and 13 C { 1 H}-NMR data agreed with the data reported in the literature. 17,18) MS-EI m=z (%): 180 (100), 165 (40), 137 (27), 77 (15), 122 (12), 91 (12).…”

Section: Methodsmentioning

confidence: 99%

Key Aroma Compounds in Roasted In-shell Peanuts

Kaneko¹,

Sakai²,

Kumazawa³

et al. 2013

Bioscience, Biotechnology, and Biochemistry

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Obtaining 4-vinylphenols by decarboxylation of natural 4-hydroxycinnamic acids under microwave irradiation

Cited by 73 publications

References 40 publications

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

Cellulose supported copper nanoparticles as a versatile and efficient catalyst for the protodecarboxylation and oxidative decarboxylation of aromatic acids under microwave heating

Key Aroma Compounds in Roasted In-shell Peanuts

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