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2D Structure
Also known as: 4065-45-6, Benzophenone-4, 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, Sungard, Benzophenone 4
Molecular Formula
C14H12O6S
Molecular Weight
308.31  g/mol
InChI Key
CXVGEDCSTKKODG-UHFFFAOYSA-N
FDA UNII
1W6L629B4K

Sulisobenzone is approved by the FDA in concentrations of up to 10% and in Canada, is approved by Health Canada at the same concentrations. It works to filter out both UVA and UVB rays, protecting the skin from sun UV damage. The UV-filter substance, sulisobenzone (BP-4) is widely used an ingredient in sunscreens and other personal care products,. It falls under the drug category of benzophenones. The benzophenones are a group of aromatic ketones that have both pharmaceutical and industrial applications. Benzophenones may be found organically in fruits such as grapes. Benzophenones are used as photoinitiators, fragrance enhancers, ultraviolet curing agents, and, occasionally, as flavor ingredients; they are also used in the manufacture of insecticides, agricultural chemicals, and pharmaceuticals and as an additive for plastics, coatings, and adhesives. As a group, benzophenones may be used to delay photodegradation or extend shelf life in toiletries and plastic surface coatings.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid
2.1.2 InChI
InChI=1S/C14H12O6S/c1-20-12-8-11(15)10(7-13(12)21(17,18)19)14(16)9-5-3-2-4-6-9/h2-8,15H,1H3,(H,17,18,19)
2.1.3 InChI Key
CXVGEDCSTKKODG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC1=C(C=C(C(=C1)O)C(=O)C2=CC=CC=C2)S(=O)(=O)O
2.2 Other Identifiers
2.2.1 UNII
1W6L629B4K
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-hydroxy-4-methoxybenzophenone-5-sulfonic Acid

