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
Identifiers
CAS Number	122-99-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:64275 ;
ChEMBL	ChEMBL1229846 ;
ChemSpider	13848467 ;
ECHA InfoCard	100.004.173
PubChem CID	31236;
UNII	HIE492ZZ3T ;
CompTox Dashboard (EPA)	DTXSID9021976 ;
	InChI InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2 Key: QCDWFXQBSFUVSP-UHFFFAOYSA-N ; InChI=1/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2 Key: QCDWFXQBSFUVSP-UHFFFAOYAU;
	SMILES c1ccc(cc1)OCCO;
Properties
Chemical formula	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)
Solubility in water	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)	1.534 (20 ℃)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Harmful if swallowed; Causes serious eye irritation
	GHS labelling:
Pictograms
Signal word	Warning
NFPA 704 (fire diamond)	3 1 0
Flash point	126 °C (259 °F; 399 K)
Autoignition; temperature	430 °C (806 °F; 703 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	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). verify (what is ?) 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.[4]

Use

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

Phenoxyethanol is produced 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.[12]

Effective concentration and contact time to kill germs with aromatic alcohols[13]
Aromatic alcohol	Concentration (%)	Contact time (minutes)
Aromatic alcohol	Concentration (%)	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
Phenethyl alcohol	2.5	2.5	2.5	2.5	5
Phenoxyethanol	1.25	15	2.5	2.5	>30
Phenoxyethanol	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, excema, and possible death.[14] It reversibly inhibits NMDAR-mediated ion currents.[15]

References

Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe (2007). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.
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.
Rosenberg, Herb (1992). "Improve Laboratory Conditions with Neutralizing Agent". The American Biology Teacher. 54 (6): 327–327. doi:10.2307/4449498. ISSN 0002-7685.
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.
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.
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.
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.

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[a-1] Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe (2007). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.

[2] Commission, British Pharmacopoeia (2009), "Phenoxyethanol", British Pharmacopoeia, vol. 2, 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] 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.

[6] Rosenberg, Herb (1992). "Improve Laboratory Conditions with Neutralizing Agent". The American Biology Teacher. 54 (6): 327–327. doi:10.2307/4449498. ISSN 0002-7685.

[7] 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.

[8] 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.

[9] 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.

[10] 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.

[11] 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.

[12] 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.

[13] Hans-P. Harke (2007), "Disinfectants", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 1–17, doi:10.1002/14356007.a08_551

[14] 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

[15] 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.