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Prestwick3_000887
Also known as: 131-57-7, 2-hydroxy-4-methoxybenzophenone, Benzophenone-3, (2-hydroxy-4-methoxyphenyl)(phenyl)methanone, 4-methoxy-2-hydroxybenzophenone, Oxybenzon
Molecular Formula
C14H12O3
Molecular Weight
228.24  g/mol
InChI Key
DXGLGDHPHMLXJC-UHFFFAOYSA-N
FDA UNII
95OOS7VE0Y

Oxybenzone is a benzophenone derivative used as a sunscreen agent. Oxybenzone absorbs UVB and UVA II rays, resulting in a photochemical excitation and absorption of energy. Upon return to ground state, the absorbed energy results in emission of longer wavelength radiation and decreased skin penetration of radiation which reduces the risk of DNA damage.
1 2D Structure

Prestwick3_000887

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2-hydroxy-4-methoxyphenyl)-phenylmethanone
2.1.2 InChI
InChI=1S/C14H12O3/c1-17-11-7-8-12(13(15)9-11)14(16)10-5-3-2-4-6-10/h2-9,15H,1H3
2.1.3 InChI Key
DXGLGDHPHMLXJC-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC1=CC(=C(C=C1)C(=O)C2=CC=CC=C2)O
2.2 Other Identifiers
2.2.1 UNII
95OOS7VE0Y
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-hydroxy-4-methoxybenzone

