CoChat
Sign Up
Cited by 35Skin Protection and AgingPhotochromic and Fluorescence ChemistryPhotopolymerization techniques and applications

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

Open access
Peyrot, Cédric, Mention, Matthieu M., Brunissen, Fanny, Balaguer, Patrick, Allais, Florent·2020·Molecules
DOI 10.3390/molecules25092178PMC PMC7248827
Open this paper in CoChat — free accountOpen PDF

Abstract

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.

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.3390/molecules25092178

Cites

Statistics

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

  • Compounds 180 and 183 possess photostability with LoA < avobenzone (11).

    “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 [145]

    In Results §2.2 (page not provided), the paper reports 3.5% loss of absorbance for its simplest coumaric derivative, versus 0.6% for avobenzone, and says the other phenolic derivatives have greater losses. Results §2.5 reports 6.4% for another phenolic derivative and says only a mixture—not the individual compounds—performed better than avobenzone. The paper uses different compound numbers, but its reported phenolic-series results run contrary to the claimed lower loss of absorbance. (LLM, conf=0.85)

    Checked by a reasoning model — may be wrong.

    Experimental — accuracy not yet measured

  • Compounds 182, 184, 187, and 191 do not interact with receptors, showing absence of agonistic (% receptor activity < 30%) and antagonistic (% receptor activity > 70%) effects.

    “Interestingly, endocrine disruption assays were performed for compounds 182, 184, 187, and 191, that revealed non-interaction with receptors, showing the absence of agonistic (% receptor activity < 30%) and antagonistic (% receptor activity > 70%) effects [145].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [145]

    Section 2.6, Endocrine Disruption Assays (page unavailable), reports that four tested molecules barely interacted with the receptors and showed no agonist or antagonist activity. It identifies them as compounds 3, 5, 8, and 12, not 182, 184, 187, and 191; the cited text also does not establish the claimed <30% and >70% activity thresholds. (LLM, conf=0.86)

    Experimental — accuracy not yet measured

  • A small library of compounds from Meldrum's acid and p-hydroxycinnamic acids (180-183), furans (184-190), and pyrroles (191-193) displays interesting UV filter properties.

    “Recently, Peyrot et al. (2020) developed a small library of compounds from Meldrum’s acid and p-hydroxycinnamic acids (180–183), furans (184–190), and pyrroles (191–193), displaying interesting UV filter properties and photostability.”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [145]

  • p-Hydroxycinnamic acid-based Meldrum's derivatives 180 and 183 possess antioxidant and anti-tyrosinase properties.

    “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 [145]

  • A small library of compounds from Meldrum's acid and p-hydroxycinnamic acids (180-183), furans (184-190), and pyrroles (191-193) displays photostability.

    “Recently, Peyrot et al. (2020) developed a small library of compounds from Meldrum’s acid and p-hydroxycinnamic acids (180–183), furans (184–190), and pyrroles (191–193), displaying interesting UV filter properties and photostability.”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [145]

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

No citation lists for this paper

No citation lists for this paper yet — checked again daily.

