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 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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) |
Refractive index (nD) | 1.534 (20 °C) |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Harmful if swallowed Causes serious eye irritation |
GHS labelling: | |
Warning | |
NFPA 704 (fire diamond) | |
Flash point | 126 °C (259 °F; 399 K) |
430 °C (806 °F; 703 K) | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 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). |
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]
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]
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]
Phenoxyethanol is effective against gram-negative and gram-positive bacteria, and the yeast Candida albicans. [16]
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 |
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]
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.
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
6H
5OH. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.
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.
Catechol, also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Small amounts of catechol occur in fruits and vegetables.
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.
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.
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.
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-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.
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.
Ethyl lactate, also known as lactic acid ethyl ester, is the organic compound with the formula CH3CH(OH)CO2CH2CH3. It is the ethyl ester of lactic acid. A colorless liquid, it is a chiral ester. Being naturally derived, it is readily available as a single enantiomer. It is commonly used as a solvent. This compound is considered biodegradable and can be used as a water-rinsible degreaser. Ethyl lactate is found naturally in small quantities in a wide variety of foods including wine, chicken, and various fruits. The odor of ethyl lactate when dilute is mild, buttery, creamy, with hints of fruit and coconut.
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.
In electrochemistry, electrosynthesis is the synthesis of chemical compounds in an electrochemical cell. Compared to ordinary redox reactions, electrosynthesis sometimes offers improved selectivity and yields. Electrosynthesis is actively studied as a science and also has industrial applications. Electrooxidation has potential for wastewater treatment as well.
Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and as a co-solvent in lithium-ion batteries. Notably, dimethyl carbonate is a weak methylating agent, and is not considered as a carcinogen. Instead, dimethyl carbonate is often considered to be a green reagent, and it is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the United States.
Gentisic acid is a dihydroxybenzoic acid. It is a derivative of benzoic acid and a minor (1%) product of the metabolic break down of aspirin, excreted by the kidneys.
2,6-Dichlorophenol is a compound with formula C6H3Cl2OH. It is one of the six isomers of dichlorophenol. It is a colorless solid. Its pKa is 6.78, which is about 100x more acidic than 2-chlorophenol (8.52) and 1000x more acidic than phenol itself (9.95).
ortho-Cresol (IUPAC name: 2-methylphenol, also known as 2-hydroxytoluene or ortho-Toluenol) is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and m-cresol.
Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a pungent and fruity odour. It is produced on a large scale industrially.
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.