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2D Structure
Also known as: 103597-45-1, Tinosorb m, Ultraviolet absorbent uv-360, Mbbt, Uv-360, Fat 75'634
Molecular Formula
C41H50N6O2
Molecular Weight
658.9  g/mol
InChI Key
FQUNFJULCYSSOP-UHFFFAOYSA-N
FDA UNII
8NT850T0YS

Bisoctrizole, or methylene bis-benzotriazolyl tetramethylbutylphenol, is a broad-spectrum organic UV filter that is marketed as Tinosorb M. It is a benzotriazole-based organic compound that absorbs, reflects, and scatters both UV-A and UV-B rays. Bisoctrizole is not approved by the FDA, but is approved in the EU and other parts of the world as a UV-filter in sunscreens, day care products and skin lightening products at a maximum concentration of 10%.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(benzotriazol-2-yl)-6-[[3-(benzotriazol-2-yl)-2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)phenyl]methyl]-4-(2,4,4-trimethylpentan-2-yl)phenol
2.1.2 InChI
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
2.1.3 InChI Key
FQUNFJULCYSSOP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)(C)CC(C)(C)C1=CC(=C(C(=C1)N2N=C3C=CC=CC3=N2)O)CC4=C(C(=CC(=C4)C(C)(C)CC(C)(C)C)N5N=C6C=CC=CC6=N5)O
2.2 Other Identifiers
2.2.1 UNII
8NT850T0YS
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Methylene Bis-benzotriazolyl Tetramethylphenol

2. Tinosorb M

2.3.2 Depositor-Supplied Synonyms

1. 103597-45-1

2. Tinosorb M

3. Ultraviolet Absorbent Uv-360

4. Mbbt

5. Uv-360

6. Fat 75'634

7. Milestab-360

8. Tinuvin-360

9. Nsc-759873

10. 8nt850t0ys

11. 2-(benzotriazol-2-yl)-6-[[3-(benzotriazol-2-yl)-2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)phenyl]methyl]-4-(2,4,4-trimethylpentan-2-yl)phenol

12. 2,2'-methylenebis[6-(benzotriazol-2-yl)-4-tert-octylphenol]

13. Fat-75634

14. Ncgc00167544-01

15. 6,6'-methylenebis(2-(2h-benzo[d][1,2,3]triazol-2-yl)-4-(2-methylheptan-2-yl)phenol)

16. Phenol, 2,2'-methylenebis(6-(2h-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)-

17. Phenol, 2,2'-methylenebis[6-(2h-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)-

18. Bisoctrizole [usan]

19. 2,2'-methylenebis

20. Bisoctrizole (usp/inn)

21. Bisoctrizole [mi]

22. Bisoctrizole [inn]

23. Dsstox_cid_26703

24. Dsstox_rid_81837

25. Unii-8nt850t0ys

26. Dsstox_gsid_46703

27. Schembl39191

28. Bisoctrizole [mart.]

29. Ultraviolet Absorber Uv-360

30. Bisoctrizole [usp-rs]

31. Bisoctrizole [who-dd]

32. Bisoctrizole [usan:usp:inn]

33. Chembl2104957

34. Dtxsid2046703

35. Bisoctrizole, Analytical Standard

36. Chebi:135865

37. Hms3264f09

38. Pharmakon1600-01503866

39. Bcp29317

40. Hy-b0897

41. Bisoctrizole [usp Monograph]

42. Tox21_112541

43. Mfcd00192289

44. Nsc759873

45. S4551

46. Uv 360

47. Zinc11677911

48. Akos015895745

49. Db11262

50. Nsc 759873

51. Ncgc00167544-02

52. Cas-103597-45-1

53. Ft-0642535

54. M1259

55. A14939

56. D03249

57. Ec 403-800-1

58. Ab01563348_01

59. A800767

60. Sr-01000883719

61. Tinosorb M Pound>>ultraviolet Absorbent Uv-360

62. J-525148

63. Q4918369

64. Sr-01000883719-1

65. Bis-[2-hydroxy-5-t-octyl-3-(benzotriazol-2-yl)-phe

66. Bis-[2-hydroxy-5-t-octyl-3-(benzotriazol-2-yl)-phenyl) Methane

67. Bis[3-(benzotriazol-2-yl)-2-hydroxy-5-tert-octylphenyl]methane

68. Bisoctrizole, United States Pharmacopeia (usp) Reference Standard

69. Methylene Bis-benzotriazolyl Tetramethylbutylphenol [inci]

70. 2,2'-methylene-bis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-yl-phenol]

71. 2,2'-methylenebis(6-(2-benzotriazolyl)-4-(1,1,3,3-tetramethylbutyl)phenol

72. 2,2'-methylenebis(6-(2-benzotriazolyl)-4-(1,1,3,3-tetramethylbutyl)phenol)

73. 2,2'-methylenebis(6-(2hbenzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol]

74. 2,2'-methylenebis[6-(2h-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], 99%

75. Bisoctrizole, Pharmaceutical Secondary Standard; Certified Reference Material

76. 2-(2h-1,2,3-benzotriazol-2-yl)-6-{[3-(2h-1,2,3-benzotriazol-2-yl)-2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)phenyl]methyl}-4-(2,4,4-trimethylpentan-2-yl)phenol

77. 3-(benzotriazol-2-yl)-2-[[2-(benzotriazol-2-yl)-6-hydroxy-4-(1,1,3,3-tetramethylbutyl)phenyl]methyl]-5-(1,1,3,3-tetramethylbutyl)phenol;2,2'-methylenebis[6-(2h-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol]

78. 6,6'-bis(2h-1,2,3-benzotriazol-2-yl)-4,4'-bis(2,4,4-trimethylpentan-2-yl)- 2,2'-methylenebiphenol

79. Phenol, 2,2'-methylenebis(6-(2h-benzotrialzol-2-yl)-4-(1,1,3,3-tetramethylbutyl)-

2.4 Create Date
2005-09-09
3 Chemical and Physical Properties
Molecular Weight 658.9 g/mol
Molecular Formula C41H50N6O2
XLogP312.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count10
Exact Mass658.39952486 g/mol
Monoisotopic Mass658.39952486 g/mol
Topological Polar Surface Area102 Ų
Heavy Atom Count49
Formal Charge0
Complexity989
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Indicated for use as a sunscreen agent in cosmetic products.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Under the conditions of _in vitro_ androgen competitive binding assay, bisoctrizole displayed no intrinsic androgenic, estrogenic, nor uterotrophic activity.


5.2 Absorption, Distribution and Excretion

Absorption

A rat and human dermal penetration study _in vitro_ indicates that bisoctrizole displays minimal absorption through the skin, with only about 0.01% and 0.06 % of the applied dose penetration through the human and rat skin membrane, respectively. Despite low dermal uptake, potential bioaccumulation after repeated skin applications cannot be excluded.


Route of Elimination

No pharmacokinetic data available.


Volume of Distribution

No pharmacokinetic data available.


Clearance

No pharmacokinetic data available.


5.3 Metabolism/Metabolites

No pharmacokinetic data available.


5.4 Biological Half-Life

No pharmacokinetic data available.


5.5 Mechanism of Action

Bisoctrizole is an organic UV-A filter that absorbs both UV-A and UV-B rays.