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Wikipedia

Oxybenzone

May 02, 2024

Oxybenzone or benzophenone-3 or BP-3 (trade names Milestab 9, Eusolex 4360, Escalol 567, KAHSCREEN BZ-3) is an organic compound belonging to the class of aromatic ketones known as benzophenones. It is a pale-yellow solid that is readily soluble in most organic solvents. It is widely used in sunscreen formulations, plastics, toys, furniture finishes, and other products to limit UV degradation.[4] In nature, oxybenzone can be found in various flowering plants.[5] The compound was first synthesised in Germany by chemists König and Kostanecki in 1906.

Oxybenzone[1]
Names
Preferred IUPAC name
(2-Hydroxy-4-methoxyphenyl)(phenyl)methanone
Other names
Oxybenzone
Benzophenone-3
2-Hydroxy-4-methoxybenzophenone
Identifiers
  • 131-57-7 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:34283 N
ChEMBL
  • ChEMBL1625 Y
ChemSpider
  • 4471 Y
DrugBank
  • DB01428 N
ECHA InfoCard 100.004.575
KEGG
  • D05309 Y
  • 4632
UNII
  • 95OOS7VE0Y Y
  • DTXSID3022405
  • 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 Y
    Key: DXGLGDHPHMLXJC-UHFFFAOYSA-N Y
  • 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 228.247 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]
Hazards[2]
NFPA 704 (fire diamond)
Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 140.5 °C (284.9 °F; 413.6 K)
Lethal dose or concentration (LD, LC):
>12800 mg/kg (oral in rats)
Pharmacology
Legal status
  • As sunscreen ingredient is banned in Thailand, Palau and Hawaii
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

The use of oxybenzone as sunscreen ingredient is currently under scrutiny by the scientific community due to controversies about its environmental impact and safety profile (see section below).[6] As a result, sunscreens containing oxybenzone have been banned from sale in Hawaii,[7] Palau,[8] and Thailand.[9]

Structure and electronic structure edit

Being a conjugated molecule, oxybenzone absorbs light at lower energies than many aromatic molecules.[10] As in related compounds, the hydroxyl group is hydrogen bonded to the ketone.[11] 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.[12]

Production edit

Oxybenzone is produced by Friedel-Crafts reaction of benzoyl chloride with 3-methoxyphenol.[13]

 

Uses edit

Oxybenzone is used in plastics as an ultraviolet light absorber and stabilizer.[13] 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.[13] Oxybenzone can also be used as a photostabilizer for synthetic resins.[13] Benzophenones can leach from food packaging, and are widely used as photo-initiators to activate a chemical that dries ink faster.[14] Despite its photoprotective qualities, much controversy surrounds oxybenzone because of its possible hormonal and photoallergenic effects, leading many countries to regulate its use.

Sunscreen edit

Oxybenzone provides a broad-spectrum ultraviolet coverage which includes 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.[15]

Due to safety concerns, the percentage of sunscreen products on the market containing oxybenzone in the USA dropped to 13% in 2023 from 60% in 2019.[16] Some brands market their sunscreens as "oxybenzone free"[17] due to the negative perception of benzophenones.

Safety edit

In vivo studies edit

The incidence of oxybenzone causing photoallergy is extremely uncommon,[18] however, oxybenzone has been associated with rare allergic reactions triggered by sun exposure. In a study of 82 patients with photoallergic contact dermatitis, just over one quarter showed photoallergic reactions to oxybenzone.[19] Evidence points to oxybenzone having contact allergen effects.[15][18] Oxybenzone is allegedly the most common allergen found in sunscreens.[20][21][22][23]

In a 2008 study of participants ages 6 and up, oxybenzone was detected in 96.8% of urine samples.[24] 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.[25] Because oxybenzone is the least lipophilic of the three most common UV filters, it is the least likely to end up trapped in the stratum corneum and the most likely to be absorbed and metabolized.[26]

When applied topically, UV filters, such as oxybenzone, are absorbed through the skin, metabolized, and excreted primarily through the urine.[27] 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).[28][29] To form DHB the methoxy functional group undergoes O-dealkylation; to form THB the same ring is hydroxylated.[27] Ring B in oxybenzone is hydroxylated to form DHMB.[27]

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.[30] The major metabolite detected was DHB and very small amounts of THB were found.[30] By utilizing the Ames test in Salmonella typhimurium strains, DHB was determined to be nonmutagenic.[31] In 2019, the U.S. Food and Drug Administration (FDA) noted in their recommendations for future study that, "While research indicates that some topical drugs can be absorbed into the body through the skin, this does not mean these drugs are unsafe."[32] Oxybenzone can be found in some plants.[33][34]

Environmental effects edit

Studies have shown possible links between oxybenzone exposure and mortality in developing coral, coral bleaching, and genetic damage to coral and marine life.[35][36][37][38][39][40] However, some of these studies have been criticised for not having control groups or representing real-world conditions.[41][42][43][44] Nevertheless, these have led to the ban of oxybenzone-containing sunscreen in many areas[45] such as Palau,[46] Hawaii,[7] nature reserves in Mexico, Bonaire, the Marshall Islands, the United States Virgin Islands, Thailand's marine natural parks,[47] the Northern Mariana Islands,[48] and Aruba.[49]

Health and environmental regulation edit

Aruba edit

Aruba banned the use of oxybenzone in sunscreens due to environmental concerns in 2019.[49]

Australia edit

As of 2023, the maximum concentration of oxybenzone in a sunscreen cannot exceed 10% according to the TGA (Therapeutic Goods Administration).[50]

Bonaire edit

As of 2019 Bonaire banned oxybenzone due to coral toxicity concerns, with regards to coral larvae[51]

Canada edit

Revised as of 2012, Health Canada allows oxybenzone for cosmetic use up to 6%.[52]

