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] It has a faint rose-like aroma.

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.

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

History and synthesis

Phenoxyethanol was first prepared by W. H. Perkin Jr. and his graduate student Edward Haworth in 1896.[9] They reacted sodium, phenol and 2-chloroethanol in anhydrous ethanol.[10] Starting from the 1920s, it has been commercially available as a cellulose acetate solvent under the trademark of "Phenyl cellosolve".[11]

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.[12]

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.[13]

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 . 10.1126/science.163.3868.681 . 1726343 . 5762931 . 1969Sci...163..681N . 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 . 10.2175/106143016X14504669767616 . 44134400 . 2016WaEnR..88..217D . 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. Book: Abstracts of the Proceedings of the Chemical Society . 1895 . Chemical Society . en.
  10. Bentley . William Henry . Haworth . Edward . Perkin . William Henry . 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 . en . 69 . 161–175 . 10.1039/CT8966900161 . 0368-1645.
  11. Book: Corporation, Union Carbide . Report . 1929 . en.
  12. 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 .
  13. Schmuck G, Steffens W, Bomhard E . 2-Phenoxyethanol: a neurotoxicant? . Archives of Toxicology . 74 . 4–5 . 281–7 . July 2000 . 10959804 . 10.1007/s002040000110. 2000ArTox..74..281S . 6999187 .

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