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Avobenzone

■POLYMER ADDITIVES

BIONUTRICHEM UV1789

25KG/Drum

Avobenzone Basic information Overview Application Properties Toxicity References Product Name: Avobenzone Synonyms: AVOBENZONE;EUSOLEX(R) 9020;4-tert-butyl-4'-methoxy-dibenzoylmethane;4-T-BUTYL-4'-METHOXY-DIBENZOYLMETHANE;1-(4-(1,1-Dimethylethyl)phenyl)-3-(4-methoxyphenyl)-1,3-propanedione;1-(4-TERT-BUTYLPHENYL)-3-(4-METHOXYPHENYL) 1,3-PROPANEDIOL;1-(P-T-BUTYLPHENYL)-3-(P-METHOXYPHENYL)-1,3-PROPANEDIONE;PARSOL 1789 CAS: 70356-09-1 MF: C20H22O3 MW: 310.39 EINECS: 274-581-6 Product Categories: API;Pharmaceutical intermediates;cosmetic raw material;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Organics;UV-Absorber;70356-09-1 Mol File: 70356-09-1.mol   Avobenzone Chemical Properties Melting point  81-84 °C Boiling point  463.6±35.0 °C(Predicted) density  1.079 storage temp.  Inert atmosphere,Room Temperature solubility  Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated) pka 9.74±0.13(Predicted) form  neat color  White to Pale Yellow λmax 356nm(EtOH)(lit.) Merck  14,888 InChIKey GTIRDWBOUTYFQO-UHFFFAOYSA-N CAS DataBase Reference 70356-09-1(CAS DataBase Reference) EPA Substance Registry System 1,3-Propanedione, 1-[4-(1,1-dimethylethyl)phenyl]-3-(4-methoxyphenyl)- (70356-09-1)   Safety Information Hazard Codes  N Risk Statements  50/53 Safety Statements  60-61 RIDADR  UN3077 9/PG 3 WGK Germany  2 HS Code  29145000 Hazardous Substances Data 70356-09-1(Hazardous Substances Data) MSDS Information Provider Language Avobenzone English   Avobenzone Usage And Synthesis Overview Avobenzone 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.[1][2]  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.[6] 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.; Application The Food and Drug Administration approved the use of avobenzone, a derivative of dibenzoylmethane, in commercial cosmetics for sunshine protection in 1988[14]. Properties Avobenzone 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]. Toxicity Although 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[14]. References //www.ewg.org/skindeep/ingredient/700596/AVOBENZONE/ 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. M.M.Petkovic ,M.R.Etinski,M.M.Ristic ,Hem.Ind.67(2013)203 M.M.Ristic ,M.Petkovic ,M.Etinski,J.Serb.Chem.Soc.77(2012)1037 G.P.Pfeifer,A.Besaratinia,Photochem.Photobiol.Sci.11(2012)90 N.A.Shaath,Photochem.Photobiol.Sci.9(2010)464 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 A.Cantrell,D.J.McGarvey,J.Photochem.Photobiol.,B64(2001)117 M.Yamaji,M.Kida,J.Phys.Chem.,A117(2013)1946 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. Description 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; Item No. 89320), as well as inhibits UVA-induced depletion of glutathione (GSH; Item No. 10007461), 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. Uses sedative, neurosedative Uses A component of sunscreen that absorbs the full spectrum of UVA rays. Uses 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. Uses 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. 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). Brand name Parsol 1789 (Givaudan S.A., Switzerland). Therapeutic Function Sunscreen agent General Description 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.   Avobenzone Preparation Products And Raw materials Raw materials Sodium carbonate-->Sulfuric acid-->Sodium amide-->Methanol-->Hydrochloric acid-->4-tert-Butylbenzoic acid-->4'-Methoxyacetophenone-->1-Propanone, 3-[4-(1,1-dimethylethyl)phenyl]-3-hydroxy-1-(4-methoxyphenyl)--->Benzoic acid, 4-(1,1-dimethylethyl)-, 1,1-dimethylethyl ester-->Methyl anisate-->Methyl 4-tert-butylbenzoate-->2-BROMO-1-(4-TERT-BUTYL-PHENYL)-ETHANONE-->Ethyl 4-methoxybenzoate-->4'-tert-Butylacetophenone-->Anisonitrile-->4-tert-Butyltoluene Tag:Avobenzone(70356-09-1) Related Product Information

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Leader Biochemical Group is a large leader incorporated industry manufacturers and suppliers of advanced refined raw materials From the year of 1996 when our factory was put into production to year of 2020, our group has successively invested in more than 52 factories with shares and subordinates.We focus on manufacture Pharm & chemicals, functional active ingredients, nutritional Ingredients, health care products, cosmetics, pharmaceutical and refined feed, oil, natural plant ingredients industries to provide top quality of GMP standards products.All the invested factories' product lines cover API and intermediates, vitamins, amino acids, plant extracts, daily chemical products, cosmetics raw materials, nutrition and health care products, food additives, feed additives, essential oil products, fine chemical products and agricultural chemical raw materials And flavors and fragrances. Especially in the field of vitamins, amino acids, pharmaceutical raw materials and cosmetic raw materials, we have more than 20 years of production and sales experience. All products meet the requirements of high international export standards and have been recognized by customers all over the world. Our manufacture basement & R&D center located in National Aerospace Economic & Technical Development Zone Xi`an Shaanxi China. Now not only relying on self-cultivation and development as well as maintains good cooperative relations with many famous research institutes and universities in China. Now, we have closely cooperation with Shanghai Institute of Organic Chemistry of Chinese Academy of Science, Beijing Institute of Material Medical of Chinese Academy of Medical Science, China Pharmaceutical University, Zhejiang University. Closely cooperation with them not only integrating Science and technology resources, but also increasing the R&D speed and improving our R&D power. Offering Powerful Tech supporting Platform for group development. Keep serve the manufacture and the market as the R&D central task, focus on the technical research.  Now there are 3 technology R & D platforms including biological extract, microorganism fermentation and chemical synthesis, and can independently research and develop kinds of difficult APIs and pharmaceutical intermediates. With the strong support of China State Institute of Pharmaceutical Industry (hereinafter short for CSIPI), earlier known as Shanghai Institute of Pharmaceutical Industry (SIPI), we have unique advantages in the R & D and industrialization of high-grade, precision and advanced products.  Now our Group technical force is abundant, existing staff more that 1000 people, senior professional and technical staff accounted for more than 50% of the total number of employees, including 15 PhD research and development personnel, 5 master′ S degree in technical and management personnel 9 people. We have advanced equipment like fermentation equipment and technology also extraction, isolation, purification, synthesis with rich production experience and strict quality control system, According to the GMP required, quickly transforming the R&D results to industrial production in time, it is our advantages and our products are exported to North and South America, Europe, Middle East, Africa, and other five continents and scale the forefront in the nation, won good international reputation.  We believe only good quality can bring good cooperation, quality is our key spirit during our production, we are warmly welcome clients and partner from all over the world contact us for everlasting cooperation, Leader will be your strong, sincere and reliable partner in China.

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