European Union edit

The European Food Safety Authority categorises benzophenones, such as oxybenzone, as persistent, bio-accumulative, toxic, and a possible human carcinogen and endocrine disruptor.[53] The Scientific Committee on Consumer Products (SCCP) of the European Commission concluded that it poses a significant risk to consumers as a contact allergenic potential.[54] It is allowed in face, hand, and lip products up to 6%, in body products up to 2.2%, and in other formulations up to 0.5%.[55]

Japan edit

Revised as of 2001, the Ministry of Health, Labour, and Welfare notification allows oxybenzone for cosmetic use up to 5%.[56]

Mexico edit

Nature Reserves across Mexico have banned the usage of sunscreens containing Oxybenzone[57]

Palau edit

The Palau government has signed a law that restricts the sale and use of sunscreen and skincare products that contain oxybenzone, and nine other chemicals. The ban came into force in 2020.[58][59]

Sweden edit

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 to break it down. No regulations have come of this study yet.[13]

Thailand edit

Thailand has prohibited sunscreens containing chemicals harmful to corals, including oxybenzone, in all its marine national parks. This decision was driven by evidence highlighting the detrimental effects of certain sunscreen ingredients on coral larvae, reproduction, and inducing reef bleaching. Violators face fines up to 100,000 baht (£2,100), although enforcement methods remain unspecified.[60]

United States edit

In 2021 the U.S. FDA changed their classification of oxybenzone and no longer regard it as GRASE (Generally Recognised As Safe and Effective)[61] due to the lack of safety data to support the classification.

The Hawaii State Legislature has legislated oxybenzone as illegal for use in sunscreens and personal care products since 2021 due to its environmental effects, such as mortality in developing coral, coral bleaching, genetic damage to coral, and other marine organisms.[7][62]

Key West has also banned the sale of sunscreens that contain the ingredients oxybenzone (and octinoxate). The ban was to be effective as of January 1, 2021.[63] However, this legislation was superseded by the Florida State Legislature by Senate Bill 172,[64] which prohibits local governments from regulating over-the-counter proprietary drugs and cosmetics (such as sunscreen containing oxybenzone and octinoxate). The statute became effective July 1, 2020.

