Sinapic Acid Esters: Octinoxate Substitutes Combining Suitable UV Protection and Antioxidant Activity
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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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Sinapic acid analogues of EHMC (21) with ester (111-124), amide (125-126), and ketone (127) groups revealed promising UV filter activity.
“Sinapic acid analogues of EHMC (21) with ester (111–124), amide (125–126), and ketone (127) groups revealed promising UV filter activity.”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [137]
The Results and Discussion report UV absorption for the ester, amide, and ketone analogues. However, the Loss of Absorbance subsection calls the phenolic esters and ketone poor UV-filter candidates because of photostability, so describing all the analogues as promising overstates the findings. No page number is available in our copy. (LLM, conf=0.87)
Experimental — accuracy not yet measuredSinapic acid analogue 111, its methylated derivative 112, aliphatic sinapate derivatives 116 and 118, and amide derivative 125 presented higher photostability than EHMC (21).
“Additionally, sinapic acid analogue 111 and its methylated derivative 112, aliphatic sinapate derivatives 116 and 118, and amide derivative 125 presented higher photostability than EHMC (21) [137].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [137]
Section 3.1 (page not provided) reports less loss of absorbance than octinoxate for compounds 1, 2, 8 and aromatic amide 15, supporting higher photostability for the corresponding cited derivatives. For the aliphatic series containing compound 6, it says primary-alcohol derivatives were 'close to or better than' octinoxate; it does not establish that compound 6 specifically was better. (LLM, conf=0.84)
Experimental — accuracy not yet measuredDerivatives 125 and 127 showed the best antioxidant activities with IC50 values lower than 8.9 ± 0.3 nmol.
“Among all compounds, the derivatives 125 and 127 showed the best antioxidant activities with IC50 values lower than 8.9 ± 0.3 nmol [137].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [137]
Section 3.2 (page unavailable) reports that compounds 15 and 17 had stronger antiradical activity than BHT, supporting the general point about antioxidant activity. It does not identify derivatives 125 and 127 or report the claimed IC50 threshold of 8.9 ± 0.3 nmol; the paper describes its measurements as EC50 values. (LLM, conf=0.82)
Experimental — accuracy not yet measuredCompounds 111 and 114-127 showed multifunctional properties, combining antioxidant and photoprotective effects.
“Interestingly, 111 and 114–127 showed multifunctional properties, combining antioxidant and photoprotective effects.”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [137]
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Xu, X., Zhang, L., Wan, Z., Fu, L., Han, Y., Wang, K., Yan, L., Li, Y., Zhang, X.-H., & Min, D. (2021) · Figshare · doi:10.6084/m9.figshare.14601972
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The Influence of p-hydroxyl group on the Synthesis of 2-Ethylhexyl 4-Hydroxycinnamate
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Self-citation
- Authors
- Peyrot, C., Mention, M. M., Brunissen, F., & Allais, F.
- Affiliations
- AgroParisTech (FR)
- Corresponding author
- Allais, Florent
- Venue
- Antioxidants
- Publisher
- MDPI AG
- Published
- 2020-08-24
- Volume
- 9
- Issue
- 9
- Pages
- 782
- ISSN
- 2076-3921 (ISSN-L)
- PMC
- PMC7554726
- OpenAlex
- W3080118992
- Cited by
- 61
- References
- 44
- Citations by year
- 2026: 4 · 2025: 6 · 2024: 13 · 2023: 8 · 2022: 11 · 2021: 18 · 2020: 1
- FWCI
- 9.31
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- Locations
- Antioxidants (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- HAL (submittedVersion, other-oa)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Funders
- Agence Nationale de la Recherche (ANR-17-CE07-0046)
- H2020 Future and Emerging Technologies (828753)
- Topics
- Health Sciences › Medicine › Dermatology › Skin Protection and Aging
- Health Sciences › Medicine › Biochemistry › Phytochemicals and Antioxidant Activities
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Keywords
- UV filters, sunscreen, UVB protection, antioxidant activity, structure-activity relationship, coral reef conservation, free phenolics
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