2. 2-hydroxy-4-methoxybenzophenone

3. Benzophenone-3

4. Eusolex 4360

5. Eusolex-4360

6. Hmbp Cpd

7. Solbar

2.3.2 Depositor-Supplied Synonyms

1. 131-57-7

2. 2-hydroxy-4-methoxybenzophenone

3. Benzophenone-3

4. (2-hydroxy-4-methoxyphenyl)(phenyl)methanone

5. 4-methoxy-2-hydroxybenzophenone

6. Oxybenzon

7. Advastab 45

8. 2-benzoyl-5-methoxyphenol

9. Ongrostab Hmb

10. Methanone, (2-hydroxy-4-methoxyphenyl)phenyl-

11. Anuvex

12. Benzophenone 3

13. Escalol 567

14. Eusolex 4360

15. Chimassorb 90

16. Uvinul 9

17. Cyasorb Uv 9

18. Oxibenzona

19. Oxybenzonum

20. Sunscreen Uv-15

21. Syntase 62

22. Uvistat 24

23. Usaf Cy-9

24. Uvinul M40

25. Spectra-sorb Uv 9

26. Nsc-7778

27. Oxybenzonum [inn-latin]

28. Oxibenzona [inn-spanish]

29. (2-hydroxy-4-methoxyphenyl)-phenylmethanone

30. Cyasorb Uv 9 Light Absorber

31. (2-hydroxy-4-methoxyphenyl)phenylmethanone

32. Uf 3

33. Uv 9

34. Benzophenone, 2-hydroxy-4-methoxy-

35. Nci-c60957

36. Tinosorb B 3

37. Uvinul 40

38. Viosorb 110

39. Uvinul M 40

40. Chebi:34283

41. 2-hydroxy-4-methoxy Benzophenone

42. Kahscreen Bz-3

43. 95oos7ve0y

44. Chembl1625

45. Mob

46. (2-hydroxy-4-methoxy-phenyl)-phenyl-methanone

47. 2-hydroxy-4-methoxy-benzophenone

48. Nsc7778

49. Ncgc00016394-07

50. Cas-131-57-7

51. Dsstox_cid_2405

52. Dsstox_rid_76576

53. Dsstox_gsid_22405

54. Smr000035344

55. Ccris 1078

56. Hsdb 4503

57. Sr-01000610567

58. Nsc 7778

59. Einecs 205-031-5

60. Unii-95oos7ve0y

61. Brn 1913145

62. Oxybenzone [usan:usp:inn]

63. Ai3-23644

64. Neo Heliopan Bb

65. Kopben-3

66. Mfcd00008387

67. Solaquin (salt/mix)

68. Spectrum_001049

69. Durascreen (salt/mix)

70. Oxybenzone [mi]

71. Oxybenzone [inn]

72. Prestwick0_000887

73. Prestwick1_000887

74. Prestwick2_000887

75. Prestwick3_000887

76. Spectrum2_001008

77. Spectrum3_000538

78. Spectrum4_000463

79. Spectrum5_001337

80. Oxybenzone [hsdb]

81. Oxybenzone [usan]

82. Oxybenzone [vandf]

83. Presun 15 (salt/mix)

84. Epitope Id:131795

85. Wln: 1or Cq Dvr

86. Ec 205-031-5

87. Oxybenzone [mart.]

88. Oxybenzone [usp-rs]

89. Oxybenzone [who-dd]

90. Oprea1_174131

91. Schembl15551

92. Bspbio_000674

93. Bspbio_002155

94. Kbiogr_000906

95. Kbioss_001529

96. Mls000039797

97. Mls001055487

98. Bidd:er0353

99. Divk1c_000184

100. Spectrum1500451

101. Spbio_001135

102. Spbio_002893

103. Benzophenone-3 [inci]

104. Oxybenzone, Analytical Standard

105. Bpbio1_000742

106. Benzophenone-3 [vandf]

107. Dtxsid3022405

108. Oxybenzone [orange Book]

109. Hms500j06

110. Kbio1_000184

111. Kbio2_001529

112. Kbio2_004097

113. Kbio2_006665

114. Kbio3_001655

115. Ninds_000184

116. Hms1570b16

117. Hms1920d16

118. Hms2091l16

119. Hms2097b16

120. Hms2424p09

121. Hms3714b16

122. Oxybenzone [usp Monograph]

123. Pharmakon1600-01500451

124. Zinc136138

125. Albb-021277

126. Bcp25880

127. Hy-a0067

128. Tox21_110418

129. Tox21_201985

130. Tox21_302852

131. Bbl003220

132. Bdbm50253134

133. Ccg-40226

134. Component Of Presun 23 (salt/mix)

135. Component Of Presun 29 (salt/mix)

136. Component Of Presun 30 (salt/mix)

137. Nsc757260

138. S4691

139. Stk057962

140. Akos000120532

141. Tox21_110418_1

142. 2-hydroxy-4-methoxybenzophenone, 98%

143. Cs-3186

144. Db01428

145. Nsc-757260

146. Idi1_000184

147. Ncgc00016394-01

148. Ncgc00016394-02

149. Ncgc00016394-03

150. Ncgc00016394-04

151. Ncgc00016394-05

152. Ncgc00016394-06

153. Ncgc00016394-08

154. Ncgc00016394-10

155. Ncgc00065306-03

156. Ncgc00065306-04

157. Ncgc00065306-05

158. Ncgc00065306-06

159. Ncgc00256323-01

160. Ncgc00259534-01

161. Ac-11987

162. As-13616

163. Shade Uvaguard Component Oxybenzone

164. Sbi-0051470.p003

165. Ab00052063

166. Ft-0612546

167. H0266

168. Oxybenzone Component Of Shade Uvaguard

169. (2-hydroxy-4-methoxyphenyl)(phenyl) Methanone

170. D05309

171. Ab00052063_13

172. A934242

173. Ae-848/01549044

174. Q518114

175. Q-200287

176. Sr-01000610567-2

177. Sr-01000610567-4

178. Brd-k59037100-001-05-5

179. Brd-k59037100-001-09-7

180. Component Of Caraloe Snow & Sun Lip Balm (salt/mix)

181. Benzophenone 3;eusolex-4360;2-hydroxy-4-methoxybenzone

182. Z1945708085

183. 2-hydroxy-4-methoxybenzophenone 100 Microg/ml In Methanol

184. 2-hydroxy-4-methoxybenzophenone 10 Microg/ml In Cyclohexane

185. Oxybenzone, United States Pharmacopeia (usp) Reference Standard

186. 2-hydroxy-4-methoxybenzophenone, Certified Reference Material, Tracecert(r)

187. Oxybenzone, Pharmaceutical Secondary Standard; Certified Reference Material

188. 1-(cyclopropylcarbonyl)-n-(4-ethoxyphenyl)-3,3-dimethylindoline-5-sulfonamide

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 228.24 g/mol
Molecular Formula C14H12O3
XLogP33.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass228.078644241 g/mol
Monoisotopic Mass228.078644241 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count17
Formal Charge0
Complexity258
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

Sunscreening Agents.