References 48 · Cited by 35

Research works printed but not linked: 42

  1. [1]Pillai S. Oresajo C. Hayward J. Ultraviolet radiation and skin aging: Roles of reactive oxygen species, inflammation and protease activation, and strategies for prevention of inflammation-induced matrix degradation - a review Int. J. Cosmet. Sci. 2005 27 17 34 10.1111/j.1467-2494.2004.00241.x 18492178 · DOI · Paper page
  2. [2]Liebel F. Kaur S. Ruvolo E. Kollias N. Southall M.D. Irradiation of Skin with Visible Light Induces Reactive Oxygen Species and Matrix-Degrading Enzymes J. Invest. Dermatol. 2012 132 1901 1907 10.1038/jid.2011.476 22318388 · DOI · Paper page
  3. [3]Sakanashi T. Sugiyama M. Suematsu T. Nakagawa T. Hidaka T. Ogura R. UV exposure alters the membrane lipid composition and cell membrane fluidity of intact cultured B-16 melanoma cells Kurume Med. J. 1988 35 159 169 10.2739/kurumemedj.35.159 2855086 · DOI
  4. [4]Philips N. Smith J. Keller T. Gonzalez S. Predominant effects of Polypodium leucotomos on membrane integrity, lipid peroxidation, and expression of elastin and matrixmetalloproteinase-1 in ultraviolet radiation exposed fibroblasts, and keratinocytes J. Dermatol. Sci. 2003 32 1 9 10.1016/S0923-1811(03)00042-2 12788523 · DOI
  5. [5]Pfeifer G.P. You Y.-H. Besaratinia A. Mutations induced by ultraviolet light Mutat. Res. Fundam. Mol. Mech. Mutagen. 2005 571 19 131 10.1016/j.mrfmmm.2004.06.057 15748635 · DOI
  6. [6]Ikehata H. Ono T. The mechanisms of UV mutagenesis J. Radiat. Res. 2011 52 115 125 10.1269/jrr.10175 21436607 · DOI
  7. [7]Godley B.F. Shamsi F.A. Liang F.-Q. Jarrett S.G. Davies S. Boulton M. Blue light induces mitochondrial DNA damage and free radical production in epithelial cells J. Biol. Chem. 2005 280 21061 21066 10.1074/jbc.M502194200 15797866 · DOI
  8. [8]Nakashima Y. Ohta S. Wolf A.M. Blue light-induced oxidative stress in live skin Free Radical Biol. Med. 2017 108 300 310 10.1016/j.freeradbiomed.2017.03.010 28315451 · DOI
  9. [9]Geiger P. Barben M. Grimm C. Samardzija M. Blue light-induced retinal lesions, intraretinal vascular leakage and edema formation in the all-cone mouse retina Cell Death Dis. 2015 6 e1985 10.1038/cddis.2015.333 26583326 PMC4670937 · DOI
  10. [10]DiNardo J.C. Downs C.A. Dermatological and environmental toxicological impact of the sunscreen ingredient oxybenzone/benzophenone-3 J. Cosmet Dermatol. 2018 17 15 19 10.1111/jocd.12449 29086472 · DOI · Paper page
  11. [11]Siller A. Blaszak S.C. Lazar M. Olasz H.E. Update About the Effects of the Sunscreen Ingredients Oxybenzone and Octinoxate on Humans and the Environment Plast Surg Nurs 2018 38 158 161 10.1097/PSN.0000000000000244 30507815 · DOI
  12. [12]Giokas D.L. Salvador A. Chisvert A. UV filters: From sunscreens to human body and the environment TrAC Trends Anal. Chem. 2007 26 360 374 10.1016/j.trac.2007.02.012 · DOI
  13. [13]Ouchene L. Litvinov I.V. Netchiporouk E. Hawaii and Other Jurisdictions Ban Oxybenzone or Octinoxate Sunscreens Based on the Confirmed Adverse Environmental Effects of Sunscreen Ingredients on Aquatic Environments J. Cutan Med. Surg 2019 23 648 649 10.1177/1203475419871592 31729915 · DOI
  14. [14]Danovaro R. Bongiorni L. Corinaldesi C. Giovannelli D. Damiani E. Astolfi P. Greci L. Pusceddu A. Sunscreens cause coral bleaching by promoting viral infections Environ. Health Perspect. 2008 116 441 447 10.1289/ehp.10966 18414624 PMC2291018 · DOI · Paper page
  15. [15]Downs C.A. Kramarsky-Winter E. Segal R. Fauth J. Knutson S. Bronstein O. Ciner F.R. Jeger R. Lichtenfeld Y. Woodley C.M. Toxicopathological Effects of the Sunscreen UV Filter, Oxybenzone (Benzophenone-3), on Coral Planulae and Cultured Primary Cells and Its Environmental Contamination in Hawaii and the U.S. Virgin Islands Arch. Environ. Contam. Toxicol. 2016 70 265 288 10.1007/s00244-015-0227-7 26487337 · DOI
  16. [16]Dunlap W.C. Shick J.M. Yamamoto Y. Sunscreens, oxidative stress and antioxidant functions in marine organisms of the Great Barrier Reef Redox Rep. 1999 4 301 306 10.1179/135100099101535142 10772069 · DOI
  17. [17]Trebse P. Polyakova O.V. Baranova M. Kralj M.B. Dolenc D. Sarakha M. Kutin A. Lebedev A.T. Transformation of avobenzone in conditions of aquatic chlorination and UV-irradiation Water Res. 2016 101 95 102 10.1016/j.watres.2016.05.067 27258620 · DOI
  18. [18]Schlumpf M. Cotton B. Conscience M. Haller V. Steinmann B. Lichtensteiger W. In vitro and in vivo estrogenicity of UV screens Environ. Health Perspect. 2001 109 239 244 10.1289/ehp.01109239 PMC1240241 11333184 · DOI
  19. [19]Schlumpf M. Schmid P. Durrer S. Conscience M. Maerkel K. Henseler M. Gruetter M. Herzog I. Reolon S. Ceccatelli R. Endocrine activity and developmental toxicity of cosmetic UV filters - an update Toxicology 2004 205 113 122 10.1016/j.tox.2004.06.043 15458796 · DOI · Paper page
  20. [20]Dunford R. Salinaro A. Cai L. Serpone N. Horikoshi S. Hidaka H. Knowland J. Chemical oxidation and DNA damage catalyzed by inorganic sunscreen ingredients FEBS Lett. 1997 418 87 90 10.1016/S0014-5793(97)01356-2 9414101 · DOI · Paper page
