Oxybenzone

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 408784649

| Chembox_ref = Merck Index, 11th Edition, 6907

| ImageFile = Oxybenzone.svg

| ImageName = Oxybenzone

| ImageClass = skin-invert

| PIN = (2-Hydroxy-4-methoxyphenyl)(phenyl)methanone

| OtherNames = Oxybenzone
Benzophenone-3
2-Hydroxy-4-methoxybenzophenone

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4471

| PubChem = 4632

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 95OOS7VE0Y

| 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

| InChIKey = DXGLGDHPHMLXJC-UHFFFAOYAX

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1625

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = DXGLGDHPHMLXJC-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 131-57-7

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D05309

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB01428

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 34283

| SMILES = O=C(c1ccc(OC)cc1O)c2ccccc2

}}

|Section2={{Chembox Properties

| C=14 | H=12 | O=3

| Density = 1.20 g cm−3{{CAS|131-57-7}} at commonchemistry.org

| MeltingPtC = 62 to 65

| Appearance = pale yellow crystals

| BoilingPtC = 224 to 227

| pKa = 7.6 (H2O){{cite journal | vauthors = Fontanals N, Cormack PA, Sherrington DC, Marcé RM, Borrull F | title = Weak anion-exchange hypercrosslinked sorbent in on-line solid-phase extraction-liquid chromatography coupling to achieve automated determination with an effective clean-up | journal = Journal of Chromatography A | volume = 1217 | issue = 17 | pages = 2855–61 | date = April 2010 | pmid = 20303088 | doi = 10.1016/j.chroma.2010.02.064 }}

}}

|Section3={{Chembox Hazards

| Hazards_ref =

| FlashPtC = 140.5

| LD50 = >12800 mg/kg (oral in rats)

| NFPA-H = 1

| NFPA-F = 1

| NFPA-R = 0

}}

|Section4={{Chembox Pharmacology

| Legal_status = As sunscreen ingredient it is banned in Thailand, Palau and Hawaii

}}

}}

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 takes the form of pale-yellow crystals that are readily soluble in most organic solvents. It is widely used in sunscreen formulations, plastics, toys, furniture finishes, and other products to limit UV degradation.{{Cite web |url=https://echa.europa.eu/substance-information/-/substanceinfo/100.004.575 |title=Oxybenzone - Substance Information - ECHA |website=echa.europa.eu |access-date=2019-05-01}} In nature, it can be found in various flowering plants (angiosperms).{{Cite web|url=https://www.cdc.gov/biomonitoring/Benzophenone-3_FactSheet.html|title=Benzophenone-3 (BP-3) Factsheet {{!}} National Biomonitoring Program {{!}} CDC|date=2019-05-24|website=www.cdc.gov|access-date=2019-05-29}} The compound was first synthesised in Germany by chemists König and Kostanecki in 1906.

The use of oxybenzone as sunscreen ingredient is currently under scrutiny by the scientific community due to controversies about the molecule's environmental impact and safety profile (see section below).{{Cite web|url=https://www.byrdie.com/oxybenzone-5185876|title=Oxybenzone Offers Sun Protection—At a Cost|website=Byrdie}} As a result, sunscreens containing oxybenzone have been banned from sale in Hawaii, Palau,{{Cite news|url=https://www.bbc.com/news/world-asia-50963080|title=Palau is first country to ban 'reef toxic' sun cream|date=January 1, 2020|via=www.bbc.com}} and Thailand.{{Cite news|url=https://www.bbc.com/news/world-asia-58092472|title=Thailand bans coral-damaging sunscreens in marine parks|date=August 4, 2021|via=www.bbc.com}}

