70356-09-1Relevant articles and documents
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)
Avobenzone is one of the most common UVA-filters in sunscreens, and is known to be photounstable. Some of the strategies used to stabilize this filter present some drawbacks like photosensitization reactions. Antioxidants are widely used as cosmetic ingredients that prevent photoageing and complement the photoprotection offered by the UV-filters preventing or reducing photogenerated reactive species. The purpose of this work was to study the effect of antioxidants in the photostabilization of avobenzone. The filter dissolved in dimethyl sulfoxide or incorporated in a sunscreen formulation was irradiated with simulated solar radiation (750 W/m2). The tested antioxidants were vitamin C, vitamin E, and ubiquinone. The area under the curve of the absorption spectrum for UVA range and the sun protection factor (SPF) were calculated. Vitamin E (1:2), vitamin C (1:0.5) and ubiquinone (1:0.5) were the more effective concentrations increasing the photostability of avobenzone. In sunscreen formulations, the most effective photostabilizer was ubiquinone which also promoted an increase in SPF. This knowledge is important to improve effectiveness of sunscreen formulation. Antioxidants can be valuable ingredients for sunscreens with a triple activity of filter stabilization, SPF boosting and photoageing prevention.
Methoxy-monobenzoylmethane protects human skin against uv-induced damage by conversion to avobenzone and radical scavenging
Carola, Christophe,Keck, Cornelia M.,Salazar, Andrew,Termer, Michael,von Hagen, Joerg
, (2021/10/20)
Avobenzone, one of the most commonly used UV filters in topical sunscreens, is susceptible to photodegradation with a consequential reduction of its UV absorbing properties. This loss of function may lead to skin irritation, photodermatosis, and photoallergic reactions caused by photodegradation byproducts. In this work, we aim to address this issue with a substance named methoxy-monobenzoylmethane (MeO-MBM), which is neither a UVB nor a UVA filter, but which converts to avobenzone, a known and approved UVA filter, under mainly UVB light irradiation. The antioxidant and intracellular radical formation properties of MeO-MBM were compared to the ones of avobenzone. The UV irradiation of MeO-MBM led to an increase in UV absorption primarily in the UVA range after conversion, both in vitro and in vivo. HPTLC and UHPLC studies illustrate the conversion of MeO-MBM to avobenzone in vitro after irradiation at 250 kJ/m2, reaching a conversion rate of 48.8%. A stable molecular antioxidant activity was observed, since 100-μM MeOMBM was measured to be 11.2% in the DPPH assay, with a decrease to 9.7% after irradiation. In comparison, the molecular antioxidant activity of 100-μM avobenzone was determined to be 0.8%. In keratinocytes, MeO-MBM reduces the intracellular ROS by 90% and avobenzone by 75% with tBHP as the inducer and by 53% and 57%, respectively, when induced by pyocyanin, indicating the redox scavenging capacity of both these molecules. These results indicate that MeO-MBM functions initially as an antioxidant material and as a photoantioxidant during its conversion process to avobenzone. This research provides insight into the development of active ingredients for topical applications with dynamic functionalities. Using this approach, we demonstrate the possibility to extend the UV protection offered to skin cells while combating cellular stress in parallel.
Novel Bifunctionalization of Activated Methylene: Base-Promoted Trifluoromethylthiolation of β-Diketones with Trifluoromethanesulfinyl Chloride
Sun, Dong-Wei,Jiang, Min,Liu, Jin-Tao
supporting information, p. 10797 - 10802 (2019/07/03)
A novel bifunctionalization of activated methylene was achieved successfully through the base-promoted trifluoromethylthiolation of β-diketones or β-ketoesters with trifluoromethanesulfinyl chloride. A series of α-trifluoromethylthiolated α-chloro-β-diketones and α-chloro-β-ketoesters were obtained in moderate to good yields under mild conditions. When β-diketones containing a phenyl group with a hydroxyl or amino substituent at the ortho position were used as substrates, intramolecular trifluoromethylthiolation/cyclization reaction took place to give the corresponding cyclic products. Furthermore, the protocol could be extended to perfluoroalkylthiolation with the sodium perfluoroalkanesulfinate/POCl3 system. On the basis of experimental results, plausible mechanisms are proposed.
High-yield production process for 1,3-diphenyl propanedione compound
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Paragraph 0085-0114, (2019/02/19)
The invention discloses a high-yield production process for a 1,3-diphenyl propanedione compound. The production process comprises the steps that a benzoate compound A, a catalyst and a solvent I areadded into a reaction kettle, then an acetophenone compound B is dropwise added into the reaction kettle at the set temperature for reaction, and after reaction, a final product is prepared through acidification, washing, desolvation and recrystallization. The production process has the characteristics that a mixed basic catalyst is adopted, compared with sodium methylate and a traditional process, the yield is increased by 10-15% and is greater than or equal to 85.0%, the production operation is easy, the environmental pollution is small, the product color is light, the distinctive aromatic odor is achieved, the quality is good, the market competitiveness is high, and the industrialization promotion is easy.
