Фенилсалицилат

Описание

Phenyl salicylate, also referred to as salol, is a member of the hydroxybenzoic acid family of organic compounds. Its chemical formula is C13H10O3. It is manufactured through the chemical reaction between phenol and salicylic acid. Phenyl salicylate is a good antiseptic that is used in the production of toothpaste. It has several medical properties, including its ability to act as an analgesic, anti-septic with antibacterial properties, and antipyretic to reduce fever. Additionally, it can be utilized for treating lower urinary tract inflammation. Although it is no longer widely used in human medicine, it is still employed in veterinary medicine.

Химические свойства

Phenyl salicylate is a white crystalline solid that has a balsamic type odor. It readily dissolves in ether, benzene, and chloroform, and can be dissolved in ethanol, but is almost insoluble in water and glycerol.

Использование

Phenyl salicylate is used as an analgesic and antipyretic. It is also used in the manufacture of polymer plastics, lacquers, waxes, polishes, adhesives, and sunscreen products(suntan oils and cremes). As light absorber to prevent discoloration of plastics. It is also a fragrance ingredient, but has limited use. in veterinary use as an external disinfectant and intestinal antiseptic agent.

Подготовка

Phenyl salicylate was synthesized by esterification of salicylic acid and phenol in the presence of catalyst sulfuric acid. The esterification liquid is neutralized, washed with water and distilled to obtain the finished product. It also can preparation by the action of phosphorus oxychloride on a mixture of phenol and salicylic acid (Merck Index, 1968).

Определение

ChEBI: Phenyl salicylate is a benzoate ester that is the phenyl ester of salicylic acid. Also known as salol, it can be formed by heating salicylic acid with phenol and is used in the manufacture of some polymers, lacquers, adhesives, waxes and polishes. It has a role as an ultraviolet filter. It is a benzoate ester, a member of phenols and a member of salicylates. It derives from a salicylic acid.

Пороговые значения вкуса

Sweet, mildly medicinal taste at concentrations near 50 ppm.

Общее описание

Phenyl salicylate is a phenyl ester of salicylic acid and is used as a medicine under the name ′salol′ as an internal antiseptic. It finds its application in paints, waxes, and varnishes as it is found to absorb UV radiation in the range of 290-325 nm. It also shows its presence in cosmetics and sunscreens as a UV filter.

Реакции воздуха и воды

Insoluble in water.

Профиль реактивности

Incompatible with bromine water, ferric salts, camphor, phenol, chloral hydrate, monobrominated camphor, thymol, or urethane in trituration. .

Пожароопасность

Flash point data for Phenyl salicylate are not available, however Phenyl salicylate is probably combustible.

Фармаколо?гия

Phenyl salicylate was found to have slight analgesic activity against pain stimuli in mice (Kameyama, 1961), but ip administration of 500 mg/kg showed no analgesic action against an electric shock applied to the tails of mice (McKenzie & Beechey, 1962). In vitro studies on cartilage and rat-liver mitochondria have shown that phenyl salicylates are more active than salicylates in uncoupling oxidative phosphorylation (Bostrom, Berntsen & Whitehouse, 1964).

Профиль безопасности

Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS

Метаболизм

According to Baas (1890) from 44 to 96% of a dose (5-8 g) of phenyl salicylate is hydrolysed in man and none of it is found in the faeces. An increase in the ethereal sulphates of the urine after its ingestion is due, no doubt, to the phenol liberated (Williams, 1959). Phenyl salicylate is hydrolysed in the gut primarily to phenol and salicylic acid, which are rapidly absorbed and excreted (Fassett, 1963), but it was not hydrolysed by a partially purified preparation of acetylarylesterase from human plasma (Augustinsson & Ekedahl, 1962). Intestinal absorption and excretion of orally administered phenyl salicylate were studied in rabbits and dogs by analysis of blood and urine samples; oral administration of glucosamine hydrochloride increased the blood concentration of phenyl salicylate but had little effect on urinary excretion (Tanaka, Kojima & Matsubara, 1961).

Методы очистки

Fractionally crystallise salol from its melt, then crystallise it from *benzene. [Beilstein 10 IV 154.]