Structure and electronic structure

Being a conjugated molecule, oxybenzone absorbs light at lower energies than many aromatic molecules.{{cite journal |vauthors=Castro GT, Blanco SE, Giordano OS |doi=10.3390/50300424 |title=UV Spectral Properties of Benzophenone. Influence of Solvents and Substituents |year=2000 |journal=Molecules |volume=5 |issue=3 |pages=424–425 |doi-access=free }} As in related compounds, the hydroxyl group is hydrogen bonded to the ketone.{{cite journal | vauthors = Lago AF, Jimenez P, Herrero R, Dávalos JZ, Abboud JL | title = Thermochemistry and gas-phase ion energetics of 2-hydroxy-4-methoxy-benzophenone (oxybenzone) | journal = The Journal of Physical Chemistry A | volume = 112 | issue = 14 | pages = 3201–8 | date = April 2008 | pmid = 18341312 | doi = 10.1021/jp7111999 | bibcode = 2008JPCA..112.3201L }} 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.{{cite journal | vauthors = Chrétien MN, Heafey E, Scaiano JC | title = Reducing adverse effects from UV sunscreens by zeolite encapsulation: comparison of oxybenzone in solution and in zeolites | journal = Photochemistry and Photobiology | volume = 86 | issue = 1 | pages = 153–61 | year = 2010 | pmid = 19930122 | doi = 10.1111/j.1751-1097.2009.00644.x | s2cid = 43408456 }}

Production

Oxybenzone is produced by the Friedel-Crafts reaction of benzoyl chloride with 3-methoxyphenol.{{cite web |title=Hazardous Substances Data Bank |url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+131-57-7 |work=2-HYDROXY-4-METHOXYBENZOPHENONE |publisher=National Library of Medicine (US), Division of Specialized Information Services |access-date=9 March 2014}}

File:Synthese von Oxybenzon.svg

Uses

Oxybenzone is used in plastics as an ultraviolet light absorber and stabilizer. 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, as a stabilizer in concentrations up to 1%, in nail polishes. Oxybenzone can also be used as a photostabilizer for synthetic resins. This substance can leach from food packaging, and is widely used as photo-initiators to activate a chemical that dries ink faster.{{cite journal | vauthors = Koivikko R, Pastorelli S, Rodríguez-Bernaldo de Quirós A, Paseiro-Cerrato R, Paseiro-Losada P, Simoneau C | title = Rapid multi-analyte quantification of benzophenone, 4-methylbenzophenone and related derivatives from paperboard food packaging | journal = Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment | volume = 27 | issue = 10 | pages = 1478–86 | date = October 2010 | pmid = 20640959 | doi = 10.1080/19440049.2010.502130 | s2cid = 8900382 | url = https://hal.archives-ouvertes.fr/hal-00608934/file/PEER_stage2_10.1080%252F19440049.2010.502130.pdf }} Despite its photoprotective qualities, much controversy surrounds oxybenzone because of possible negative hormonal and photoallergenic effects, leading many countries to regulate use in sunscreen products.

= Sunscreen =

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.{{cite journal |vauthors=Burnett ME, Wang SQ |date=April 2011 |title=Current sunscreen controversies: a critical review |journal=Photodermatology, Photoimmunology & Photomedicine |volume=27 |issue=2 |pages=58–67 |doi=10.1111/j.1600-0781.2011.00557.x |pmid=21392107 |s2cid=29173997 |doi-access=}}

Due to toxicity and environmental concerns, the percentage of sunscreen products on the market containing oxybenzone in the USA dropped to 13% in 2023 from 60% in 2019.{{Cite web |last=Edney|first=Anna |date=2023-05-24 |title=There's Still Scary Stuff in Sunscreen |url=https://www.bloomberg.com/news/articles/2023-05-24/many-sunscreens-still-have-potentially-dangerous-chemicals#xj4y7vzkg|access-date=2023-08-15|website=www.bloomberg.com |language=en}} Some brands market their sunscreens as "oxybenzone free"{{Cite web |last1=Slijkerman |first1=Diana |last2=Bol |first2=Sharon |date=May 2018 |title=UV filter pollution Bonaire by tourism - Lac Bay monitoring and survey results 2017 - Research Report C023/18 |url=https://library.wur.nl/WebQuery/wurpubs/fulltext/446117 |website=Wageningen University}} due to the generally negative perception of benzophenones by both the consuming public and scientific researchers.