ONE-STEP, FAST, 18F-19F ISOTOPIC EXCHANGE RADIOLABELING OF DIFLUORO-DIOXABORININS AND USE OF SUCH COMPOUNDS IN TREATMENT
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Paragraph 0019; 0206-0207, (2019/12/15)
A compound according to Formula (I) or a pharmaceutically acceptable salt and/or solvate thereof, wherein X1 and X2 are each independently 18F or 19F; R1 and R2 are each independently alkyl, amine, perfluoroalkyl, alkenyl, alkynyl, aryl, or aralkenyl; and R3 is H, halo, alkyl, alkyl ester, alkenyl, alkynyl, aryl, or aralkenyl; or wherein: R1 and R3 or R2 and R3 join to form a 6-membered cycloalkyl or heterocyclyl; or R1 and R3, R2 and R3, or R1, R2, and R3 join to form a substituted or unsubstituted polycyclic ring, wherein the polycyclic ring comprises fused cycloalkyl, heterocycloalkyl, aryl, or heteroaryl rings.
Synthesis method of avobenzone
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Paragraph 0016; 0017; 0020; 0021, (2019/07/10)
The invention relates to a synthesis method of avobenzone. The synthesis method uses concentrated sulfuric acid as an acid medium to provide a needed acidic condition for carboxyl esterification, theesterification reaction belongs to a relatively common reaction in organic synthesis reactions, the reaction operation is simple, the post-treatment is easy, and the purity of the obtained product does not need special purification, and the purity, yield and other aspects are ensured, so that the synthesis method is relatively suitable for industrialized large-scale production. Sodium amide with strong alkalinity is used as a basic reagent for the Claise condensation reaction, and the final product is crystallized from a dichloromethane solution by using petroleum ether with less polarity in the post-treatment of the reaction, so that the post-treatment operation of this step is greatly simplified, the purity of the obtained product is relatively high, and the yield is also greatly improved. Crystallization and recrystallization methods are basically adopted in the post-treatment of the reactions, so that the yield is improved, and the post-treatment is easy, so that a method for industrial production is provided.
A process for preparing arab League Fu Benzong method
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Paragraph 0066; 0108; 0109; 0113; 0114; 0118-0119; 0123-0124, (2017/08/26)
The invention provides a method for preparing avobenzone. The method comprises the steps that p-tert-butylbenzaldehyde and p-methoxyacetophenone serve as raw materials, a condensation reaction is performed under the alkaline condition, and prepared condensation products are oxidized into the avobenzone under the action of an oxidizing agent. The preparation method is simple, convenient, easy to perform and few in reaction steps, the preparation condition is mild and easy to control, and the prepared avobenzone is light in color, good in quality, pure in smell, high in market competitiveness and capable of easily achieving industrialization popularization.
A arab League Fu Benzong synthetic method
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, (2017/07/04)
The invention discloses a synthetic method of avobenzone. The avobenzone is prepared by subjecting phenetole and methylbenzene, as starting materials, to alkylation, oxidation, esterification, acylation and condensation reaction. During oxidation, the oxidant potassium permanganate is added to a reaction system six times, thus thermal decomposition and deacidification of the potassium permanganate is avoided, and reaction yield is higher. During esterification, with methylsulphonic acid as catalyst, P-tert-butyl benzoic acid and methanol are subjected to reflux reaction for 8 hours according to a molar ratio: 1:7; the methanol is added in two stages for reaction, and the problem that water diversion fails in the reaction process is solved. During acylation, phosphotungstic acid is used as catalyst, reaction selectivity is improved, post-reaction treatment is simpler, and reaction yield is higher; the phosphotungstic acid is recyclable, thus cost is saved and industrial production is more benefited.
Variations in the blaise reaction: Conceptually new synthesis of 3-amino enones and 1,3-diketones
Rao, H. Surya Prakash,Muthanna, Nandurka
supporting information, p. 1525 - 1532 (2015/03/04)
Organic compounds with 3-amino enone or 1,3-diketone functional groups are extremely important, as they can be converted into a plethora of heterocyclic or carbocyclic compounds, or can be used as ligands in metal complexes. We have achieved a new, easy, straightforward and convenient synthesis of 3-amino enones and 1,3-diketones starting from aryl/heteroaryl/alkyl nitriles and 1-aryl/alkyl 2-bromoethanones. The reaction is a variation of the classical Blaise reaction, and it works with zinc and trimethylsilyl chloride as an activator. By running the hydrolysis of the reaction intermediate with HCl (3 N aq.) at 0-30 °C or at 100 °C, it is possible to form either 3-amino enones or 1,3-diketones, respectively. The newly developed method was used for the synthesis of avobenzone, an ingredient of sun-screen lotions. Furthermore, an easy synthesis of (Z)-3-amino-1-[4-(tertbutyl) phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one, with UV/Vis absorption characteristics similar to those of avobenzone, was also achieved.
Cosmetic compositions
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, (2014/07/08)
Suggested is a cosmetic compositions comprising (a) a crosspolymer obtained from copolymerisation of at least two different polyols and at least one dicarboxylic acid and (b) at least one fragrance.
