Phenoxyethanol

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 for cellulose acetate, 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, phenol and 2-chloroethanol in anhydrous ethanol. Starting from the 1920s, it has been commercially available as a cellulose acetate 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 and gram-positive bacteria, and the yeast 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

References

1. {{Ullmann. (2007)
2. (2009). "British Pharmacopoeia". Stationery Office.
3. (2010). "CRC Handbook of Chemistry and Physics". CRC Press.
4. (2007). "Antimicrobial preservative use in parenteral products: Past and present". Journal of Pharmaceutical Sciences.
5. (1972). "Phenoxyethanol as a Fungal Enzyme Extractant and Preservative". Mycologia.
6. Rosenberg, Herb. (1992). "Improve Laboratory Conditions with Neutralizing Agent". The American Biology Teacher.
7. (1969). "Phenoxyethanol: Protein Preservative for Taxonomists". Science.
8. (2015). "Behaviour of sea lamprey (Petromyzon marinus L.) at man-made obstacles during upriver spawning migration: use of telemetry to assess efficacy of weir modifications for improved passage". Biology and Environment: Proceedings of the Royal Irish Academy.
9. (2016). "Cytokine Responses in Gills of Capoeta umbla as Biomarkers of Environmental Pollution". Water Environment Research.
10. (1989). "Phenoxyethanol as a nontoxic preservative in the dissection laboratory". Acta Anat (Basel).
11. (2003). "市販化粧水中のフェノキシエタノールおよびパラベン類の分析法に関する研究". Kokuritsu Iyakuhin Shokuhin Eisei Kenkyūjo Hōkoku.
12. (1895). "Abstracts of the Proceedings of the Chemical Society". Chemical Society.
13. (1896). "On γ-phenoxy-derivatives of malonic acid and acetic acid, and various compounds used in the synthesis of these acids". Journal of the Chemical Society, Transactions.
14. Corporation, Union Carbide. (1929). "Report".
15. (1994). "The antimicrobial activity of phenoxyethanol in vaccines". Lett Appl Microbiol.
16. Hans-P. Harke. (2007). "Ullmann's Encyclopedia of Industrial Chemistry". Wiley.
17. (2010). "Rook's Textbook of Dermatology". Wiley-Blackwell.
18. (July 2000). "2-Phenoxyethanol: a neurotoxicant?". Archives of Toxicology.
19. (2017). "Anaerobic biodegradation of (Emerging) organic contaminants in the aquatic environment". Water Research.