Oxybenzone

Oxybenzone[1]
Oxybenzone
Names
Preferred IUPAC name
(2-Hydroxy-4-methoxyphenyl)(phenyl)methanone
Other names
Oxybenzone
Benzophenone-3
2-Hydroxy-4-methoxybenzophenone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.575 Edit this at Wikidata
KEGG
UNII
  • 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
  • O=C(c1ccc(OC)cc1O)c2ccccc2
Properties
C14H12O3
Molar mass 228.247 g·mol−1
Appearance pale yellow crystals
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):
>12800 mg/kg (oral in rats)
Pharmacology
Legal status
  • As sunscreen ingredient it 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 ?)

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.[4] In nature, it can be found in various flowering plants (angiosperms).[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 the molecule's 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.