National Library of Medicine's Medical Subject Headings. Oxybenzone. Online file (MeSH, 2017). Available from, as of July 6, 2017: https://www.nlm.nih.gov/mesh/2017/mesh_browser/MBrowser.html


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Oxybenzone is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of July 6, 2017: https://clinicaltrials.gov/


Ultraviolet screen.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1290


Topical Sunscreen Agent providing UVA/UVB coverage and approved for use by the FDA at concentrations up to 6%.

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


For more Therapeutic Uses (Complete) data for 2-Hydroxy-4-methoxybenzophenone (9 total), please visit the HSDB record page.


4.2 Drug Warning

... /Benzophenone-3/ undergoes conjugation in the body to make it water soluble. However, we do not know at what age the ability to conjugate is fully developed, and therefore for children physical filters such as titanium dioxide and/or zinc oxide might still be considered a more appropriate sunscreen component.

PMID:12472548 Gustavsson Gonzalez H et al; Clin Exp Dermatol 27 (8): 691-4 (2002)


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 2017; Drug Information 2017. Bethesda, MD. 2017


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 2017; Drug Information 2017. Bethesda, MD. 2017


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 2017; Drug Information 2017. Bethesda, MD. 2017


For more Drug Warnings (Complete) data for 2-Hydroxy-4-methoxybenzophenone (8 total), please visit the HSDB record page.


4.3 Drug Indication

Used as an ingredient in sunscreen and other cosmetics.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Oxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone.


5.2 MeSH Pharmacological Classification

Sunscreening Agents

Chemical or physical agents that protect the skin from sunburn and erythema by absorbing or blocking ultraviolet radiation. (See all compounds classified as Sunscreening Agents.)


5.3 Absorption, Distribution and Excretion

Route of Elimination

In vivo studies show oxybenzone is abosorbed transdermally (through the skin) and is excreted in the urine.


...The disposition of Benzophenone-3 in rats dosed orally, intravenously and topically, has been investigated. (14)C-Benzophenone-3 was administered orally at dosages of 3, 28, 293 and 2570 mg/kg, dermally at approximate dosages of 0.2, 0.6, 0.8 and 3.2 mg/kg and intravenously at a dosage of 4.6 mg/kg. The dermal dosage of 0.6 mg/kg involved the use of a sunscreen lotion as vehicle, while the other dermal dosage levels concerned alcoholic solutions of the compound. Through all routes and dosages, Benzophenone-3 appeared to be well-absorbed and urinary secretion clearly showed to be the major route of elimination, followed by the fecal route. Only trace amounts appeared to be measured in tissues after 72 hours.

European Commission; Reports of the Scientific Committee on Consumer Products (SCCP): Benzophenone-3 Colipa No. S38 (131-57-7) p. 25 (2006). Available from, as of July 6, 2017: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_078.pdf


Benzophenone-3 formed part of a battery of five UV filters for which standard operating procedures for their rapid analysis in various skin layers, were established. Benzophenone-3 was included at 4.9% in a cosmetic formulation (composition not stated) applied at 3 mg/sq cm on fresh dermatomed (+/- 344 um) human skin (6 samples from different donors) put on static diffusion cells. The 3 mL receptor fluid (pH 7.4) was maintained at 32 C and consisted of 1% bovine serum albumin, 0.9% NaCl, 0.02% KCl and 0.04% gentamycin in distilled water. The transepidermal water loss (TEWL) was recorded at each site with a Tewameter. After an exposure time of 16 hours, the skin was washed and dried with cotton swabs. The receptor fluid was collected and 16 strippings were carried out on the skin surface to determine the stratum corneum (SC) content and subsequently the epidermis was separated from the dermis. Analysis was performed by isocratic RP-HPLC2 with UV detection. Benzophenone-3 quantification led to the following results: Total amount applied 147 ug/sq cm (3 mg cream/sq cm, 4.9% Benzophenone-3); Stratum corneum (SC) 8.5 +/- 3.3 ug/sq cm; Epidermis 0.3 +/- 0.2 ug/sq cm; Dermis 0.4 +/- 0.1 ug/sq cm; Receptor fluid 1.0 +/- 0.4 ug/sq cm; Washing solution 85.7% +/- 4.5%; Recovery 93.4% +/- 3.1%. The results indicate that the SC adsorbed the greatest proportion of the applied amount (5.8%), while about 0.5% was absorbed in the viable skin and 0.7% was analyzed in the receptor fluid. ... They estimate the dermal absorption of Benzophenone-3 in respect to bioavailability after topical application to freshly dermatomed human skin for 16 hours as 1.7 ug/sq cm (1.0 ug/sq cm receptor fluid, 0.4 ug/sq cm dermis, 0.3 ug/sq cm epidermis), corresponding to 1.16% of the applied dose.

