Oxybenzone

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"Benzone" redirects here. It is not to be confused with benzene.
Oxybenzone[1]
Oxybenzone
Names
IUPAC name
(2-Hydroxy-4-methoxyphenyl)-phenylmethanone
Other names
Oxybenzone
Benzophenone-3
2-Hydroxy-4-methoxybenzophenone
Identifiers
131-57-7 YesY
ChEBI CHEBI:34283 N
ChEMBL ChEMBL1625 YesY
ChemSpider 4471 YesY
DrugBank DB01428 N
Jmol 3D model Interactive image
KEGG D05309 YesY
PubChem 4632
UNII 95OOS7VE0Y YesY
  • 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 YesY
    Key: DXGLGDHPHMLXJC-UHFFFAOYSA-N YesY
  • InChI=1/C14H12O3/c1-17-11-7-8-12(13(15)9-11)14(16)10-5-3-2-4-6-10/h2-9,15H,1H3
    Key: DXGLGDHPHMLXJC-UHFFFAOYAX
  • O=C(c1ccc(OC)cc1O)c2ccccc2
Properties
C14H12O3
Molar mass 228.25 g·mol−1
Density 1.20 g cm−3[2]
Melting point 62 to 65 °C (144 to 149 °F; 335 to 338 K)
Boiling point 224 to 227 °C (435 to 441 °F; 497 to 500 K)
Acidity (pKa) 7.6 (H2O)[3]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Oxybenzone or benzophenone-3 (trade names Milestab 9, Eusolex 4360, Escalol 567, KAHSCREEN BZ-3) is an organic compound. It is a white solid that is readily soluble in most organic solvents. Oxybenzone belongs to the class of aromatic ketones known as benzophenones. It is a component of many sunscreen lotions.

Structure and electronic structure

Being a conjugated molecule, oxybenzone absorbs at lower energies than many aromatic molecules.[4] As in related compounds, the hydroxyl group is hydrogen bonded to the ketone.[5] This interaction contributes to oxybenzone's light-absorption properties. At low temperatures, however, it is possible to observe both the phosphorescence and the triplet-triplet absorption spectrum. At 175 K the triplet lifetime is 24 ns. The short lifetime has been attributed to a fast intramolecular hydrogen transfer between the oxygen of the C=O and the OH.[6]

Production

Oxybenzone is produced by Friedel-Crafts reaction of benzoyl chloride with 3-methoxyphenol(3-hydroxyanisole).[7]

Uses

Oxybenzone is used in plastics as an ultraviolet light absorber and stabilizer.[7] It is used, along with other benzophenones, in sunscreens, hair sprays, and cosmetics because they help prevent potential damage from sunlight exposure. It is also found, in concentrations up to 1%, in nail polishes.[7] Oxybenzone can also be used as a photostabilizer for synthetic resins.[7] Benzophenones can leach from food packaging, and are widely used as photo-initiators used to start a chemical that dries ink faster.[8]

As a sunscreen, it provides broad-spectrum ultraviolet coverage, including UVB and short-wave UVA rays. As a photoprotective agent, it has an absorption profile spanning from 270 to 350 nm with absorption peaks at 288 and 350 nm.[9] It is one of the most widely used organic UVA filters in sunscreens today.[9] It is also found in nail polish, fragrances, hairspray, and cosmetics as a photostabilizer. Despite its photoprotective qualities, much controversy surrounds oxybenzone because of its possible hormonal and photoallergenic effects, leading many countries to regulate its use.

Safety and controversy

Some debate focuses on the potential of oxybenzone as an endocrine disruptor.[9] According to the Environmental Working Group (EWG) oxybenzone is ineffective and harmful.[10] Similar concerns have been expressed for related products including avobenzone, octisalate, octocrylene, homosalate, and octinoxate.[11] Due to the advent of PABA-free sunscreens, oxybenzone is now the most common allergen found in sunscreens.[12][13][14][15]

In vivo studies

Among common sunscreen chemicals, oxybenzone is associated with allergic reactions triggered by sun exposure. In a study of 82 patients with photoallergic contact dermatitis, over one quarter showed photoallergic reactions to oxybenzone.[16]

