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

pka

8.71±0.10(Predicted)

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 Number

736

BRN 

393969

Stability:

Light sensitive. Incompatible with strong oxidants. Flammable.

CAS DataBase Reference

118-55-8(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 2-hydroxy-, phenyl ester(118-55-8)

EPA Substance Registry System

Phenyl salicylate (118-55-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

2

RTECS 

VO6125000

TSCA 

Yes

HS Code 

29182300

MSDS

• Language:English Provider:Disperse Dye Blue EXSF
• Language:English Provider:ACROS
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Phenyl salicylate Usage And Synthesis

Description

Phenyl 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.

References

https://pubchem.ncbi.nlm.nih.gov/compound/Phenyl_salicylate#section=Top
http://www.wisegeek.com/what-are-the-medical-uses-of-phenyl-salicylate.htm

Chemical Properties

white crystalline solid with an aromatic odour

Chemical Properties

Phenyl salicylate has a distinctive aromatic odor and taste.

Occurrence

Has apparently not been reported to occur in nature.

Uses

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. It is also a fragrance ingredient, but has limited use.

Uses

In 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.

Uses

Phenyl 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.

Definition

ChEBI: 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.

Preparation

By the action of phosphorus oxychloride on a mixture of phenol and salicylic acid (Merck Index, 1968).

Toxicity evaluation

The 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 Description

White crystals. Insoluble in water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

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

Fire Hazard

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

Pharmacology

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).

Safety Profile

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

Chemical Synthesis

Prepared 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.

Metabolism

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).

Purification Methods

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

Phenyl salicylate(118-55-8)Related Product Information

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