Oxybenzone

Structural formula
General
Surname	Oxybenzone
other names	2-hydroxy-4-methoxybenzophenone BENZOPHENONE-3 ( INCI )
Molecular formula	C 14 H 12 O 3
Brief description	yellowish odorless solid
External identifiers / databases
CAS number 131-57-7 EC number 205-031-5 ECHA InfoCard 100.004.575 PubChem 4632 ChemSpider 4471 DrugBank DB01428 Wikidata Q518114
properties
Molar mass	228.25 g mol −1
Physical state	firmly
density	1.32 g cm −3
Melting point	> 62 ° C
boiling point	315 ° C
solubility	practically insoluble in water (3 mg l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 410 P: 273-391-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxybenzone is a chemical compound from the group of substituted benzophenones .

Extraction and presentation

Oxybenzone can be obtained by Friedel-Crafts acylation of benzoyl chloride with 3-methoxyphenol .

properties

Oxybenzone is a flammable, difficult to ignite, yellowish, odorless solid that is practically insoluble in water.

use

Oxybenzone is used as a broad spectrum filter for UV-B and UV-A rays in sunscreens (in a concentration of 1 to 6%) and polymers . It acts as a reagent in the gravimetric determination of copper (II). It is also used to make poly [(2-hydroxy-4-methoxybenzophenone) propylene], a polymeric ligand suitable for the synthesis of metal / ligand polychelates.

safety

Oxybenzone is classified as a photoallergen . However, some studies do not consider this to be statistically relevant. For the compound, hormonal effects are also shown in very high concentrations in some studies, but these have no significant influence on the human organism. Due to the widespread use of the compound and the ambiguous results of the studies, the compound is on the list of CoRAP substances .

The Pacific state of Palau has banned the use of the compound in sunscreens since January 1, 2020, and the US state of Hawaii from January 1, 2021. The reason for this are studies that show that the compound has damaged coral reefs.

Individual evidence

1. ↑ Entry on BENZOPHENONE-3 in the CosIng database of the EU Commission, accessed on January 1, 2020.
2. ↑ ^{a b c d e f g h i} Entry on oxybenzone in the GESTIS substance database of the IFA , accessed on July 16, 2018(JavaScript required) .
3. ↑ ^{a b} Entry on 2-hydroxy-4-methoxybenzophenone in the Hazardous Substances Data Bank , accessed on July 16, 2018.
4. ^ ^{A b} Henry Lim: Photodermatology, An Issue of Dermatologic Clinics, E-Book . Elsevier Health Sciences, 2014, ISBN 978-0-323-31180-9 , pp. 434 ( limited preview in Google Book search).
5. ↑ Data sheet 2-Hydroxy-4-methoxybenzophenone, 98 +% from AlfaAesar, accessed on July 16, 2018 ( PDF )(JavaScript required) .
6. ↑ Joseph C. DiNardo, Craig A Downs: Dermatological and environmental toxicological impact of the sunscreen ingredient oxybenzone / benzophenone-3. In: Journal of Cosmetic Dermatology. 17, 2018, p. 15, doi : 10.1111 / jocd.12449 .
7. ↑ Patricia P. Agin, Karen Ruble, Steven J. Hermansky, Timothy J. McCarthy: Rates of allergic sensitization and irritation to oxybenzone-containing sunscreen products: a quantitative meta-analysis of 64 exaggerated use studies. In: Photodermatology, Photoimmunology & Photomedicine. 24, 2008, p. 211, doi : 10.1111 / j.1600-0781.2008.00363.x .
8. ↑ Pacific Islands: Palau bans sunscreens that poison corals . In: Spiegel Online . January 1, 2020 ( spiegel.de [accessed January 1, 2020]).
9. ↑ Protection of the corals: Hawaii prohibits certain sun creams , www.tagesschau.de, July 5, 2018 ( archived version of July 5, 2018 , accessed on February 20, 2020).
10. ↑ The Guardian: Hawaii becomes first US state to ban sunscreens harmful to coral reefs | Travel | The Guardian , accessed November 2, 2018.
11. ↑ CA Downs, Esti Kramarsky-Winter and a .: 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 US Virgin Islands. In: Archives of Environmental Contamination and Toxicology. 70, 2016, p. 265, doi : 10.1007 / s00244-015-0227-7 .