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Bisoctrizole

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Bisoctrizole
Skeletal formula of bisoctrizole
Space-filling model of the bisoctrizole molecule
Names
Preferred IUPAC name
2,2′-Methylenebis[6-(2H-1,2,3-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol]
Other names
UV-360
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.100.550Edit this at Wikidata
UNII
  • InChI=1S/C41H50N6O2/c1-38(2,3)24-40(7,8)28-20-26(36(48)34(22-28)46-42-30-15-11-12-16-31(30)43-46)19-27-21-29(41(9,10)25-39(4,5)6)23-35(37(27)49)47-44-32-17-13-14-18-33(32)45-47/h11-18,20-23,48-49H,19,24-25H2,1-10H3 checkY
    Key: FQUNFJULCYSSOP-UHFFFAOYSA-N checkY
  • InChI=1/C41H50N6O2/c1-38(2,3)24-40(7,8)28-20-26(36(48)34(22-28)46-42-30-15-11-12-16-31(30)43-46)19-27-21-29(41(9,10)25-39(4,5)6)23-35(37(27)49)47-44-32-17-13-14-18-33(32)45-47/h11-18,20-23,48-49H,19,24-25H2,1-10H3
    Key: FQUNFJULCYSSOP-UHFFFAOYAP
  • n1c6ccccc6nn1c2cc(cc(c2O)Cc5cc(cc(n3nc4ccccc4n3)c5O)C(C)(C)CC(C)(C)C)C(C)(C)CC(C)(C)C
Properties
C41H50N6O2
Molar mass658.88 g/mol
Melting point195.7 °C (384.3 °F; 468.8 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Bisoctrizole (INN[1]/USAN,[2] marketed byBASF asTinosorb M, by DSM Nutritional Products asParsol Max, by Everlight Chemical asEversorb M, and by MPI asMilestab 360,INCI methylene bis-benzotriazolyl tetramethylbutylphenol) is aphenolic benzotriazole that is added tosunscreens to absorbUV rays.[3] It is a broad-spectrumultraviolet radiation absorber, absorbing UVB as well as UVA rays.[3] It also reflects and scatters UV.[citation needed]

Bisoctrizole is what is termed a hybrid UV absorber, which has been described as an organic UV filter produced in microfine organic particles (< 200 nm),[verification needed][4][better source needed][5][non-primary source needed] like microfinezinc oxide andtitanium dioxide.[dubiousdiscuss][citation needed] Where other organic UV absorbers dissolved in either the oily or aqueous phases, bisoctrizole dissolves poorly in both.[citation needed]

Hence, bisoctrizole is formulated in sunscreen preparations as a 50%suspension, the absorber added to the water phase,[contradictory] and mineral micropigments usually added to the oil phase.[citation needed] The bisoctrizole particles are stabilized by thesurfactantdecyl glucoside.[citation needed] The compound shows very littlephotodegradation, and has a stabilizing effect on other UV absorbers,octyl methoxycinnamate (octinoxate) in particular.[citation needed]

In primary research reports, bisoctrizole has been reported to minimally penetrate skin,[6][non-primary source needed] and has been described as lackingestrogenic effectsin vitro.[7][non-primary source needed]

Bisoctrizole has not yet been approved by theU.S. Food and Drug Administration (FDA),[citation needed] but is approved in the EU and other parts of the world.[8][better source needed][9][10][full citation needed]

References

[edit]
  1. ^WHO Staff (2005)."Recommended International Nonproprietary Names: List 54, International Nonproprietary Names for Pharmaceutical Substances (INN) [Entry 'bisoctrizolum']".WHO Drug Information.19 (3). Archived fromthe original on October 19, 2009. RetrievedJuly 5, 2022.
  2. ^National Library of Medicine Staff (July 5, 2022)."Bisoctrizole".Chem.NLM.NIH.gov. RetrievedJuly 5, 2022.
  3. ^abLatha, MS; Martis, Jacintha; Shobha, V; Shinde, Rutuja Sham; Bangera, Sudhakar; Krishnankutty, Binny; Bellary, Shantala; Varughese, Sunoj; Rao, Prabhakar; Naveen Kumar, B.R. (January 2013)."Sunscreening Agents A Review".Journal of Clinical and Aesthetic Dermatology.6 (1):16–26.PMC 3543289.PMID 23320122.
  4. ^Ciba Staff (July 5, 2022)."TINOSORB® M, Broad-spectrum UV Filter for the Water Phase".BASF.com. RetrievedJuly 5, 2022.
  5. ^Herzog, B.; Mongiat, S.; Deshayes, C.; Neuhaus, M.; Sommer, K.; Mantler, A. (2002). "In vivo and in vitro assessment of UVA protection by sunscreen formulations containing either butyl methoxy dibenzoyl methane, methylene bis-benzotriazolyl tetramethylbutylphenol, or microfine ZnO".International Journal of Cosmetic Science.24 (3):170–85.doi:10.1046/j.1467-2494.2002.00137.x.PMID 18498509.S2CID 37553401.[non-primary source needed]
  6. ^Mavon A, Miquel C, Lejeune O, Payre B, Moretto P (2007). "In vitro percutaneous absorption and in vivo stratum corneum distribution of an organic and a mineral sunscreen".Skin Pharmacol Physiol.20 (1):10–20.doi:10.1159/000096167.PMID 17035717.S2CID 22041398.[non-primary source needed]
  7. ^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.[non-primary source needed]
  8. ^Kapes, Beth (July 1, 2005)."Docs Rally for Better Sun Protection".ModernMedicine.com. Archived fromthe original on October 9, 2007. RetrievedJuly 5, 2022.
  9. ^"Eur-Lex.Europa.eu PDF"(PDF). Archived fromthe original(PDF) on 2008-08-14. Retrieved2007-08-19.
  10. ^Australian Regulatory Guidelines for OTC Medicines, Chapter 10.[full citation needed]

External links

[edit]
Sunscreening agentscurrently approved by one or more agencies (e.g.US FDA,SCCS,TGA)
  • UVA: 400–315 nm
  • UVB: 315–290 nm
UVA filters
UVB filters
UVA+UVB filters
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