ChemicalBook > Product Catalog > API > Synthetic Anti-infective Drugs > Antiseptics & Disinfectants Drugs > Phenyl salicylate
Phenyl salicylate Chemical Properties
- Melting point:41-43 °C(lit.)
- Boiling point:172-173 °C12 mm Hg(lit.)
- Density 1.250g/cm3
- FEMA 3960 | PHENYL SALICYLATE
- refractive index 1.5090 (estimate)
- Flash point:>230 °F
- storage temp. room temp
- solubility dioxane: 0.1 g/mL, clear, colorless
- form Fine Crystalline Powder
- color White
- Water Solubility Soluble in alcohol, ether, chloroform, turpentine, acetone and benzene. Sparingly soluble in chloroformbenzene. Insoluble in water.
- Merck 14,7310
- JECFA Number736
- BRN 393969
- Stability:Light sensitive. Incompatible with strong oxidants. Flammable.
- CAS DataBase Reference118-55-8(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzoic acid, 2-hydroxy-, phenyl ester(118-55-8)
- EPA Substance Registry SystemPhenyl salicylate (118-55-8)
Phenyl salicylate Usage And Synthesis
- DescriptionPhenyl salicylate (chemical formula: C13H10O3) belongs to the family of hydroxybenzoic acid which are compound containing a hydroxybenzoic acid or its derivative. It is manufactured through the chemical reaction between phenol and salicylic acid. Phenyl salicylate has several medical properties. It can be used as analgesic to relieve pain, as an antiseptic with antibacterial effect as well as a kind of antipyretic for the treatment of fever. It is also used for the treatment of inflammation triggered by the lower urinary tract. However, it is no longer commonly applied to human medicine, but is still used in veterinary medicine.
- Chemical Propertieswhite crystalline solid with an aromatic odour
- Chemical PropertiesPhenyl salicylate has a distinctive aromatic odor and taste.
- OccurrenceHas apparently not been reported to occur in nature.
- UsesPhenyl 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. It is also a fragrance ingredient, but has limited use.
- UsesIn the manufacture of various polymers for the plastics industry, also in lacquers, adhesives, waxes, polishes. In suntan oils and cremes. As light absorber to prevent discoloration of plastics. Has some plasticizer properties.
- UsesPhenyl salicylate is used as analgesie; antipyretie; anti-rheumatie agent; manufacture of polymer plastics, lacquers, waxes, polishes, and adhesives; in suntan oils and creams; light absorber to prevent discoloration of plastics; in veterinary use as an external disinfectant and intestinal antiseptic agent.
- DefinitionChEBI: 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.
- PreparationBy the action of phosphorus oxychloride on a mixture of phenol and salicylic acid (Merck Index, 1968).
- Toxicity evaluationThe acute oral LD50 value in rats was reported as 3 g/kg and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Levenstein, 1975). The probable LD in man is 50-500 mg/kg. The toxic effects of phenyl salicylate are similar to those of phenol but do not include a corrosive action on the alimentary canal (Dittmer, 1959).
- General DescriptionWhite crystals. Insoluble in water.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileIncompatible with bromine water, ferric salts, camphor, phenol, chloral hydrate, monobrominated camphor, thymol, or urethane in trituration. .
- Fire HazardFlash point data for Phenyl salicylate are not available, however Phenyl salicylate is probably combustible.
- PharmacologyPhenyl 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).
- Safety ProfileModerately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS
- Chemical SynthesisPrepared by a synthetic process whereby the phenol group is made to unite with the salicylic acid radical. Also obtained by heating salicylic acid, the air being excluded.
- MetabolismAccording 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).
- Purification MethodsFractionally crystallise salol from its melt, then crystallise it from *benzene. [Beilstein 10 IV 154.]
Phenyl salicylate Preparation Products And Raw materials
- BLUE DYE Phenyl salicylate Triphenyl phosphate Diphenyl ether Phenylacetic acid Dimethyl phthalate TRIS(TRIMETHYLSILYL) PHOSPHATE PHENETHYL SALICYLATE Triphenyl phosphite Sodium salicylate DISPERSE BLUE 102 Methyl acrylate PHENYL VALERATE Benzyl benzoate DISPERSE DYE Phenyl chloroformate Dimethyl succinate Isoamyl o-hydroxybenzoate
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