Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate

Organic compound used in sunscreen From Wikipedia, the free encyclopedia

Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate (INCI; sometimes abbreviated MCE) is an organic compound used in sunscreens to absorb UVA radiation. It is marketed as Mexoryl 400 by L'Oréal, and as UVMune by L'Oréal's subsidiary La Roche Posay.[1] MCE has an absorption maximum at 385 nm, which is in the long-wave UVA range (UVA1, 360−400 nm).[2][3][4][5][6][7][8] It is used exclusively in products manufactured by L'Oréal.[9] MCE was developed by L'Oréal and BASF.[1]

Quick facts Names, Identifiers ...
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).
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Properties

MCE is a yellow solid in the form of powder or small chunks.[2] At 25 °C, it is soluble in phenoxyethanol, dimethyl capramide, ethoxydiglycol, dimethyl isosorbide, and alcohol (ethanol), which are ingredients used in cosmetics.[2][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.[2] In 2025, it was approved for use by the TGA in Australia[16] up to a maximum concentration of 3%.[17] It is not currently recognised or approved by the FDA for use in cosmetics in the US.

See also

References

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