Chemistry: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 | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
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PubChem CID
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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 | |
| Main hazards | Harmful if swallowed Causes serious eye irritation |
| GHS pictograms | 
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| GHS Signal word | 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). | |
 verify (what is   ?)
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| Infobox references | |
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]
Use
Phenoxyethanol has germicidal and germistatic properties.[2] It is often used together with quaternary ammonium compounds.
Phenoxyethanol is used as a perfume fixative; an insect repellent; an antiseptic;[3] a solvent for cellulose acetate, dyes, inks, and resins; a preservative for pharmaceuticals, cosmetics and lubricants;[4] an anesthetic in fish aquaculture;[5][6] and in organic synthesis.
Phenoxyethanol is an alternative to formaldehyde-releasing preservatives.[7] In Japan and the European Union, its concentration in cosmetics is restricted to 1%.[8]
Production
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.[9]
Efficacy
Phenoxyethanol is effective against gram-negative and gram-positive bacteria, and the yeast Candida albicans.[10]
| 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.[11] It reversibly inhibits NMDAR-mediated ion currents.[12]
References
- ↑ 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. https://www.jstor.org/stable/3757974.
- ↑ 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.
- ↑ 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. https://www.jstor.org/stable/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. https://www.jstor.org/stable/10.3318/bioe.2015.14.
- ↑ 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. ISSN 1061-4303. https://www.jstor.org/stable/44134400.
- ↑ "Phenoxyethanol as a nontoxic preservative in the dissection laboratory". Acta Anat (Basel) 136 (2): 155–8. 1989. doi:10.1159/000146816. PMID 2816264.
- ↑ "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.
- ↑ Cite error: Invalid
<ref>tag; no text was provided for refs nameda - ↑ "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.
- ↑ 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
- ↑ "2-Phenoxyethanol: a neurotoxicant?". Archives of Toxicology 74 (4–5): 281–7. July 2000. doi:10.1007/s002040000110. PMID 10959804.
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