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Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate

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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]

Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate
Names
IUPAC names
  • 2-ethoxyethyl (2Z)-2-cyano-2-[3-(3-methoxypropylamino) cyclohex-2-en-1-ylidene]acetate
  • 2-ethoxyethyl 2-cyano-2-[(1Z)-3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene]acetate
Other names
  • Mexoryl 400
  • Colipa No. S 87
  • C-1701 B_C_3
  • C-1701 Merocyanine
Identifiers
3D model (JSmol)
23320776
ChemSpider
EC Number
  • 700-860-3
  • InChI=1S/C17H26N2O4/c1-3-22-10-11-23-17(20)16(13-18)14-6-4-7-15(12-14)19-8-5-9-21-2/h12,19H,3-11H2,1-2H3/b16-14-
    Key: NPNDSRGIZUPLNP-PEZBUJJGSA-N
  • CCOCCOC(=O)C(=C1CCCC(=C1)NCCCOC)C#N
Properties
C17H26N2O4
Molar mass 322.405 g·mol−1
Appearance Yellow solid in the form of powder or small chunks
Melting point 85–120 °C (185–248 °F; 358–393 K)
Boiling point 306–315 °C (583–599 °F; 579–588 K)
Solubility in Ethanol 13% w/w
log P 1.7
Acidity (pKa) 13.3
UV-vis (λmax) 385
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Properties

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MCE is a yellow solid in the form of powder or small chunks.[1] At 25°C, it is soluble in phenoxyethanol, dimethyl capramide, ethoxydiglycol, dimethyl isosorbide, and alcohol (ethanol), which are ingredients used in cosmetics.[1][10][11][12][13][14]

It is considered a cyclic merocyanine.[15]

Safety and regulation

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In 2019, MCE was approved for use up to a maximum concentration of 3% as a UV filter in cosmetics in the EU.[1] It is not currently recognised or approved by the FDA for use in cosmetics in the US.

References

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  1. ^ a b c d "Scientific Committee on Consumer Safety" (PDF). europa.eu. Retrieved 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". JID Innovations. 2 (1). doi:10.1016/j.xjidi.2021.100070. ISSN 2667-0267. PMC 8762479. PMID 35072138.
  3. ^ Aguilera, José; Gracia-Cazaña, Tamara; Gilaberte, Yolanda (2023-10-01). "New developments in sunscreens". Photochemical & Photobiological Sciences. 22 (10): 2473–2482. Bibcode:2023PhPhS..22.2473A. doi:10.1007/s43630-023-00453-x. ISSN 1474-9092. PMID 37543534.
  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. 23 (15): 8243. doi:10.3390/ijms23158243. ISSN 1422-0067. PMC 9368482. PMID 35897826.
  5. ^ PubChem. "2-ethoxyethyl (2Z)-2-cyano-2-[3-(3-methoxypropylamino)cyclohex-2-en-1-ylidene]acetate". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-07-30.
  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". JEADV Clinical Practice. 1 (3): 229–239. doi:10.1002/jvc2.38. ISSN 2768-6566.
  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. 38 (1): 214–222. doi:10.1111/jdv.19486. ISSN 0926-9959. PMID 37655436.
  8. ^ "L'Oréal Breaks the Ultra-long UVA Code with UVMune 400". Cosmetics & Toiletries. 2022-05-24. Retrieved 2024-07-28.
  9. ^ "La Roche-Posay UVMune 400: Science and Review". Lab Muffin Beauty Science. 2024-06-10. Retrieved 2024-07-28.
  10. ^ PubChem. "Phenoxyethanol". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-07-29.
  11. ^ PubChem. "N,N-Dimethyldecanamide". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-07-29.
  12. ^ PubChem. "Diethylene Glycol Monoethyl Ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-07-29.
  13. ^ PubChem. "Dimethyl isosorbide". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-07-29.
  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. 3 (1): 26. doi:10.1186/1745-6673-3-26. ISSN 1745-6673. PMC 2596158. PMID 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. doi:10.1016/j.tetlet.2014.01.113. ISSN 0040-4039.


 

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