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Phenoxyethanol

Phenoxyethanol[1][2][3]
Names
Preferred IUPAC name
2-Phenoxyethan-1-ol
Other names
Phenoxyethanol
Ethylene glycol monophenyl ether
Phenoxytolarosol
Dowanol EP / EPH
Protectol PE
Emery 6705
Rose ether
1-Hydroxy-2-phenoxyethane
β-hydroxyethyl phenyl ether
Phenyl cellosolve
Phenoxetol®
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.173 Edit this at Wikidata
UNII
  • InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2 checkY
    Key: QCDWFXQBSFUVSP-UHFFFAOYSA-N checkY
  • InChI=1/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2
    Key: QCDWFXQBSFUVSP-UHFFFAOYAU
  • c1ccc(cc1)OCCO
Properties
C8H10O2
Molar mass 138.166 g·mol−1
Appearance Colorless oily liquid
Odor faint rose-like
Density 1.102 g/cm3
Melting point −2 °C (28 °F; 271 K)
Boiling point 247 °C (477 °F; 520 K)
26 g/kg
Solubility Chloroform, Alkali, diethyl ether: soluble
Solubility in peanut oil slightly
Solubility in olive oil slightly
Solubility in acetone miscible
Solubility in ethanol miscible
Solubility in glycerol miscible
Vapor pressure 0.001 kPa (0.00015 psi)
Thermal conductivity 0.169 W/(m⋅K)
1.534 (20 °C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful if swallowed
Causes serious eye irritation
GHS labelling:
GHS07: Exclamation mark
Warning
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 126 °C (259 °F; 399 K)
430 °C (806 °F; 703 K)
Lethal dose or concentration (LD, LC):
1850 mg/kg (rat, oral)
Related compounds
Related compounds
 phenetole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.[4] It has a faint rose-like aroma.[5]

Use

Phenoxyethanol has germicidal and germistatic properties.[6] It is often used together with quaternary ammonium compounds.

Phenoxyethanol is used as a perfume fixative; an insect repellent; an antiseptic;[7] a solvent for cellulose acetate, dyes, inks, and resins; a preservative for pharmaceuticals, cosmetics and lubricants;[8] an anesthetic in fish aquaculture;[9][10] and in organic synthesis.

It is an alternative to formaldehyde-releasing preservatives.[11] In Japan and the European Union, its concentration in cosmetics is restricted to 1%.[12]

History and synthesis

Phenoxyethanol was first prepared by W. H. Perkin Jr. and his graduate student Edward Haworth in 1896.[13] They reacted sodium, phenol and 2-chloroethanol in anhydrous ethanol.[14] Starting from the 1920s, it has been commercially available as a cellulose acetate solvent under the trademark of "Phenyl cellosolve".[15]

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.[1]

Efficacy

Phenoxyethanol is effective against gram-negative and gram-positive bacteria, and the yeast Candida albicans.[16]

Effective concentration and contact time to kill germs with aromatic alcohols[5]
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.[17] It reversibly inhibits NMDAR-mediated ion currents.[18]

References

  1. ^ a b 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 978-3527306732.
  2. ^ Commission, British Pharmacopoeia (2009), "Phenoxyethanol", British Pharmacopoeia, vol. 2, Stationery Office, ISBN 978-0-11-322799-0
  3. ^ David R. Lide, ed. (2010), CRC Handbook of Chemistry and Physics (90th ed.), CRC Press
  4. ^ 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.
  5. ^ a b 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
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.
  13. ^ Abstracts of the Proceedings of the Chemical Society. Chemical Society. 1895.
  14. ^ 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.
  15. ^ Corporation, Union Carbide (1929). Report.
  16. ^ 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.
  17. ^ 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
  18. ^ 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.
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