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Bemotrizinol

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Bemotrizinol
Names
Preferred IUPAC name
2,2′-[6-(4-Methoxyphenyl)-1,3,5-triazine-2,4-diyl]bis{5-[(2-ethylhexyl)oxy]phenol}
Other names
Tinosorb S
Bis-ethylhexyloxyphenol methoxyphenyl triazine
Anisotriazine
Identifiers
3D model (JSmol)
Abbreviations BEMT
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.109.468 Edit this at Wikidata
EC Number
  • 606-111-6
UNII
  • InChI=1S/C38H49N3O5/c1-6-10-12-26(8-3)24-45-30-18-20-32(34(42)22-30)37-39-36(28-14-16-29(44-5)17-15-28)40-38(41-37)33-21-19-31(23-35(33)43)46-25-27(9-4)13-11-7-2/h14-23,26-27,42-43H,6-13,24-25H2,1-5H3 checkY
    Key: XVAMCHGMPYWHNL-UHFFFAOYSA-N checkY
  • InChI=1/C38H49N3O5/c1-6-10-12-26(8-3)24-45-30-18-20-32(34(42)22-30)37-39-36(28-14-16-29(44-5)17-15-28)40-38(41-37)33-21-19-31(23-35(33)43)46-25-27(9-4)13-11-7-2/h14-23,26-27,42-43H,6-13,24-25H2,1-5H3
    Key: XVAMCHGMPYWHNL-UHFFFAOYAK
  • CCC(CCCC)COc4ccc(c1nc(nc(n1)c2ccc(cc2O)OCC(CC)CCCC)c3ccc(OC)cc3)c(O)c4
Properties
C38H49N3O5
Molar mass 627.826 g·mol−1
Hazards
GHS labelling:
H413
P273, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

Bemotrizinol (INN, USAN, INCI name bis-ethylhexyloxyphenol methoxyphenyl triazine, BEMT;[1][2][3] marketed as Escalol S, Parsol Shield, and Tinosorb S) is an oil-soluble organic compound that is added to sunscreens to absorb UV rays.

Bemotrizinol is a broad-spectrum UV absorber, absorbing both UVB and UVA rays. It has two absorption peaks, 310 and 340 nm.[4] It is highly photostable. Even after 50 MEDs (minimal erythemal doses), 98.4% remains intact. It helps prevent the photodegradation of other sunscreen actives like avobenzone.[5] Tinosorb S Aqua, recently developed by BASF, is bemotrizinol in a PMMA matrix dispersed in water. This makes it possible to add bemotrizinol to the water phase.[6]

Bemotrizinol has strong synergistic effects on the SPF when formulated with bisoctrizole, ethylhexyl triazone, or iscotrizinol.[7] It is the most effective UV absorber available measured by SPF, based on the maximum concentration permitted by European legislation.[8]

It has been approved in the European Union since 2000,[9] and some other parts of the world,[which?] including Australia.[10][11] In June 2026, bemotrizinol was approved for use in sunscreens in the United States.[12]

Unlike some other organic sunscreen actives, it shows no estrogenic effects in vitro.[13]

References

[edit]
  1. ↑ "Statement on a nonproprietary name adopted by the USAN Council: BEMOTRIZINOL". Archived from the original on 29 September 2007. Retrieved 19 August 2007.
  2. ↑ "International Nonproprietary Names for Pharmaceutical Substances (INN): Proposed International Nonproprietary Names: List 92" (PDF). WHO Drug Information. 18 (4). 2004. Archived from the original (PDF) on 19 September 2007. Retrieved 19 September 2008.
  3. ↑ "International Nonproprietary Names for Pharmaceutical Substances (INN): Recommended INN: List 54 / Recommended International Nonproprietary Names: List 54" (PDF). WHO Drug Information. 19 (3). 2005. Archived from the original (PDF) on 16 October 2009. Retrieved 28 September 2008.
  4. ↑ Vielhaber G, Grether-Beck S, Koch O, Johncock W, Krutmann J (March 2006). "Sunscreens with an absorption maximum of > or =360 nm provide optimal protection against UVA1-induced expression of matrix metalloproteinase-1, interleukin-1, and interleukin-6 in human dermal fibroblasts". Photochem Photobiol Sci. 5 (3): 275–82. doi:10.1039/b516702g. PMID 16520862.
  5. ↑ Chatelain E, Gabard B (September 2001). "Photostabilization of Butyl methoxydibenzoylmethane (Avobenzone) and Ethylhexyl methoxycinnamate by Bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter". Photochem Photobiol. 74 (3): 401–6. doi:10.1562/0031-8655(2001)074<0401:POBMAA>2.0.CO;2 (inactive 16 July 2025). PMID 11594052. S2CID 29879472.{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)
  6. ↑ "Tinosorb® S Aqua / New UV Filter Technology for the Water Phase" (PDF). BASF. Archived from the original (PDF) on 5 September 2011. Retrieved 15 April 2011.
  7. ↑ "BASF – Global Home" (PDF). [dead link]
  8. ↑ Couteau C, Pommier M, Paparis E, Coiffard LJ (June 2007). "Study of the efficacy of 18 sun filters authorized in European Union tested in vitro". Pharmazie. 62 (6): 449–52. doi:10.1691/ph.2007.6.6247. PMID 17663193.
  9. ↑ Osterwalder U, Luther H, Herzog B (2001). "Über den Lichtschutzfaktor hinaus - neue effiziente und photostabile UVA-Filter". Bundesgesundheitsblatt - Gesundheitsforschung - Gesundheitsschutz. 44 (5): 463–470. doi:10.1007/s001030170019. S2CID 36985446.
  10. ↑ "NEW-WAVE SUNSCREENS: Active ingredient makers are frustrated by the long list of sunscreens and UV-A testing protocols that are still awaiting FDA decisions". Chemical & Engineering News. 83 (15): 18–22. 11 April 2005. doi:10.1021/cen-v083n015.p018.
  11. ↑ "Australian Regulatory Guidelines for OTC Medicines - Chapter 10" (PDF). Archived from the original (PDF) on 31 August 2007.
  12. ↑ "FDA Expands Sunscreen Options for the First Time in 20 Years" (Press release). U.S. Food and Drug Administration (FDA). 9 June 2026. Retrieved 9 June 2026. Public Domain This article incorporates text from this source, which is in the public domain.
  13. ↑ Ashby J, Tinwell H, Plautz J, Twomey K, Lefevre PA (December 2001). "Lack of binding to isolated estrogen or androgen receptors, and inactivity in the immature rat uterotrophic assay, of the ultraviolet sunscreen filters Tinosorb M-active and Tinosorb S". Regul Toxicol Pharmacol. 34 (3): 287–91. doi:10.1006/rtph.2001.1511. PMID 11754532.
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