Avobenzone Chemical Properties
- Melting point:81-84 °C
- Boiling point:463.6±35.0 °C(Predicted)
- Density 1.079
- form neat
- Merck 14,888
- CAS DataBase Reference70356-09-1(CAS DataBase Reference)
- EPA Substance Registry System1,3-Propanedione, 1-[4-(1,1-dimethylethyl)phenyl]-3-(4-methoxyphenyl)- (70356-09-1)
Avobenzone Usage And Synthesis
- OverviewAvobenzone is a sunscreen agent that protects against the full spectrum of UV light. Of all sunscreen agents, avobenzone has one of the largest absorbance spectrums, absorbing light between 320 – 400 nm (peak absorption ~ 360 nm). Exposure to UV rays is a leading cause of skin cancer, and so use of an effective sunscreen, like avobenzone or avobenzone in combination with other agents, helps to lower risk of developing skin cancer. Avobenzone is specifically the most effective sunscreen agent against UVA rays. Avobenzone is susceptible to photodegredation, and therefore it is important that avobenzone be combined with photostabilizers in the final sunscreen product. It's been considered a relatively safe chemical, but recent research suggests otherwise. Avobenzone degrades in the sun, resulting in the release of free radicals that may actually increase the risk for cancer.
Figure 1 the chemical structure of Avobenzone
Ultraviolet (UV) light is harmful for skin cells since it can damage genetic material.[3–5] The ozone layer absorbs radiation below 290 nm and thus cosmetic sunscreens need to filter radiation in UV-A (320–380 nm) and UV-B (290–320 nm) bands. Although there are many available UV-B filters, proper UV-A filters are deficient. 1-(4-tert-Butylphenyl)-3-(4-methoxyphenyl) propane-1, 3-dione (trade name avobenzone (AB)) is the most widely used UV-A absorber in cosmetic sunscreens. Despite its importance as a UV-A absorber, the photodynamics of AB are not completely understood[7-9]. This is due to a fact that photoexcited AB transforms into several transient tautomeric forms the lifetimes of which range from ps to ms.[10-13] These tautomerizations together with photodegradation are responsible for a complete loss of UV-A protection under irradiation.;
- ApplicationThe Food and Drug Administration approved the use of avobenzone, a derivative of dibenzoylmethane, in commercial cosmetics for sunshine protection in 1988.
- PropertiesAvobenzone belongs to a dibenzoyl methane derivative. It is oil soluble ingredient. Since it is very sensitive to light, photostablizers are added in the sunscreen product to increase its stability and duration of action. Avobenzone has an absorption maximum of 357 nm. Sunscreens containing avobenzone is indicated for providing protection from the sun. In addition to limiting the skin's exposure to the sun, using sunscreen agents may help reduce long-term sun damage such as premature aging of the skin and skin cancer. It is capable of blocking UVA I, UVA II and UVB wavelengths, thereby limiting the impact of UV rays on skin. Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent[15, 16].
- ToxicityAlthough avobenzone itself has very low toxicity, when exposed to light in a chlorinated water solution, avobenzone can be broken down into a combination of aromatic acids, aldehydes, phenols and acetyl benzenes, several of which are highly toxic.
- Karlsson I, Hillerström L, Stenfeldt AL, Mårtensson J, Börje A. "Photodegradation of dibenzoylmethanes: potential cause of photocontact allergy to sunscreens." Chemical Research in Toxicology. November 2009. doi: 10.1021/tx900284e.
- D. Veierov, T. Bercovici, E. Fischer, Y. Mazur, A. Yogev, J. Am. Chem. Soc. 99 (1977) 2723
- H. Gonzenbach, T. J. Hill, T. G. Truscott, J. Photochem. Photobiol., B 16 (1992) 377
- P.K.Verma,F.Koch,A.Steinbacher,P.Nuernberger,T.Brixner,J.Am.Chem.Soc.136 (2014) 14981
- A. D. Dunkelberger, R. D. Kieda, B. M. Marsh, F. F. Crim, J. Phys. Chem., A 119 (2015) 6155
- P. K. Verma, A. Steinbacher, F. Koch, P. Nuernberger, T. Brixner, Phys. Chem. Chem. Phys. 17 (2015) 8459
- Zawadiak J, Mrzyczek M (October 2012). "Influence Of Substituent On UV Absorption And Keto–Enol Tautomerism Equilibrium Of Dibenzoylmethane Derivatives". Spectrochim Acta a Mol Biomol Spectrosc. 96: 815–819. Bibcode:2012 AcSpA..96..815Z. doi:10.1016/j.saa.2012.07.109. PMID 22925908.
- Vielhaber G, Grether-Beck S, Koch O, Johncock W, Krutmann J (March 2006). "Sunscreens with an absorption maximum of > or =360 nm provide optimal protection against UVA1-induced expression of matrix metalloproteinase-1, interleukin-1, and interleukin-6 in human dermal fibroblasts". Photochem Photobiol Sci. 5 (3): 275&ndash, 282. doi:10.1039/b516702g. PMID 16520862.
- Usessedative, neurosedative
- UsesA component of sunscreen that absorbs the full spectrum of UVA rays.
- Usesavobenzone (BMDM, butyl methoxydibenzoylmethane) is a sun-A screen chemical that offers broad-range protection against uVA rays. It is associated with some photoinstability, which can be overcome in the overall sunscreen formulation. It is approved for use up to 3 percent in the united States and 5 percent in the european union. Avobenzone is noted to rarely be photosensitizing.
- UsesAvobenzone provides strong absorption through a large portion of the UVA spectrum including the majority of the UVA I range with peak absorption at 360 nm. Photostability refers to the ability of a molecule to remain intact with irradiation. It is potentially a problem with all UV filters, but particularly with the use of avobenzone. This effect may degrade other sunscreens in a formulation including octyl methoxycinnamate. Octocrylene and some of the newer sunscreens including BEMT stabilized avobenzone. Non-UV filters such as diethylhexyl 2,6 naphthalate may also be used. These molecules function as triplet–triplet quenchers. Overall formulation with avobenzone is therefore particularly critical.
- brand nameParsol 1789 (Givaudan S.A., Switzerland).
- 4'-METHYL-3-PHENYLPROPIOPHENONE Avobenzone tert-Butyl methyl ether Dibenzoylmethane PHENYL VALERATE 4-tert-Butylphenol 4-tert-Butylcatechol Phenylhydrazine 2-Methoxyethanol Methyl 4-tert-butylbenzoate Methoxy tert-Butyldimethylsilyl chloride tert-Butyl hydroperoxide Buprofezin Butyl acrylate butyl rubber Cyhalofop-butyl PBP
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