Safety

= ''In vivo'' studies =

The incidence of oxybenzone causing skin eruptions is extremely uncommon,{{cite journal |vauthors=Darvay A, White IR, Rycroft RJ, Jones AB, Hawk JL, McFadden JP |date=October 2001 |title=Photoallergic contact dermatitis is uncommon |journal=The British Journal of Dermatology |volume=145 |issue=4 |pages=597–601 |doi=10.1046/j.1365-2133.2001.04458.x |pmid=11703286 |s2cid=34414844}} 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.{{cite journal | vauthors = Rodríguez E, Valbuena MC, Rey M, Porras de Quintana L | title = Causal agents of photoallergic contact dermatitis diagnosed in the national institute of dermatology of Colombia | journal = Photodermatology, Photoimmunology & Photomedicine | volume = 22 | issue = 4 | pages = 189–92 | date = August 2006 | pmid = 16869867 | doi = 10.1111/j.1600-0781.2006.00212.x | s2cid = 36123270 }} Evidence points to oxybenzone having contact allergen effects. Oxybenzone is allegedly the most common allergen found in sunscreens.{{cite book |last1=Rietschel |first1=Robert L. |url=https://books.google.com/books?id=dQBAzfyCeQ8C |title=Fisher's Contact Dermatitis |last2=Fowler |first2=Joseph F. |date=2008 |publisher=PMPH-USA |isbn=9781550093780 |edition=6th |location=Hamilton |page=460 |access-date=8 February 2015 |name-list-style=vanc}}{{cite journal |vauthors=DeLeo VA, Suarez SM, Maso MJ |date=November 1992 |title=Photoallergic contact dermatitis. Results of photopatch testing in New York, 1985 to 1990 |journal=Archives of Dermatology |volume=128 |issue=11 |pages=1513–8 |doi=10.1001/archderm.1992.01680210091015 |pmid=1444508}}{{cite journal |vauthors=Scheuer E, Warshaw E |date=March 2006 |title=Sunscreen allergy: A review of epidemiology, clinical characteristics, and responsible allergens |journal=Dermatitis |volume=17 |issue=1 |pages=3–11 |doi=10.2310/6620.2006.05017 |pmid=16800271 |s2cid=42168353}}{{cite journal |vauthors=Zhang XM, Nakagawa M, Kawai K, Kawai K |date=January 1998 |title=Erythema-multiforme-like eruption following photoallergic contact dermatitis from oxybenzone |journal=Contact Dermatitis |volume=38 |issue=1 |pages=43–4 |doi=10.1111/j.1600-0536.1998.tb05637.x |pmid=9504247 |s2cid=35237413}}

In a 2008 study of participants ages 6 and up, oxybenzone was detected in 96.8% of urine samples.{{cite journal | vauthors = Calafat AM, Wong LY, Ye X, Reidy JA, Needham LL | title = Concentrations of the sunscreen agent benzophenone-3 in residents of the United States: National Health and Nutrition Examination Survey 2003--2004 | journal = Environmental Health Perspectives | volume = 116 | issue = 7 | pages = 893–7 | date = July 2008 | pmid = 18629311 | pmc = 2453157 | doi = 10.1289/ehp.11269 | bibcode = 2008EnvHP.116..893C }} 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.{{cite journal | vauthors = Gonzalez H, Farbrot A, Larkö O, Wennberg AM | title = Percutaneous absorption of the sunscreen benzophenone-3 after repeated whole-body applications, with and without ultraviolet irradiation | journal = The British Journal of Dermatology | volume = 154 | issue = 2 | pages = 337–40 | date = February 2006 | pmid = 16433806 | doi = 10.1111/j.1365-2133.2005.07007.x | s2cid = 1001823 }} 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.{{cite journal | vauthors = Hanson KM, Gratton E, Bardeen CJ | title = Sunscreen enhancement of UV-induced reactive oxygen species in the skin | journal = Free Radical Biology & Medicine | volume = 41 | issue = 8 | pages = 1205–12 | date = October 2006 | pmid = 17015167 | doi = 10.1016/j.freeradbiomed.2006.06.011 | s2cid = 13999532 | url = http://www.escholarship.org/uc/item/9f14s2dd }}