References edit

  1. ^ Merck Index, 11th Edition, 6907
  2. ^ a b 131-57-7 at commonchemistry.org
  3. ^ Fontanals N, Cormack PA, Sherrington DC, Marcé RM, Borrull F (April 2010). "Weak anion-exchange hypercrosslinked sorbent in on-line solid-phase extraction-liquid chromatography coupling to achieve automated determination with an effective clean-up". Journal of Chromatography A. 1217 (17): 2855–61. doi:10.1016/j.chroma.2010.02.064. PMID 20303088.
  4. ^ "Oxybenzone - Substance Information - ECHA". echa.europa.eu. Retrieved 2019-05-01.
  5. ^ "Benzophenone-3 (BP-3) Factsheet | National Biomonitoring Program | CDC". www.cdc.gov. 2019-05-24. Retrieved 2019-05-29.
  6. ^ "Oxybenzone Offers Sun Protection—At a Cost". Byrdie.
  7. ^ a b c Folley A (2 May 2018). "Hawaii lawmakers approve ban on sunscreens with chemicals harmful to coral reefs". The Hill. Retrieved 2 May 2018.
  8. ^ "Palau is first country to ban 'reef toxic' sun cream". January 1, 2020 – via www.bbc.com.
  9. ^ "Thailand bans coral-damaging sunscreens in marine parks". August 4, 2021 – via www.bbc.com.
  10. ^ Castro GT, Blanco SE, Giordano OS (2000). "UV Spectral Properties of Benzophenone. Influence of Solvents and Substituents". Molecules. 5 (3): 424–425. doi:10.3390/50300424.
  11. ^ Lago AF, Jimenez P, Herrero R, Dávalos JZ, Abboud JL (April 2008). "Thermochemistry and gas-phase ion energetics of 2-hydroxy-4-methoxy-benzophenone (oxybenzone)". The Journal of Physical Chemistry A. 112 (14): 3201–8. Bibcode:2008JPCA..112.3201L. doi:10.1021/jp7111999. PMID 18341312.
  12. ^ Chrétien MN, Heafey E, Scaiano JC (2010). "Reducing adverse effects from UV sunscreens by zeolite encapsulation: comparison of oxybenzone in solution and in zeolites". Photochemistry and Photobiology. 86 (1): 153–61. doi:10.1111/j.1751-1097.2009.00644.x. PMID 19930122. S2CID 43408456.
  13. ^ a b c d e "Hazardous Substances Data Bank". 2-HYDROXY-4-METHOXYBENZOPHENONE. National Library of Medicine (US), Division of Specialized Information Services. Retrieved 9 March 2014.
  14. ^ Koivikko R, Pastorelli S, Rodríguez-Bernaldo de Quirós A, Paseiro-Cerrato R, Paseiro-Losada P, Simoneau C (October 2010). "Rapid multi-analyte quantification of benzophenone, 4-methylbenzophenone and related derivatives from paperboard food packaging" (PDF). Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment. 27 (10): 1478–86. doi:10.1080/19440049.2010.502130. PMID 20640959. S2CID 8900382.
  15. ^ a b Burnett ME, Wang SQ (April 2011). "Current sunscreen controversies: a critical review". Photodermatology, Photoimmunology & Photomedicine. 27 (2): 58–67. doi:10.1111/j.1600-0781.2011.00557.x. PMID 21392107. S2CID 29173997.
  16. ^ Edney, Anna (2023-05-24). "There's Still Scary Stuff in Sunscreen". www.bloomberg.com. Retrieved 2023-08-15.
  17. ^ Slijkerman, Diana; Bol, Sharon (May 2018). "UV filter pollution Bonaire by tourism - Lac Bay monitoring and survey results 2017 - Research Report C023/18". Wageningen University.
  18. ^ a b Darvay A, White IR, Rycroft RJ, Jones AB, Hawk JL, McFadden JP (October 2001). "Photoallergic contact dermatitis is uncommon". The British Journal of Dermatology. 145 (4): 597–601. doi:10.1046/j.1365-2133.2001.04458.x. PMID 11703286. S2CID 34414844.
  19. ^ Rodríguez E, Valbuena MC, Rey M, Porras de Quintana L (August 2006). "Causal agents of photoallergic contact dermatitis diagnosed in the national institute of dermatology of Colombia". Photodermatology, Photoimmunology & Photomedicine. 22 (4): 189–92. doi:10.1111/j.1600-0781.2006.00212.x. PMID 16869867. S2CID 36123270.
  20. ^ Rietschel RL, Fowler JF (2008). Fisher's Contact Dermatitis (6th ed.). Hamilton: PMPH-USA. p. 460. ISBN 9781550093780. Retrieved 8 February 2015.
  21. ^ DeLeo VA, Suarez SM, Maso MJ (November 1992). "Photoallergic contact dermatitis. Results of photopatch testing in New York, 1985 to 1990". Archives of Dermatology. 128 (11): 1513–8. doi:10.1001/archderm.1992.01680210091015. PMID 1444508.
  22. ^ Scheuer E, Warshaw E (March 2006). "Sunscreen allergy: A review of epidemiology, clinical characteristics, and responsible allergens". Dermatitis. 17 (1): 3–11. doi:10.2310/6620.2006.05017. PMID 16800271. S2CID 42168353.
  23. ^ Zhang XM, Nakagawa M, Kawai K, Kawai K (January 1998). "Erythema-multiforme-like eruption following photoallergic contact dermatitis from oxybenzone". Contact Dermatitis. 38 (1): 43–4. doi:10.1111/j.1600-0536.1998.tb05637.x. PMID 9504247. S2CID 35237413.
  24. ^ Calafat AM, Wong LY, Ye X, Reidy JA, Needham LL (July 2008). "Concentrations of the sunscreen agent benzophenone-3 in residents of the United States: National Health and Nutrition Examination Survey 2003--2004". Environmental Health Perspectives. 116 (7): 893–7. doi:10.1289/ehp.11269. PMC 2453157. PMID 18629311.
  25. ^ Gonzalez H, Farbrot A, Larkö O, Wennberg AM (February 2006). "Percutaneous absorption of the sunscreen benzophenone-3 after repeated whole-body applications, with and without ultraviolet irradiation". The British Journal of Dermatology. 154 (2): 337–40. doi:10.1111/j.1365-2133.2005.07007.x. PMID 16433806. S2CID 1001823.
  26. ^ Hanson KM, Gratton E, Bardeen CJ (October 2006). "Sunscreen enhancement of UV-induced reactive oxygen species in the skin". Free Radical Biology & Medicine. 41 (8): 1205–12. doi:10.1016/j.freeradbiomed.2006.06.011. PMID 17015167. S2CID 13999532.
  27. ^ a b c Chisvert A, León-González Z, Tarazona I, Salvador A, Giokas D (November 2012). "An overview of the analytical methods for the determination of organic ultraviolet filters in biological fluids and tissues". Analytica Chimica Acta. 752: 11–29. doi:10.1016/j.aca.2012.08.051. PMID 23101648.
  28. ^ Okereke CS, Kadry AM, Abdel-Rahman MS, Davis RA, Friedman MA (1993). "Metabolism of benzophenone-3 in rats". Drug Metabolism and Disposition. 21 (5): 788–91. PMID 7902237.
  29. ^ Okereke CS, Abdel-Rhaman MS, Friedman MA (August 1994). "Disposition of benzophenone-3 after dermal administration in male rats". Toxicology Letters. 73 (2): 113–22. doi:10.1016/0378-4274(94)90101-5. PMID 8048080.
  30. ^ a b Sarveiya V, Risk S, Benson HA (April 2004). "Liquid chromatographic assay for common sunscreen agents: application to in vivo assessment of skin penetration and systemic absorption in human volunteers". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 803 (2): 225–31. doi:10.1016/j.jchromb.2003.12.022. PMID 15063329.
  31. ^ "Hazardous Substances Data Bank". 2,4-Dihydroxybenzophenone. National Library of Medicine (US), Division of Specialized Information Services. Retrieved 19 April 2014.
