Oxybenzone

Oxybenzone Basic information
description Chemical properties Application and Synthesis Improvement of UV - 9 Production Process
Product Name:Oxybenzone
Synonyms:component of Presun 30;Cyasorb uv 9;Cyasorb uv 9 light absorber;cyasorbuv9;Escalol 567;Eusolex 4360;Methanone, (2-hydroxy-4-methoxyphenyl)phenyl-;Methanone,(2-hydroxy-4-methoxyphenyl)phenyl-
CAS:131-57-7
MF:C14H12O3
MW:228.24
EINECS:205-031-5
Product Categories:UVINUL M40;Aromatic Benzophenones & Derivatives (substituted);Organics;Additives for Plastic;Industrial/Fine Chemicals;131-57-7
Mol File:131-57-7.mol
Oxybenzone Structure
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
pka7.56±0.35(Predicted)
color White to light yellow
Odorylsh. cryst., rose-like odor
Water Solubility <0.1 g/100 mL at 20 ºC
Merck 14,6954
BRN 1913145
InChIKeyDXGLGDHPHMLXJC-UHFFFAOYSA-N
LogP3.45 at 40℃
CAS DataBase Reference131-57-7(CAS DataBase Reference)
NIST Chemistry ReferenceOxybenzone(131-57-7)
EPA Substance Registry System2-Hydroxy-4-methoxybenzophenone (131-57-7)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37
RIDADR UN 3077 9/PG III
WGK Germany 2
RTECS DJ1575000
TSCA Yes
HazardClass 9
PackingGroup III
HS Code 29145000
Hazardous Substances Data131-57-7(Hazardous Substances Data)
ToxicityLD50 orally in rats: >12.8 g/kg (Lewerenz)
MSDS Information
ProviderLanguage
2-Hydroxy-4-methoxybenzophenone English
SigmaAldrich English
ACROS English
ALFA English
Oxybenzone Usage And Synthesis
descriptionOxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone. It forms colorless crystals that are readily soluble in most organic solvents. It 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.
Chemical propertieslight yellow crystalline powder, soluble in ethanol, acetone and other organic solvents, insoluble in water.
Application and SynthesisUV-9 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 ℃. This product hardly absorb visible light, it applies to light-colored transparent products. This product 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. UV-9 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. UV-9 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, it 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.
Improvement of UV - 9 Production ProcessUsing mixed acid as catalyst, trichloromethylbenzene and resorcinol were condensed into intermediate 2,4-dihydroxydiphenyl ketone in aqueous phase, and then the catalyst was treated with phase transfer catalyst, etherification of the target product UV-9.
Chemical Propertieswhite to light yellow crystalline powder
UsesOxybenzone 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.
UsesUltraviolet light absorber and stabilizer, especially in plastics and paints.
UsesSunscreen. UV stabilizer
Usesbenzophenone-3 (oxybenzone) is an oil-soluble uV absorber and filter with absorption rates within the uVA and uVB peak ranges. It has an approved usage level of up to 6 percent in the united States and 10 percent in the european union. Benzophenone-3 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 it with causing photocontact allergy. It is considered a non-comedogenic raw material.
Usesultraviolet screen
Usesoxybenzone (benzophenone-3) is the drug name for an FDAapproved uV filter and absorber.
PreparationPreparation by partial methylation of 2,4- dihydroxy-benzophenone,
? with methyl iodide in the presence of sodium hydroxide;
? with a methyl halide;
? with dimethyl sulfate in the presence of sodium hydroxide or alkaline solution.


DefinitionChEBI: 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.
Brand nameUvinul M40 (BASF).
Synthesis Reference(s)Tetrahedron, 42, p. 885, 1986 DOI: 10.1016/S0040-4020(01)87495-0
General DescriptionWhite to off-white or light yellow powder.
Air & Water ReactionsInsoluble in water.
Fire HazardFlash point data for Oxybenzone are not available; however, Oxybenzone is probably combustible.
Flammability and ExplosibilityNonflammable
Contact allergensBZP-3 is used as a direct sunscreen agent and in antiaging creams. Allergic reactions have been reported. Cross-reactivity is expected in an average of one in four patients photoallergic to ketoprofen.
Safety ProfilePoison by intraperitoneal route. Mddly toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
2,2'-Thiobis(4-tert-octylphenolato)-n-butylamine nickel(II) 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone Tinuvin-1130 2,2'-Dihydroxy-4-methoxybenzophenone Benazol P 2-(2'-Hydroxy-4'-benzoyloxyphenyl)-5-chlorobenzotriazole MELICOPIDINE STERIGMATOCYSTIN Ultraviolet absorbent Methoxy High efficiency ultraviolet absorbent UV-419 2-(2H-Benzothiazol-2-yl)-6-(dodecyl)-4-methylphenol Ultraviolet absorbent UV-214 OXYBENZONE USP(CRM STANDARD) Tinuvin-1130 METHOXYPHENONE CHLOROPHOSPHONAZO III 1,2,3,4-TETRAMETHOXY-10-METHYLACRIDONE

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