European Commission; Reports of the Scientific Committee on Consumer Products (SCCP): Benzophenone-3 Colipa No. S38 (131-57-7) p. 10 (2006). Available from, as of July 6, 2017: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_078.pdf


The results of a study investigating the urinary content of Benzophenone-3 after topical application to human volunteers can be considered as an indication for low bioavailability. A commercial available sunscreen containing 4% Benzophenone-3 was topically applied in an amount of 40 g to the average body area of 2.0 sq m of each of 11 volunteers and urine samples were collected subsequently during 48 hours. Although the urine is known as the major excretion route for absorbed and bioavailable material, only 0.4% (corresponding a median of 9.8 mg/volunteer) of the applied Benzophenone-3 dose was recovered in the urine within the 48 hours sampling period.

European Commission; Reports of the Scientific Committee on Consumer Products (SCCP): Benzophenone-3 Colipa No. S38 (131-57-7) p. 26 (2006). Available from, as of July 6, 2017: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_078.pdf


In this study, 32 volunteers were treated with 2 mg/sq cm of a basic cream formulation on a daily basis for 4 days during the first week, followed by the same treatment regime with a sunscreen containing 30% of UV-filters in total (10% 4-Methylbenzylidene Camphor, 10% Benzophenone-3 and 10% Ethylhexyl Methoxycinnamate) during the second week. Blood was collected at several time intervals on the first day of treatment and subsequently on a daily basis. All three compounds were detected in their parent forms both in plasma (Benzophenone-3 up to 300 ng/mL) and urine, showing that there is a substantial skin penetration, dermal uptake and urinary excretion in humans.

European Commission; Reports of the Scientific Committee on Consumer Products (SCCP): Benzophenone-3 Colipa No. S38 (131-57-7) p. 26 (2006). Available from, as of July 6, 2017: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_078.pdf


For more Absorption, Distribution and Excretion (Complete) data for 2-Hydroxy-4-methoxybenzophenone (22 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

...The metabolism and disposition of Benzophenone-3 when administered orally in rats and mice and dermally in the rat at a uniform single dosage of 100 mg/kg bw /were described/. The same metabolites /were/ detected in all cases: 2,4-Dihydroxybenzone (DHB), 2,2'-dihydroxy-4-methoxybenzone (DHMB) and 2,3,4-trihydroxybenzophenone (THB). They have been identified in their free and conjugated (glucuronidated or sulfonated) forms.

European Commission; Reports of the Scientific Committee on Consumer Products (SCCP): Benzophenone-3 Colipa No. S38 (131-57-7) p. 26 (2006). Available from, as of July 6, 2017: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_078.pdf


Benzophenone-3 (2-hydroxy-4-methoxybenzophenone; BP-3) is widely used as sunscreen for protection of human skin and hair from damage by ultraviolet (UV) radiation. In this study, we examined the metabolism of BP-3 by rat and human liver microsomes, and the estrogenic and anti-androgenic activities of the metabolites. When BP-3 was incubated with rat liver microsomes in the presence of NADPH, 2,4,5-trihydroxybenzophenone (2,4,5-triOH BP) and 3-hydroxylated BP-3 (3-OH BP-3) were newly identified as metabolites, together with previously detected metabolites 5-hydroxylated BP-3 (5-OH BP-3), a 4-desmethylated metabolite (2,4-diOH BP) and 2,3,4-trihydroxybenzophenone (2,3,4-triOH BP). In studies with recombinant rat cytochrome P450, 3-OH BP-3 and 2,4,5-triOH BP were mainly formed by CYP1A1. BP-3 was also metabolized by human liver microsomes and CYP isoforms. In estrogen reporter (ER) assays using estrogen-responsive CHO cells, 2,4-diOH BP exhibited stronger estrogenic activity, 2,3,4-triOH BP exhibited similar activity, and 5-OH BP-3, 2,4,5-triOH BP and 3-OH BP-3 showed lower activity as compared to BP-3. Structural requirements for activity were investigated in a series of 14 BP-3 derivatives. When BP-3 was incubated with liver microsomes from untreated rats or phenobarbital-, 3-methylcholanthrene-, or acetone-treated rats in the presence of NADPH, estrogenic activity was increased. However, liver microsomes from dexamethasone-treated rats showed decreased estrogenic activity due to formation of inactive 5-OH BP-3 and reduced formation of active 2,4-diOH BP. Anti-androgenic activity of BP-3 was decreased after incubation with liver microsomes.