  32. ^ Office of the Commissioner (2019-05-09). "FDA finalizes recommendations for studying absorption of active ingredients in topically-applied OTC monograph drugs". FDA.
  33. ^ "Benzophenone-3 (BP-3) Factsheet". www.cdc.gov. 2017-12-01. Retrieved 2019-05-01.
  34. ^ "Benzophenone-3 (BP-3) Factsheet | National Biomonitoring Program | CDC". www.cdc.gov. 2019-05-24. Retrieved 2019-05-29.
  35. ^ Danovaro R, Bongiorni L, Corinaldesi C, Giovannelli D, Damiani E, Astolfi P, et al. (April 2008). "Sunscreens cause coral bleaching by promoting viral infections". Environmental Health Perspectives. 116 (4): 441–7. doi:10.1289/ehp.10966. PMC 2291018. PMID 18414624.
  36. ^ Downs CA, Kramarsky-Winter E, Segal R, Fauth J, Knutson S, Bronstein O, et al. (February 2016). "Toxicopathological Effects of the Sunscreen UV Filter, Oxybenzone (Benzophenone-3), on Coral Planulae and Cultured Primary Cells and Its Environmental Contamination in Hawaii and the U.S. Virgin Islands". Archives of Environmental Contamination and Toxicology. 70 (2): 265–88. doi:10.1007/s00244-015-0227-7. PMID 26487337. S2CID 4243494.
  37. ^ Watkins, Yasmine S. D.; Sallach, J. Brett (September 2021). "Investigating the exposure and impact of chemical UV filters on coral reef ecosystems: Review and research gap prioritization". Integrated Environmental Assessment and Management. 17 (5): 967–981. doi:10.1002/ieam.4411. ISSN 1551-3777. PMID 33734562. S2CID 232300774.
  38. ^ Vuckovic, Djordje; Tinoco, Amanda I.; Ling, Lorraine; Renicke, Christian; Pringle, John R.; Mitch, William A. (2022-05-06). "Conversion of oxybenzone sunscreen to phototoxic glucoside conjugates by sea anemones and corals". Science. 376 (6593): 644–648. Bibcode:2022Sci...376..644V. doi:10.1126/science.abn2600. ISSN 0036-8075. PMID 35511969. S2CID 248543542.
  39. ^ Schneider, Samantha L.; Lim, Henry W. (2019-01-01). "Review of environmental effects of oxybenzone and other sunscreen active ingredients". Journal of the American Academy of Dermatology. 80 (1): 266–271. doi:10.1016/j.jaad.2018.06.033. ISSN 0190-9622. PMID 29981751. S2CID 51600562.
  40. ^ Downs, C. A.; Bishop, Elizabeth; Diaz-Cruz, M. Silvia; Haghshenas, S. Abbas; Stien, Didier; Rodrigues, Alice M. S.; Woodley, Cheryl M.; Sunyer-Caldú, Adrià; Doust, Shadan Nasseri; Espero, William; Ward, Gene; Farhangmehr, Aref; Tabatabaee Samimi, S. Maryam; Risk, Michael J.; Lebaron, Philippe (2022-03-01). "Oxybenzone contamination from sunscreen pollution and its ecological threat to Hanauma Bay, Oahu, Hawaii, U.S.A." Chemosphere. 291 (Pt 2): 132880. Bibcode:2022Chmsp.291m2880D. doi:10.1016/j.chemosphere.2021.132880. hdl:10261/257615. ISSN 0045-6535. PMID 34780745. S2CID 244095190.
  41. ^ Hughes T. "There's insufficient evidence your sunscreen harms coral reefs".
  42. ^ Downs, Craig A.; Cruz, Orion T.; Remengesau, Tommy E. (May 2022). "Sunscreen pollution and tourism governance: Science and innovation are necessary for biodiversity conservation and sustainable tourism". Aquatic Conservation: Marine and Freshwater Ecosystems. 32 (5): 896–906. doi:10.1002/aqc.3791. ISSN 1052-7613. S2CID 247347759.
  43. ^ Mirsky, Rachel S; Prado, Giselle; Svoboda, Ryan M; Rigel, Darrell S (2018-09-07). "Oxybenzone and Sunscreens: A Critical Review of the Evidence and a Plan for Discussion with Patients". SKIN the Journal of Cutaneous Medicine. 2 (5). doi:10.25251/2.5.0. ISSN 2574-1624. S2CID 81525466.
  44. ^ "PubPeer criticism of Downs, et al".
  45. ^ Narla, Shanthi; Lim, Henry W. (2020-01-01). "Sunscreen: FDA regulation, and environmental and health impact". Photochemical & Photobiological Sciences. 19 (1): 66–70. doi:10.1039/c9pp00366e. ISSN 1474-9092. PMID 31845952. S2CID 209388568.
  46. ^ McGrath M (November 2018). "Coral: Palau to ban sunscreen products to protect reefs". BBC News. BBC. Retrieved 2020-01-01.
  47. ^ "Thailand bans coral-damaging sunscreens". France 24. 2021-08-04. Retrieved 2022-11-02.
  48. ^ Torres, Governor Ralph (April 2020). "COMMONWEAlTH of the NORTHERN l\fARlANA ISLANDS - OFFICE OF THE GOVERNOR" (PDF). Commonwealth Law Revision Commission.
  49. ^ a b Overheid, Aruba (2019-11-21). "Single use plastic, the use of Styrofoam and Oxybenzone prohibited!". www.government.aw. Retrieved 2022-11-02.
  50. ^ "Active ingredients currently restricted for use in therapeutic sunscreens" (PDF). Australian Government: TGA, ARGS, Department of Health and Aged Care. May 2023. p. 40.
  51. ^ Stephanie Pappas (2018-05-17). "Another Tropical Paradise Enacts a Sunscreen Ban". livescience.com. Retrieved 2023-08-18.
  52. ^ "Guidance Document Sunscreen Monograph". Health Canada. 2012-12-03. Retrieved 9 March 2014.
  53. ^ "Endocrine Disruptors: from Scientific Evidence to Human Health Protection" (PDF). European Parliament. European Parliament - Policy Department for Citizens' Rights and Constitutional Affairs - Directorate General for Internal Policies of the Union PE 608.866. March 2019.
  54. ^ Aguirre C. . The International Dermal Institute. Archived from the original on 19 May 2014. Retrieved 9 March 2014.
  55. ^ "COMMISSION REGULATION (EU) 2022/1176".
  56. ^ "Standards for Cosmetics" (PDF). Ministry of Health and Welfare Notification No.331 of 2000. Japanese Government. Retrieved 9 March 2014.
  57. ^ Miller, Ingo B.; Pawlowski, Sascha; Kellermann, Matthias Y.; Petersen-Thiery, Mechtild; Moeller, Mareen; Nietzer, Samuel; Schupp, Peter J. (2021-06-26). "Toxic effects of UV filters from sunscreens on coral reefs revisited: regulatory aspects for "reef safe" products". Environmental Sciences Europe. 33 (1): 74. doi:10.1186/s12302-021-00515-w. ISSN 2190-4715.
  58. ^ McGrath M (November 2018). "Palau to ban sunscreen to save coral reefs". BBC News.
  59. ^ "The Republic of Palau Adopts the World's Strictest National Sunscreen Standard – PalauGov.pw". Retrieved 2023-08-18.
  60. ^ "Thailand bans coral-damaging sunscreens in marine parks". BBC News. 2021-08-04. Retrieved 2023-08-18.
  61. ^ Research, Center for Drug Evaluation and (2021-11-16). "Questions and Answers: FDA posts deemed final order and proposed order for over-the-counter sunscreen". FDA.
  62. ^ Galamgam J, Linou N, Linos E (November 2018). "Sunscreens, cancer, and protecting our planet". The Lancet. Planetary Health. 2 (11): e465–e466. doi:10.1016/S2542-5196(18)30224-9. PMID 30396433.
  63. ^ Filosa G (February 5, 2019). "Key West bans the sale of sunscreens that hurt coral reefs in the Keys". Miami Herald. Retrieved 6 February 2019.
  64. ^ "SB 172: Florida Drug and Cosmetic Act". The Florida Senate. Retrieved 2020-11-10.

