Chloroxylenol

Structural formula
General
Surname	Chloroxylenol
other names	4-chloro-3,5-dimethylphenol ( IUPAC ); para -chloro- meta- xylenol; PCMX;
Molecular formula	C 8 H 9 ClO
Brief description	beige crystals with a phenolic odor
External identifiers / databases
EC number	201-793-8
ECHA InfoCard	100.001.631
PubChem	2723
DrugBank	DB11121
Wikidata	Q426460
Drug information
ATC code	D08 AE05
properties
Molar mass	156.61 g mol −1
Physical state	firmly
Melting point	114-116 ° C
boiling point	246 ° C
solubility	practically insoluble in water (250 mg l −1 at 20 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 302-315-317-319
	P: 280-302 + 352-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlorxylenol ( para -Chlor- meta -Xylenol, PCMX, 4-chloro-3,5-dimethylphenol ) is a halogenated phenol that is used as a disinfectant . It is included in the list of essential medicines by the World Health Organization .

presentation

Chloroxylenol is by chlorination of 3,5-xylenol accessible.

use

Chlorxylenol is used in a wide variety of antibacterial soaps , hand sanitisers, and antiseptics . It is also used as a preservative in cosmetics, paints and other products. Chlorxylenol is non-toxic for humans in the concentrations used (0.5–4%), and skin irritation can occasionally occur. It was first registered for use as a fungicide in the United States in 1959. Possible contamination with dioxins, which can occur during the manufacturing process, is of concern.

Chlorxylenol shows good effectiveness against bacteria ( bactericidal ) and fungi ( fungicidal ), especially against gram-positive pathogens. However, the antimicrobial activity is highly dependent on the formulation . The mechanism of action of chloroxylenol in particular has not been well studied, but is probably no different from other phenols; the reactive hydroxyl groups form hydrogen bonds with macromolecules, especially proteins , which leads to disruption of enzyme functions and membrane integrity.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on 4-chloro-3,5-dimethylphenol in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ Entry on 4-chloro-3,5-xylenol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ WHO Model List of Essential Medicines (PDF file; 432 kB) , accessed on September 20, 2012.
↑ Hager's Handbook of Pharmaceutical Practice , p. 921 ( limited preview in Google book search).
↑ ^a ^b Gerald E. McDonnell: Antisepsis, disinfection, and sterilization: types, action, and resistance , Wiley-Blackwell, Washington DC 2007, ISBN 978-1-55581-392-5 , pp. 133-140 ( restricted preview in Google Book Search).
↑ Chloroxylenol (EPA Registration) (PDF file; 25 kB).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f Entry on 4-chloro-3,5-dimethylphenol in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[CLP_100.001.631-2] Entry on 4-chloro-3,5-xylenol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[3] WHO Model List of Essential Medicines (PDF file; 432 kB) , accessed on September 20, 2012.

[4] Hager's Handbook of Pharmaceutical Practice , p. 921 ( limited preview in Google book search).

[McDonnell-5] Gerald E. McDonnell: Antisepsis, disinfection, and sterilization: types, action, and resistance , Wiley-Blackwell, Washington DC 2007, ISBN 978-1-55581-392-5 , pp. 133-140 ( restricted preview in Google Book Search).

[6] Chloroxylenol (EPA Registration) (PDF file; 25 kB).