Phenoxyethanol is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula C₆H₅OC₂H₄OH. It is a colorless oily liquid. It can be classified as a glycol ether and a phenol ether. It is a common preservative in vaccine formulations. It has a faint rose-like aroma.

Use

Phenoxyethanol has germicidal and germistatic properties. It is often used together with quaternary ammonium compounds. Phenoxyethanol is used as a perfume fixative; an insect repellent; an antiseptic; a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

for

cellulose acetate In biochemistry, cellulose acetate refers to any acetate ester of cellulose, usually cellulose diacetate. It was first prepared in 1865. A bioplastic, cellulose acetate is used as a film base in photography, as a component in some coatings, and ...

, dyes, inks, and resins; a preservative for pharmaceuticals, cosmetics and lubricants; an anesthetic in fish aquaculture; and in organic synthesis. It is an alternative to formaldehyde-releasing preservatives. In Japan and the European Union, its concentration in cosmetics is restricted to 1%.

History and synthesis

Phenoxyethanol was first prepared by W. H. Perkin Jr. and his graduate student Edward Haworth in 1896. They reacted

sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

and 2-chloroethanol in anhydrous ethanol. Starting from the 1920s, it has been commercially available as a

solvent under the trademark of "Phenyl cellosolve". The compound is produced in the industry by the hydroxyethylation of phenol ( Williamson synthesis), for example, in the presence of alkali-metal hydroxides or alkali-metal borohydrides.

Efficacy

Phenoxyethanol is effective against

gram-negative Gram-negative bacteria are bacteria that, unlike gram-positive bacteria, do not retain the crystal violet stain used in the Gram staining method of bacterial differentiation. Their defining characteristic is that their cell envelope consists ...

and

gram-positive bacteria In bacteriology, gram-positive bacteria are bacteria that give a positive result in the Gram stain test, which is traditionally used to quickly classify bacteria into two broad categories according to their type of cell wall. The Gram stain ...

, and the

yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom (biology), kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are est ...

Candida albicans.

Safety

Phenoxyethanol is a vaccine preservative and potential allergen, which may result in a nodular reaction at the site of injection. Possible symptoms include rashes, eczema, and possible death. It reversibly inhibits NMDAR-mediated ion currents.

Environmental considerations

In view of phenoxyethanol's widespread use, its biodegradation has been examined. One pathway entails initial conversion to phenol and acetaldehyde.

References

{{reflist, 2 Hydroxyethyl compounds Glycol ethers Household chemicals Antiseptics Phenol ethers