When applied topically, UV filters, such as oxybenzone, are absorbed through the skin, metabolized, and excreted primarily through the urine.{{cite journal | vauthors = Chisvert A, León-González Z, Tarazona I, Salvador A, Giokas D | title = An overview of the analytical methods for the determination of organic ultraviolet filters in biological fluids and tissues | journal = Analytica Chimica Acta | volume = 752 | pages = 11–29 | date = November 2012 | pmid = 23101648 | doi = 10.1016/j.aca.2012.08.051 | bibcode = 2012AcAC..752...11C }} 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).{{cite journal | vauthors = Okereke CS, Kadry AM, Abdel-Rahman MS, Davis RA, Friedman MA | title = Metabolism of benzophenone-3 in rats | journal = Drug Metabolism and Disposition | volume = 21 | issue = 5 | pages = 788–91 | year = 1993 | doi = 10.1016/S0090-9556(25)08162-0 | pmid = 7902237 }}{{cite journal | vauthors = Okereke CS, Abdel-Rhaman MS, Friedman MA | title = Disposition of benzophenone-3 after dermal administration in male rats | journal = Toxicology Letters | volume = 73 | issue = 2 | pages = 113–22 | date = August 1994 | pmid = 8048080 | doi = 10.1016/0378-4274(94)90101-5 }} To form DHB the methoxy functional group undergoes O-dealkylation; to form THB the same ring is hydroxylated. Ring B in oxybenzone is hydroxylated to form DHMB.

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.{{cite journal | vauthors = Sarveiya V, Risk S, Benson HA | title = Liquid chromatographic assay for common sunscreen agents: application to in vivo assessment of skin penetration and systemic absorption in human volunteers | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 803 | issue = 2 | pages = 225–31 | date = April 2004 | pmid = 15063329 | doi = 10.1016/j.jchromb.2003.12.022 }} The major metabolite detected was DHB and very small amounts of THB were found. By utilizing the Ames test in Salmonella typhimurium strains, DHB was determined to be nonmutagenic."Hazardous Substances Data Bank". 2,4-Dihydroxybenzophenone. National Library of Medicine (US), Division of Specialized Information Services. Retrieved 19 April 2014. 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."{{Cite journal| author = Office of the Commissioner |date=2019-05-09|title=FDA finalizes recommendations for studying absorption of active ingredients in topically-applied OTC monograph drugs|url=https://www.fda.gov/news-events/fda-brief/fda-finalizes-recommendations-studying-absorption-active-ingredients-topically-applied-otc-monograph|journal=FDA|language=en}} Oxybenzone can also occur as a natural product.{{Cite web |date=2017-12-01 |title=Benzophenone-3 (BP-3) Factsheet |url=https://www.cdc.gov/biomonitoring/Benzophenone-3_FactSheet.html |access-date=2019-05-01 |website=www.cdc.gov}}{{Cite web |date=2019-05-24 |title=Benzophenone-3 (BP-3) Factsheet {{!}} National Biomonitoring Program {{!}} CDC |url=https://www.cdc.gov/biomonitoring/Benzophenone-3_FactSheet.html |access-date=2019-05-29 |website=www.cdc.gov}}

