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Revision as of 13:57, 15 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - updated 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit Latest revision as of 04:19, 2 November 2024 edit undoCitation bot (talk | contribs)Bots5,458,626 edits Removed parameters. | Use this bot. Report bugs. | #UCB_CommandLineTag: Manual revert 
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{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 401815812 | verifiedrevid = 424200371
| ImageFile = Bemotrizinol.png | ImageFile = Bemotrizinol 2D-Structural Formula V1.svg
| ImageSize = | ImageSize = 300
| IUPACName = 2,2′- bis{5-phenol} | PIN = 2,2′-bis{5-phenol}
| OtherNames = Tinosorb S<br>Bis-ethylhexyloxyphenol methoxyphenyl triazine<br>Anisotriazine | OtherNames = Tinosorb S<br>Bis-ethylhexyloxyphenol methoxyphenyl triazine<br>Anisotriazine
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| Abbreviations = BEMT | Abbreviations = BEMT
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=10645286 | ChemSpiderID=10645286
| EINECS = | EINECS = 606-111-6
| PubChem = | PubChem = 11954320
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2104956
| SMILES = CCC(CCCC)COc4ccc(c1nc(nc(n1)c2ccc(cc2O)OCC(CC)CCCC)c3ccc(OC)cc3)c(O)c4 | SMILES = CCC(CCCC)COc4ccc(c1nc(nc(n1)c2ccc(cc2O)OCC(CC)CCCC)c3ccc(OC)cc3)c(O)c4
| 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 | 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
| RTECS = | RTECS =
| MeSHName = | MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = | ChEBI = 135857
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = | KEGG =
}}
| ATCCode_prefix =
⚫ |Section2={{Chembox Properties
| ATCCode_suffix =
| C=38 | H=49 | N=3 | O=5
| ATC_Supplemental = }}
⚫ | Section2 = {{Chembox Properties
| Formula = C<sub>38</sub>H<sub>49</sub>N<sub>3</sub>O<sub>5</sub>
| MolarMass = 627.81 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| Melting_notes = | MeltingPt_notes =
| BoilingPt = | BoilingPt =
| Boiling_notes = | BoilingPt_notes =
| Solubility = | Solubility =
| SolubleOther = | SolubleOther =
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| pKa = | pKa =
| pKb = }} | pKb = }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| EUClass =
| EUIndex =
| MainHazards = | MainHazards =
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| NFPA-O = | NFPA-S =
| RPhrases = | GHSPictograms =
| SPhrases = | GHSSignalWord =
| RSPhrases = | GHS_ref =
| HPhrases = {{H-phrases|413}}
| PPhrases = {{P-phrases|273|501}}
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| ExploLimits = | ExploLimits =
| PEL = }} | PEL = }}
}} }}

'''Bemotrizinol''' (]<ref>http://whqlibdoc.who.int/druginfo/18_4_2004_INN92.pdf</ref><ref>http://whqlibdoc.who.int/druginfo/INN_2005_list54.pdf</ref>/],<ref>http://www.ama-assn.org/ama1/pub/upload/mm/365/bemotrizinol.doc</ref> ] bis-ethylhexyloxyphenol methoxyphenyl triazine) is an oil-soluble ] that is added to ]s to absorb ] rays. It is marketed as '''Tinosorb S''' by ] and as '''Escalol S''' by International Specialty Products. A recent development is Tinosorb S Aqua, which is bemotrizinol in a ] matrix dispersed in water. This makes it possible to add bemotrizinol to the water phase.<ref>Tinosorb S Aqua info</ref>
'''Bemotrizinol''' (]<ref>{{Cite web | url=http://whqlibdoc.who.int/druginfo/18_4_2004_INN92.pdf | title=Home | access-date=2008-09-19 | archive-url=https://web.archive.org/web/20070919195045/http://whqlibdoc.who.int/druginfo/18_4_2004_INN92.pdf | archive-date=2007-09-19 | url-status=dead }}</ref><ref>{{Cite web | url=http://whqlibdoc.who.int/druginfo/INN_2005_list54.pdf | title=Home | access-date=2008-09-28 | archive-url=https://web.archive.org/web/20091016221356/http://whqlibdoc.who.int/druginfo/INN_2005_list54.pdf | archive-date=2009-10-16 | url-status=dead }}</ref>/],<ref>{{Cite web |url=http://www.ama-assn.org/ama1/pub/upload/mm/365/bemotrizinol.doc |title=Archived copy |access-date=2007-08-19 |archive-url=https://web.archive.org/web/20070929140612/http://www.ama-assn.org/ama1/pub/upload/mm/365/bemotrizinol.doc |archive-date=2007-09-29 |url-status=dead }}</ref> ] bis-ethylhexyloxyphenol methoxyphenyl triazine) is an oil-soluble ] that is added to ]s to absorb ] rays. It is marketed as Parsol Shield, Tinosorb S, and Escalol S.


