Expeditious and sustainable two-step synthesis of sinapoyl- l -malate and analogues: towards non-endocrine disruptive bio-based and water-soluble bioactive compounds
Open accessAbstract
Straightforward and sustainable two-step route to bioactive sinapoyl- l -malate and analogues using Meldrum's acid opening and Knoevenagel-Doebner condensation.
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Compounds 142, 151, and 154-157 revealed photostability with LoA values less than 20%.
“Moreover, 142, 151, and 154–157 revealed photostability with LoA values less than 20% [24].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [24]
The available summary passage (no page or section supplied) says the compounds studied showed promise as photostable UV filters. It does not identify compounds 142, 151, or 154–157 or report LoA values below 20%, so those specifics remain unsupported by our copy. (LLM, conf=0.78)
Experimental — accuracy not yet measuredCompounds 180 and 183 have potential as multifunctional agents for cosmetic application.
“Moreover, p-hydroxycinnamic acid-based Meldrum’s derivatives (180 and 183) possess antioxidant and anti-tyrosinase properties, photoprotective characteristics, namely against UVA radiation and blue light, and photostability (with LoA < avobenzone (11)) [145] reinforcing their potential as multifunctional agents for cosmetic application [24].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [24]
The available passage on the study’s targets reports photostable UV-filter, antioxidant and preservative properties and says their water solubility facilitates incorporation into cosmetic formulations. It supports multifunctional cosmetic potential for sinapoyl-L-malate and its analogues, but does not identify compounds 180 and 183 or establish that those numbered compounds are among the targets studied. (LLM, conf=0.80)
Experimental — accuracy not yet measuredAmong compounds 142-157, compounds 142, 144, 147, and 150-157 showed promising photoprotective activity with LoA < avobenzone (11), and antioxidant activity, with 151 and 155-157 being the most promising.
“Among all the compounds, 142–157, 142, 144, 147, and 150–157 showed promising photoprotective activity with LoA < avobenzone (11), and antioxidant activity, being 151 and 155–157 the most promising.”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [24]
The paper text available in our copy reports that the synthesized compounds showed promise as photostable UV filters and antioxidants. It does not identify compounds 142, 144, 147, or 150–157, compare their LoA with avobenzone, or single out 151 and 155–157 as most promising. (LLM, conf=0.85)
Experimental — accuracy not yet measuredThe free carboxylic acid in compounds 142-157 could facilitate their incorporation into sunscreen formulation.
“All compounds presented good water solubility, as a result of the presence of a free carboxylic acid in their structure which could facilitate the incorporation into sunscreen’s formulation.”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [24]
All compounds 142-157 presented good water solubility due to the presence of a free carboxylic acid in their structure.
“All compounds presented good water solubility, as a result of the presence of a free carboxylic acid in their structure which could facilitate the incorporation into sunscreen’s formulation.”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [24]
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Cites
Natural Antioxidants: Multiple Mechanisms to Protect Skin From Solar Radiation
Dunaway, S., Odin, R., Zhou, L., Ji, L., Zhang, Y., & Kadekaro, A. L. (2018) · Frontiers in Pharmacology · doi:10.3389/fphar.2018.00392 · Cited by 280 · see citing works
Towards symmetry driven and nature inspired UV filter design
Horbury, M. D., Holt, E. L., Mouterde, L. M. M., Balaguer, P., Cebrián, J., Blasco, L., Allais, F., & Stavros, V. G. (2019) · Nature Communications · doi:10.1038/s41467-019-12719-z · Cited by 73 · see citing works
Self-citationHubner, A., Sobreira, F., Vetore Neto, A., Pinto, C. A. S. D. O., Dario, M. F., Díaz, I. E. C., Lourenço, F. R., Rosado, C., Baby, A. R., & Bacchi, E. M. (2019) · Antioxidants · doi:10.3390/antiox8110530 · Cited by 60 · see citing works
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UV Filters: Challenges and Prospects
Jesus, A., Sousa, E., Cruz, M., Cidade, H., Lobo, J., & Almeida, I. (2022) · Pharmaceuticals · doi:10.3390/ph15030263 · Cited by 132 · see citing works
- Authors
- Peyrot, C., Mention, M. M., Fournier, R., Brunissen, F., Couvreur, J., Balaguer, P., & Allais, F.
- Affiliations
- AgroParisTech (FR)
- Inserm (FR)
- Corresponding author
- Allais, Florent
- ORCID
- Venue
- Green Chemistry
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2020
- Volume
- 22
- Issue
- 19
- Pages
- 6510-6518
- ISSN
- 1463-9262 (ISSN-L)
- 1463-9270
- OpenAlex
- W3087551354
- Cited by
- 29
- References
- 3
- Citations by year
- 2026: 3 · 2025: 3 · 2024: 6 · 2023: 4 · 2022: 7 · 2021: 6
- FWCI
- 1.75
- Type
- journal article
- Language
- en
- Open access
- Licence
- Locations
- Green Chemistry (publishedVersion)
- HAL (submittedVersion, cc-by-nc)
- Funders
- H2020 Future and Emerging Technologies (828753)
- Agence Nationale de la Recherche (ANR-17-CE07-0046)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Health Sciences › Medicine › Pharmacology › Synthesis of Organic Compounds
- Keywords
- two-step synthesis
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