PMID:25528284 Watanabe Y et al; Toxicol Appl Pharmacol 282 (2): 119-28 (2015)


... This study was performed to investigate the pharmacokinetics of benzophenone-3 (BZ-3) after oral administration at 100 mg/kg bw in male Sprague-Dawley rats. ... Urine and feces analysis indicate that urine was the major route of excretion, followed by feces. Further analysis of urine samples also indicates that conjugation of BZ-3 with glucuronic acid was the major systemic elimination route for the compound.

PMID:7782565 Kadry AM et al; J Appl Toxicol 15 (2): 97-102 (1995)


... The disposition of benzophenone-3 (BZ-3) was investigated after dermal administration of 100 mg/kg bw in Sprague-Dawley rats. ... Three metabolites were identified in plasma, 2,4-dihydroxybenzophenone (DHB) and 2,2'-dihydroxy-4-methoxybenzophenone (DHMB) were the major metabolites detected in the plasma, while 2,3,4-trihydroxybenzophenone (THB) was detected in trace amounts. Tissue distribution studies revealed that THB was the major metabolite followed by DHB (both free and conjugated) in all tissues examined. The liver contained the highest amount followed by the kidney, spleen and testes, respectively.

PMID:8048080 Okereke CS et al; Toxicol Lett 73 (2): 113-22 (1994)


Benzophenone-3 (2-hydroxy-4-methoxybenzophenone; BP-3) is widely used as sunscreen for protection of human skin and hair from damage by ultraviolet (UV) radiation. In this study, we examined the metabolism of BP-3 by rat and human liver microsomes, and the estrogenic and anti-androgenic activities of the metabolites. When BP-3 was incubated with rat liver microsomes in the presence of NADPH, 2,4,5-trihydroxybenzophenone (2,4,5-triOH BP) and 3-hydroxylated BP-3 (3-OH BP-3) were newly identified as metabolites, together with previously detected metabolites 5-hydroxylated BP-3 (5-OH BP-3), a 4-desmethylated metabolite (2,4-diOH BP) and 2,3,4-trihydroxybenzophenone (2,3,4-triOH BP). In studies with recombinant rat cytochrome P450, 3-OH BP-3 and 2,4,5-triOH BP were mainly formed by CYP1A1. BP-3 was also metabolized by human liver microsomes and CYP isoforms. In estrogen reporter (ER) assays using estrogen-responsive CHO cells, 2,4-diOH BP exhibited stronger estrogenic activity, 2,3,4-triOH BP exhibited similar activity, and 5-OH BP-3, 2,4,5-triOH BP and 3-OH BP-3 showed lower activity as compared to BP-3. Structural requirements for activity were investigated in a series of 14 BP-3 derivatives. When BP-3 was incubated with liver microsomes from untreated rats or phenobarbital-, 3-methylcholanthrene-, or acetone-treated rats in the presence of NADPH, estrogenic activity was increased. However, liver microsomes from dexamethasone-treated rats showed decreased estrogenic activity due to formation of inactive 5-OH BP-3 and reduced formation of active 2,4-diOH BP. Anti-androgenic activity of BP-3 was decreased after incubation with liver microsomes.

PMID:25528284 Watanabe Y et al; Toxicol Appl Pharmacol 282 (2): 119-28 (2015)


5.5 Biological Half-Life

... This study was performed to investigate the pharmacokinetics of benzophenone-3 (BZ-3) after oral administration at 100 mg/kg bw in male Sprague-Dawley rats. ... The elimination pattern was biphasic with alpha and beta half-lives of elimination of 0.88 and 15.90 hr, respectively.

