Phenoxyethanol

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Phenoxyethanol[1][2][3]
2-phenoxyethanol-Line-Structure.svg
Phenoxyethanol 3d structure.png
Names
IUPAC name
2-Phenoxyethanol
Other names
Phenoxyethanol
Ethylene glycol monophenyl ether
Phenoxytolarosol
Dowanol EP / EPH
Emery 6705
Rose ether
1-Hydroxy-2-phenoxyethane
β-hydroxyethyl phenyl ether
Phenyl cellosolve
Identifiers
122-99-6 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:64275 N
ChEMBL ChEMBL1229846 N
ChemSpider 13848467 YesY
ECHA InfoCard 100.004.173
PubChem 31236
UNII HIE492ZZ3T YesY
Properties
C8H10O2
Molar mass 138.17 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 arachis oil slightly
Solubility in olive oil slightly
Solubility in acetone miscible
Solubility in ethanol miscible
Solubility in glycerol miscible
Vapor pressure 0.001 kPa
Thermal conductivity 0.169 W/(m⋅K)
1.534 (20 ℃)
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 121 °C (250 °F; 394 K)
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 YesYN ?)
Infobox references

Phenoxyethanol is a germicidal and germistatic glycol ether, phenol ether, and aromatic alcohol often used together with quaternary ammonium compounds.

Use[edit]

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.[4] In Japan and the EU, its concentration in cosmetics is restricted to 1%.[5]

Production[edit]

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[edit]

Phenoxyethanol is effective against gram-negative and gram-positive bacteria, and the yeast Candida albicans.[6]

Effective concentration and contact time to kill germs with aromatic alcohols[7]
Aromatic alcohol Concentration, % Contact time, min
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.[8] It is neurotoxic.[9] Ingestion may cause CNS and respiratory depression, vomiting and diarrhea in infants, particularly when combined with chlorphenesin.[10]

References[edit]

  1. ^ 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 (7th ed.), Wiley, doi:10.1002/14356007.a19_313 
  2. ^ "Phenoxyethanol", British Pharmacopoeia, 2, 2009, ISBN 978-0-11-322799-0 
  3. ^ David R. Lide, ed. (2010), CRC Handbook of Chemistry and Physics (90th ed.), CRC Press 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ Hans-P. Harke (2007), "Disinfectants", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 1–17, doi:10.1002/14356007.a08_551 
  8. ^ M. H. Beck; S. M. Wilkinson (2010), "Contact Dermatitis: Allergic", in Tony Burns; Stephen Breathnach; Neil Cox; Christopher Griffiths, Rook's Textbook of Dermatology, 2 (8th ed.), Wiley-Blackwell, p. 26.46, ISBN 978-1-4051-6169-5 
  9. ^ 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. 
  10. ^ "FDA Warns Consumers Against Using Mommy's Bliss Nipple Cream".