  21. [22]Jonasson S. Gustafsson A. Koch B. Bucht A. Inhalation exposure of nano-scaled titanium dioxide (TiO2) particles alters the inflammatory responses in asthmatic mice Inhalation Toxicol. 2013 25 179 191 10.3109/08958378.2013.770939 23480194 · DOI
  22. [23]Chen T. Hu J. Chen C. Pu J. Cui X. Jia G. Cardiovascular effects of pulmonary exposure to titanium dioxide nanoparticles in ApoE knockout mice J. Nanosci. Nanotechnol. 2013 13 3214 3222 10.1166/jnn.2013.7147 23858833 · DOI
  23. [24]Mention M.M. Flourat A.L. Peyrot C. Allais F. Biomimetic regioselective and high-yielding Cu(i)-catalyzed dimerization of sinapate esters in green solvent Cyrene™: Towards sustainable antioxidant and anti-UV ingredients Green Chem. 2020 22 2077 2085 10.1039/D0GC00122H · DOI
  24. [26]Dean J. Kusaka R. Walsh P. Allais F. Zwier T. Plant Sunscreens in the UV-B: Ultraviolet Spectroscopy of Jet-cooled Sinapoyl Malate, Sinapic Acid, and Sinapate Ester Derivatives J. Am. Chem. Soc. 2014 136 14780 10.1021/ja5059026 25295994 · DOI
  25. [27]Luo J. Liu Y. Yang S. Flourat A.L. Allais F. Han K. Ultrafast Barrierless Photoisomerization and Strong Ultraviolet Absorption of Photoproducts in Plant Sunscreens J. Phys. Chem. Lett. 2017 8 1025 1030 10.1021/acs.jpclett.7b00083 28177249 · DOI
  26. [28]Mouterde L.M.M. Flourat A.L. Cannet M.M.M. Ducrot P.-H. Allais F. Chemoenzymatic total synthesis of a naturally occurring (5-5′)/(8′-O-4″) dehydrotrimer of ferulic acid Eur. J. Org. Chem. 2013 2013 173 179 10.1002/ejoc.201201290 · DOI
  27. [29]Sandhu H.S. Sapra S. Gupta M. Nepali K. Gautam R. Yadav S. Kumar R. Jachak S.M. Chugh M. Gupta M.K. Synthesis and biological evaluation of arylidene analogues of Meldrum’s acid as a new class of antimalarial and antioxidant agents Bioorg. Med. Chem. 2010 18 5626 5633 10.1016/j.bmc.2010.06.033 20621497 · DOI
  28. [30]Thirupathi G. Venkatanarayana M. Dubey P.K. Kumari Y.B. L-Tyrosine as an Eco-Friendly and Efficient Catalyst for Knoevenagel Condensation of Arylaldehydes with Meldrum’s Acid in Solvent-Free Condition under Grindstone Method Org. Chem. Int. 2012 2012 191584 10.1155/2012/191584 · DOI
  29. [33]Mierina I. Jure M. Zeberga S. Makareviciene V. Zicane D. Tetere Z. Ravina I. Novel type of carbon-centered antioxidants arylmethyl Meldrum’s acids − inhibit free radicals Eur. J. Lipid Sci. Technol. 2017 119 1700172 10.1002/ejlt.201700172 · DOI
  30. [35]Vashi N.A. Kundu R.V. Facial hyperpigmentation: Causes and treatment Br. J. Dermatol. 2013 169 41 56 10.1111/bjd.12536 24098900 · DOI
  31. [36]Boissy R.E. Visscher M. de Long M.A. DeoxyArbutin: A novel reversible tyrosinase inhibitor with effective in vivo skin lightening potency Exp. Dermatol. 2005 14 601 608 10.1111/j.0906-6705.2005.00337.x 16026582 · DOI
  32. [37]Chakraborty A.K. Funasaka Y. Komoto M. Ichihashi M. Effect of arbutin on melanogenic proteins in human melanocytes Pigment. Cell Res. 1998 11 206 212 10.1111/j.1600-0749.1998.tb00731.x 9711535 · DOI
  33. [38]Chawla S. deLong M.A. Visscher M.O. Wickett R.R. Manga P. Boissy R.E. Mechanism of tyrosinase inhibition by deoxyArbutin and its second-generation derivatives Br. J. Dermatol. 2008 159 1267 1274 10.1111/j.1365-2133.2008.08864.x 18811684 · DOI
  34. [39]Hori I. Nihei K. Kubo I. Structural criteria for depigmenting mechanism of arbutin Phytother. Res. 2004 18 475 479 10.1002/ptr.1456 15287073 · DOI
  35. [40]Lee Y.S. Park J.H. Kim M.H. Seo S.H. Kim H.J. Synthesis of tyrosinase inhibitory kojic acid derivative Arch. Pharm. (Weinheim) 2006 339 111 114 10.1002/ardp.200500213 16511808 · DOI
  36. [41]Neeley E. Fritch G. Fuller A. Wolfe J. Wright J. Flurkey W. Variations in IC50 values with purity of mushroom tyrosinase Int. J. Mol. Sci. 2009 10 3811 3823 10.3390/ijms10093811 19865520 PMC2769143 · DOI
  37. [42]Thanaporn A. Boonme P. Formulation and characterization of sunscreen creams with synergistic efficacy on SPF by combination of UV filters J. Appl. Pharm. Sci. 2013 3 001 005 10.7324/JAPS.2013.3801 · DOI
  38. [43]Maipas S. Nicolopoulou-Stamati P. Sun lotion chemicals as endocrine disruptors Hormones 2015 14 32 46 10.1007/BF03401379 25885102 · DOI
  39. [44]Wang J. Pan L. Wu S. Lu L. Xu Y. Zhu Y. Guo M. Zhuang S. Recent advances on endocrine disrupting effects of UV filters Int. J. Environ. Res. Public Health 2016 13 782 10.3390/ijerph13080782 27527194 PMC4997468 · DOI
  40. [45]Crews D. McLachlan J.A. Epigenetics, evolution, endocrine disruption, health, and disease Endocrinology 2006 147 S4 S10 10.1210/en.2005-1122 16690812 · DOI
  41. [46]Mishra K. Ojha H. Chaudhury N.K. Estimation of antiradical properties of antioxidants using DPPH[rad] assay: A critical review and results Food Chem. 2012 130 1036 1043 10.1016/j.foodchem.2011.07.127 · DOI
  42. [47]Masamoto Y. Ando H. Murata Y. Shimoishi Y. Tada M. Takahata K. Mushroom tyrosinase inhibitory activity of esculetin isolated from seeds of Euphorbia lathyris L. Biosci. Biotechnol. Biochem. 2003 67 631 634 10.1271/bbb.67.631 12723615 · DOI

