Phenoxyethanol

Last updated
Phenoxyethanol [1] [2] [3]
2-phenoxyethanol-Line-Structure.svg
Phenoxyethanol 3d structure.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2 Yes check.svgY
    Key: QCDWFXQBSFUVSP-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceColorless 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:
GHS-pictogram-exclam.svg
Warning
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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 alcoholConcentration (%)Contact time (minutes)
Escherichia coli Pseudomonas aeruginosa Proteus mirabilis Staphylococcus aureus
Benzyl alcohol 1>30>30>30>30
Phenethyl alcohol 1.252.52.52.5>30
2.52.52.52.55
Phenoxyethanol1.25152.52.5>30
2.52.52.52.5>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]

Related Research Articles

<span class="mw-page-title-main">Benzoic acid</span> Organic compound (C6H5COOH)

Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

<span class="mw-page-title-main">Phenols</span> Chemical compounds in which hydroxyl group is attached directly to an aromatic ring

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

<span class="mw-page-title-main">Imide</span> Class of chemical compounds

In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis. In terms of commercial applications, imides are best known as components of high-strength polymers, called polyimides. Inorganic imides are also known as solid state or gaseous compounds, and the imido group (=NH) can also act as a ligand.

<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

<span class="mw-page-title-main">Dimethyl sulfate</span> Chemical compound

Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis. Me2SO4 is a colourless oily liquid with a slight onion-like odour. Like all strong alkylating agents, Me2SO4 is toxic. Its use as a laboratory reagent has been superseded to some extent by methyl triflate, CF3SO3CH3, the methyl ester of trifluoromethanesulfonic acid.

<span class="mw-page-title-main">Oligodynamic effect</span> Toxic effect of metal ions on living cells

The oligodynamic effect is a biocidal effect of metals, especially heavy metals, that occurs even in low concentrations. This effect is attributed to the antibacterial behavior of metal ions, which are absorbed by bacteria upon contact and damage their cell membranes.

In organic chemistry, an azo coupling is an reaction between a diazonium compound and another aromatic compound that produces an azo compound. In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile, and the activated carbon, serves as a nucleophile. Classical coupling agents are phenols and naphthols. Usually the diazonium reagent attacks at the para position of the coupling agent. When the para position is occupied, coupling occurs at a ortho position, albeit at a slower rate.

<span class="mw-page-title-main">1,4-Benzoquinone</span> Chemical compound

1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

<span class="mw-page-title-main">Carbonate ester</span> Chemical group (R–O–C(=O)–O–R)

In organic chemistry, a carbonate ester is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R−O−C(=O)−O−R' and they are related to esters, ethers and also to the inorganic carbonates.

2,6-Di-<i>tert</i>-butylphenol Chemical compound

2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH3)3C)2C6H3OH. This colorless solid alkylated phenol and its derivatives are used industrially as UV stabilizers and antioxidants for hydrocarbon-based products ranging from petrochemicals to plastics. Illustrative of its usefulness, it prevents gumming in aviation fuels.

<span class="mw-page-title-main">Nitrilotriacetic acid</span> Chemical compound

Nitrilotriacetic acid (NTA) is the aminopolycarboxylic acid with the formula N(CH2CO2H)3. It is a colourless solid. Its conjugate base nitrilotriacetate is used as a chelating agent for Ca2+, Co2+, Cu2+, and Fe3+.

<span class="mw-page-title-main">Cigarette filter</span> Filter in cigarettes that reduce nicotine, tar and carbon monoxide

A cigarette filter, also known as a filter tip, is a component of a cigarette, along with cigarette paper, capsules and adhesives. Filters were introduced in the early 1950s.

<span class="mw-page-title-main">Anthraquinones</span> Type of compounds

For the parent molecule 9,10-anthraquinone, see anthraquinone

<span class="mw-page-title-main">Lignocellulosic biomass</span> Plant dry matter

Lignocellulose refers to plant dry matter (biomass), so called lignocellulosic biomass. It is the most abundantly available raw material on the Earth for the production of biofuels. It is composed of two kinds of carbohydrate polymers, cellulose and hemicellulose, and an aromatic-rich polymer called lignin. Any biomass rich in cellulose, hemicelluloses, and lignin are commonly referred to as lignocellulosic biomass. Each component has a distinct chemical behavior. Being a composite of three very different components makes the processing of lignocellulose challenging. The evolved resistance to degradation or even separation is referred to as recalcitrance. Overcoming this recalcitrance to produce useful, high value products requires a combination of heat, chemicals, enzymes, and microorganisms. These carbohydrate-containing polymers contain different sugar monomers and they are covalently bound to lignin.

<span class="mw-page-title-main">Crotonaldehyde</span> Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

<span class="mw-page-title-main">Oxazines</span> E heterocyclic organic compounds containing one oxygen and one nitrogen atom

Oxazines are heterocyclic organic compounds containing one oxygen and one nitrogen atom in a cyclohexa-1,4-diene ring. Isomers exist depending on the relative position of the heteroatoms and relative position of the double bonds.

<span class="mw-page-title-main">Phenylmercury acetate</span> Chemical compound

Phenylmercuric acetate is an organomercury compound used as a preservative, disinfectant, and antitranspirant.

In organic chemistry, alkynylation is an addition reaction in which a terminal alkyne is added to a carbonyl group to form an α-alkynyl alcohol.

<span class="mw-page-title-main">Isopropenyl acetate</span> Chemical compound

Isopropenyl acetate is an organic compound, which is the acetate ester of the enol tautomer of acetone. This colorless liquid is significant commercially as the principal precursor to acetylacetone. In organic synthesis, it is used to prepare enol acetates of ketones and acetonides from diols.

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