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
CAS Number	122-99-6  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:64275  N
ChEMBL	ChEMBL1229846  N
ChemSpider	13848467  Y
ECHA InfoCard	100.004.173
PubChem CID	31236
UNII	HIE492ZZ3T  Y
CompTox Dashboard (EPA)	DTXSID90873407 DTXSID9021976, DTXSID90873407
InChI InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2 Y Key: QCDWFXQBSFUVSP-UHFFFAOYSA-N Y 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 °C)
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). N  verify  (what is  YN ?) 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] 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]

Environmental considerations

In view of phenoxyethanol's widespread use, its biodegradation has been examined. One pathway entails initial conversion to phenol and acetaldehyde. ^[19]

References

1. 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   978-3-527-30673-2.
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. 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. PMID   26931532.
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.
19. Ghattas, Ann-Kathrin; Fischer, Ferdinand; Wick, Arne; Ternes, Thomas A. (2017). "Anaerobic biodegradation of (Emerging) organic contaminants in the aquatic environment". Water Research. 116: 268–295. Bibcode:2017WatRe.116..268G. doi: 10.1016/j.watres.2017.02.001 . PMID   28347952.