A green chemical synthesis of coumarin-3-carboxylic and cinnamic acids using crop-derived products and waste waters as solvents

Fiorito, Serena; Taddeo, Vito Alessandro; Genovese, Salvatore; Epifano, Francesco

doi:10.1016/j.tetlet.2016.09.023

Cited by 40 publications

(26 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…This compound was synthesized based on numerous reports, which documented the use of Meldrum’s acid as a substrate for the synthesis of coumarin 3-carboxylic acid derivatives [19,20,21]. A number of these papers refer to various crop-derived products such as juices, extracts, or even waste waters employed as both media and catalysts in the Knoevenagel condensation-like reactions of Meldrum’s acid [5,22]. It is particularly worth emphasizing that the majority of these reactions were carried out at eco-friendly conditions such as room temperature, aqueous media, and only a slightly acidic pH.…”

Section: Resultsmentioning

confidence: 99%

Anti-Hypochlorite and Catalytic Activity of Commercially Available Moringa oleifera Diet Supplement

et al. 2019

View full text Add to dashboard Cite

Aiming at the assessment of the pro-health, and especially anti-hypochlorite properties of Moringa oleifera species a representative, commercially available Moringa oleifera dietary supplement was used as a substrate for the preparation of aqueous Moringa extract. The anti-hypochlorite activity of the extract was assessed using the hypochlorite-specific coumarin-based fluorescence turn-off sensor, namely 7-diethylamino-coumarin-3-carboxylic acid (7-DCCA). This compound was synthesized via the Knoevenagel condensation of 4-diethylamino-2-hydroxybenzaldehyde with Meldrum’s acid and the Moringa extract was employed as a medium and catalyst. Moreover, the total phenolic content (TPC) as well as the reactive oxygen species (ROS)–scavenging ability of the aqueous Moringa extract were determined. The results obtained demonstrated the applicability of Moringa extract as an anti-hypochlorite agent. Additionally, the satisfactory yield of the 7-DCCA obtained suggests the usefulness of the extract as a catalyst and the reaction medium. The antioxidative potential of the extract was notably lower than that of the standard (TROLOX). Determination of TPC in 100 g of the dry weight (DW) of studied material revealed a high number of polyphones present.

show abstract

Section: Resultsmentioning

confidence: 99%

Anti-Hypochlorite and Catalytic Activity of Commercially Available Moringa oleifera Diet Supplement

et al. 2019

View full text Add to dashboard Cite

show abstract

“…In particular, the potential of pseudo-ternary systems made of water/alcohol/essential oils is being currently explored, and recent developments are reported, for example, as mosquito-repellent formulations 61,62 or as a medium for enzymatic and chemical reactions. 20,22,63 To understand these systems, with the aim of tailoring them to the desired need, a detailed knowledge of the microscopic structure is mandatory, and, SANS provides a unique tool, as shown in this work for the case of Limoncello.…”

Section: Discussionmentioning

confidence: 99%

Looking into Limoncello: The Structure of the Italian Liquor Revealed by Small-Angle Neutron Scattering

Chiappisi

Grillo

2018

ACS Omega

View full text Add to dashboard Cite

Limoncello, the Italian liquor based on lemon essential oils, is becoming increasingly popular around the world. This digestive is not only an iconic representative of Italian food culture, but it is also a complex colloidal system, made of essential oils, ethanol, sucrose, and water. Smell, aroma, taste, and appearance of Limoncello do, of course, depend on the components, in particular on the peculiar essential oil mixture. Accordingly, several studies are available in the literature investigating the composition of various Limoncellos. However, the microscopic structure plays an equally important role when it comes to the sensory properties of food and beverages. In this work, small-angle neutron scattering was used to probe the microscopic structure of Limoncello, revealing the presence of spontaneously formed 100 nm-sized droplets over a large range of composition and temperature. The results are not limited to this famous drink but can be extended to the rapidly developing formulations based on water-insoluble oils, water, and alcohols.

show abstract

“…The aqueous extracts were used as a catalyst and medium in the synthesis of the coumarin-derived fluorescent probe 7-DCCA ( Figure 4). These experiments were inspired by the fact that a wide variety of crop-derived products, such as fruit juices or extracts, were employed as both media and catalysts in the synthesis of coumarin derivatives via the Knoevenagel condensation mechanism [40,41]. In the case of TROLOX, the concentrations needed were in the range 0.011-0.013 mg/mL, while for the berry extracts, the IC50 values are in the range of 0.46 mg/mL for açaí at pH 7.4 to 2.86 mg/mL for Schisandra at pH 3.…”

Section: Synthesis Of Hypochlorite-sensitive Fluorescent Probe 7-dccamentioning

confidence: 99%

Anti-Hypochlorite, Antioxidant, and Catalytic Activity of Three Polyphenol-Rich Super-Foods Investigated with the Use of Coumarin-Based Sensors

et al. 2020

View full text Add to dashboard Cite

The anti-hypochlorite activity of açaí (Euterpe oleracea Mart.), goji (Lycium barbarum L.) and schisandra (Schisandra chinensis) fruit extracts were assessed by determining the reactive chlorine species (RCS)-scavenging ability of these three “super-food” berries. In addition, the aqueous extracts obtained were employed as both the media and the catalyst in a green chemistry approach to the synthesis of a coumarin-based fluorescence turn-off sensor, which was then used for anti-hypochlorite activity testing. The aqueous extracts were also assessed for total phenolic content (TPC), using the Folin–Ciocalteu method, and the antioxidant activity using the ABTS+• assay. Moreover, the main water-soluble polyphenolic constituents of the extracts were identified by the HPLC-PDA-ESI-MS technique. Among the extracts tested, açaí demonstrated the highest anti-hypochlorite and antioxidant activities, while the highest TPC value was found for the goji extract. All extracts demonstrated modest catalytic activity as Knoevenagel condensation catalysts.

show abstract

A green chemical synthesis of coumarin-3-carboxylic and cinnamic acids using crop-derived products and waste waters as solvents

Cited by 40 publications

References 20 publications

Anti-Hypochlorite and Catalytic Activity of Commercially Available Moringa oleifera Diet Supplement

Anti-Hypochlorite and Catalytic Activity of Commercially Available Moringa oleifera Diet Supplement

Looking into Limoncello: The Structure of the Italian Liquor Revealed by Small-Angle Neutron Scattering

Anti-Hypochlorite, Antioxidant, and Catalytic Activity of Three Polyphenol-Rich Super-Foods Investigated with the Use of Coumarin-Based Sensors

Contact Info

Product

Resources

About