Phenylsalicylat

Bezeichnung:Phenylsalicylat

CAS-Nr118-55-8

Englisch Name:Phenyl salicylate

CBNumberCB9322550

SummenformelC13H10O3

Molgewicht214.22

MOL-Datei118-55-8.mol

Synonyma

Phenylsalicylat

Phenylsalicylat physikalisch-chemischer Eigenschaften

Schmelzpunkt	41-43 °C (lit.)
Siedepunkt	172-173 °C/12 mmHg (lit.)
Dichte	1.250g/cm3
Brechungsindex	1.5090 (estimate)
FEMA	3960 \| PHENYL SALICYLATE
Flammpunkt	>230 °F
storage temp.	2-8°C
Löslichkeit	dioxane: 0.1 g/mL, clear, colorless
pka	8.71±0.10(Predicted)
Aggregatzustand	Fine Crystalline Powder
Farbe	White
Geruch (Odor)	at 100.00 %. mild sweet fruity balsam
Geruchsart	balsamic
Biologische Quelle	synthetic
Wasserlöslichkeit	Soluble in alcohol, ether, chloroform, turpentine, acetone and benzene. Sparingly soluble in chloroformbenzene. Insoluble in water.
Merck	14,7310
JECFA Number	736
BRN	393969
Dielectric constant	6.3（50.0℃）
Stabilität	Light sensitive. Incompatible with strong oxidants. Flammable.
Kosmetik-Inhaltsstoffe Funktionen	ANTIMICROBIAL PERFUMING DENATURANT
InChI	1S/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H
InChIKey	ZQBAKBUEJOMQEX-UHFFFAOYSA-N
SMILES	Oc1ccccc1C(=O)Oc2ccccc2
LogP	3.55
CAS Datenbank	118-55-8(CAS DataBase Reference)
NIST chemische Informationen	Benzoic acid, 2-hydroxy-, phenyl ester(118-55-8)
EPA chemische Informationen	Phenyl salicylate (118-55-8)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36-24/25
RIDADR	UN 3077 9 / PGIII
WGK Germany	2
RTECS-Nr.	VO6125000
TSCA	TSCA listed
HS Code	29182300
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Aquatic Chronic 2 Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1

Gefahreninformationscode (GHS)

Phenyl salicylate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
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.
Chemische Eigenschaften
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.
Verwenden
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.
synthetische
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).
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.
Taste threshold values
Sweet, mildly medicinal taste at concentrations near 50 ppm.
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).
Allgemeine Beschreibung
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.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
Incompatible with bromine water, ferric salts, camphor, phenol, chloral hydrate, monobrominated camphor, thymol, or urethane in trituration. .
Brandgefahr
Flash point data for Phenyl salicylate are not available, however Phenyl salicylate is probably combustible.
Pharmakologie
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).
Sicherheitsprofil
Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS
Stoffwechsel
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).
läuterung methode
Fractionally crystallise salol from its melt, then crystallise it from *benzene. [Beilstein 10 IV 154.]
Einzelnachweise
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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