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Bisoctrizole

Chemical compound From Wikipedia, the free encyclopedia

Bisoctrizole

Bisoctrizole (INN[1]/USAN,[2] marketed by BASF as Tinosorb M, by DSM Nutritional Products as Parsol Max , by Everlight Chemical as Eversorb M, and by MPI as Milestab 360, INCI methylene bis-benzotriazolyl tetramethylbutylphenol) is a phenolic benzotriazole that is added to sunscreens to absorb UV rays.[3] It is a broad-spectrum ultraviolet radiation absorber, absorbing UVB as well as UVA rays.[3] It also reflects and scatters UV.[citation needed]

Quick Facts Names, Identifiers ...
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 InfoCard 100.100.550
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 Y
    Key: FQUNFJULCYSSOP-UHFFFAOYSA-N Y
  • 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 mass 658.88 g/mol
Melting point 195.7 °C (384.3 °F; 468.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Close

Bisoctrizole is what is termed is 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 microfine zinc oxide and titanium dioxide.[dubious discuss][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 the surfactant decyl glucoside.[citation needed] The compound shows very little photodegradation, 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 lacking estrogenic effects in vitro.[7][non-primary source needed]

Bisoctrizole has not yet been approved by the U.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

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