1-[4-(1,1-Dimethylethyl)phenyl]-3-(4-methoxyphenyl)propan-1,3-dion

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H413：Kann für Wasserorganismen schädlich sein, mit langfristiger Wirkung.

• Sicherheit

  P273：Freisetzung in die Umwelt vermeiden.

  P501：Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Avobenzone Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.

• S-Sätze Betriebsanweisung:

  S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
  S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.

• Beschreibung

  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.

• Originator

  Avobenzone,AroKor Holdings Inc.

• Verwenden

  A component of sunscreen that absorbs the full spectrum of UVA rays.

• Verwenden

  sedative, neurosedative

• Verwenden

  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.

• Verwenden

  avobenzone (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.

• Definition

  ChEBI: Avobenzone is a member of dihydrochalcones.

• Manufacturing Process

  356.0 g (2 mol) of p-t-butylbenzoic acid, 243.0 g (7.6 mol) of methyl alcohol and 35.0 g of sulfuric acid (96%) are added to a four-necked round flask which is provided with a stirrer and a condenser. The mixture is held for 8 h at reflux temperature with slight stirring. The condenser is then replaced by a distillation column and the excess methyl alcohol is distilled off, towards the end under a slight vacuum but without the temperature exceeding 100°C. The mixture is cooled and poured on to ice. The phases are left to separate, the organic phase is washed with ice-water, with a saturated sodium carbonate solution in the presence of ice and finally with ice until neutral. The organic phase is dried over sodium sulfate and there is thus obtained a precipitate. By distillation on a Widmer column (120 mm) there are obtained 345.0 g (90% yield) of the p-t-butylbenzoic acid methyl ester, boiling point 76°C/0.02 mmHg.
  2 methods of producing of 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane from p-t-butylbenzoic acid methyl ester:
  1). To a round flask which has been well dried and flushed with nitrogen are added 85.0 g (1.1 mol) of sodium amide (50% suspension in toluene) and 180.0 g of isopropyl ether and there are now added dropwise thereto at a temperature of 50°-60°C 150.2 g (1 mol) of acetylanisole in 180.0 g of isopropyl ether. Reaction sets in immediately and a white paste-like mass forms. After completion of the addition, the mixture is stirred for a further 0.5 h and then 192.3 g of p-t-butylbenzoic acid methyl ester are added rapidly at 25°-30°C. The mixture is stirred for 0.5 h at room temperature, then for 3 h at 60°-70°C and left to stand for 12 h. 200.0 g of ice are then added and the mixture is acidified with 128.0 g (1.1 mol) of technical hydrochloric acid and 200 ml of ice-water. The mixture is stirred until the sodium salt of the product has dissolved. The phases are separated and the organic phase is washed with ice-water until neutral. The organic phase is concentrated on a rotary evaporator and there are thus recovered 290.0 g of isopropyl ether. The yield of 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane, melting point 83.5°C is 199.8 g (64.5%) (recrystallisation from methanol).
  2). 36.0 g (1.2 mol) of 80% sodium amide and 300.0 g of dry toluene are added to a round flask which was flushed with nitrogen. The mixture is heated to 50°C and 150.2 g (1 mol) of acetylanisole in 309.0 g of toluene are added within 1.5 h. After completion of the addition, the mixture is held at 50°C for 15 min and there are then added thereto at this temperature within 1 h 50 min 192.3 g (1 mol) of p-t-butylbenzoic acid methyl ester. The mixture is stirred for a further 1 h at 50°C and then heated at 100°C for 1 h, after which time the product has separated out in the form of a solid precipitate. The mixture is left to stand for 12 h and there are then added thereto 300 ml of ice-water followed by a mixture of 100 ml of pure hydrochloric acid and 250 ml of ice-water. The phases are separated and the organic phase is washed twice with water. The organic phase is dried over sodium sulfate and treated simultaneously with 20.0 g of active carbon. After filtration, the filtrate is concentrated until crystallisation begins. 50 ml of hexane are added, the mixture is cooled and then filtered over a Buchner funnel. There is obtained a total yield of 220.91 g (71.2%) of the desired 4-(1,1-dimethylethyl)-4'- methoxydibenzoylmethane, of melting point 83.5°C (recrystallisation from 600 ml of methanol).

• Trademarks

  Parsol 1789 (Givaudan S.A., Switzerland).

• Therapeutic Function

  Sunscreen agent

• Allgemeine Beschreibung

  Avobenzone is an UVA filter. It is used in sunscreen lotions and cosmetic formulations. It has maximum absorption at ca 340–350 nm, decreasing under UV irradiation resulting in loss of the UVA protecting effect. Its photostability is very sensitive as it is stable in polar protic solvent and is photolabile in nonpolar solvents.

• Flammability and Explosibility

  Non flammable

Avobenzone Upstream-Materialien And Downstream Produkte

1-[4-(1,1-Dimethylethyl)phenyl]-3-(4-methoxyphenyl)propan-1,3-dion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(554)Suppliers

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