4-クロロ-3,5-ジメチルフェノール

外観

白色〜わずかにうすい褐色, 結晶〜結晶性粉末

定義

本品は、次の化学式で表されるハロゲン化フェノール誘導体である。

溶解性

エタノール及びアセトンに溶ける。

用途

有機合成原料、消毒・殺菌剤原料。

化粧品の成分用途

防腐剤、殺菌剤、消臭剤

効能

抗菌薬, 消毒薬

化学的特性

4-Chloro-3,5-dimethylphenol is white or cream crystalline powder with a characteristic odour

使用

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).

調製方法

Chloroxylenol is prepared by treating 3,5-dimethylphenol with chlorine or sulfuryl chloride (SO₂Cl₂).

一般的な説明

The degradation of 4-chloro-3,5-dimethylphenol (PCMX) by Fenton-like process using nanoparticulate zero-valent iron (nZVI) and hydrogen peroxide (H₂O₂) was studied.

応用例（製薬）

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.

农业用途

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.

製品名

BAR-FUNGAL PLUS®[C]; BIO SLIME®[C]; DESSON®; DETTOL®; ECOTRU®; ESPADOL®; HUSEPT®; HUSEPT EXTRA®; NIPACIDE®; OTTASEPT®[C]; OTTASEPT® EXTRA[C]; PCMX; RBA 777®

臨床応用

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).

安全性プロファイル

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-.

安全性

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.
LD₅₀ (mouse, IP): 0.115 g/kg
LD₅₀ (rat, dermal): >2.0 g/kg
LD₅₀ (rat, oral): 3.83 g/kg

貯蔵

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.

純化方法

Crystallise the phenol from *benzene or toluene. [Beilstein 6 IV 3152.]

不和合性

4-Chloro-3,5-dimethylphenol has been reported to be incompatible with nonionic surfactants and methylcellulose.

規制状況(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%.