Environmental effects

Studies have shown possible links between oxybenzone exposure and mortality in coral larvae, coral bleaching, and to genetic damage in marine invertebrates.{{cite journal | vauthors = Danovaro R, Bongiorni L, Corinaldesi C, Giovannelli D, Damiani E, Astolfi P, Greci L, Pusceddu A | display-authors = 6 | title = Sunscreens cause coral bleaching by promoting viral infections | journal = Environmental Health Perspectives | volume = 116 | issue = 4 | pages = 441–7 | date = April 2008 | pmid = 18414624 | pmc = 2291018 | doi = 10.1289/ehp.10966 | bibcode = 2008EnvHP.116..441D }}{{cite journal | vauthors = Downs CA, Kramarsky-Winter E, Segal R, Fauth J, Knutson S, Bronstein O, Ciner FR, Jeger R, Lichtenfeld Y, Woodley CM, Pennington P, Cadenas K, Kushmaro A, Loya Y | display-authors = 6 | title = 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 | journal = Archives of Environmental Contamination and Toxicology | volume = 70 | issue = 2 | pages = 265–88 | date = February 2016 | pmid = 26487337 | doi = 10.1007/s00244-015-0227-7 | bibcode = 2016ArECT..70..265D | s2cid = 4243494 | url = https://repository.library.noaa.gov/view/noaa/13720 }}{{Cite journal |last1=Watkins |first1=Yasmine S. D. |last2=Sallach |first2=J. Brett |date=September 2021 |title=Investigating the exposure and impact of chemical UV filters on coral reef ecosystems: Review and research gap prioritization |url=https://onlinelibrary.wiley.com/doi/10.1002/ieam.4411 |journal=Integrated Environmental Assessment and Management |language=en |volume=17 |issue=5 |pages=967–981 |doi=10.1002/ieam.4411 |pmid=33734562 |bibcode=2021IEAM...17..967W |s2cid=232300774 |issn=1551-3777}}{{Cite journal |last1=Vuckovic |first1=Djordje |last2=Tinoco |first2=Amanda I. |last3=Ling |first3=Lorraine |last4=Renicke |first4=Christian |last5=Pringle |first5=John R. |last6=Mitch |first6=William A. |date=2022-05-06 |title=Conversion of oxybenzone sunscreen to phototoxic glucoside conjugates by sea anemones and corals |journal=Science |language=en |volume=376 |issue=6593 |pages=644–648 |doi=10.1126/science.abn2600 |issn=0036-8075 |pmid=35511969 |bibcode=2022Sci...376..644V |s2cid=248543542|doi-access=free }}{{Cite journal |last1=Schneider |first1=Samantha L. |last2=Lim |first2=Henry W. |date=2019-01-01 |title=Review of environmental effects of oxybenzone and other sunscreen active ingredients |url=https://www.sciencedirect.com/science/article/pii/S0190962218321893 |journal=Journal of the American Academy of Dermatology |language=en |volume=80 |issue=1 |pages=266–271 |doi=10.1016/j.jaad.2018.06.033 |pmid=29981751 |s2cid=51600562 |issn=0190-9622|url-access=subscription }}{{Cite journal |last1=Downs |first1=C. A. |last2=Bishop |first2=Elizabeth |last3=Diaz-Cruz |first3=M. Silvia |last4=Haghshenas |first4=S. Abbas |last5=Stien |first5=Didier |last6=Rodrigues |first6=Alice M. S. |last7=Woodley |first7=Cheryl M. |last8=Sunyer-Caldú |first8=Adrià |last9=Doust |first9=Shadan Nasseri |last10=Espero |first10=William |last11=Ward |first11=Gene |last12=Farhangmehr |first12=Aref |last13=Tabatabaee Samimi |first13=S. Maryam |last14=Risk |first14=Michael J. |last15=Lebaron |first15=Philippe |date=2022-03-01 |title=Oxybenzone contamination from sunscreen pollution and its ecological threat to Hanauma Bay, Oahu, Hawaii, U.S.A. |url=https://www.sciencedirect.com/science/article/pii/S004565352103352X |journal=Chemosphere |language=en |volume=291 |issue=Pt 2 |pages=132880 |doi=10.1016/j.chemosphere.2021.132880 |pmid=34780745 |bibcode=2022Chmsp.29132880D |hdl=10261/257615 |s2cid=244095190 |issn=0045-6535|hdl-access=free }} However, some of these studies have been criticised for not having control groups or representing real-world conditions.