OXYBENZONE

Oxybenzone is an organic compound used in sunscreens. 
Oxybenzone is a derivative of benzophenone. 
Oxybenzone forms colorless crystals that are readily soluble in most organic solvents. 

CAS:    131-57-7
MF:    C14H12O3
MW:    228.24
EINECS:    205-031-5

Synonyms
component of Presun 29;component of Presun 30;Cyasorb uv 9;Cyasorb uv 9 light absorber;cyasorbuv9;Escalol 567;Eusolex 4360;Lankromark LE296;oxybenzone;131-57-7;2-HYDROXY-4-METHOXYBENZOPHENONE;Benzophenone-3;2-Benzoyl-5-methoxyphenol;Advastab 45;(2-hydroxy-4-methoxyphenyl)(phenyl)methanone;4-Methoxy-2-hydroxybenzophenone;Oxibenzona;Oxybenzon;Anuvex;Ongrostab HMB;Oxybenzonum;Escalol 567;Chimassorb 90;Uvinul 9;Syntase 62;Uvistat 24;Cyasorb UV 9;Methanone, (2-hydroxy-4-methoxyphenyl)phenyl-;Sunscreen UV-15;Usaf cy-9;Uvinul M40;Benzophenone 3;Spectra-sorb UV 9;Eusolex 4360;Oxibenzonum;NSC-7778;Cyasorb UV 9 Light Absorber;Oxybenzonum [INN-Latin];UF 3;UV 9;(2-Hydroxy-4-methoxyphenyl)phenylmethanone;Oxibenzona [INN-Spanish];(2-hydroxy-4-methoxyphenyl)-phenylmethanone;Benzophenone, 2-hydroxy-4-methoxy-;Tinosorb b 3;2-hydroxy-4-methoxy benzophenone;NCI-C60957;Viosorb 110;CCRIS 1078;CHEBI:34283;HSDB 4503;UNII-95OOS7VE0Y;NSC 7778;EINECS 205-031-5;95OOS7VE0Y;Uvinul 40;BRN 1913145;DTXSID3022405;Uvinul M 40;AI3-23644;NSC7778;MFCD00008387;MOB;CHEMBL1625;Oxybenzone [USAN:USP:INN];DTXCID002405;(2-hydroxy-4-methoxy-phenyl)-phenyl-methanone;2-hydroxy-4-methoxy-benzophenone;EC 205-031-5;NCGC00016394-07;CAS-131-57-7;SHADE UVAGUARD COMPONENT OXYBENZONE;Oxybenzonum (INN-Latin);Oxibenzona (INN-Spanish);(2-hydroxy-4-methoxyphenyl)(phenyl) methanone;OXYBENZONE (MART.);OXYBENZONE [MART.];OXYBENZONE (USP-RS);OXYBENZONE [USP-RS];Oxybenzone (USAN:USP:INN);OXYBENZONE (USP MONOGRAPH);OXYBENZONE [USP MONOGRAPH];SMR000035344;SR-01000610567;BP-3;Neo heliopan BB;Bebak Baby Sun;Oxybenzonum (Latin);Solaquin (Salt/Mix);Oxybenzone (Standard);Spectrum_001049;DuraScreen (Salt/Mix);OXYBENZONE [MI];KAHSCREEN BZ-3;OXYBENZONE [INN];Prestwick0_000887;Prestwick1_000887;Prestwick2_000887;Prestwick3_000887;Spectrum2_001008;Spectrum3_000538;Spectrum4_000463;Spectrum5_001337;SUNSCREEN UV 15;OXYBENZONE [HSDB];OXYBENZONE [USAN];OXYBENZONE [VANDF];PreSun 15 (Salt/Mix);ADUVEX 24;Epitope ID:131795;SUMISORB 110;WLN: 1OR CQ DVR;SEESORB 101;OXYBENZONE [WHO-DD];Oprea1_174131;SCHEMBL15551;BSPBio_000674;BSPBio_002155;KBioGR_000906;KBioSS_001529;MLS000039797;MLS001055487;BIDD:ER0353;DivK1c_000184;SPECTRUM1500451;2-HYDROXY-4-METHOXYBENZOPHENONE (OXYBENZONE);SPBio_001135;SPBio_002893

