Phenoxyethanol Explained

Phenoxyethanol is the organic compound 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.[1]

Use

Phenoxyethanol has germicidal and germistatic properties.[2] It is often used together with quaternary ammonium compounds.

Phenoxyethanol is used as a perfume fixative; an insect repellent; an antiseptic;[3] a solvent for cellulose acetate, dyes, inks, and resins; a preservative for pharmaceuticals, cosmetics and lubricants;[4] an anesthetic in fish aquaculture;[5] [6] and in organic synthesis.

Phenoxyethanol is an alternative to formaldehyde-releasing preservatives.[7] In Japan and the European Union, its concentration in cosmetics is restricted to 1%.[8]

Production

Phenoxyethanol is produced by the hydroxyethylation of phenol (Williamson synthesis), for example, in the presence of alkali-metal hydroxides or alkali-metal borohydrides. Phenoxyethanol has a long history of use, with its discovery credited to the German chemist Otto Schott in the early 20th century. Since then, it has been extensively studied and applied in various industries.

Efficacy

Phenoxyethanol is effective against gram-negative and gram-positive bacteria, and the yeast Candida albicans.[9]

Aromatic alcohol! rowspan=2
Concentration (%)Contact time (minutes)
Escherichia coliPseudomonas aeruginosaProteus mirabilisStaphylococcus aureus
Benzyl alcohol1>30>30>30>30
Phenethyl alcohol1.252.52.52.5>30
2.52.52.52.55
Phenoxyethanol1.25152.52.5>30
2.52.52.52.5>30

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.[10]

Notes and References

  1. 10.1002/jps.20976. Antimicrobial preservative use in parenteral products: Past and present. 2007. Meyer. Brian K.. Ni. Alex. Hu. Binghua. Shi. Li. Journal of Pharmaceutical Sciences. 96. 12. 3155–3167. 17722087.
  2. Nolan . Richard A. . Nolan . William G. . 1972 . Phenoxyethanol as a Fungal Enzyme Extractant and Preservative . Mycologia . 64 . 6 . 1344–1349 . 10.2307/3757974 . 3757974 . 0027-5514.
  3. Rosenberg . Herb . 1992 . Improve Laboratory Conditions with Neutralizing Agent . The American Biology Teacher . 54 . 6 . 327 . 10.2307/4449498 . 4449498 . 0002-7685.
  4. Nakanishi . Mikiye . Wilson . Allan C. . Nolan . Richard A. . Gorman . George C. . Bailey . George S. . 1969 . Phenoxyethanol: Protein Preservative for Taxonomists . Science . 163 . 3868 . 681–683 . 1726343 . 0036-8075.
  5. Rooney . Seán M. . Wightman . Glen . Ó'Conchúir . Ruairi . King . James J. . 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 . 115B . 2 . 125–136 . 10.3318/bioe.2015.14 . 10.3318/bioe.2015.14 . 0791-7945.
  6. Danabas . Durali . Yildirim . Nuran Cikcikoglu . Yildirim . Numan . Onal . Ayten Oztufekci . Uslu . Gulsad . Unlu . Erhan . Danabas . Seval . Ergin . Cemil . Tayhan . Nilgun . 2016 . Cytokine Responses in Gills of Capoeta umbla as Biomarkers of Environmental Pollution . Water Environment Research . 88 . 3 . 217–222 . 44134400 . 1061-4303.
  7. Acta Anat (Basel) . 1989 . 136 . 2 . 155–8 . Phenoxyethanol as a nontoxic preservative in the dissection laboratory . Wineski LE, English AW . 2816264 . 10.1159/000146816.
  8. Tokunaga H, Takeuchi O, Ko R, Uchino T, Ando M . 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 . Studies for analyzing phenoxyethanol and parabens in commercial lotions . ja . Kokuritsu Iyakuhin Shokuhin Eisei Kenkyūjo Hōkoku . 121 . 25–9 . 2003 . 14740401 .
  9. Lett Appl Microbiol . 1994 . 18 . 2 . 115–6 . The antimicrobial activity of phenoxyethanol in vaccines . Lowe I, Southern J . 7764595 . 10.1111/j.1472-765X.1994.tb00820.x. 12124463 .
  10. Schmuck G, Steffens W, Bomhard E . 2-Phenoxyethanol: a neurotoxicant? . Archives of Toxicology . 74 . 4–5 . 281–7 . July 2000 . 10959804 . 10.1007/s002040000110. 6999187 .

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