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Phenoxyethanol
Chemical compound

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. It has a faint rose-like aroma.

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Use

Phenoxyethanol has germicidal and germistatic properties.3 It is often used together with quaternary ammonium compounds.

Phenoxyethanol is used as a perfume fixative; an insect repellent; an antiseptic;4 a solvent for cellulose acetate, dyes, inks, and resins; a preservative for pharmaceuticals, cosmetics and lubricants;5 an anesthetic in fish aquaculture;67 and in organic synthesis.

It is an alternative to formaldehyde-releasing preservatives.8 In Japan and the European Union, its concentration in cosmetics is restricted to 1%.9

History and synthesis

Phenoxyethanol was first prepared by W. H. Perkin Jr. and his graduate student Edward Haworth in 1896.10 They reacted sodium, phenol and 2-chloroethanol in anhydrous ethanol.11 Starting from the 1920s, it has been commercially available as a cellulose acetate solvent under the trademark of "Phenyl cellosolve".12

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.13

Efficacy

Phenoxyethanol is effective against gram-negative and gram-positive bacteria, and the yeast Candida albicans.14

Effective concentration and contact time to kill germs with aromatic alcohols15
Aromatic alcoholConcentration (%)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.16 It reversibly inhibits NMDAR-mediated ion currents.17

Environmental considerations

In view of phenoxyethanol's widespread use, its biodegradation has been examined. One pathway entails initial conversion to phenol and acetaldehyde.18

References

  1. Meyer, Brian K.; Ni, Alex; Hu, Binghua; Shi, Li (2007). "Antimicrobial preservative use in parenteral products: Past and present". Journal of Pharmaceutical Sciences. 96 (12): 3155–3167. doi:10.1002/jps.20976. PMID 17722087. /wiki/Doi_(identifier) ↩

  2. Hans-P. Harke (2007), "Disinfectants", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 1–17, doi:10.1002/14356007.a08_551, ISBN 978-3-527-30673-2 978-3-527-30673-2 ↩

  3. Nolan, Richard A.; Nolan, William G. (1972). "Phenoxyethanol as a Fungal Enzyme Extractant and Preservative". Mycologia. 64 (6): 1344–1349. doi:10.2307/3757974. ISSN 0027-5514. JSTOR 3757974. https://www.jstor.org/stable/3757974 ↩

  4. Rosenberg, Herb (1992). "Improve Laboratory Conditions with Neutralizing Agent". The American Biology Teacher. 54 (6): 327. doi:10.2307/4449498. ISSN 0002-7685. JSTOR 4449498. https://www.jstor.org/stable/4449498 ↩

  5. 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. Bibcode:1969Sci...163..681N. doi:10.1126/science.163.3868.681. ISSN 0036-8075. JSTOR 1726343. PMID 5762931. https://www.jstor.org/stable/1726343 ↩

  6. 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. doi:10.3318/bioe.2015.14. ISSN 0791-7945. JSTOR 10.3318/bioe.2015.14. https://www.jstor.org/stable/10.3318/bioe.2015.14 ↩

  7. 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. Bibcode:2016WaEnR..88..217D. doi:10.2175/106143016X14504669767616. ISSN 1061-4303. JSTOR 44134400. PMID 26931532. https://www.jstor.org/stable/44134400 ↩

  8. Wineski LE, English AW (1989). "Phenoxyethanol as a nontoxic preservative in the dissection laboratory". Acta Anat (Basel). 136 (2): 155–8. doi:10.1159/000146816. PMID 2816264. /wiki/Doi_(identifier) ↩

  9. Tokunaga H, Takeuchi O, Ko R, Uchino T, Ando M (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" [Studies for analyzing phenoxyethanol and parabens in commercial lotions] (PDF). Kokuritsu Iyakuhin Shokuhin Eisei Kenkyūjo Hōkoku (in Japanese) (121): 25–9. PMID 14740401. http://www.nihs.go.jp/library/eikenhoukoku/2003/2003_notes_25.pdf ↩

  10. Abstracts of the Proceedings of the Chemical Society. Chemical Society. 1895. https://books.google.com/books?id=uCZEAQAAMAAJ&pg=RA1-PA40 ↩

  11. 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. 69: 161–175. doi:10.1039/CT8966900161. ISSN 0368-1645. https://books.google.com/books?id=qQnjBugq3X0C&pg=PA165 ↩

  12. Corporation, Union Carbide (1929). Report. https://books.google.com/books?id=aBchAQAAMAAJ&q=Phenyl+cellosolve ↩

  13. Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe; Wilfried Paulus (2007). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3-527-30673-2. 978-3-527-30673-2 ↩

  14. Lowe I, Southern J (1994). "The antimicrobial activity of phenoxyethanol in vaccines". Lett Appl Microbiol. 18 (2): 115–6. doi:10.1111/j.1472-765X.1994.tb00820.x. PMID 7764595. S2CID 12124463. /wiki/Doi_(identifier) ↩

  15. Hans-P. Harke (2007), "Disinfectants", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 1–17, doi:10.1002/14356007.a08_551, ISBN 978-3-527-30673-2 978-3-527-30673-2 ↩

  16. M. H. Beck; S. M. Wilkinson (2010), "Contact Dermatitis: Allergic", in Tony Burns; Stephen Breathnach; Neil Cox; Christopher Griffiths (eds.), Rook's Textbook of Dermatology, vol. 2 (8th ed.), Wiley-Blackwell, p. 26.46, ISBN 978-1-4051-6169-5 978-1-4051-6169-5 ↩

  17. Schmuck G, Steffens W, Bomhard E (July 2000). "2-Phenoxyethanol: a neurotoxicant?". Archives of Toxicology. 74 (4–5): 281–7. Bibcode:2000ArTox..74..281S. doi:10.1007/s002040000110. PMID 10959804. S2CID 6999187. /wiki/Bibcode_(identifier) ↩

  18. Ghattas, Ann-Kathrin; Fischer, Ferdinand; Wick, Arne; Ternes, Thomas A. (2017). "Anaerobic biodegradation of (Emerging) organic contaminants in the aquatic environment". Water Research. 116: 268–295. Bibcode:2017WatRe.116..268G. doi:10.1016/j.watres.2017.02.001. PMID 28347952. https://doi.org/10.1016%2Fj.watres.2017.02.001 ↩