Oxybenzone is used as an ingredient in sunscreen and other cosmetics because it absorbs UV-A ultraviolet rays.
Oxybenzone absorbs UVB and UVA II rays, resulting in a photochemical excitation and absorption of energy. 
Upon return to ground state, the absorbed energy results in emission of longer wavelength radiation and decreased skin penetration of radiation which reduces the risk of DNA damage.
A hydroxybenzophenone that is benzophenone which is substituted at the 2- and 4-positions of one of the benzene rings by hydroxy and methoxy groups respectively.
Oxybenzone is an organic compound belonging to the class of aromatic ketones known as benzophenones. 
Oxybenzone takes the form of pale-yellow crystals that are readily soluble in most organic solvents. 
Oxybenzone is widely used in sunscreen formulations, plastics, toys, furniture finishes, and other products to limit UV degradation.

In nature, Oxybenzone can be found in various flowering plants (angiosperms).
Oxybenzone 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).
As a result, sunscreens containing oxybenzone have been banned from sale in Hawaii, Palau, and Thailand.
Oxybenzone is produced by the Friedel-Crafts reaction of benzoyl chloride with 3-methoxyphenol.
Oxybenzone is a commonly used UV filter in sun tans and skin protectants. 
Oxybenzone act as endocrine disrupting chemicals (EDCs) and can pass through the placental and blood-brain barriers. 
Oxybenzone impairs autophagy, alters epigenetic status, and disrupts retinoid X receptor signaling in apoptotic neuronal cells.
Oxybenzone is a solid oil soluble UVA/UVB sunscreen. 

Protects polymers and organic substances in cosmetic products. 
Stabilizes complex formulations and color cosmetics.
Oxybenzone, often labeled as oxybenzone in sunscreen products, is a widely used chemical compound in cosmetics and sunscreens. 
Oxybenzone's chemical formula is C14H12O3. 
This organic UV filter serves as a sunblock agent, absorbing and dissipating harmful ultraviolet (UV) rays, particularly UVB and some UVA radiation. 
Oxybenzone3 helps protect the skin from sunburn and UV-induced damage, making it a common ingredient in sunscreens, lotions, and lip balms. 
Despite its effectiveness in shielding against sun damage, concerns about its potential hormone-disrupting properties have led to ongoing research and the exploration of alternative UV filters in the cosmetic industry.

Oxybenzone Chemical Properties
Melting point: 62-64 °C(lit.)
Boiling point: 150-160 °C5 mm Hg(lit.)
Density: 1,3 g/cm3
Vapor pressure: 0.001Pa at 25℃
Refractive index: 1.5805 (estimate)
Fp: 216°C
Storage temp.: 2-8°C
Solubility: 95% ethanol: soluble50mg/mL, clear, colorless
Form: Crystalline Powder
pka: 7.56±0.35(Predicted)
Color: White to light yellow
Odor: ylsh. cryst., rose-like odor
Water Solubility: <0.1 g/100 mL at 20 ºC
Merck: 14,6954
BRN: 1913145
InChIKey: DXGLGDHPHMLXJC-UHFFFAOYSA-N
LogP: 3.45 at 40℃
CAS DataBase Reference: 131-57-7(CAS DataBase Reference)
NIST Chemistry Reference: Oxybenzone(131-57-7)
EPA Substance Registry System: Oxybenzone (131-57-7)

Uses    
Oxybenzone is an organic compound used in sunscreens. Oxybenzone is used as an ingredient in sunscreen and other cosmetics because it absorbs UVB and short-wave UVA (ultraviolet) rays. 
Oxybenzone was one of the first compounds incorporated into sunscreen formulations to offer enhanced UVA protection because its absorption spectrum extends to less than 350 nm.
Ultraviolet light absorber and stabilizer, especially in plastics and paints.
Oxybenzone is an oil-soluble uV absorber and filter with absorption rates within the uVA and uVB peak ranges. 
Oxybenzone has an approved usage level of up to 6 percent in the united States and 10 percent in the european union. 
Oxybenzone enhances SPF and is popular among sunscreen formulators given a concern over potential safety problems associated with more traditional sunscreen chemicals. 
However, some reports associate Oxybenzone with causing photocontact allergy. 
Oxybenzone is considered a non-comedogenic raw material.
oxybenzone (benzophenone-3) is the drug name for an FDAapproved uV filter and absorber.

