Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate explained

Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate (INCI) is an organic compound used in sunscreens to absorb UVA radiation. It is marketed as Mexoryl 400 by L'Oréal. MCE has an absorption maximum of 385 nm, which is in the long-wave UVA range (UVA1, 360−400 nm).[1] [2] [3] [4] [5] [6] [7] Like Mexoryl SX (Ecamsule) and Mexoryl XL (Drometrizole trisiloxane), it is used exclusively in products manufactured by L'Oréal.[8] MCE was developed by L'Oréal and BASF.[9]

Properties

MCE is a yellow solid in the form of powder or small chunks. At 25°C, it is soluble in phenoxyethanol, dimethyl capramide, ethoxydiglycol, dimethyl isosorbide, and alcohol (ethanol), which are ingredients used in cosmetics.[10] [11] [12] [13] [14]

It is considered a cyclic merocyanine.[15]

Safety and regulation

In 2019, MCE was approved for use up to a maximum concentration of 3% as a UV filter in cosmetics in the EU. It is not currently recognised or approved by the FDA for use in cosmetics in the US.

References

  1. Web site: Scientific Committee on Consumer Safety . europa.eu . 28 July 2024.
  2. Marionnet . Claire . de Dormael . Romain . Marat . Xavier . Roudot . Angélina . Gizard . Julie . Planel . Emilie . Tornier . Carine . Golebiewski . Christelle . Bastien . Philippe . Candau . Didier . Bernerd . Françoise . January 2022 . Sunscreens with the New MCE Filter Cover the Whole UV Spectrum: Improved UVA1 Photoprotection In Vitro and in a Randomized Controlled Trial . . 2 . 1 . 10.1016/j.xjidi.2021.100070 . 2667-0267 . 8762479 . 35072138.
  3. Aguilera . José . Gracia-Cazaña . Tamara . Gilaberte . Yolanda . 2023-10-01 . New developments in sunscreens . Photochemical & Photobiological Sciences . en . 22 . 10 . 2473–2482 . 10.1007/s43630-023-00453-x . 37543534 . 1474-9092. free . 2023PhPhS..22.2473A .
  4. Bernerd . Françoise . Passeron . Thierry . Castiel . Isabelle . Marionnet . Claire . January 2022 . The Damaging Effects of Long UVA (UVA1) Rays: A Major Challenge to Preserve Skin Health and Integrity . International Journal of Molecular Sciences . en . 23 . 15 . 8243 . 10.3390/ijms23158243 . free . 1422-0067 . 9368482 . 35897826.
  5. Web site: PubChem . 2-ethoxyethyl (2Z)-2-cyano-2-[3-(3-methoxypropylamino)cyclohex-2-en-1-ylidene]acetate ]. 2024-07-30 . pubchem.ncbi.nlm.nih.gov . en.
  6. de Dormael . Romain . Bernerd . Francoise . Bastien . Philippe . Candau . Didier . Roudot . Angelina . Tricaud . Caroline . September 2022 . Improvement of photoprotection with sunscreen formulas containing the cyclic merocyanine UVA1 absorber MCE: In vivo demonstration under simulated and real sun exposure conditions in three randomised controlled trials . . en . 1 . 3 . 229–239 . 10.1002/jvc2.38 . 2768-6566. free .
  7. Flament . F. . Mercurio . D. G. . Muller . B. . Li . J. . Tricaud . C. . Bernerd . F. . Roudot . A. . Candau . D. . Passeron . T. . January 2024 . The impact of methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate (MCE) UVA1 filter on pigmentary and ageing signs: An outdoor prospective 8-week randomized, intra-individual comparative study in two populations of different genetic background . Journal of the European Academy of Dermatology and Venereology . en . 38 . 1 . 214–222 . 10.1111/jdv.19486 . 37655436 . 0926-9959. free .
  8. Web site: 2022-05-24 . L'Oréal Breaks the Ultra-long UVA Code with UVMune 400 . 2024-07-28 . Cosmetics & Toiletries . en-us.
  9. Web site: 2024-06-10 . La Roche-Posay UVMune 400: Science and Review . 2024-07-28 . Lab Muffin Beauty Science . en-US.
  10. Web site: PubChem . Phenoxyethanol . 2024-07-29 . pubchem.ncbi.nlm.nih.gov . en.
  11. Web site: PubChem . N,N-Dimethyldecanamide . 2024-07-29 . pubchem.ncbi.nlm.nih.gov . en.
  12. Web site: PubChem . Diethylene Glycol Monoethyl Ether . 2024-07-29 . pubchem.ncbi.nlm.nih.gov . en.
  13. Web site: PubChem . Dimethyl isosorbide . 2024-07-29 . pubchem.ncbi.nlm.nih.gov . en.
  14. Lachenmeier . Dirk W . 2008-11-13 . Safety evaluation of topical applications of ethanol on the skin and inside the oral cavity . Journal of Occupational Medicine and Toxicology . en . 3 . 1 . 26 . 10.1186/1745-6673-3-26 . free . 1745-6673 . 2596158 . 19014531.
  15. Winkler . Barbara . Hoeffken . Hans Wolfgang . Eichin . Kai . Houy . Wolfgang . 2014-03-05 . A cyclic merocyanine UV-A absorber: mechanism of formation and crystal structure . Tetrahedron Letters . 55 . 10 . 1749–1751 . 10.1016/j.tetlet.2014.01.113 . 0040-4039.

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