Biomimetic regioselective and high-yielding Cu(<scp>i</scp>)-catalyzed dimerization of sinapate esters in green solvent Cyrene™: towards sustainable antioxidant and anti-UV ingredients

Mention, Matthieu M.; Flourat, Amandine L.; Peyrot, Cédric; Allais, Florent

doi:10.1039/d0gc00122h

Cited by 34 publications

(31 citation statements)

References 35 publications

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“…Data are reported as follows: chemical shift (δ ppm), multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, sept = septet, dd = doublet of doublet, td = triplet of doublet, m = multiplet), coupling constant (Hz), integration and assignment. 13 C NMR spectra were recorded on a Bruker Fourier 300 In addition, sinapic acid has already demonstrated its great potential as a starting material for UV filter production [26,27]. Moreover, naturally occurring sinapoyl malate plays the role of a UV filter at the leaves' surface to protect them from the harmful effects of UV radiation [28].…”

Section: Chemical Synthesismentioning

confidence: 99%

“…This is particularly surprising as it is well known that sinapic acid is the most efficient in terms of absorbance among p-hydroxycinnamic acids. In addition, sinapic acid has already demonstrated its great potential as a starting material for UV filter production [26,27]. Moreover, naturally occurring sinapoyl malate plays the role of a UV filter at the leaves' surface to protect them from the harmful effects of UV radiation [28].…”

Section: Introductionmentioning

confidence: 99%

“…Several physico-chemical studies have made it possible to better understand the protection mechanism of those molecules [29,30]. Recent work on the highly selective β-β dimerization of sinapic acid esters has highlighted their great potential both as UV filters and antioxidants [26]. Based on these observations, we decided to focus our efforts on the synthesis of renewable sinapic-acid-based octinoxate analogues with dual properties (i.e., UV filter, antioxidant).…”

Section: Introductionmentioning

confidence: 99%

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Sinapic Acid Esters: Octinoxate Substitutes Combining Suitable UV Protection and Antioxidant Activity

et al. 2020

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In 2021, Hawaii will permanently ban the use and sale of octinoxate-based sunscreens as studies have shown serious impacts of such UV filters on the coral reef. This ban, which could be generalized to other countries, highlights the extreme need to offer alternative UV filters that are not only effective in terms of sun protection, but also healthy with regards to human health and the environment. In this context, a wide library of p-hydroxycinnamic esters deriving from naturally occurring sinapic acid has been synthesized using a Knoevenagel–Doebner condensation. The UV filtering activities as well as the antioxidant properties of these sinapic acid esters were then investigated. The results showed promising UVB protection and antioxidant efficacy. A Structure–Activity Relationship (SAR) study on the sinapic acid esters highlighted the need of a free phenol to, as expected, observe antioxidant activity, but also to obtain a higher intensity of protection. Moreover, the nature of the ester moiety also proved to be a key structural feature for the UV absorbance, as higher steric hindrance on the ester moiety leads to more active compounds. The judicious structural design of sinapic esters thus provides promising compounds combining UV protection and antioxidant activity.

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Section: Chemical Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Sinapic Acid Esters: Octinoxate Substitutes Combining Suitable UV Protection and Antioxidant Activity

et al. 2020

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“…In this context, lignin and related chemicals (e.g., lignans, phenolic acids) appear as a valuable source of sustainable aromatic building blocks [1,2]. Indeed, p-hydroxycinnamic acids and their derivatives can be readily extracted from different biomasses and be further (chemo-)enzymatically modified [3][4][5][6] to provide them with physicochemical and biological properties of interest in various fields, such as antioxidants [7][8][9] and anti-UV compounds [10][11][12]. However, p-hydroxycinnamic acids and their derivatives are not only poorly water soluble, but also they are usually present in relatively small quantities in biomass, thus greatly limiting their uses at the industrial scale.…”

Section: Introductionmentioning

confidence: 99%

Sustainable Synthesis of p-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical Scavengers

et al. 2020

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p-Hydroxycinnamic diacids are reaction intermediates of the classical Knoevenagel–Doebner condensation between malonic acid and benzaldehydes. As they are generally obtained in low yields, they remain relatively under-studied and under-exploited. Herein, we developed and optimized a sustainable synthetic procedure allowing the production of these compounds in good to high yields (60–80%) using proline as the catalyst and ethanol as the solvent. Study of their antioxidant and anti-UV activities revealed that these p-hydroxycinnamic diacids were not only potent radical scavengers but also efficient UV filters exhibiting high photostability.

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“…Conjugated or aromatic compounds are known for their abilities to absorb specific wavelengths, especially ultraviolet ones [24][25][26]. Some of them are bio-sourced or biodegradable (i.e., phenolic and furfural derivatives) and less harmful.…”

Section: Introductionmentioning

confidence: 99%

Innovative Bio-Based Organic UV-A and Blue Light Filters from Meldrum’s Acid

et al. 2020

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Faced with the ban of some organic UV filters such as octinoxate or avobenzone, especially in Hawaii, it became essential to offer new alternatives that are both renewable and safe for humans and the environment. In this context, a class of bio-based molecules displaying interesting UV filter properties and great (photo)stability has been developed from Meldrum’s acid and bio-based and synthetic p-hydroxycinnamic acids, furans and pyrroles. Moreover, p-hydroxycinnamic acid-based Meldrum’s derivatives possess valuable secondary activities sought by the cosmetic industry such as antioxidant and anti-tyrosinase properties. The evaluation of the properties of mixture of judiciously chosen Meldrum’s acid derivatives highlighted the possibility to modulate secondary activity while maintaining excellent UV protection. Meldrum’s acid derivatives are not only competitive when benchmarked against organic filters currently on the market (i.e., avobenzone), but they also do not exhibit any endocrine disruption activity.

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Biomimetic regioselective and high-yielding Cu(i)-catalyzed dimerization of sinapate esters in green solvent Cyrene™: towards sustainable antioxidant and anti-UV ingredients

Abstract: β–β′ dimers of sinapate esters are anti-UV and antiradical chemicals.

Cited by 34 publications

References 35 publications

Sinapic Acid Esters: Octinoxate Substitutes Combining Suitable UV Protection and Antioxidant Activity

Sinapic Acid Esters: Octinoxate Substitutes Combining Suitable UV Protection and Antioxidant Activity

Sustainable Synthesis of p-Hydroxycinnamic Diacids through Proline-Mediated Knoevenagel Condensation in Ethanol: An Access to Potent Phenolic UV Filters and Radical Scavengers

Innovative Bio-Based Organic UV-A and Blue Light Filters from Meldrum’s Acid

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