{{cite web |last=Hughes |first=Terry |name-list-style=vanc |title=There's insufficient evidence your sunscreen harms coral reefs |date=4 February 2019 |url=https://theconversation.com/theres-insufficient-evidence-your-sunscreen-harms-coral-reefs-109567}}{{Cite journal |last1=Downs |first1=Craig A. |last2=Cruz |first2=Orion T. |last3=Remengesau |first3=Tommy E. |date=May 2022 |title=Sunscreen pollution and tourism governance: Science and innovation are necessary for biodiversity conservation and sustainable tourism |journal=Aquatic Conservation: Marine and Freshwater Ecosystems |language=en |volume=32 |issue=5 |pages=896–906 |doi=10.1002/aqc.3791 |s2cid=247347759 |issn=1052-7613|doi-access=free |bibcode=2022ACMFE..32..896D }}{{Cite journal |last1=Mirsky |first1=Rachel S |last2=Prado |first2=Giselle |last3=Svoboda |first3=Ryan M |last4=Rigel |first4=Darrell S |date=2018-09-07 |title=Oxybenzone and Sunscreens: A Critical Review of the Evidence and a Plan for Discussion with Patients |url=https://jofskin.org/index.php/skin/article/view/385 |journal=SKIN the Journal of Cutaneous Medicine |volume=2 |issue=5 |doi=10.25251/2.5.0 |s2cid=81525466 |issn=2574-1624|doi-access=free }}{{Cite web |title=PubPeer criticism of Downs, et al. |date=February 2016 |url=https://pubpeer.com/publications/E3A59C5143AF504D4577F5D710C39A |last1=Downs |first1=C. A. |last2=Kramarsky-Winter |first2=Esti |last3=Segal |first3=Roee |last4=Fauth |first4=John |last5=Knutson |first5=Sean |last6=Bronstein |first6=Omri |last7=Ciner |first7=Frederic R. |last8=Jeger |first8=Rina |last9=Lichtenfeld |first9=Yona |last10=Woodley |first10=Cheryl M. |last11=Pennington |first11=Paul |last12=Cadenas |first12=Kelli |last13=Kushmaro |first13=Ariel |last14=Loya |first14=Yossi }} Nevertheless, these have led to the ban of oxybenzone-containing sunscreen in many areas{{Cite journal |last1=Narla |first1=Shanthi |last2=Lim |first2=Henry W. |date=2020-01-01 |title=Sunscreen: FDA regulation, and environmental and health impact |url=https://doi.org/10.1039/c9pp00366e |journal=Photochemical & Photobiological Sciences |language=en |volume=19 |issue=1 |pages=66–70 |doi=10.1039/c9pp00366e |pmid=31845952 |bibcode=2020PhPhS..19...66N |s2cid=209388568 |issn=1474-9092|url-access=subscription }} such as Palau,{{Cite news |last=McGrath |first=Matt |name-list-style=vanc |date=November 2018 |title=Coral: Palau to ban sunscreen products to protect reefs |work=BBC News |publisher=BBC |url=https://www.bbc.co.uk/news/science-environment-46046064 |access-date=2020-01-01}} Hawaii, nature reserves in Mexico, Bonaire, the Marshall Islands, the United States Virgin Islands, Thailand's marine natural parks,{{Cite web |date=2021-08-04 |title=Thailand bans coral-damaging sunscreens |url=https://www.france24.com/en/live-news/20210804-thailand-bans-coral-damaging-sunscreens |access-date=2022-11-02 |website=France 24 |language=en}} the Northern Mariana Islands,{{Cite web |last=Torres |first=Governor Ralph |date=April 2020 |title=COMMONWEAlTH of the NORTHERN l\fARlANA ISLANDS - OFFICE OF THE GOVERNOR |url=https://cnmilaw.org/pdf/public_laws/21/pl21-20.pdf |website=Commonwealth Law Revision Commission}} and Aruba.

