Chemistry:Phenoxyethanol

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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.[2]

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;[6][7] 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]

Aromatic alcohol Concentration (%) Contact time (minutes)
Escherichia coli Pseudomonas aeruginosa Proteus mirabilis Staphylococcus aureus
Benzyl alcohol 1 >30 >30 >30 >30
Phenethyl alcohol 1.25 2.5 2.5 2.5 >30
2.5 2.5 2.5 2.5 5
Phenoxyethanol 1.25 15 2.5 2.5 >30
2.5 2.5 2.5 2.5 >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.[15] It reversibly inhibits NMDAR-mediated ion currents.[16]

Environmental considerations

In view of phenoxyethanol's widespread use, its biodegradation has been examined. One pathway entails initial conversion to phenol and acetaldehyde.[17]

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. 
  2. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named :0
  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. 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. 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. doi:10.1126/science.163.3868.681. ISSN 0036-8075. PMID 5762931. Bibcode: 1969Sci...163..681N. 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. 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 et al. (2016). "Cytokine Responses in Gills of Capoeta umbla as Biomarkers of Environmental Pollution". Water Environment Research 88 (3): 217–222. doi:10.2175/106143016X14504669767616. ISSN 1061-4303. PMID 26931532. Bibcode: 2016WaEnR..88..217D. https://www.jstor.org/stable/44134400. 
  8. ↑ "Phenoxyethanol as a nontoxic preservative in the dissection laboratory". Acta Anat (Basel) 136 (2): 155–8. 1989. doi:10.1159/000146816. PMID 2816264. 
  9. ↑ "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" (in ja). Kokuritsu Iyakuhin Shokuhin Eisei Kenkyūjo Hōkoku (121): 25–9. 2003. PMID 14740401. http://www.nihs.go.jp/library/eikenhoukoku/2003/2003_notes_25.pdf. 
  10. ↑ (in en) 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" (in en). 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) (in en). Report. https://books.google.com/books?id=aBchAQAAMAAJ&q=Phenyl+cellosolve. 
  13. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named a
  14. ↑ "The antimicrobial activity of phenoxyethanol in vaccines". Lett Appl Microbiol 18 (2): 115–6. 1994. doi:10.1111/j.1472-765X.1994.tb00820.x. PMID 7764595. 
  15. ↑ M. H. Beck; S. M. Wilkinson (2010), "Contact Dermatitis: Allergic", in Tony Burns; Stephen Breathnach; Neil Cox et al., Rook's Textbook of Dermatology, 2 (8th ed.), Wiley-Blackwell, p. 26.46, ISBN 978-1-4051-6169-5 
  16. ↑ "2-Phenoxyethanol: a neurotoxicant?". Archives of Toxicology 74 (4–5): 281–7. July 2000. doi:10.1007/s002040000110. PMID 10959804. Bibcode: 2000ArTox..74..281S. 
  17. ↑ 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. doi:10.1016/j.watres.2017.02.001. PMID 28347952. Bibcode: 2017WatRe.116..268G. 



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