| Identification | More | [Name]
Phenyl salicylate | [CAS]
118-55-8 | [Synonyms]
2-HYDROXYBENZOIC ACID PHENYL ESTER
AURORA KA-3673
Disperse Dye Blue EXSF
FEMA 3960
LABOTEST-BB LT00053052
'LGC' (2411)
'LGC' (2613)
O-HYDROXYBENZOIC ACID PHENYL ESTER
PHENYL 2-HYDROXYBENZOATE
PHENYL-O-HYDROXYBENZOATE
PHENYL SALICYLATE
SALICYLIC ACID PHENYL ESTER
SALOL
2-hydroxy-benzoicaciphenylester
2-Phenoxycarbonylphenol
Benzoicacid,2-hydroxy-,phenylester
Fenylester kyseliny salicylove
fenylesterkyselinysalicylove
Musol
Phenol salicylate | [EINECS(EC#)]
204-259-2 | [Molecular Formula]
C13H10O3 | [MDL Number]
MFCD00002213 | [Molecular Weight]
214.22 | [MOL File]
118-55-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline solid with an aromatic odour | [Melting point ]
41-43 °C (lit.) | [Boiling point ]
172-173 °C/12 mmHg (lit.) | [density ]
1.250g/cm3 | [FEMA ]
3960 | [refractive index ]
1.5090 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [solubility ]
dioxane: 0.1 g/mL, clear, colorless
| [form ]
Fine Crystalline Powder | [pka]
8.71±0.10(Predicted) | [color ]
White | [Odor]
at 100.00 %. mild sweet fruity balsam | [Stability:]
Light sensitive. Incompatible with strong oxidants. Flammable. | [Odor Type]
balsamic | [Water Solubility ]
Soluble in alcohol, ether, chloroform, turpentine, acetone and benzene. Sparingly soluble in chloroformbenzene. Insoluble in water. | [JECFA Number]
736 | [Merck ]
14,7310 | [BRN ]
393969 | [Dielectric constant]
6.3（50.0℃） | [LogP]
3.55 | [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]
118-55-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
2
| [RTECS ]
VO6125000
| [TSCA ]
Yes | [HS Code ]
29182300 | [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 |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
Phenyl salicylate is a white crystalline solid with a distinctive aromatic odor and taste. Soluble in ether, benzene and chloroform, soluble in ethanol, almost insoluble in water and glycerol. | [Uses]
Phenyl salicylate(118-55-8) 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.
| [Definition]
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. | [Preparation]
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). | [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]
Phenyl salicylate(118-55-8) 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. | [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). | [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.] | [References]
https://pubchem.ncbi.nlm.nih.gov/compound/Phenyl_salicylate
http://www.wisegeek.com/what-are-the-medical-uses-of-phenyl-salicylate.htm
https://en.wikipedia.org/wiki/Phenyl_salicylate
https://www.sigmaaldrich.com/SG/en/product/sial/phr1152 |
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