Oxybenzone

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Oxybenzone[1]
Oxybenzone
File:Oxybenzone.gif
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 131-57-7 YesY
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style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula C14H12O3
Molar mass 228.24 g/mol
Melting point

62-65 °C

Boiling point

224-227 °C

 YesY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Oxybenzone (trade names Eusolex 4360, Escalol 567) is an organic compound used in sunscreens. It forms colorless crystals that are readily soluble in most organic solvents. A 2008 study by the US Centers for Disease Control and Prevention found the compound to be present in 96.8% of human urine samples analyzed as part of the National Health and Nutrition Examination Survey.[2]

It is used as an ingredient in sunscreen and other cosmetics because it absorbs UVB and short-wave UVA (ultraviolet) rays.[3] In the EU products intended for skin protection with 0.5% or more oxybenzone must be labeled "Contains Oxybenzone".[4]

This organic compound has been shown to penetrate into the skin where it acts as a photosensitizer. This results in an increased production of free radicals under illumination,[5] possibly making this substance a photocarcinogen.[citation needed] This study concludes that "determining what, if any, type of damage is done by ROS generated by UV filters needs to be explored." The fact that researchers have not discovered how free radicals possibly caused by this sunscreen agent compare with the damage known to be caused by UV ray exposure makes prohibition of it questionable at this point.[citation needed]

This study is of oxybenzone and two other sunscreen active ingredients. Two years after the study this information is now reaching consumers,[6] but it can still be found in many sunscreens.

Oxybenzone is a derivative of benzophenone, which can attack DNA when illuminated. It generates strand breaks and various photoproducts.[7] Already in 1993 the use of oxybenzone had been strongly criticized, based on its similarity to benzophenone.[7]

The photomutagenic properties of these compounds might be a contributing factor to the increased melanoma incidence that has been found in sunscreen users. Other possibilities include consequent overexposure to sun without UVA protection and vitamin D deficiency from overuse of sunscreen. (see sunscreen controversy).

References

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  1. *Merck Index, 11th Edition, 6907.
  2. Antonia M. Calafat, Lee-Yang Wong, Xiaoyun Ye, John A. Reidy, and Larry L. Needham (2008). "Concentrations of the Sunscreen Agent, Benzophenone-3, in Residents of the United States: National Health and Nutrition Examination Survey 2003–2004" (in press). Environmental Health Perspectives. 116 (7): 893–7. doi:10.1289/ehp.11269. PMC 2453157Freely accessible. PMID 18629311. 
  3. Skin cancer foundation: Understanding UVA and UVB
  4. UV Absorber Portfolio Performance Data and Regulatory Status, cosmetics.basf.de
  5. Hanson Kerry M.; Gratton Enrico; Bardeen Christopher J. (2006). "Sunscreen enhancement of UV-induced reactive oxygen species in the skin". Free Radical Biology and Medicine. 41 (8): 1205–1212. doi:10.1016/j.freeradbiomed.2006.06.011. PMID 17015167. 
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  7. 7.0 7.1 Knowland, John; McKenzie, Edward A.; McHugh, Peter J.; Cridland, Nigel A. (1993). "Sunlight-induced mutagenicity of a common sunscreen ingredient". FEBS Letters. 324(3): 309–313. doi:10.1016/0014-5793(93)80141-G.