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Oxybenzone information


Oxybenzone[1]
Oxybenzone
Names
Preferred IUPAC name
(2-Hydroxy-4-methoxyphenyl)(phenyl)methanone
Other names
Oxybenzone
Benzophenone-3
2-Hydroxy-4-methoxybenzophenone
Identifiers
CAS Number
  • 131-57-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:34283 ☒N
ChEMBL
  • ChEMBL1625 checkY
ChemSpider
  • 4471 checkY
DrugBank
  • DB01428 ☒N
ECHA InfoCard 100.004.575 Edit this at Wikidata
KEGG
  • D05309 checkY
PubChem CID
  • 4632
UNII
  • 95OOS7VE0Y checkY
CompTox Dashboard (EPA)
  • DTXSID3022405 Edit this at Wikidata
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 checkY
    Key: DXGLGDHPHMLXJC-UHFFFAOYSA-N checkY
  • 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
SMILES
  • O=C(c1ccc(OC)cc1O)c2ccccc2
Properties
Chemical formula
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)
NFPA 704 four-colored diamondHealth 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):
LD50 (median dose)
>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 checkY☒N ?)
Infobox references

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.

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]

  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. ^ Cite error: The named reference :6 was invoked but never defined (see the help page).
  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.

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Oxybenzone

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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...

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Lipophilicity

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detergents because fluorocarbons are not lipophilic.[citation needed] Oxybenzone, a common cosmetic ingredient often used in sunscreens, penetrates the...

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Octyl methoxycinnamate

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research by the FDA on six common petrochemical UV filters (avobenzone, oxybenzone, octocrylene, homosalate, octisalate, and octinoxate) found that they...

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Retrieved 17 February 2024. Avoid sunscreens that contain the "Toxic 3 Os" of oxybenzone, octinoxate and octocrylene – they are prohibited in the United States...

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Uvinul

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hydroxybenzoyl hexyl benzoate (Uvinul A Plus) Ethylhexyl triazone (Uvinul T 150) Oxybenzone (Uvinul M 40) Octinoxate (Uvinul MC 80 (N)) Octocrylene (Uvinul N 539...

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Brandon Truaxe

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methylisothiazolinone, animal oils, coal tar dyes, formaldehyde, mercury and oxybenzone. Under his leadership, annual revenue was headed to $300 million in sales...

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Benzophenone-n, a class of compounds derived from benzophenone, including Oxybenzone Dioxybenzone and mostly used in sunscreens This disambiguation page lists...

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sunscreen that was deposited into Hanauma Bay every day. Sunscreen containing oxybenzone and octinoxate has been banned from the Hawaiian islands due to the deadly...

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include camphor, beeswax, menthol, petrolatum, phenol, vitamin E, aloe and oxybenzone. However, there are many variants of ChapStick, each with its own composition...

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Helioplex

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broad-spectrum ultraviolet (UVA and UVB) skin protection containing avobenzone and oxybenzone made by Neutrogena. Avobenzone-containing products have decreasing efficiency...

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Photodermatitis

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lemon oil (may be present in fragrances) PABA (found in sunscreens) Oxybenzone (UVA and UVB chemical blocker also in sunscreens) Salicylanilide (found...

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Overtourism

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Antarctica, which steadily increased during the 2010s. In Aruba, the chemical Oxybenzone in sunscreen is harming coral reefs and marine life. In 2019, a proposed...

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Coral bleaching

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mineral dust from African dust storms caused by drought pollutants such as oxybenzone, butylparaben, octyl methoxycinnamate, or enzacamene: four common sunscreen...

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Environmental Working Group

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made unfair "sweeping generalizations" about newer chemicals (such as oxybenzone) in its report and that its recommended products were based only on "very...

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Personal care products

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(February 2016). "Toxicopathological Effects of the Sunscreen UV Filter, Oxybenzone (Benzophenone-3), on Coral Planulae and Cultured Primary Cells and Its...

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1039/b516702g. PMID 16520862. S2CID 37910033. "Why Evaluate the Sunscreen Active Oxybenzone (Benzophenone-3) for Carcinogenicity and Reproductive Toxicology or Consider...

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statewide ban on sunscreens that contained the controversial chemicals oxybenzone and octinoxate. The bill also included a ban on the pesticide chlorpyrifos...

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as potential sources of new drugs. Substituted benzophenones such as oxybenzone and dioxybenzone are used in many sunscreens. The use of benzophenone-derivatives...

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sunscreen, ingredients that absorb UVA/UVB rays, such as avobenzone, oxybenzone and octyl methoxycinnamate, are organic chemical absorbers or "blockers"...

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Pyrimidine dimer

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the UV light from the sun through the use of organic compounds, such as oxybenzone or avobenzone. These compounds are able to absorb UV energy from the sun...

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harmful to coral reefs than sunscreens that include chemicals such as oxybenzone, octocrylene and octinoxate. Nanosized titanium dioxide is found in the...

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(February 2016). "Toxicopathological Effects of the Sunscreen UV Filter, Oxybenzone (Benzophenone-3), on Coral Planulae and Cultured Primary Cells and Its...

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(February 2016). "Toxicopathological Effects of the Sunscreen UV Filter, Oxybenzone (Benzophenone-3), on Coral Planulae and Cultured Primary Cells and Its...

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