Avobenzone is a full-spectrum ultraviolet A (UVA) blocker. It inhibits UVA-induced increases in melanin levels and tyrosinase activity in B16/F10 melanoma cells (IC30s = 21.94 and 24.25 μM, respectively). Avobenzone (30 μM) also inhibits UVA-induced production of reactive oxygen species (ROS) and 8-hydroxy-2''-deoxyguanosine (8-OH-dG; ), as well as inhibits UVA-induced depletion of glutathione (GSH; ), in B16/F10 cells. It increases nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2) and upregulates the antioxidant response element (ARE) in UVA-irradiated B16/F10 cells when used at at a concentration of 30 μM. Formulations containing avobenzone have been used as a sun protectant in sunscreen products.
The CAS number of Avobenzone is 70356-09-1.
Synonyms for Avobenzone 70356-09-1:1-(4-Methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione;1-(4-tert-Butylphenyl)-3-(4-methoxyphenyl)propan-1,3-dione;4-(1,1-Dimethylethyl)-4'-methoxydibenzoylmethane;4-Methoxy-4'-tert-butyldibenzoylmethane;4-tert-Butyl-4'-methoxydibenzoylmethane;1,3-Propanedione,1-[4-(1,1-dimethylethyl)phenyl]-3-(4-methoxyphenyl)-;Butylmethoxydibenzoylmethane;Escalol 517;Eusolex 9020;NeoHeliopan 357;Parsol 1789;Parsol A;Parsol RTM 1789;Photoplex;
Avobenzone 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.
InChI:InChI=1/C20H22O3/c1-2-3-10-15-23-20(18(21)16-11-6-4-7-12-16)19(22)17-13-8-5-9-14-17/h4-9,11-14,20H,2-3,10,15H2,1H3
Relevant articles related to Avobenzone:
Article |
Source |
Photodegradation of avobenzone: Stabilization effect of antioxidants |
Afonso,Horita,Sousa E Silva,Almeida,Amaral,Lob?o,Costa,Miranda, Margarida S.,Esteves Da Silva, Joaquim C.G.,Sousa Lobo , p. 36 - 40 (2014) |
High-yield production process for 1,3-diphenyl propanedione compound |
- Paragraph 0085-0114, (2019/02/19) |
ONE-STEP, FAST, 18F-19F ISOTOPIC EXCHANGE RADIOLABELING OF DIFLUORO-DIOXABORININS AND USE OF SUCH COMPOUNDS IN TREATMENT |
- Paragraph 0019; 0206-0207, (2019/12/15) |
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