Phenoxyethanol

Source: Wikipedia, the free encyclopedia.
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
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.004.173 Edit this at Wikidata
UNII
  • 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
  • c1ccc(cc1)OCCO
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)
1.534 (20 °C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful if swallowed
Causes serious eye irritation
GHS labelling:
GHS07: Exclamation mark
Warning
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 126 °C (259 °F; 399 K)
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).
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Phenoxyethanol is the

glycol ether and a phenol ether. It is a common preservative in vaccine formulations.[4]

Use

Phenoxyethanol has

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 (

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.[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)
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.

NMDAR-mediated ion currents.[15]

References

  1. ^
    ISBN 978-3527306732
    .
  2. ISBN 978-0-11-322799-0
  3. ^ David R. Lide, ed. (2010), CRC Handbook of Chemistry and Physics (90th ed.), CRC Press
  4. PMID 17722087
    .
  5. JSTOR 3757974
    .
  6. JSTOR 4449498
    .
  7. JSTOR 1726343
    .
  8. JSTOR 10.3318/bioe.2015.14
    .
  9. JSTOR 44134400
    .
  10. PMID 2816264
    .
  11. PMID 14740401
    .
  12. S2CID 12124463
    .
  13. doi:10.1002/14356007.a08_551
  14. ISBN 978-1-4051-6169-5
  15. S2CID 6999187
    .
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