May 02, 2024
oxybenzone, benzophenone, trade, names, milestab, eusolex, 4360, escalol, kahscreen, organic, compound, belonging, class, aromatic, ketones, known, benzophenones, pale, yellow, solid, that, readily, soluble, most, organic, solvents, widely, used, sunscreen, fo. Oxybenzone or benzophenone 3 or BP 3 trade names Milestab 9 Eusolex 4360 Escalol 567 KAHSCREEN BZ 3 is an organic compound belonging to the class of aromatic ketones known as benzophenones It is a pale yellow solid that is readily soluble in most organic solvents It is widely used in sunscreen formulations plastics toys furniture finishes and other products to limit UV degradation 4 In nature oxybenzone can be found in various flowering plants 5 The compound was first synthesised in Germany by chemists Konig and Kostanecki in 1906 Oxybenzone 1 Names Preferred IUPAC name 2 Hydroxy 4 methoxyphenyl phenyl methanone Other names OxybenzoneBenzophenone 32 Hydroxy 4 methoxybenzophenone Identifiers CAS Number 131 57 7 Y 3D model JSmol Interactive image ChEBI CHEBI 34283 N ChEMBL ChEMBL1625 Y ChemSpider 4471 Y DrugBank DB01428 N ECHA InfoCard 100 004 575 KEGG D05309 Y PubChem CID 4632 UNII 95OOS7VE0Y Y CompTox Dashboard EPA DTXSID3022405 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 YKey DXGLGDHPHMLXJC UHFFFAOYSA N YInChI 1 C14H12O3 c1 17 11 7 8 12 13 15 9 11 14 16 10 5 3 2 4 6 10 h2 9 15H 1H3Key DXGLGDHPHMLXJC UHFFFAOYAX SMILES O C c1ccc OC cc1O c2ccccc2 Properties Chemical formula C 14H 12O 3 Molar mass 228 247 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 Hazards 2 NFPA 704 fire diamond 110 Flash point 140 5 C 284 9 F 413 6 K Lethal dose or concentration LD LC LD50 median dose gt 12800 mg kg oral in rats Pharmacology Legal status As sunscreen ingredient is banned in Thailand Palau and Hawaii Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references The use of oxybenzone as sunscreen ingredient is currently under scrutiny by the scientific community due to controversies about its environmental impact and safety profile see section below 6 As a result sunscreens containing oxybenzone have been banned from sale in Hawaii 7 Palau 8 and Thailand 9 Contents 1 Structure and electronic structure 2 Production 3 Uses 3 1 Sunscreen 4 Safety 4 1 In vivo studies 5 Environmental effects 6 Health and environmental regulation 6 1 Aruba 6 2 Australia 6 3 Bonaire 6 4 Canada 6 5 European Union 6 6 Japan 6 7 Mexico 6 8 Palau 6 9 Sweden 6 10 Thailand 6 11 United States 7 ReferencesStructure and electronic structure editBeing a conjugated molecule oxybenzone absorbs light at lower energies than many aromatic molecules 10 As in related compounds the hydroxyl group is hydrogen bonded to the ketone 11 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 12 Production editOxybenzone is produced by Friedel Crafts reaction of benzoyl chloride with 3 methoxyphenol 13 nbsp Uses editOxybenzone is used in plastics as an ultraviolet light absorber and stabilizer 13 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 13 Oxybenzone can also be used as a photostabilizer for synthetic resins 13 Benzophenones can leach from food packaging and are widely used as photo initiators to activate a chemical that dries ink faster 14 Despite its photoprotective qualities much controversy surrounds oxybenzone because of its possible hormonal and photoallergenic effects leading many countries to regulate its use Sunscreen edit Oxybenzone provides a broad spectrum ultraviolet coverage which includes 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 15 Due to safety concerns the percentage of sunscreen products on the market containing oxybenzone in the USA dropped to 13 in 2023 from 60 in 2019 16 Some brands market their sunscreens as oxybenzone free 17 due to the negative perception of benzophenones Safety editIn vivo studies edit The incidence of oxybenzone causing photoallergy is extremely uncommon 18 however oxybenzone has been associated with rare allergic reactions triggered by sun exposure In a study of 82 patients with photoallergic contact dermatitis just over one quarter showed photoallergic reactions to oxybenzone 19 Evidence points to oxybenzone having contact allergen effects 15 18 Oxybenzone is allegedly the most common allergen found in sunscreens 20 21 22 23 In a 2008 study of participants ages 6 and up oxybenzone was detected in 96 8 of urine samples 24 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 25 Because oxybenzone is the least lipophilic of the three most common UV filters it is the least likely to end up trapped in the stratum corneum and the most likely to be absorbed and metabolized 26 When applied topically UV filters such as oxybenzone are absorbed through the skin metabolized and excreted primarily through the urine 27 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 28 29 To form DHB the methoxy functional group undergoes O dealkylation to form THB the same ring is hydroxylated 27 Ring B in oxybenzone is hydroxylated to form DHMB 27 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 30 The major metabolite detected was DHB and very small amounts of THB were found 30 By utilizing the Ames test in Salmonella typhimurium strains DHB was determined to be nonmutagenic 31 In 2019 the U S Food and Drug