Authors
Peyrot, C., Mention, M. M., Brunissen, F., Balaguer, P., & Allais, F.
Affiliations
  • AgroParisTech (FR)
  • Inserm (FR)
Corresponding author
Allais, Florent
ORCID
Venue
Molecules
Publisher
MDPI AG
Published
2020-05-06
Volume
25
Issue
9
Pages
2178
ISSN
1420-3049 (ISSN-L)
DOI
10.3390/molecules25092178
PMC
PMC7248827
OpenAlex
W3022667728
Cited by
35
References
48
Citations by year
2026: 3 · 2025: 6 · 2024: 4 · 2023: 7 · 2022: 6 · 2021: 5 · 2020: 4
FWCI
4.01
Type
journal article
Language
en
Open access
Licence
Locations
  • Molecules (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
  • Physical Sciences › Materials Science › Materials Chemistry › Photochromic and Fluorescence Chemistry
  • Physical Sciences › Chemistry › Organic Chemistry › Photopolymerization techniques and applications
Keywords
Meldrum's acid derivatives, p-hydroxycinnamic acid, furan, pyrrole, photostability, antioxidant activity, tyrosinase inhibition, endocrine disruption
MeSH terms
Biocompatible Materials, Biphenyl Compounds, Cell Line, Coumaric Acids, Dioxanes, Furans, Humans, Picrates, Pyrroles, Monophenol Monooxygenase, Ultraviolet Rays, Free Radical Scavengers, Endocrine Disruptors

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review