Description
Chloroxylenol is a bactericide and antiseptic used mainly in public health situations. Available data is limited. It is moderately toxic to aquatic species. Mammalian toxicity is low and, whilst it may be an eye irritant, no data is available that suggests it may cause more serious health impacts.
Chemical Properties
4-Chloro-3,5-dimethylphenol is white or cream crystalline powder with a characteristic odour
Chemical Properties
White or cream-colored crystals or crystalline powder with a
characteristic phenolic odor. Volatile in steam.
Originator
Septiderm ,Fougera ,US,1960
Uses
antibacterial, topical and urinary antiseptic
Uses
Antiseptic and germicide; for mildew prevention. Claimed to be about 60 times as potent as phenol.
Uses
4-Chloro-3,5-dimethylphenol is an antiseptic and germicide. Chloroxylenol is used for mildew prevention. Chloroxylenol is also an antibacterial; antiseptic (topical and urinary).
Definition
ChEBI: 4-chloro-3,5-dimethylphenol is a member of the class of phenols that is 3,5-xylenol which is substituted at position 4 by chlorine. It is bactericidal against most Gram-positive bacteria but less effective against Staphylococci and Gram-negative bacteria, and often inactive against Pseudomonas species. It is ineffective against bacterial spores. It has a role as an antiseptic drug, a disinfectant and a molluscicide. It is a member of phenols and a member of monochlorobenzenes. It is functionally related to a 3,5-xylenol.
Production Methods
Chloroxylenol is prepared by treating 3,5-dimethylphenol with chlorine or sulfuryl chloride (SO
2Cl
2).
Manufacturing Process
546 g of intermediate xylenol fraction having a crystallizing point of 45°C
mixed with an equal weight of m-5-xylenol are placed in a suitable vessel,
equipped with stirring gear, and 273 g of sulfuryl chloride are added slowly.
The temperature rises in the course of the reaction to about 40°C. When all
the sulfuryl chloride is added the reaction mixture is heated to 80°C and theacid gases removed as far as possible by air-blowing or any other suitable
means. On cooling a quantity of the required chlor-xylenol separates out and
is removed from the mother liquor. Further quantities of the material required
can be isolated by vacuum distillation of the mother liquors and further
crystallization. In all, 200 to 208 g of material substantially 2-chlor-m-5-
xylenol can be obtained having a melting point of 112°C to 115°C. The
material can be purified if desired by crystallization from a solvent such as a
hydrocarbon.
Therapeutic Function
Topical antiseptic; Disinfectant
General Description
The degradation of 4-chloro-3,5-dimethylphenol (PCMX) by Fenton-like process using nanoparticulate zero-valent iron (nZVI) and hydrogen peroxide (H
2O
2) was studied.
Pharmaceutical Applications
4-Chloro-3,5-dimethylphenol is a common constituent of many proprietary disinfectants used for skin and wound disinfection.
As a pharmaceutical excipient, 4-Chloro-3,5-dimethylphenol is commonly used in low concentrations as an antimicrobial preservative in topical formulations such as creams and ointments. 4-Chloro-3,5-dimethylphenol is also used in a number of cosmetic formulations.
Therapeutically, 4-Chloro-3,5-dimethylphenol has been investigated as a treatment for acne vulgaris, for treating infected root canals, and as an antifungal agent when impregnated into medical devices. 4-Chloro-3,5-dimethylphenol is included in drug products approved for topical antifungal, topical acne and topical dandruff/seborrheic dermatitis/psoriasis treatments.
Agricultural Uses
Microbiocide: 4-Chloro-3,5-dimethylphenol was first registered in the U.S. for use as a fungicide and is now applied as an antimicrobial for control of bacteria, algae and fungi in adhesives, emulsions, paints and wash tanks. It is registered for use in household and domestic dwellings, laundry equipment, bathrooms, diaper pails and in industrial water and aqueous systems. Not listed for use in EU countries. Registered for use in the U.S. There are 64 global suppliers.
Trade name
BAR-FUNGAL PLUS®[C]; BIO SLIME®[C]; DESSON®; DETTOL®; ECOTRU®; ESPADOL®; HUSEPT®; HUSEPT EXTRA®; NIPACIDE®; OTTASEPT®[C]; OTTASEPT® EXTRA[C]; PCMX; RBA 777®
Mechanism of action
Causes disruption of cell membrane potentials, blocking production of adenosine triphosphate
Clinical Use
p-Chloro-m-xylenol (PC-MX; Metasep) is a nonirritating antiseptic agent with broad-spectrum antibacterial and antifungal properties. It is marketed in a 2% concentration as a shampoo. It has also been used topically for the treatment of tinea (ringworm) infections such as athlete s foot (tinea pedis) and jock itch (tinea cruris).
Safety Profile
Poison by
intraperitoneal route. Moderately toxic by
ingestion. An experimental teratogen. An
eye irritant. An antimicrobial agent. See also
CHLOROPHENOLS and
CHLORINATED HYDROCARBONS,
AROMATIC. When heated to
decomposition it emits toxic fumes of Cl-.
Safety
Chloroxylenol is generally regarded as a relatively nontoxic and
nonirritant material when used as an excipient in topical products.
However, chloroxylenol has been placed in Toxicity Category I for
eye irritation effects. In addition, allergic skin reactions have
been reported. Taken orally, chloroxylenol is mildly toxic and
ingestion of a chloroxylenol-containing disinfectant product has
been associated with reports of fatal or severe instances of selfpoisoning.
LD
50 (mouse, IP): 0.115 g/kg
LD
50 (rat, dermal): >2.0 g/kg
LD
50 (rat, oral): 3.83 g/kg
storage
Chloroxylenol is stable at normal room temperature, but is volatile
in steam. Contact with natural rubber should be avoided. Aqueous
solutions of chloroxylenol are susceptible to microbial contamination
and appropriate measures should be taken to prevent
contamination during storage or dilution. Chloroxylenol should
be stored in polyethylene, mild steel or stainless steel containers,
which should be well-closed and kept in a cool, dry place.
Chloroxylenol does not absorb at wavelengths >290 nm and has
been reported to be stable to sunlight for up to 24 hours.
Purification Methods
Crystallise the phenol from *benzene or toluene. [Beilstein 6 IV 3152.]
Incompatibilities
4-Chloro-3,5-dimethylphenol has been reported to be incompatible with nonionic surfactants and methylcellulose.
Regulatory Status
Included in the FDA Inactive Ingredients Database (otic preparations;
topical creams and emulsions). Included in nonparenteral
medicines licensed in the UK. Approved in Europe as a preservative
in cosmetics with a maximum authorized concentration of
0.5%.
References
[1] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7529 - 7537
[2] Patent: US2350677, 1940,
[3] Fortsch. Ch., Phys., 1924, vol. 18, p. 38,51
[4] Journal of the Chemical Society [Section] C: Organic, 1970, p. 1982 - 1986
Pesticide Type
Fungicide; Veterinary substance