Administration FDA noted in their recommendations for future study that While research indicates that some topical drugs can be absorbed into the body through the skin this does not mean these drugs are unsafe 32 Oxybenzone can be found in some plants 33 34 Environmental effects editStudies have shown possible links between oxybenzone exposure and mortality in developing coral coral bleaching and genetic damage to coral and marine life 35 36 37 38 39 40 However some of these studies have been criticised for not having control groups or representing real world conditions 41 42 43 44 Nevertheless these have led to the ban of oxybenzone containing sunscreen in many areas 45 such as Palau 46 Hawaii 7 nature reserves in Mexico Bonaire the Marshall Islands the United States Virgin Islands Thailand s marine natural parks 47 the Northern Mariana Islands 48 and Aruba 49 Health and environmental regulation editAruba edit Aruba banned the use of oxybenzone in sunscreens due to environmental concerns in 2019 49 Australia edit As of 2023 the maximum concentration of oxybenzone in a sunscreen cannot exceed 10 according to the TGA Therapeutic Goods Administration 50 Bonaire edit As of 2019 Bonaire banned oxybenzone due to coral toxicity concerns with regards to coral larvae 51 Canada edit Revised as of 2012 Health Canada allows oxybenzone for cosmetic use up to 6 52 European Union edit The European Food Safety Authority categorises benzophenones such as oxybenzone as persistent bio accumulative toxic and a possible human carcinogen and endocrine disruptor 53 The Scientific Committee on Consumer Products SCCP of the European Commission concluded that it poses a significant risk to consumers as a contact allergenic potential 54 It is allowed in face hand and lip products up to 6 in body products up to 2 2 and in other formulations up to 0 5 55 Japan edit Revised as of 2001 the Ministry of Health Labour and Welfare notification allows oxybenzone for cosmetic use up to 5 56 Mexico edit Nature Reserves across Mexico have banned the usage of sunscreens containing Oxybenzone 57 Palau edit The Palau government has signed a law that restricts the sale and use of sunscreen and skincare products that contain oxybenzone and nine other chemicals The ban came into force in 2020 58 59 Sweden edit 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 to break it down No regulations have come of this study yet 13 Thailand edit Thailand has prohibited sunscreens containing chemicals harmful to corals including oxybenzone in all its marine national parks This decision was driven by evidence highlighting the detrimental effects of certain sunscreen ingredients on coral larvae reproduction and inducing reef bleaching Violators face fines up to 100 000 baht 2 100 although enforcement methods remain unspecified 60 United States edit In 2021 the U S FDA changed their classification of oxybenzone and no longer regard it as GRASE Generally Recognised As Safe and Effective 61 due to the lack of safety data to support the classification The Hawaii State Legislature has legislated oxybenzone as illegal for use in sunscreens and personal care products since 2021 due to its environmental effects such as mortality in developing coral coral bleaching genetic damage to coral and other marine organisms 7 62 Key West has also banned the sale of sunscreens that contain the ingredients oxybenzone and octinoxate The ban was to be effective as of January 1 2021 63 However this legislation was superseded by the Florida State Legislature by Senate Bill 172 64 which prohibits local governments from regulating over the counter proprietary drugs and cosmetics such as sunscreen containing oxybenzone and octinoxate The statute became effective July 1 2020 References edit Merck Index 11th Edition 6907 a b 131 57 7 at commonchemistry org Fontanals N Cormack PA Sherrington DC Marce RM Borrull F April 2010 Weak anion exchange hypercrosslinked sorbent in on line solid phase extraction liquid chromatography coupling to achieve automated determination with an effective clean up Journal of Chromatography A 1217 17 2855 61 doi 10 1016 j chroma 2010 02 064 PMID 20303088 Oxybenzone Substance Information ECHA echa europa eu Retrieved 2019 05 01 Benzophenone 3 BP 3 Factsheet National Biomonitoring Program CDC www cdc gov 2019 05 24 Retrieved 2019 05 29 Oxybenzone Offers Sun Protection At a Cost Byrdie a b c Folley A 2 May 2018 Hawaii lawmakers approve ban on sunscreens with chemicals harmful to coral reefs The Hill Retrieved 2 May 2018 Palau is first country to ban reef toxic sun cream January 1 2020 via www bbc com Thailand bans coral damaging sunscreens in marine parks August 4 2021 via www bbc com Castro GT Blanco SE Giordano OS 2000 UV Spectral Properties of Benzophenone Influence of Solvents and Substituents Molecules 5 3 424 425 doi 10 3390 50300424 Lago AF Jimenez P Herrero R Davalos JZ Abboud JL April 2008 Thermochemistry and gas phase ion energetics of 2 hydroxy 4 methoxy benzophenone oxybenzone The Journal of Physical Chemistry A 112 14 3201 8 Bibcode 2008JPCA 112 3201L doi 10 1021 jp7111999 PMID 18341312 Chretien MN Heafey E Scaiano JC 2010 Reducing adverse effects from UV sunscreens by zeolite encapsulation comparison of oxybenzone in solution