In a 2008 study of participants ages 6 and up, oxybenzone was detected in 96.8% of urine samples.[17] Humans can absorb anywhere from 0.4% to 8.7% of oxybenzone after one topical application of sunscreen, as measured in urine excretions. This number can increase after multiple applications over the same period of time.[18] Oxybenzone is particularly penetrative because it is the most lipophilic of the three most common UV filters.[19]

When applied topically UV filters, such as oxybenzone, are absorbed through the skin, metabolized, and excreted primarily through the urine.[20] The method of biotransformation, the process by which a foreign compound is chemically transformed to form a metabolite, was determined by Okereke and colleagues through oral and dermal administration of oxybenzone to rats. The scientists analyzed blood, urine, feces, and tissue samples and found three metabolites: 2,4-dihydroxybenzophenone(DHB), 2,2-dihydroxy-4-methoxybenzophenone (DHMB) and 2,3,4-trihydroxybenzophenone (THB).[21][22] To form DHB the methoxy functional group undergoes o-dealkylation; to form THB the same ring is hydroxylated.[20] Ring B in oxybenzone is hydroxylated to form DHMB.[20]

A study done in 2004 measured the levels of oxybenzone and its metabolites in urine. After topical application to human volunteers, results revealed that up to 1% of the applied dose was found in the urine.[23] The major metabolite detected was DHB and very small amounts of THB were found.[23] By utilizing the Ames test in Salmonella typhimurium strains, DHB was determinted to be nonmutagenic.[24]

Effects on coral

Benzophenones (along with three other active ingredients) in sunscreens have been linked to coral bleaching and die-offs.[25][26][27] A 2015 study published by the Archives of Environmental Contamination and Toxicology directly linked oxybenzone to the declining health of coral reefs popular with tourists.[28]

Regulation

Australia

Revised as of 2007, the National Industrial Chemicals Notification and Assessment Scheme (NICNAS)) Cosmetic Guidelines allow oxybenzone for cosmetic use up to 10%.[29]

Canada

Revised as of 2012, Health Canada allows oxybenzone for cosmetic use up to 6%.[30]

European Union

The Scientific Committee on Consumer Products (SCCP) of the European Commission concluded in 2008 that it does not pose a significant risk to consumers, apart from contact allergenic potential.[31] It is allowed in cosmetics up to 10%.

Japan

Revised as of 2001, the Ministry of Health, Labour, and Welfare notification allows oxybenzone for cosmetic use up to 5%.[32]

Sweden

The Swedish Research Council has determined that sunscreens with oxybenzone are unsuitable for use in young children, because children under the age of two years have not fully developed the enzymes that are believed break it down. No regulations have come of this study yet.[7]

United States

Oxybenzone was approved for use in the US by the FDA in the early 1980s. Revised as of April 1, 2013, the FDA allows oxybenzone in cosmetic products up to 6%.[33]

References

  1. ↑ Merck Index, 11th Edition, 6907
  2. ↑ Template:CAS
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ 7.0 7.1 7.2 7.3 7.4 Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Koivikko, R; Pastorelli, S; Rodríguez-Bernaldo de Quirós, A; Paseiro-Cerrato, R; Paseiro-Losada, P; Simoneau, C (2010). “Rapid multi-analye quantification of benzophenone, 4-methylbenzophenone and related derivatives form paperboard food packaging”. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2010 Oct;27(10):1478-86. doi: 10.1080/19440049.2010.502130. Retrieved 8 February 2015. PMID 20640959.
  9. ↑ 9.0 9.1 9.2 Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Centers for Disease Control. CDC: Americans Carry Body Burden of Toxic Sunscreen Chemical. Environmental Working Group. EWG, 25 March 2008. Web. 14 March 2014.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  20. ↑ 20.0 20.1 20.2 Lua error in package.lua at line 80: module 'strict' not found.
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  22. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  23. ↑ 23.0 23.1 Lua error in package.lua at line 80: module 'strict' not found.
  24. ↑ "Hazardous Substances Data Bank". 2,4-Dihydroxybenzophenone. National Library of Medicine (US), Division of Specialized Information Services. Retrieved 19 April 2014.
  25. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  26. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  27. ↑ http://www.badgerbalm.com/s-35-coral-reef-safe-sunscreen.aspx
  28. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  29. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  30. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  31. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  32. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  33. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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