118-55-8 Usage
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
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 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
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
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 118-55-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 8 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 118-55:
(5*1)+(4*1)+(3*8)+(2*5)+(1*5)=48
48 % 10 = 8
So 118-55-8 is a valid CAS Registry Number.
InChI:InChI=1/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H
118-55-8Relevant articles and documents
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Bader,Kotowicz
, p. 5417 (1953)
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Cu(OTf)2-mediated Chan-Lam reaction of carboxylic acids to access phenolic esters
Zhang, Lingli,Zhang, Guoying,Zhang, Manli,Cheng, Jiang
, p. 7472 - 7474 (2010)
A Cu(OTf)2-mediated Chan-Lam reaction of carboxylic acids with arylboronic acids is described. It represents a facile and practical methodology to access phenolic esters in moderate to good yields. The procedure tolerates a series of functional groups, such as methoxycarbonyl, acetoxy, free phenolic hydroxyl, vinyl, nitro, trifluoromethyl, methoxyl, bromo, chloro, iodo, and acetyl groups.
Synthesis, characterization and catalytic activity studies on cordierite honeycomb coated with ZrO2 based solid super acids
Mohamed Shamshuddin,Shyam Sundar,Thimmaraju,Venkatesh,Vatsalya,Senthilkumar
, p. 799 - 807 (2012)
Cordierite honeycomb coated with solid acids such as ZrO2, Mo/ZrO2 and W/ZrO2 were synthesized. These solid acid catalysts were also synthesized in their powder forms. The catalytic materials were characterized for their physicochemical properties such as surface area, surface acidity, crystallinity and morphology by using techniques such as BET, NH3-TPD/n-butylamine back titration, powder XRD and SEM respectively. The catalytic activity of these catalytic materials was determined in an acid catalyzed transesterification reaction of methyl salicylate with phenol to synthesize phenyl salicylate (salol). The effect of concentration of Mo or W ions on ZrO2, nature of the catalyst (whether honeycomb coated or powder form), reaction temperature, reaction time and reusability of the catalytic material in transesterification was studied. Formation of diphenyl ether as a by-product was observed on increasing the concentration of Mo or W ions on ZrO2 and also at higher reaction temperature. The catalytic activity of catalytic materials was correlated with surface acidity and the crystalline phases of catalytic material. Transesterification reactions were also carried out with methyl salicylate and benzyl alcohol or cyclohexanol to synthesize their respective salicylate esters. A probable mechanism of transesterification of methyl salicylate with an alcohol is also proposed. The honeycomb catalysts were found to be efficient, ecofriendly, economical and reusable catalysts compared to their powder forms.
Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids
Tripathy, Alisha Rani,Yatham, Veera Reddy,Yedase, Girish Suresh
, p. 25207 - 25210 (2021/08/05)
We report herein a cerium photocatalyzed aryl migration from an aryl ether to a carboxylic acid group through radical-Smiles rearrangement. This operationally simple protocol utilizes inexpensive CeCl3as a photocatalyst and converted a variety of 2-aryloxybenzoic acids into aryl-2-hydroxybenzoates in good yields.
Rhodium-Catalyzed Carbonylative Synthesis of Aryl Salicylates from Unactivated Phenols
Ai, Han-Jun,Zhang, Youcan,Zhao, Fengqian,Wu, Xiao-Feng
supporting information, p. 6050 - 6054 (2020/10/02)
A rhodium-catalyzed carbonylative transformation of unactivated phenols to aryl salicylates is described. This protocol is characterized by utilizing 1,3-rhodium migration as the key step to provide direct access to synthesize ohydroxyaryl esters. Various desired aryl o-hydroxybenzoates were produced in moderate to excellent yields with bis(dicyclohexylphosphino)ethane (DCPE) as the ligand. Interestingly, diphenyl carbonate was formed as the main product when 1,3-bis(diphenylphosphino)propane (DPPP) was used as the ligand. A plausible reaction mechanism is proposed.