and in zeolites Photochemistry and Photobiology 86 1 153 61 doi 10 1111 j 1751 1097 2009 00644 x PMID 19930122 S2CID 43408456 a b c d e Hazardous Substances Data Bank 2 HYDROXY 4 METHOXYBENZOPHENONE National Library of Medicine US Division of Specialized Information Services Retrieved 9 March 2014 Koivikko R Pastorelli S Rodriguez Bernaldo de Quiros A Paseiro Cerrato R Paseiro Losada P Simoneau C October 2010 Rapid multi analyte quantification of benzophenone 4 methylbenzophenone and related derivatives from paperboard food packaging PDF Food Additives amp Contaminants Part A Chemistry Analysis Control Exposure amp Risk Assessment 27 10 1478 86 doi 10 1080 19440049 2010 502130 PMID 20640959 S2CID 8900382 a b Burnett ME Wang SQ April 2011 Current sunscreen controversies a critical review Photodermatology Photoimmunology amp Photomedicine 27 2 58 67 doi 10 1111 j 1600 0781 2011 00557 x PMID 21392107 S2CID 29173997 Edney Anna 2023 05 24 There s Still Scary Stuff in Sunscreen www bloomberg com Retrieved 2023 08 15 Slijkerman Diana Bol Sharon May 2018 UV filter pollution Bonaire by tourism Lac Bay monitoring and survey results 2017 Research Report C023 18 Wageningen University a b Darvay A White IR Rycroft RJ Jones AB Hawk JL McFadden JP October 2001 Photoallergic contact dermatitis is uncommon The British Journal of Dermatology 145 4 597 601 doi 10 1046 j 1365 2133 2001 04458 x PMID 11703286 S2CID 34414844 Rodriguez E Valbuena MC Rey M Porras de Quintana L August 2006 Causal agents of photoallergic contact dermatitis diagnosed in the national institute of dermatology of Colombia Photodermatology Photoimmunology amp Photomedicine 22 4 189 92 doi 10 1111 j 1600 0781 2006 00212 x PMID 16869867 S2CID 36123270 Rietschel RL Fowler JF 2008 Fisher s Contact Dermatitis 6th ed Hamilton PMPH USA p 460 ISBN 9781550093780 Retrieved 8 February 2015 DeLeo VA Suarez SM Maso MJ November 1992 Photoallergic contact dermatitis Results of photopatch testing in New York 1985 to 1990 Archives of Dermatology 128 11 1513 8 doi 10 1001 archderm 1992 01680210091015 PMID 1444508 Scheuer E Warshaw E March 2006 Sunscreen allergy A review of epidemiology clinical characteristics and responsible allergens Dermatitis 17 1 3 11 doi 10 2310 6620 2006 05017 PMID 16800271 S2CID 42168353 Zhang XM Nakagawa M Kawai K Kawai K January 1998 Erythema multiforme like eruption following photoallergic contact dermatitis from oxybenzone Contact Dermatitis 38 1 43 4 doi 10 1111 j 1600 0536 1998 tb05637 x PMID 9504247 S2CID 35237413 Calafat AM Wong LY Ye X Reidy JA Needham LL July 2008 Concentrations of the sunscreen agent benzophenone 3 in residents of the United States National Health and Nutrition Examination Survey 2003 2004 Environmental Health Perspectives 116 7 893 7 doi 10 1289 ehp 11269 PMC 2453157 PMID 18629311 Gonzalez H Farbrot A Larko O Wennberg AM February 2006 Percutaneous absorption of the sunscreen benzophenone 3 after repeated whole body applications with and without ultraviolet irradiation The British Journal of Dermatology 154 2 337 40 doi 10 1111 j 1365 2133 2005 07007 x PMID 16433806 S2CID 1001823 Hanson KM Gratton E Bardeen CJ October 2006 Sunscreen enhancement of UV induced reactive oxygen species in the skin Free Radical Biology amp Medicine 41 8 1205 12 doi 10 1016 j freeradbiomed 2006 06 011 PMID 17015167 S2CID 13999532 a b c Chisvert A Leon Gonzalez Z Tarazona I Salvador A Giokas D November 2012 An overview of the analytical methods for the determination of organic ultraviolet filters in biological fluids and tissues Analytica Chimica Acta 752 11 29 doi 10 1016 j aca 2012 08 051 PMID 23101648 Okereke CS Kadry AM Abdel Rahman MS Davis RA Friedman MA 1993 Metabolism of benzophenone 3 in rats Drug Metabolism and Disposition 21 5 788 91 PMID 7902237 Okereke CS Abdel Rhaman MS Friedman MA August 1994 Disposition of benzophenone 3 after dermal administration in male rats Toxicology Letters 73 2 113 22 doi 10 1016 0378 4274 94 90101 5 PMID 8048080 a b Sarveiya V Risk S Benson HA April 2004 Liquid chromatographic assay for common sunscreen agents application to in vivo assessment of skin penetration and systemic absorption in human volunteers Journal of Chromatography B Analytical Technologies in the Biomedical and Life Sciences 803 2 225 31 doi 10 1016 j jchromb 2003 12 022 PMID 15063329 Hazardous Substances Data Bank 2 4 Dihydroxybenzophenone National Library of Medicine US Division of Specialized Information Services Retrieved 19 April 2014 Office of the Commissioner 2019 05 09 FDA finalizes recommendations for studying absorption of active ingredients in topically applied OTC monograph drugs FDA Benzophenone 3 BP 3 Factsheet www cdc gov 2017 12 01 Retrieved 2019 05 01 Benzophenone 3 BP 3 Factsheet National Biomonitoring Program CDC www cdc gov 2019 05 24 Retrieved 2019 05 29 Danovaro R Bongiorni L Corinaldesi C Giovannelli D Damiani E Astolfi P et al April 2008 Sunscreens cause coral bleaching by promoting viral infections Environmental Health Perspectives 116 4 441 7 doi 10 1289 ehp 10966 PMC 2291018 PMID 18414624 Downs CA Kramarsky Winter E Segal R Fauth J Knutson S Bronstein O et al February 2016 Toxicopathological Effects of the Sunscreen UV Filter Oxybenzone Benzophenone 3 on Coral Planulae and Cultured