Health and environmental regulation

= Aruba =

Aruba banned the use of oxybenzone in sunscreens due to environmental concerns in 2019.{{Cite web |last=Overheid |first=Aruba |date=2019-11-21 |title=Single use plastic, the use of Styrofoam and Oxybenzone prohibited! |url=https://www.government.aw/news/news_47033/item/single-use-plastic-the-use-of-styrofoam-and-oxybenzone-prohibited_46498.html |access-date=2022-11-02 |website=www.government.aw |language=en}}

= Australia =

As of 2023, the maximum concentration of oxybenzone in a sunscreen cannot exceed 10% according to the TGA (Therapeutic Goods Administration).{{Cite web |date=May 2023 |title=Active ingredients currently restricted for use in therapeutic sunscreens |url=https://www.tga.gov.au/sites/default/files/australian-regulatory-guidelines-for-sunscreens.pdf |website=Australian Government: TGA, ARGS, Department of Health and Aged Care |page=40}}

= Bonaire =

As of 2019 Bonaire banned oxybenzone due to coral toxicity concerns, with regards to coral larvae{{Cite web |author1=Stephanie Pappas |date=2018-05-17 |title=Another Tropical Paradise Enacts a Sunscreen Ban |url=https://www.livescience.com/62598-bonaire-island-bans-sunscreen.html |access-date=2023-08-18 |website=livescience.com |language=en}}

= Canada =

Revised as of 2012, Health Canada allows oxybenzone for cosmetic use up to 6%.{{cite web|title=Guidance Document Sunscreen Monograph|url=http://www.hc-sc.gc.ca/dhp-mps/consultation/natur/sunscreen-ecransolaire-eng.php|publisher=Health Canada|access-date=9 March 2014|date=2012-12-03}}

= European Union =

The European Food Safety Authority categorises all the benzophenones, such as oxybenzone, as persistent, bio-accumulative, toxic, and a possible human carcinogen and endocrine disruptor.{{Cite web |date=March 2019 |title=Endocrine Disruptors: from Scientific Evidence to Human Health Protection |url=https://www.europarl.europa.eu/RegData/etudes/STUD/2019/608866/IPOL_STU(2019)608866_EN.pdf |website=European Parliament |publisher=European Parliament - Policy Department for Citizens' Rights and Constitutional Affairs - Directorate General for Internal Policies of the Union PE 608.866}} 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.{{cite web |last=Aguirre |first=Claudia |name-list-style=vanc |title=Shedding Light on Sun Safety – Part Two |url=http://dermalinstitute.com/us/library/66_article_Shedding_Light_on_Sun_Safety_Part_Two.html |publisher=The International Dermal Institute |access-date=9 March 2014 |archive-date=19 May 2014 |archive-url=https://web.archive.org/web/20140519123813/http://dermalinstitute.com/us/library/66_article_Shedding_Light_on_Sun_Safety_Part_Two.html |url-status=dead }} 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%.{{cite web |url=https://eur-lex.europa.eu/legal-content/EN/TXT/HTML/?uri=CELEX:32022R1176&qid=1657638963313&from=en#d1e32-53-1|title=COMMISSION REGULATION (EU) 2022/1176}}

= Japan =

Revised as of 2001, the Ministry of Health, Labour, and Welfare notification allows oxybenzone for cosmetic use up to 5%.{{cite web |title=Standards for Cosmetics |url=http://www.mhlw.go.jp/file/06-Seisakujouhou-11120000-Iyakushokuhinkyoku/0000032704.pdf |work=Ministry of Health and Welfare Notification No.331 of 2000 |publisher=Japanese Government |access-date=9 March 2014}}

