Bisoctrizole

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Bisoctrizole
Skeletal formula of bisoctrizole
Space-filling model of the bisoctrizole molecule
Names
IUPAC name
2,2′-methanediylbis[6-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol]
Identifiers
103597-45-1 N
ChEMBL ChEMBL2104957 N
ChemSpider 2808671 YesY
Jmol 3D model Interactive image
PubChem 3571576
UNII 8NT850T0YS YesY
  • 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 YesY
    Key: FQUNFJULCYSSOP-UHFFFAOYSA-N YesY
  • 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 YesYN ?)
Infobox references

Bisoctrizole (INN[1][2]/USAN,[3] marketed by BASF as Tinosorb M and by MPI as Milestab 360, 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]

References

  1. ↑ http://whqlibdoc.who.int/druginfo/18_4_2004_INN92.pdf
  2. ↑ http://whqlibdoc.who.int/druginfo/INN_2005_list54.pdf
  3. ↑ http://www.ama-assn.org/ama1/pub/upload/mm/365/bisoctrizol.doc
  4. ↑ Ciba TINOSORB M
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Manage Account - Modern Medicine
  9. ↑ CL1976L0768EN0150010.0001 1..107
  10. ↑ Australian Regulatory Guidelines for OTC Medicines - Chapter 10

External links

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