Phenoxyethanol

Phenoxyethanol

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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
CAS Number	122-99-6 Y
ChEBI	CHEBI:64275 N
ChEMBL	ChEMBL1229846 N
ChemSpider	13848467 Y
Jmol 3D model	Interactive image
PubChem	31236
UNII	HIE492ZZ3T Y
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	138.17 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)
Solubility in water	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)
Refractive index (nD)	1.534 (20 ℃)
Vapor pressure	{{{value}}}
Related compounds
Related compounds	phenetole
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Infobox references

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

Use

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

Production

Phenoxyethanol is produced by the hydroxyethylation of phenol (Williamson synthesis), for example, in the presence of alkali-metal hydroxides or alkali-metal borohydrides.

Efficacy

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

Effective concentration and contact time to kill germs with aromatic alcohols

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

Phenoxyethanol is a vaccine preservative and potential allergen, which may result in a nodular reaction at the site of injection. It is neurotoxic. Ingestion may cause CNS and respiratory depression, vomiting and diarrhea in infants, particularly when combined with chlorphenesin.