= Mexico =

Nature Reserves across Mexico have banned the usage of sunscreens containing Oxybenzone{{Cite journal |last1=Miller |first1=Ingo B. |last2=Pawlowski |first2=Sascha |last3=Kellermann |first3=Matthias Y. |last4=Petersen-Thiery |first4=Mechtild |last5=Moeller |first5=Mareen |last6=Nietzer |first6=Samuel |last7=Schupp |first7=Peter J. |date=2021-06-26 |title=Toxic effects of UV filters from sunscreens on coral reefs revisited: regulatory aspects for "reef safe" products |journal=Environmental Sciences Europe |volume=33 |issue=1 |pages=74 |doi=10.1186/s12302-021-00515-w |issn=2190-4715 |doi-access=free }}

= Palau =

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.{{Cite news |url=https://www.bbc.com/news/science-environment-46046064 |title=Palau to ban sunscreen to save coral reefs |work=BBC News |date=November 2018 |last1=McGrath |first1=Matt |name-list-style=vanc }}{{Cite web |title=The Republic of Palau Adopts the World's Strictest National Sunscreen Standard – PalauGov.pw |url=https://www.palaugov.pw/the-republic-of-palau-adopts-the-worlds-strictest-national-sunscreen-standard/ |access-date=2023-08-18 |language=en-US}}

= 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 to break it down. No regulations have come of this study yet.

= Thailand =

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.{{Cite news |date=2021-08-04 |title=Thailand bans coral-damaging sunscreens in marine parks |language=en-GB |work=BBC News |url=https://www.bbc.com/news/world-asia-58092472 |access-date=2023-08-18}}

= United States =

In 2021 the U.S. FDA changed their classification of oxybenzone and no longer regard it as GRASE (Generally Recognised As Safe and Effective){{Cite journal |last=Research |first=Center for Drug Evaluation and |date=2021-11-16 |title=Questions and Answers: FDA posts deemed final order and proposed order for over-the-counter sunscreen |url=https://www.fda.gov/drugs/understanding-over-counter-medicines/questions-and-answers-fda-posts-deemed-final-order-and-proposed-order-over-counter-sunscreen |archive-url=https://web.archive.org/web/20210924142839/https://www.fda.gov/drugs/understanding-over-counter-medicines/questions-and-answers-fda-posts-deemed-final-order-and-proposed-order-over-counter-sunscreen |url-status=dead |archive-date=September 24, 2021 |journal=FDA |language=en}} 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.{{cite news |last1=Folley |first1=Aris |name-list-style=vanc |date=2 May 2018 |title=Hawaii lawmakers approve ban on sunscreens with chemicals harmful to coral reefs |work=The Hill |url=https://thehill.com/business-a-lobbying/385823-hawaii-lawmakers-pass-bill-banning-sunscreens-with-chemicals-harmful-to/ |access-date=2 May 2018}}{{cite journal |vauthors=Galamgam J, Linou N, Linos E |date=November 2018 |title=Sunscreens, cancer, and protecting our planet |journal=The Lancet. Planetary Health |volume=2 |issue=11 |pages=e465–e466 |doi=10.1016/S2542-5196(18)30224-9 |pmid=30396433 |doi-access=free}}

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.{{cite news |last1=Filosa |first1=Gwen |name-list-style=vanc |title=Key West bans the sale of sunscreens that hurt coral reefs in the Keys |url=https://www.miamiherald.com/news/local/community/florida-keys/article225224305.html |access-date=6 February 2019 |work=Miami Herald |date=February 5, 2019}} However, this legislation was superseded by the Florida State Legislature by Senate Bill 172,{{Cite web |title=SB 172: Florida Drug and Cosmetic Act |url=https://www.flsenate.gov/Session/Bill/2020/172 |access-date=2020-11-10 |website=The Florida Senate}} 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