Salicylate sunscreens

Diglycol/CHDM/isophthalates/SIP copolymer sunscreen protectant, skin care Hydrolyzed lupine protein sunscreen vehicle, creams C12-15 alkyl benzoate sunscreen vehicle, oils C12-15 alkyl benzoate sunscreen, anti-UV-A Pansy (Viola tricolor) extract sunscreen, cosmetics TEA-salicylate sunscreen, topical p-Aminobenzoic acid Cinnamal sunscreening agent, cosmetics Guanine Homosalate suntan lamp monitors Thallium (I) chloride suntan lotions 3-Methylumbelliferone suntan preps. 

Benzyl Chloride. Benzyl chloride is manufactured by high temperature free-radical chlorination of toluene. The yield of benzyl chloride is maximized by use of excess toluene in the feed. More than half of the benzyl chloride produced is converted by butyl benzyl phthalate by reaction with monosodium butyl phthalate. The remainder is hydrolyzed to benzyl alcohol, which is converted to ahphatic esters for use in soaps, perfume, and davors. Benzyl salicylate is used as a sunscreen in lotions and creams. By-product benzal chloride can be converted to benzaldehyde, which is also produced directiy by oxidation of toluene and as a by-product during formation of benzoic acid. By-product ben zotrichl oride is not hydrolyzed to make benzoic acid but is allowed to react with benzoic acid to yield benzoyl chloride. 

Other molecules with the benzine ring and carboxyl group also have side chains added to make them better sunscreens. Two popular ones are 2-ethylhexyl salicylate ... 

Other salicylates used as sunscreens are 4-isopropylbenzyl salicylate, and triethanolamine salicylate, which goes by the trade name Tro-lamine Salicylate. 

When treating acne vulgaris, topical and systemic therapies (if indicated) are initiated 2 to 4 weeks prior to peeling. Topical antibiotics and benzoyl peroxide based products can be used daily and discontinued 1 or 2 days prior to peeling. However, unless a deeper peel is desired, retinoids should be discontinued 7-10 days prior to salicylic acid peeling. Broad-spectrum sunscreens (UVA and UVB) should be worn daily (see Photo damage. Sunscreen section). 

These sunscreen ingredients include octyl-dimethyl-PABA (UVB), 2-ethylhexyl-p-meth-oxycinnamate (UVB),octocrylene (UVA/UVB), octyl salicylate (UVB), benzophenones (UVB/ UVA), and methyl anthranilate (UVA). Avoben-zone or Parsol 1789 and mexoryl, a benzylidene camphor, block UVA. Mexoryl is the most efficient of the UVA organic sunscreens [10]. Many sunscreen formulations combine ingredients to maximize photoprotection. 

Sunscreens are transparent organic substances that penetrate into the skin and absorb ultraviolet radiation. Common classes of sunscreens include benzophe-nones, PABA derivatives, cinnamates, salicylates, and dibenzoylmethanesJ3 Ben-zophenones have a primary protective range in the UVA region and include oxy-benzone (Fig. 12.9.1), 270-350 nm dioxybenzone (Fig. 12.9.2), 206-380 nm ... 

Ultraviolet sunscreen agents, salicylic acid esters as, 22 12, 16 Umami receptor, 24 248 Umami sensation, 11 523, 565 Umber... 

Hypersensitivity to sulfonamides or chemically related drugs (eg, sulfonylureas, thiazide and loop diuretics, carbonic anhydrase inhibitors, sunscreens with PABA, local anesthetics) pregnancy at term lactation infants less than 2 months of age (except in congenital toxoplasmosis as adjunct with pyrimethamine) porphyria salicylate hypersensitivity. 

Contraindications Hypersensitivitytocarbonicanhydraseinhibitors, local anesthetics, salicylates, sulfonamides, sulfonylureas, sunscreens containing PABA, or thiazide or loop diuretics intestinal or urinary tract obstruction porphyria severe hepatic or renal dysfunction... 

The main commercial applications for salicylate esters are as uv sunscreen agents and as flavor and fragrance agents. Several have application as topical analgesics. A number of salicylate esters of commercial interest and their physical properties are listed in Table 8. 

Homomenthyl salicylate (homosalate), employed as a sunscreen agent, is on a list of 21 compounds for OTC sunscreen products, recommended by the FDA advisory review panel on OTC bum and sunburn prevention as both "safe and effective" (30). Menthyl salicylate (6) is also a sunscreen agent. 

Perfumes, Flavors, Cosmetics, and Soap. Many naturally occurring esters in essential oils and some synthetic esters are important fragrance and flavor compounds (61,62). They are used in perfumes, flavors, cosmetics, soaps, deteigents, and air fresheners. Benzyl, butyl, ethyl, methyl, and phenyl esters of benzoic acid are used as flavors, perfumes, and food preservatives. Glyceryl 4-aminobenzoate [13644-7] and 2-ethylhexyl 4-dimethylaminobenzoate [21245-02-3] are used in cosmetic sunscreen preparations. Alkyl esters of 4-hydroxybenzoic acid, called parabens, have been used under various names for fungus infections of the skin, and as preservatives in lotions and creams (101). Soap and cosmetic fragrances use large amounts of amyl and benzyl salicylate. Benzyl salicylate [118-58-1] is also used in deodorant sprays. 2-Ethylhexyl salicylate [118-60-5] and 2-ethylhexyl 4-methoxycinnamate [5466-77-3] are used in sunscreen formulations (102). 

Another very common use of phenolic compounds is in sunscreens. The presence of the aromatic ring results in the effective absorbance of the UV-B radiation (between 280 and 315 nm) from the sun and thus prevents sunburns. The most common active ingredient in many sunscreens is p-aminobenzoic acid (PABA 7.1), which is actually not a phenolic compound. This compound has been widely used since the 1970 s but is less popular nowadays due to the formation of skin rashes and acne. As a result many sunscreens are now PABA-free. Alternative active ingredients include salicylates such as octylsalicylate (7.2), cinnamates such as octyl methylcinnamate (7.3), benzophenone (7.4) and the related compound oxybenzone (7.5), and anthranilates, such as menthylanthranilate (7.6). Octyl methylcinnamate (7.3) is insoluble in water and is therefore commonly... 

Walters, K.A. Brain, K.R. Howes, D. James, V.J. Kraus, A.L. Teetsel, N.M. Toulon, M. Watkinson, A.C. Gettings, S.D. Percutaneous penetration of octyl salicylate from representative sunscreen formulations through human skin in vitro. Fd. Chem. Toxicol. 1997, 35, 1219-1225. 

The chemical sunscreens approved for OTC use in the United States are classified into seven classes aminobenzoates (previously known as PABA and PABA derivatives), salicylates, cinnamates, benzophenones, an-thranilates, dibenzoylmethane derivatives, and one miscellaneous chemical (phenyl-ben-... 

Octyl methoxycinnamate Salicylates / Anthranilates Methyl salicylate Menthyl salicylate Menthyl anthranilate Octyl salicylate Physical Sunscreens... 

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