2. 5-benzoyl-4-hydroxy-2-methoxybenzene Sulfonic Acid

3. Benzophenone-4

4. Bp-4 Benzophenone

5. Sulisobenzone, Monosodium Salt

6. Uval

2.3.2 Depositor-Supplied Synonyms

1. 4065-45-6

2. Benzophenone-4

3. 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic Acid

4. 2-hydroxy-4-methoxybenzophenone-5-sulfonic Acid

5. Sungard

6. Benzophenone 4

7. Uval

8. Seesorb 101s

9. Syntase 230

10. Uvinul Ms 40

11. Spectra-sorb Uv 284

12. Benzenesulfonic Acid, 5-benzoyl-4-hydroxy-2-methoxy-

13. Sulisobenzona

14. Sulisobenzonum

15. 2-hydroxy-4-methoxy-5-sulfobenzophenone

16. Ms 40

17. Uvinuc Ms 40

18. Sulfisobenzone

19. Uvinul Ms-40

20. Uvasorb S 5

21. Escalol 577

22. Viosorb 111

23. Uvinul D 5030

24. Nsc-60584

25. 1-phenol-4-sulfonic Acid, 2-benzoyl-5-methoxy-

26. 3-benzoyl-4-hydroxy-6-methoxybenzenesulfonic Acid

27. 2-benzoyl-5-methoxy-1-phenol-4-sulfonic Acid

28. 1w6l629b4k

29. Mfcd00024962

30. Nsc-760350

31. Uval Sodium Salt

32. Ncgc00159404-02

33. Ncgc00159404-04

34. Nsc 60584

35. Dsstox_cid_22436

36. Dsstox_rid_80023

37. Dsstox_gsid_42436

38. Uvinul Ms 40 Sodium Salt

39. Cyasorb Uv 284 Sodium Salt

40. Sulisobenzonum [inn-latin]

41. Sulisobenzona [inn-spanish]

42. Cas-4065-45-6

43. Nsc60584

44. Nsc654266

45. Hsdb 7422

46. Uvinul Ms-40 Substanz

47. 6628-37-1

48. Einecs 223-772-2

49. Brn 2889165

50. Unii-1w6l629b4k

51. Sulisobenzone [usan:usp:inn]

52. 5-benzoyl-4-hydroxy-2-methoxybenzene Sulfonic Acid

53. Sungard (tn)

54. Hmbs

55. Benzenesulfonic Acid, 5-benzoyl-4-hydroxy-2-methoxy-, Sodium Salt

56. Uval (*sodium Salt*)

57. Uvinul Ms40

58. Cbmicro_016354

59. Sulisobenzone (usp/inn)

60. Sulisobenzone [mi]

61. Ec 223-772-2

62. Sulisobenzone [inn]

63. 5-benzoyl-4-hydroxy-2-methoxybenzolsulfonsaeure

64. Spectra-sorb U.v. 284

65. Sulisobenzone [hsdb]

66. Sulisobenzone [usan]

67. Schembl16330

68. 2-hydroxy-4-methoxy-5-sulfonylbenzophenone(bp-4)

69. 5-benzoyl-4-hydroxy-2-methoxy-benzenesulfonic Acid

70. Mls004734662

71. Sulfisobenzone [vandf]

72. Sulisobenzone [mart.]

73. Benzophenone-4 [inci]

74. Sulisobenzone [usp-rs]

75. Sulisobenzone [who-dd]

76. Cyasorb Uv 284 (salt/mix)

77. Chembl2059073

78. Dtxsid2042436

79. 4-hydroxy-2-methoxy-5-(phenylcarbonyl)benzenesulfonic Acid

80. Chebi:135312

81. Sulisobenzone, Analytical Standard

82. Uvinul Ms 40 (*sodium Salt*)

83. Albb-025816

84. Cyasorb Uv 284 (*sodium Salt*)

85. Hy-b1162

86. Zinc1690324

87. Tox21_111639

88. Tox21_202332

89. Tox21_303469

90. S4652

91. Sulisobenzone [usp Monograph]

92. Akos015895600

93. Tox21_111639_1

94. Ccg-267557

95. Cs-4610

96. Db11185

97. Sulisobenzone (usan) (*sodium Salt*)

98. Ncgc00159404-03

99. Ncgc00159404-05

100. Ncgc00257488-01

101. Ncgc00259881-01

102. Ac-19869

103. As-12605

104. Smr001262265

105. Sy036839

106. 5-benzoyl-4-hydroxy-2-methoxy-besylic Acid

107. Db-049626

108. Ft-0612547

109. H0466

110. 2-benzoyl-5-methoxy-1-phenol-4-sulphonic Acid

111. D05964

112. F11240

113. A825218

114. J-509633

115. Q7636301

116. 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic Acid Ammoniate

117. 1-phenol-4-sulfonic Acid, 2-benzoyl-5-methoxy-, Sodium Salt

118. 4-hydroxy-2-methoxy-5-(oxo-phenylmethyl)benzenesulfonic Acid

119. Sulisobenzone, United States Pharmacopeia (usp) Reference Standard

120. 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic Acid, >=97.0% (hplc)

121. 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic Acid 100 Microg/ml In Methanol

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 308.31 g/mol
Molecular Formula C14H12O6S
XLogP32.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass308.03545927 g/mol
Monoisotopic Mass308.03545927 g/mol
Topological Polar Surface Area109 Ų
Heavy Atom Count21
Formal Charge0
Complexity462
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 Therapeutic Uses

Daily use of a sunscreen with a high SPF (greater than 15) on usually exposed skin is recommended for residents of areas of high ... /solar radiation/ who work outdoors or ... /enjoy/ regular outdoor recreation. Daily use of a sunscreen can reduce the cumulative ... /solar/ exposure that causes actinic keratoses and squamous-cell carcinoma.

IARC Working Group on the Evaluation of Cancer-Preventive Agents (2001) Sunscreens (IARC Handbooks of Cancer Prevention, Vol. 5), Lyon, IARC; Unit of Chemoprevention: Cancer-Preventive Effects of Sunscreens.


Sunscreen agents are indicated for the prevention of sunburn. In addition to limiting the skin's exposure to the sun, using sunscreen agents regularly when in the sun may help reduce long-term sun damage such as premature aging of the skin and skin cancer. /Sunscreen agents, topical; Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.


