Menthyl anthranilate

Not to be confused with Methyl anthranilate.
Menthyl anthranilate
Names
IUPAC name
(1R,3R,4S)-p-Menthan-3-yl 2-aminobenzoate
Systematic IUPAC name
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 2-aminobenzoate
Other names
Meradimate; Menthyl-o-aminobenzoate; Anthranilic acid menthyl ester; Anthranilic acid p-menth-3-yl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.664 Edit this at Wikidata
UNII
  • InChI=1S/C17H25NO2/c1-11(2)13-9-8-12(3)10-16(13)20-17(19)14-6-4-5-7-15(14)18/h4-7,11-13,16H,8-10,18H2,1-3H3/t12-,13+,16-/m1/s1
    Key: SOXAGEOHPCXXIO-DVOMOZLQSA-N
  • InChI=1/C17H25NO2/c1-11(2)13-9-8-12(3)10-16(13)20-17(19)14-6-4-5-7-15(14)18/h4-7,11-13,16H,8-10,18H2,1-3H3/t12-,13+,16-/m1/s1
    Key: SOXAGEOHPCXXIO-DVOMOZLQBB
  • O=C(O[C@H]1[C@@H](CC[C@H](C1)C)C(C)C)c2ccccc2N
Properties
C17H25NO2
Molar mass 275.392 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Menthyl anthranilate (meradimate) is a sunscreening agent. It is one of the 17 ingredients approved by the Food and Drug Administration for use in over-the-counter sunscreen products.[1][2][3]

  1. ^ "The Skin Cancer Foundation's Guide to Sunscreens". Skin Cancer Foundation. Retrieved March 15, 2013.
  2. ^ Rodrigues, Natércia d.N.; Cole-Filipiak, Neil C.; Turner, Matt A.P.; Krokidi, Konstantina; Thornton, Georgia L.; Richings, Gareth W.; Hine, Nicholas D.M.; Stavros, Vasilios G. (2018). "Substituent position effects on sunscreen photodynamics: A closer look at methyl anthranilate". Chemical Physics. 515: 596–602. Bibcode:2018CP....515..596R. doi:10.1016/j.chemphys.2018.08.001.
  3. ^ Rodrigues, N.D.N.; Cole-Filipiak, N.C.; Horbury, M.D.; Staniforth, M.; Karsili, T.N.V.; Peperstraete, Y.; Stavros, V.G. (2018). "Photophysics of the sunscreen ingredient menthyl anthranilate and its precursor methyl anthranilate: A bottom-up approach to photoprotection". Journal of Photochemistry and Photobiology A: Chemistry. 353: 376–384. Bibcode:2018JPPA..353..376R. doi:10.1016/j.jphotochem.2017.11.042.