Phenoxyethanol
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| 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)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.173 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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) |
Refractive index (nD)
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1.534 (20 °C) |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Harmful if swallowed Causes serious eye irritation |
| GHS labelling: | |
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| Warning | |
| NFPA 704 (fire diamond) | |
| Flash point | 126 °C (259 °F; 399 K) |
| 430 °C (806 °F; 703 K) | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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1850 mg/kg (rat, oral) |
| Related compounds | |
Related compounds
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phenetole |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[4]
Use
[edit]Phenoxyethanol has germicidal and germistatic properties.[5] It is often used together with quaternary ammonium compounds.
Phenoxyethanol is used as a perfume fixative; an insect repellent; an antiseptic;[6] a solvent for cellulose acetate, dyes, inks, and resins; a preservative for pharmaceuticals, cosmetics and lubricants;[7] an anesthetic in fish aquaculture;[8][9] and in organic synthesis.
Phenoxyethanol is an alternative to formaldehyde-releasing preservatives.[10] In Japan and the European Union, its concentration in cosmetics is restricted to 1%.[11]
Production
[edit]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.[1]
Efficacy
[edit]Phenoxyethanol is effective against gram-negative and gram-positive bacteria, and the yeast Candida albicans.[12]
| 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
[edit]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.[14] It reversibly inhibits NMDAR-mediated ion currents.[15]
References
[edit]- ^ 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.
- ^ Commission, British Pharmacopoeia (2009), "Phenoxyethanol", British Pharmacopoeia, vol. 2, ISBN 978-0-11-322799-0
- ^ David R. Lide, ed. (2010), CRC Handbook of Chemistry and Physics (90th ed.), CRC Press
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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. ISSN 0036-8075. JSTOR 1726343.
- ^ 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.
- ^ 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. ISSN 1061-4303. JSTOR 44134400.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Hans-P. Harke (2007), "Disinfectants", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 1–17, doi:10.1002/14356007.a08_551
- ^ 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
- ^ Schmuck G, Steffens W, Bomhard E (July 2000). "2-Phenoxyethanol: a neurotoxicant?". Archives of Toxicology. 74 (4–5): 281–7. doi:10.1007/s002040000110. PMID 10959804. S2CID 6999187.