4.2 Drug Warning

The manufacturers of sunscreen preparations with propellants warn that concentrating and subsequently inhaling the fumes from these preparations may be harmful or fatal. /Propellants/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013


Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013


Little information is available regarding the safety of chronic sunscreen usage, but commercially available physical and chemical sunscreens appear to have a low incidence of adverse effects. Derivatives of PABA, benzophenone, cinnamic acid, and salicylate and 2-phenylbenzimidazole-5-sulfonic acid have caused skin irritation including burning, stinging, pruritus, and erythema on rare occasions. /Sunscreens/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013


Sunscreens should not be used as a means of extending the duration of solar exposure, such as prolonging sunbathing, and should not be used as a substitute for clothing on usually unexposed sites, such as the trunk and buttocks. /Sunscreens/

IARC Working Group on the Evaluation of Cancer-Preventive Agents (2001) Sunscreens (IARC Handbooks of Cancer Prevention, Vol. 5), Lyon, IARC; Unit of Chemoprevention: Cancer-Preventive Effects of Sunscreens.


For more Drug Warnings (Complete) data for SULISOBENZONE (11 total), please visit the HSDB record page.


4.3 Drug Indication

Sunscreening agents are used to prevent sunburn, actinic keratosis, and premature skin aging and to reduce the incidence of skin cancer.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Benzophenone sunscreens, applied topically, protect the skin from these harmful effects of ultraviolet light by chemically absorbing light energy (photons). Correct use of sunscreens serves to reduce the risk of sunburn. Sunscreen agents prevent the occurrence of squamous-cell carcinoma of the skin when used mainly during unintentional sun exposure. No conclusion can be drawn about the cancer-preventive activity of topical use of sunscreens against both basal-cell carcinoma and cutaneous melanoma. Use of sunscreens can extend the duration of intentional sun exposure, such as bathing in the sun.


5.2 Absorption, Distribution and Excretion

Absorption

Does not penetrate the skin to a large degree, but enhances the ability of other chemicals to penetrate.


Route of Elimination

This drug's main metabolite is excreted in urine conjugated with glucuronic acid. No p-hydroxybenzohydrol was detected in urine or feces, in a study of pharmacokinetics in rats.


Solvents used in sunscreen products affect the stability and binding of the drug to the skin; in general, alcoholic solvents allow for the most rapid and deepest epidermal penetration of sunscreens. It appears that sunscreen agents are absorbed by the intact epidermis to varying degrees. /Sunscreens/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013


5.3 Metabolism/Metabolites

Benzophenone's main metabolic pathway in the rabbit is by reduction to benzhydrol. A small amount (1%) is converted to p-hydroxybenzophenone following oral administration to rats.


5.4 Mechanism of Action

A surface coating of benzophenones decreases the amount of UV radiation absorbed by the skin by limiting the total amount of energy that reaches the skin. Benzophenone sunscreens, applied topically, protect the skin from these harmful effects of ultraviolet light by chemically absorbing light energy (photons). As this occurs, the benzophenone molecule becomes activated to higher energy levels. As the excited molecule returns to its ground state, the energy is released in the form of thermal energy. The hydroxyl group in the ortho position to the carbonyl group is believed to be a structural requirement for the benzophenones' absorption of UV light. This structural arrangement also contributes to the electronic stability of the molecule. Benzophenones absorb energy throughout the UV range, although the maximum UV absorbance is between 284 and 287 nm for the 2-hydroxybenzophenones.


Benzophenone sunscreens, applied topically, protect the skin from these harmful effects of ultraviolet light by chemically absorbing light energy (photons). As this occurs, the Benzophenone molecule becomes excited to higher energy levels. As the excited molecule returns to its ground state, the energy is released in the form of thermal energy. The hydroxyl group in the ortho position to the carbonyl group is believed to be a structural requirement for the Benzophenones' absorption of UV light. This structural arrangement also contributes to the electronic stability of the molecule. Thus, a surface coating of Benzophenones decreases the amount of UV radiation absorbed by the skin by limiting the total amount of energy that reaches the skin. Benzophenones absorb energy throughout the UV range, though maximum absorbance is between 284 and 287 nm for the 2-hydroxybenzophenones ...

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Benzophenones-1, -3, -4, -5, -9, and -11; Journal of the American College of Toxicology 2 (5): 35-78 (1983). Available form, as of September 12, 2013: https://online.personalcarecouncil.org/ctfa-static/online/lists/cir-pdfs/pr219.pdf


Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.