Oxybenzone

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Oxybenzone
IUPAC name	(2-Hydroxy-4-methoxyphenyl)- phenylmethanone
Other names	Oxybenzone Benzophenone-3
Identifiers
CAS number	[131-57-7]
SMILES	O=C(C2=CC=CC=C2)C1=C(O)C=C(OC)C=C1
Properties
Molecular formula	C14H12O3
Molar mass	228.24 g/mol
Melting point	66 °C
Boiling point	°C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Oxybenzone (trade names: Eusolex 4360, Escalol 567) is an organic compound used in sunscreens. It is a derivative of benzophenone. 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.^[1]

It is used as an ingredient in sunscreen and other cosmetics because it absorbs UV-A ultraviolet rays. In the EU products intended for skin protection with 0.5% or more oxybenzone must be labeled "Contains Oxybenzone".^[2]

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, which makes this substance a photocarcinogen.^[3] Two years after the study this information is now finally reaching the consumers,^[4] but this photocarcinogen can still be found in many sunscreens.

Oxybenzone is a derivative of benzophenone, which is well known to attack DNA when iluminated. It generates strand breaks and various photoproducts.^[5] Already in 1993 the use of oxybenzone had been strongly criticized, based on its similarity to benzophenone.^[5]

The photomutagenic properties of these compounds might be a contributing factor to the increased melanoma incidence that has been found in sunscreen users (see sunscreen controversy).

[edit] See also

• Dioxybenzone
• Avobenzone
• Octinoxate
• Octisalate

[edit] References

• Merck Index, 11th Edition, 6907.

1. ^ Antonia M. Calafat, Lee-Yang Wong, Xiaoyun Ye, John A. Reidy, and Larry L. Needham. "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. doi:10.1289/ehp.11269. 
2. ^ http://www.cosmetics.basf.de/(ofnv5uj3xy3zfy45hgjburu3)/pdf/Overview%20UV%20Absorber%20Portfolio_Performance%20Data%20and%20Regulatory%20Status.PDF
3. ^ 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. 
4. ^ Simon Pitman. EWG campaign highlights study on sunscreen ingredient.
5. ^ ^{a b} 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.