Padimate A
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Padimate A
Padimate A is an organic compound that is an ingredient in some sunscreens. It is an ester derivative of PABA. This aromatic chemical absorbs ultraviolet rays thereby preventing sunburn. However, its chemical structure and behaviour is similar to an industrial free radical generator. In Europe this chemical was withdrawn in 1989 for unstated reasons. In the US it was never approved for use in sunscreens. Photobiology The photobiological properties of padimate O and padimate A resemble that of Michler's ketone. These compounds have been shown to increase the lethal effects of UV-radiation on cells. This photochemistry is relevant to the sunscreen controversy. See also *Padimate O Padimate O is an organic compound related to the water-soluble compound PABA (4-aminobenzoic acid) that is used as an ingredient in some sunscreens. This yellowish water-insoluble oily liquid is an ester formed by the condensation of 2-ethylhex ..., a related sunscreen ingredient References 4-A ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Sunscreen
Sunscreen, also known as sunblock or sun cream, is a photoprotective topical product for the skin that mainly absorbs, or to a much lesser extent reflects, some of the sun's ultraviolet (UV) radiation and thus helps protect against sunburn and most importantly prevent skin cancer. Sunscreens come as lotions, sprays, gels, foams (such as an expanded foam lotion or whipped lotion), sticks, powders and other topical products. Sunscreens are common supplements to clothing, particularly sunglasses, sunhats and special sun protective clothing, and other forms of photoprotection (such as umbrellas). The first sunscreen in the world was invented in Australia, by chemist H.A. Milton Blake, in 1932 formulating with the UV filter 'salol' (phenyl salicylate) at a concentration of 10%. Its protection was verified by the University of Adelaide and it was also produced commercially by Blake's company, Hamilton Laboratories. Despite sunscreen being relatively new, sun protection practices ha ...
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Ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties. '' Nomenclature Etymology Th ...
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4-Aminobenzoic Acid
4-Aminobenzoic acid (also known as ''para''-aminobenzoic acid or PABA because the two functional groups are attached to the benzene ring across from one another in the ''para'' position) is an organic compound with the formula H2NC6H4CO2H. PABA is a white solid, although commercial samples can appear gray. It is slightly soluble in water. It consists of a benzene ring substituted with amino and carboxyl groups. The compound occurs extensively in the natural world. Production and occurrence In industry, PABA is prepared mainly by two routes: * Reduction of 4-nitrobenzoic acid * Hoffman degradation of the monoamide derived from terephthalic acid. Food sources of PABA include liver, brewer's yeast (and unfiltered beer), kidney, molasses, mushrooms, and whole grains. A review on this compound. Biology Biochemistry PABA is an intermediate in the synthesis of folate by bacteria, plants, and fungi. Many bacteria, including those found in the human intestinal tract such as ''E ...
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Ultraviolet
Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nanometer, nm (with a corresponding frequency around 30 Hertz, PHz) to 400 nm (750 Hertz, THz), shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight, and constitutes about 10% of the total electromagnetic radiation output from the Sun. It is also produced by electric arcs and specialized lights, such as mercury-vapor lamps, tanning lamps, and black lights. Although long-wavelength ultraviolet is not considered an ionizing radiation because its photons lack the energy to ionization, ionize atoms, it can cause chemical reactions and causes many substances to glow or fluorescence, fluoresce. Consequently, the chemical and biological effects of UV are greater than simple heating effects, and many practical applications of UV radiation derive from its interactions with organic molecules. Short-wave ultraviolet light damages DNA and sterilizes surf ...
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Michler's Ketone
Michler's ketone is an organic compound with the formula of CH3)2NC6H4sub>2CO. This electron-rich derivative of benzophenone is an intermediate in the production of dyes and pigments, for example Methyl violet. It is also used as a photosensitizer. It is named after the German chemist Wilhelm Michler. Synthesis The ketone is prepared today as it was originally by Michler using the Friedel-Crafts acylation of dimethylaniline (C6H5NMe2) using phosgene (COCl2) or equivalent reagents such as triphosgene :COCl2 + 2 C6H5NMe2 → (Me2NC6H4)2CO + 2 HCl → salt The related tetraethyl compound (Et2NC6H4)2CO, also a precursor to dyes, is prepared similarly. Uses Michler's ketone is an intermediate in the synthesis of dyes and pigments for paper, textiles, and leather. Condensation with various aniline derivatives gives several of the dyes called methyl violet, such as crystal violet. Condensation of Michler's ketone with ''N''-phenyl-1-naphthylamine gives the dye Victoria Blue ...
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Sunscreen Controversy
Sunscreen, also known as sunblock or sun cream, is a photoprotective topical product for the skin that mainly absorbs, or to a much lesser extent reflects, some of the sun's ultraviolet (UV) radiation and thus helps protect against sunburn and most importantly prevent skin cancer. Sunscreens come as lotions, sprays, gels, foams (such as an expanded foam lotion or whipped lotion), sticks, powders and other topical products. Sunscreens are common supplements to clothing, particularly sunglasses, sunhats and special sun protective clothing, and other forms of photoprotection (such as umbrellas). The first sunscreen in the world was invented in Australia, by chemist H.A. Milton Blake, in 1932 formulating with the UV filter 'salol' (phenyl salicylate) at a concentration of 10%. Its protection was verified by the University of Adelaide and it was also produced commercially by Blake's company, Hamilton Laboratories. Despite sunscreen being relatively new, sun protection practices hav ...
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Padimate O
Padimate O is an organic compound related to the water-soluble compound PABA (4-aminobenzoic acid) that is used as an ingredient in some sunscreens. This yellowish water-insoluble oily liquid is an ester formed by the condensation of 2-ethylhexanol with dimethylaminobenzoic acid. Other names for padimate O include 2-ethylhexyl 4-dimethylaminobenzoate, Escalol 507, octyldimethyl PABA, and OD-PABA. Photobiology Padimate O absorbs ultraviolet rays, thereby preventing direct DNA damage by UV-B. However, the thus-excited padimate O molecule may then react with DNA to produce indirect DNA damage, similar to the effects of ionizing radiation. An ''in vitro'' yeast study conducted in 1993 demonstrated the sunlight-induced mutagenicity of padimate O. The photobiological properties of padimate O resemble those of Michler's ketone, which is considered photocarcinogenic in rats and mice. These findings suggest that padimate O might also be photocarcinogenic. However, multiple ''in vivo' ...
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