xibornol

Chemical properties

Crystalline solid or viscous, yellowish liquid.

Originator

Nanbacine,Fournier,France,1976

The Uses of xibornol

Antibacterial agent, rubber antioxidant.

Definition

ChEBI: A bridged compound that is 3,4-xylenol carrying an additional isobornyl substituent at position 6. A lipophilic antibacterial drug mainly used in spray dosage forms for the local treatment of infection and inflammation of the throat.

Manufacturing Process

100 g of 3,4-xylenol and 150 g of camphene are melted in a two-necked flask equipped with a reflux condenser and a thermometer. 10 g of stannic chloride are added in small quantities; the temperature is kept between 70°C and 80°C for 4 hours. The mass is then allowed to cool and 300 ml of benzene and 300 ml of water are added. The aqueous layer is decanted off, and the supernatant organic layer is washed, first with 1,200 ml of 10% potassium hydroxide and then with water until neutral. The benzene is driven off and the mass is distilled. The fraction which passes between 203°C and 223°C/200 mm Hg is collected and recrystallized in petroleum ether.
100 mg of the recrystallized product is dissolved in 10 ml of hexane.
This solution is then slowly passed through a chromatographic alumina column, 20 cm in length and 16 mm in diameter, containing 20 g of alumina (Prolabo).
The column is then eluted with benzene and 2 ml fractions of the eluent are collected as soon as the product appears in the eluent. The presence of the product is detected by means of the color change in the collected eluent after adding 1 drop of 2% ferric chloride and 2 drops of 5% potassium ferricyanide solution.
18 ml of a first fraction are collected, the next 2 ml of eluent are discarded and then a second fraction of 20 ml is collected. Removal of the solvent from the first fraction by distillation leaves a product having a melting point of between 94°C and 96°C and removal of the solvent from the second fraction leaves a product having a melting point between 86°C and 88°C.
The product remaining from the first fraction is 6-isobornyl-3,4-xylenol while that from the second fraction is its isomer 6-exo-isocamphenyl-3,4-xylenol.

Therapeutic Function

Antibacterial