Bemotrizinol is a broad-spectrum UV absorber, absorbing UVB as well as UVA rays. It has two absorption peaks, 310 and 340&nbsp;nm.<ref>{{cite journal Bemotrizinol is a broad-spectrum UV absorber, absorbing UVB as well as UVA rays. It has two absorption peaks, 310 and 340&nbsp;nm.<ref>{{cite journal
| title=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 | title=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
| year=2006| month=March| pmid=16520862 | date=March 2006| pmid=16520862
| author=Vielhaber G, Grether-Beck S, Koch O, Johncock W, Krutmann J | vauthors=Vielhaber G, Grether-Beck S, Koch O, Johncock W, Krutmann J
| journal= Photochem Photobiol Sci| volume=5 | pages=275&ndash;82 | journal= Photochem Photobiol Sci| volume=5 | pages=275&ndash;82
| doi=10.1039/b516702g | doi=10.1039/b516702g
| issue=3 | issue=3
}}</ref> It is highly photostable. Even after 50 ]s (minimal erythemal doses), 98.4% remains intact. It helps prevent the ] of other sunscreen actives like ].<ref>{{cite journal }}</ref> It is highly photostable. Even after 50 MEDs (minimal ] doses), 98.4% remains intact. It helps prevent the ] of other sunscreen actives like ].<ref>{{cite journal
| title = Photostabilization of Butyl methoxydibenzoylmethane (Avobenzone) and Ethylhexyl methoxycinnamate by Bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter | title = Photostabilization of Butyl methoxydibenzoylmethane (Avobenzone) and Ethylhexyl methoxycinnamate by Bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter
| year = 2001| month=September| pmid=11594052 | date=September 2001| pmid=11594052
| author = Chatelain E, Gabard B. | vauthors = Chatelain E, Gabard B
| journal = Photochem Photobiol| volume=74 | pages=401–6 | journal = Photochem Photobiol| volume=74 | pages=401–6
| doi = 10.1562/0031-8655(2001)074<0401:POBMAA>2.0.CO;2 | doi = 10.1562/0031-8655(2001)074<0401:POBMAA>2.0.CO;2
| issue = 3 | issue = 3
| s2cid=29879472}}</ref> Tinosorb S Aqua, recently developed by ], is bemotrizinol in a ] matrix dispersed in water. This makes it possible to add bemotrizinol to the water phase.<ref>{{Cite web|url=http://www.basf-chemtrade.de/images/stories/broschueren/PCI/100413_tinosorb_s_aqua.pdf|title=basf-chemtrade.de|website=www.basf-chemtrade.de|access-date=2011-04-15|archive-url=https://web.archive.org/web/20110905022305/http://www.basf-chemtrade.de/images/stories/broschueren/PCI/100413_tinosorb_s_aqua.pdf|archive-date=2011-09-05|url-status=dead}}</ref>
}}</ref>


