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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.173
Edit this at Wikidata
PubChem CID
UNII
InChI
  • InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2 checkY
    Key: QCDWFXQBSFUVSP-UHFFFAOYSA-N checkY
  • 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):
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 checkY☒N ?)
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. It is often used together with quaternary ammonium compounds.

Phenoxyethanol is used as a perfume fixative; an insect repellent; an antiseptic; a solvent for cellulose acetate, dyes, inks, and resins; a preservative for pharmaceuticals, cosmetics and lubricants; an anesthetic in fish aquaculture; and in organic synthesis.

Phenoxyethanol is an alternative to formaldehyde-releasing preservatives.[5] In Japan and the European Union, its concentration in cosmetics is restricted to 1%.[6]

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.[7]

Effective concentration and contact time to kill germs with aromatic alcohols[8]
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.[9] It reversibly inhibits NMDAR-mediated ion currents.[10]

References

  1. 1 2 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. ↑ 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ Hans-P. Harke (2007), "Disinfectants", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 1–17, doi:10.1002/14356007.a08_551
  9. ↑ 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
  10. ↑ 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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