Primary Cells and Its Environmental Contamination in Hawaii and the U S Virgin Islands Archives of Environmental Contamination and Toxicology 70 2 265 88 doi 10 1007 s00244 015 0227 7 PMID 26487337 S2CID 4243494 Watkins Yasmine S D Sallach J Brett September 2021 Investigating the exposure and impact of chemical UV filters on coral reef ecosystems Review and research gap prioritization Integrated Environmental Assessment and Management 17 5 967 981 doi 10 1002 ieam 4411 ISSN 1551 3777 PMID 33734562 S2CID 232300774 Vuckovic Djordje Tinoco Amanda I Ling Lorraine Renicke Christian Pringle John R Mitch William A 2022 05 06 Conversion of oxybenzone sunscreen to phototoxic glucoside conjugates by sea anemones and corals Science 376 6593 644 648 Bibcode 2022Sci 376 644V doi 10 1126 science abn2600 ISSN 0036 8075 PMID 35511969 S2CID 248543542 Schneider Samantha L Lim Henry W 2019 01 01 Review of environmental effects of oxybenzone and other sunscreen active ingredients Journal of the American Academy of Dermatology 80 1 266 271 doi 10 1016 j jaad 2018 06 033 ISSN 0190 9622 PMID 29981751 S2CID 51600562 Downs C A Bishop Elizabeth Diaz Cruz M Silvia Haghshenas S Abbas Stien Didier Rodrigues Alice M S Woodley Cheryl M Sunyer Caldu Adria Doust Shadan Nasseri Espero William Ward Gene Farhangmehr Aref Tabatabaee Samimi S Maryam Risk Michael J Lebaron Philippe 2022 03 01 Oxybenzone contamination from sunscreen pollution and its ecological threat to Hanauma Bay Oahu Hawaii U S A Chemosphere 291 Pt 2 132880 Bibcode 2022Chmsp 291m2880D doi 10 1016 j chemosphere 2021 132880 hdl 10261 257615 ISSN 0045 6535 PMID 34780745 S2CID 244095190 Hughes T There s insufficient evidence your sunscreen harms coral reefs Downs Craig A Cruz Orion T Remengesau Tommy E May 2022 Sunscreen pollution and tourism governance Science and innovation are necessary for biodiversity conservation and sustainable tourism Aquatic Conservation Marine and Freshwater Ecosystems 32 5 896 906 doi 10 1002 aqc 3791 ISSN 1052 7613 S2CID 247347759 Mirsky Rachel S Prado Giselle Svoboda Ryan M Rigel Darrell S 2018 09 07 Oxybenzone and Sunscreens A Critical Review of the Evidence and a Plan for Discussion with Patients SKIN the Journal of Cutaneous Medicine 2 5 doi 10 25251 2 5 0 ISSN 2574 1624 S2CID 81525466 PubPeer criticism of Downs et al Narla Shanthi Lim Henry W 2020 01 01 Sunscreen FDA regulation and environmental and health impact Photochemical amp Photobiological Sciences 19 1 66 70 doi 10 1039 c9pp00366e ISSN 1474 9092 PMID 31845952 S2CID 209388568 McGrath M November 2018 Coral Palau to ban sunscreen products to protect reefs BBC News BBC Retrieved 2020 01 01 Thailand bans coral damaging sunscreens France 24 2021 08 04 Retrieved 2022 11 02 Torres Governor Ralph April 2020 COMMONWEAlTH of the NORTHERN l fARlANA ISLANDS OFFICE OF THE GOVERNOR PDF Commonwealth Law Revision Commission a b Overheid Aruba 2019 11 21 Single use plastic the use of Styrofoam and Oxybenzone prohibited www government aw Retrieved 2022 11 02 Active ingredients currently restricted for use in therapeutic sunscreens PDF Australian Government TGA ARGS Department of Health and Aged Care May 2023 p 40 Stephanie Pappas 2018 05 17 Another Tropical Paradise Enacts a Sunscreen Ban livescience com Retrieved 2023 08 18 Guidance Document Sunscreen Monograph Health Canada 2012 12 03 Retrieved 9 March 2014 Endocrine Disruptors from Scientific Evidence to Human Health Protection PDF European Parliament European Parliament Policy Department for Citizens Rights and Constitutional Affairs Directorate General for Internal Policies of the Union PE 608 866 March 2019 Aguirre C Shedding Light on Sun Safety Part Two The International Dermal Institute Archived from the original on 19 May 2014 Retrieved 9 March 2014 COMMISSION REGULATION EU 2022 1176 Standards for Cosmetics PDF Ministry of Health and Welfare Notification No 331 of 2000 Japanese Government Retrieved 9 March 2014 Miller Ingo B Pawlowski Sascha Kellermann Matthias Y Petersen Thiery Mechtild Moeller Mareen Nietzer Samuel Schupp Peter J 2021 06 26 Toxic effects of UV filters from sunscreens on coral reefs revisited regulatory aspects for reef safe products Environmental Sciences Europe 33 1 74 doi 10 1186 s12302 021 00515 w ISSN 2190 4715 McGrath M November 2018 Palau to ban sunscreen to save coral reefs BBC News The Republic of Palau Adopts the World s Strictest National Sunscreen Standard PalauGov pw Retrieved 2023 08 18 Thailand bans coral damaging sunscreens in marine parks BBC News 2021 08 04 Retrieved 2023 08 18 Research Center for Drug Evaluation and 2021 11 16 Questions and Answers FDA posts deemed final order and proposed order for over the counter sunscreen FDA Galamgam J Linou N Linos E November 2018 Sunscreens cancer and protecting our planet The Lancet Planetary Health 2 11 e465 e466 doi 10 1016 S2542 5196 18 30224 9 PMID 30396433 Filosa G February 5 2019 Key West bans the sale of sunscreens that hurt coral reefs in the Keys Miami Herald Retrieved 6 February 2019 SB 172 Florida Drug and Cosmetic Act The Florida Senate Retrieved 2020 11 10 Retrieved from https en wikipedia org w index php title Oxybenzone amp oldid 1219265931, wikipedia, wiki, book, books, library,

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