Bemotrizinol has strong ] effects on the SPF when formulated with ], ] or ].<ref>http://www.ciba.com/tinosorb-s_brochure.pdf</ref> It is the most effective UV absorber available measured by SPF, based on the maximum concentration permitted by European legislation.<ref>{{cite journal Bemotrizinol has strong ] effects on the SPF when formulated with ], ] or ].<ref>{{Cite web | url=http://www.ciba.com/tinosorb-s_brochure.pdf | title=BASF – Global Home}} {{dead link|date=September 2019}}</ref> It is the most effective UV absorber available measured by SPF, based on the maximum concentration permitted by European legislation.<ref>{{cite journal
| title = Study of the efficacy of 18 sun filters authorized in European Union tested in vitro | title = Study of the efficacy of 18 sun filters authorized in European Union tested in vitro
| year = 2007| month=June| pmid=17663193 | date=June 2007| pmid=17663193
| author = Couteau C, Pommier M, Paparis E, Coiffard LJ | vauthors = Couteau C, Pommier M, Paparis E, Coiffard LJ
| journal = Pharmazie| volume=62 | pages=449–52 | journal = Pharmazie| volume=62 | pages=449–52
| issue = 6 | issue = 6
| doi=10.1691/ph.2007.6.6247
}}</ref> }}</ref>


Bemotrizinol is not approved by the United States ], but is approved in the European Union since the year 2000<ref>.</ref> and other parts of the world, including Australia.<ref>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'', April 11, 2005, Volume 83, Number 15, pp. 18–22. </ref><ref></ref> As of 2022,<ref>{{cite news |last1=Mull |first1=Amanda |title=You're Not Allowed to Have the Best Sunscreens in the World |url=https://www.theatlantic.com/technology/archive/2022/07/us-sunscreen-ingredients-outdated-technology-better-eu-asia/661433/ |access-date=2 July 2022 |work=The Atlantic |date=1 July 2022 |language=en}}</ref> bemotrizinol is not approved by the United States ] for use in sunscreens, but has been approved in the European Union since 2000<ref>{{cite journal | doi = 10.1007/s001030170019 | title = Über den Lichtschutzfaktor hinaus - neue effiziente und photostabile UVA-Filter | journal = Bundesgesundheitsblatt - Gesundheitsforschung - Gesundheitsschutz | volume = 44 | issue = 5 | pages = 463–470 | year = 2001 | last1 = Osterwalder | first1 = U. | last2 = Luther | first2 = H. | last3 = Herzog | first3 = B. | s2cid = 36985446 }}</ref> and some other parts of the world, including Australia.<ref>{{cite journal | title = 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 | journal = ] | date = April 11, 2005 | volume = 83 | issue = 15 | pages = 18–22 | url = http://pubs.acs.org/cen/coverstory/83/8315sunscreens.html | doi = 10.1021/cen-v083n015.p018 | url-access = subscription }}</ref><ref>{{Cite web|url=http://www.tga.gov.au/docs/pdf/argom_10.pdf|archiveurl=https://web.archive.org/web/20070831075404/http://tga.gov.au/docs/pdf/argom_10.pdf|url-status=dead|title=Australian Regulatory Guidelines for OTC Medicines - Chapter 10<!-- Bot generated title -->|archivedate=August 31, 2007}}</ref>


Unlike some other organic sunscreen actives, it shows no estrogenic effects ].<ref>{{cite journal| title=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| year=2001| month=December| pmid=11754532| author=Ashby J, Tinwell H, Plautz J, Twomey K, Lefevre PA| journal= Regul Toxicol Pharmacol| volume=34 | pages=287–91| doi=10.1006/rtph.2001.1511| issue=3}}</ref> Unlike some other organic sunscreen actives, it shows no estrogenic effects ].<ref>{{cite journal| title=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|date=December 2001| pmid=11754532| vauthors=Ashby J, Tinwell H, Plautz J, Twomey K, Lefevre PA| journal= ]| volume=34 | pages=287–91| doi=10.1006/rtph.2001.1511| issue=3}}</ref>


==References== ==References==
{{reflist}} {{reflist}}

==External links==
*


{{Sunscreening agents}} {{Sunscreening agents}}
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