Phenoxyethanol
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| Names | |
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| 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] It has a faint rose-like aroma.[5]
Use
[edit]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
[edit]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
[edit]Phenoxyethanol is effective against gram-negative and gram-positive bacteria, and the yeast Candida albicans.[16]
| 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.[17] It reversibly inhibits NMDAR-mediated ion currents.[18]
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.
- ^ 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
- ^ 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.
- ^ Abstracts of the Proceedings of the Chemical Society. Chemical Society. 1895.
- ^ 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 (0): 161–175. doi:10.1039/CT8966900161. ISSN 0368-1645.
- ^ Corporation, Union Carbide (1929). Report.
- ^ 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.
- ^ 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.