Bisoctrizole

Title: Bisoctrizole
CAS Registry Number: 103597-45-1
CAS Name: 2,2¢-Methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol]
Additional Names: MBBT
Trademarks: Tinosorb M (Ciba); Tinuvin 360 (Ciba)
Molecular Formula: C41H50N6O2
Molecular Weight: 658.87
Percent Composition: C 74.74%, H 7.65%, N 12.76%, O 4.86%
Literature References: UV-A filter with dual mechanism of action. Photostable organic molecule with broad UV absorption; microfine structure causes light scattering and reflection. Prepn and use in light stabilizer formulations: N. Kubota, A. Nishimura, EP 180992; eidem, US 4681905 (1986, 1987 both to Adeka Argus). Light stabilization of polymers: G. Rytz et al., Angew. Makromol. Chem. 247, 213 (1997). Skin photoprotection study: C. Gélis et al., Photodermatol. Photoimmunol. Photomed. 19, 242 (2003). HPLC determn in suncare formulations: C. G. Smyrniotakis, H. A. Archontaki, J. Chromatogr. A 1031, 319 (2004). UV attenuating properties of microparticles: B. Herzog et al., J. Colloid Interface Sci. 276, 354 (2004).
Properties: Slightly yellow powder, mp 195°. Flash pt: >200°C. d20 1.2. Vapor pressure (25°): 6´10-13 Pa. Soly at 20° (%w/w): water < 0.001; acetone 0.05; chloroform 100; n-hexane 0.03; methylene chloride 75; toluene 34. Absorption max (chloroform): 308, 349 nm (e 31895). Absorption max (n-heptane): 348 nm (e 31600).
Melting point: mp 195°
Flash point: Flash pt: >200°C
Absorption maximum: Absorption max (chloroform): 308, 349 nm (e 31895); Absorption max (n-heptane): 348 nm (e 31600)
Density: d20 1.2
Use: Light stabilizer in polymers and resins.
Therap-Cat: Ultraviolet screen.
Keywords: Ultraviolet Screen.
Bisoprolol Bisoxatin Acetate Bisphenol B Bispyribac Bitertanol

Bisoctrizole
Bisoctrizole
Identifiers
CAS number 103597-45-1 N
PubChem 3571576
ChemSpider 2808671 YesY
UNII 8NT850T0YS YesY
Jmol-3D images Image 1
Properties
Molecular formula C41H50N6O2
Molar mass 658.88 g/mol
Melting point 195.7 °C
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Bisoctrizole (INN[1][2]/USAN,[3] marketed by BASF as Tinosorb M, INCI methylene bis-benzotriazolyl tetramethylbutylphenol) is a benzotriazole-based organic compound that is added to sunscreens to absorb UV rays.

Bisoctrizole is a broad-spectrum ultraviolet radiation absorber, absorbing UVB as well as UVA rays. It also reflects and scatters UV. Bisoctrizole is a hybrid UV absorber, the only organic UV filter produced and microfine organic particles (< 200 nm),[4][5] like microfine zinc oxide and titanium dioxide. Where other organic UV absorbers need to be dissolved in either the oil or water phase, bisoctrizole dissolves poorly in both.

Bisoctrizole is added to the water phase of a sunscreen as a 50% suspension, whereas mineral micropigments are usually added to the oil phase. The bisoctrizole particles are stabilized by the surfactant decyl glucoside.

Bisoctrizole shows very little photodegradation and has a stabilizing effect on other UV absorbers, octyl methoxycinnamate (octinoxate) in particular.

When formulated into a sunscreen, bisoctrizole has minimal skin penetration.[6] Unlike some other organic sunscreen actives, it shows no estrogenic effects in vitro.[7]

Bisoctrizole is not approved by the U.S. Food and Drug Administration (FDA), but is approved in the EU and other parts of the world.[8][9][10]