PMID:7782565 Kadry AM et al; J Appl Toxicol 15 (2): 97-102 (1995)


... The disposition of benzophenone-3 (BZ-3) was investigated after dermal administration of 100 mg/kg bw in Sprague-Dawley rats. Blood samples were collected at various intervals and the parent compound and its metabolites were analyzed by HPLC. Absorption was rapid ... The half-life of absorption was 3.45 hr... . Disappearance from the plasma was biphasic with different half-lives (1.3 for alpha phase and 15.05 hr for beta phase) ... .

PMID:8048080 Okereke CS et al; Toxicol Lett 73 (2): 113-22 (1994)


5.6 Mechanism of Action

Oxybenzone absorbs UV-A ultraviolet rays, preventing them from reaching the skin.


Hirschsprung's disease (HSCR) is neonatal intestinal abnormality which derived from the failure of enteric neural crest cells migration to hindgut during embryogenesis from 5 to 12 weeks. Currently, the knowledge of environmental factors contributing to HSCR is still scarce. Benzophenone-3 (BP-3) is one of the most widely used UV filters, and has weak estrogen and strong anti-androgenic effects. In order to examine the effect of maternal BP-3 exposure on development of offspring and explore the potential mechanism, we conducted case and control study and in vitro study. In this work, BP-3 concentrations in maternal urine was detected by ultra-high performance liquid chromatography. Besides, we investigated the cytotoxicity and receptor tyrosine kinase (RET) expression in cells exposed to BP-3. The results showed that maternal BP-3 exposure was associated with offspring's HSCR in the population as well as inhibited migration of 293T and SH-SY5Y cells. What's more, we discovered dose-response relationship between RET expression and BP-3 exposure dose, and miR-218 and some other genes involved in SLIT2/ROBO1-miR-218-RET/PLAG1 pathway were also related to BP-3 exposure. Therefore, we deduced that BP-3 influenced cell migration via SLIT2/ROBO1-miR-218-RET/PLAG1 pathway. Our study firstly revealed the relationship between maternal BP-3 exposure and HSCR as well as its potential mechanism.

PMID:26454118 Huo W et al; Chemosphere 144: 1091-7 (2016)


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.


Radiation is absorbed by chemical sunscreens when the electron energy level of the drug is raised from its ground state to a higher energy level or excited state. Chromophore groups (C=C, C=O, O-N=O) with loosely held electrons are easily excited by radiation. Compounds which have several chromophore groups in optimal positions have high absorbance over a broad range of wavelengths. Chemical sunscreens are usually agents that absorb not less than 85% of UVB radiation (thus preventing burning) but may permit transmission of UVA radiation (thus allowing tanning). Some sunscreens may absorb wavelengths over a range that is slightly wider or narrower than that of UVB. All PABA derivatives absorb wavelengths of approximately 290-320 nm, benzophenone derivatives absorb wavelengths of approximately 250-360 nm, cinnamic acid derivatives absorb wavelengths of 280-320 nm, and salicylate derivatives and other miscellaneous chemical sunscreens absorb wavelengths of about 270-320 nm.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017


The wavelength to which the skin is maximally sensitive had been accepted for many years to be 296.7 nm; however, recent evidence suggests that the most erythemogenic UVB wavelength may be slightly lower (e.g., somewhere in the range of 292-295 nm). In addition, of the stronger burning wavelengths that reach the earth's surface, most are approximately 310 nm. Therefore, sunscreens that maximally absorb UVB radiation near either of these wavelengths are particularly effective at preventing sunburn. Maximum absorbance occurs at about 290 nm for PABA, at about 295 nm for glyceryl-p-aminobenzoate, and at about 310 nm for the remaining PABA derivatives. Maximum absorbance occurs at 280-290 nm for benzophenone derivatives, at 310 nm for cinnamic acid derivatives with the exception of diethanolamine-p-methoxycinnamate which has its maximum absorbance at 290 nm, and at 300-305 nm for salicylate derivatives and other miscellaneous sunscreens. /Sunscreens/

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017


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