Oxybenzone is used in plastics as an ultraviolet light absorber and stabilizer.
Oxybenzone is used, along with other benzophenones, in sunscreens, hair sprays, and cosmetics because they help prevent potential damage from sunlight exposure. 
Oxybenzone 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.
Oxybenzone can leach from food packaging, and is widely used as photo-initiators to activate a chemical that dries ink faster.
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.
Oxybenzone is used in plastics as an ultraviolet light absorber and stabilizer. 
Oxybenzone is used, along with otherbenzophenones, in sunscreens, hair sprays, and cosmetics because they help prevent potential damage from sunlight exposure. 

Oxybenzone is also found, in concentrations up to 1%, in nail polishes. 
Oxybenzone can also be used as a photostabilizer for synthetic resins. 
Oxybenzone can leach from food packaging, and are widely used as photo-initiators used to start a chemical that dries ink faster.
Oxybenzone is used as an ingredient in sunscreen and other cosmetics.
Oxybenzone is a key ingredient in sunscreens and cosmetics. 
Oxybenzone's primary role is to protect the skin from the harmful effects of UV radiation. Oxybenzone absorbs UVB and some UVA rays, shielding the skin from sunburn and UV-induced damage. 
Oxybenzone is a popular choice in sunscreens due to its broad-spectrum UV protection capabilities. 
Additionally, Oxybenzone is used in various cosmetics like lip balms and moisturizers to provide UV protection and prevent sun damage, making it an essential component in the fight against skin aging and skin cancer caused by excessive sun exposure.

Sunscreen
Oxybenzone provides a broad-spectrum ultraviolet coverage which includes UVB and short-wave UVA rays. 
As a photoprotective agent, Oxybenzone has an absorption profile spanning from 270 to 350 nm with absorption peaks at 288 and 350 nm.
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.
Some brands market their sunscreens as "oxybenzone free" due to the generally negative perception of benzophenones by both the consuming public and scientific researchers.

Application and Synthesis    
Oxybenzone is a light yellow or white crystalline powder, also known as sunscreen 2, BP-3, suitable for polyvinyl chloride, polyvinylidene chloride, polymethyl methacrylate , unsaturated polyester, ABS resin and cellulose resin and other plastics, the maximum absorption wavelength range of 280-340 nm, the general amount of 0.1-1.5%, good thermal stability, does not decompose at 200 ℃. 
Oxybenzone hardly absorb visible light, it applies to light-colored transparent products. Oxybenzone can also be used for paints and synthetic rubber. 
For the broad-spectrum UV absorbers, with high absorption rate, non-toxic, non-teratogenic effect, light, thermal stability. 
Oxybenzone can absorb UV-A and UV-B together, is the US FDA approved Class I sunscreen and being used with a higher frequency in the US and European countries. 
Oxybenzone is widely used in sunscreen cream, cream, honey, lotion, oil and other sunscreen cosmetics, but also as a product from the photosensitive and discoloration of the anti-discoloration agent. 
In addition, Oxybenzone is usually used for PVC and unsaturated polyester and many other fields, because UV-9 has good compatibility with many kinds of plastics and resins.

Structure and electronic structure
Being a conjugated molecule, oxybenzone absorbs light at lower energies than many aromatic molecules.
As in related compounds, the hydroxyl group is hydrogen bonded to the ketone.
This interaction contributes to oxybenzone's light-absorption properties. 
At low temperatures, however, Oxybenzone 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.

Environmental effects
Studies have shown possible links between oxybenzone exposure and mortality in coral larvae, coral bleaching, and to genetic damage in marine invertebrates.
However, some of these studies have been criticised for not having control groups or representing real-world conditions.
Nevertheless, these have led to the ban of oxybenzone-containing sunscreen in many areas such as Palau, Hawaii, nature reserves in Mexico, Bonaire, the Marshall Islands, the United States Virgin Islands, Thailand's marine natural parks, the Northern Mariana Islands, and Aruba.