122-99-6 Usage
Description
Phenoxyethanol is an organic chemical compound, a glycol ether often used in dermatological products such as skin creams and sunscreen. It is a colorless oily liquid. It is a bactericide (usually used in conjunction with quaternary ammonium compounds). Phenoxyethanol is used in many applications such as cosmetics, vaccines and pharmaceuticals as a preservative.
Chemical Properties
Different sources of media describe the Chemical Properties of 122-99-6 differently. You can refer to the following data:
1. clear colorless liquid
2. Phenoxyethanol is a colorless, slightly viscous liquid with a faint
pleasant odor and burning taste.
Characteristics
Phenoxyethanol is a tried-and-tested preservative, which is welltolerated by the skin and has a low allergy risk. It can be used over a wide pH range. This means that other preservatives can lose their effectiveness if the product is not within the right pH range. It does not smell unpleasant or change the color of the product, which can be the case when using natural antimicrobial substances.
Uses
Different sources of media describe the Uses of 122-99-6 differently. You can refer to the following data:
1. phenoxyethanol is a broad-range preservative with fungicidal, bactericidal, insecticidal, and germicidal properties. It has a relatively low sensitizing factor in leave-on cosmetics. Phenoxyethanol can be used in concentrations of 0.5 to 2.0 percent, and in combination with other preservatives such as sorbic acid or parabens. In addition, it is used as a solvent for aftershaves, face and hair lotions, shampoos, and skin creams of all types. It can be obtained from phenol.
2. Ethylene glycol phenyl ether at a
1.0% level acts as a preservative in personal care products.
3. Phenoxyethanol is a preservative used in consumer and health care products, including vaccines, pen inks, ear drops, shampoos, skin cleansers, moisturizers, sun care products, and topical medicaments. The preservative Euxyl-K 400 also contains 2-phenoxyethanol, in combination with methyldibromoglutaronitrile.
Phenoxyethanol is commonly used in cosmetics for its antibacterial and antifungal properties. It is increasingly being used in vaccines as a substitute for thiomersal and is also a component of pen inks and, more rarely, ear drops.Reactions to phenoxyethanol have rarely been reported. Three cases of CoU induced by phenoxyethanol in cosmetics have been reported.2-Phenoxyethanol is used as a single agent and in combination with other preservatives such as 1,2-dibromo-2,4-dicyanobutane (Euxyl K 400) and parabens, or in conjunction with quaternary ammonium compounds.The possibility of immunological IgE-mediated reaction could not be confirmed because specific IgE against 2-phenoxyethanol was negative.
4. Antimicrobial preservative; also used topically in treatment of bacterial infections.
Production Methods
Phenoxyethanol is prepared by treating phenol with ethylene oxide
in an alkaline medium.
Synthesis Reference(s)
The Journal of Organic Chemistry, 40, p. 1356, 1975 DOI: 10.1021/jo00897a043
General Description
Colorless liquid with a pleasant odor. Density 1.02 g / cm3. An irritant.
Air & Water Reactions
Oxidizes in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. Water soluble.
Reactivity Profile
2-Phenoxyethanol may react violently with strong oxidizing agents. May generate flammable and/or toxic gases with alkali metals, nitrides, and other strong reducing agents. May initiate the polymerization of isocyanates and epoxides.
Health Hazard
May cause moderate eye irritation and moderate corneal injury. Excessive exposure may cause skin irritation and hemolysis.
Fire Hazard
2-Phenoxyethanol is combustible.
Flammability and Explosibility
Notclassified
Pharmaceutical Applications
Phenoxyethanol is an antimicrobial preservative used in cosmetics
and topical pharmaceutical formulations at a concentration of
0.5–1.0%; it may also be used as a preservative and antimicrobial
agent for vaccines.Therapeutically, a 2.2% solution or 2.0%
cream has been used as a disinfectant for superficial wounds, burns,
and minor infections of the skin and mucous membranes.
Phenoxyethanol has a narrow spectrum of activity and is thus
frequently used in combination with other preservatives,
Industrial uses
2-Phenoxyethanol is used as a preservative in cosmetic formulations at a maximum concentration of 1.0%.
2-Phenoxyethanol is a broad spectrum preservative which has excellent activity against a wide range of Gram negative and Gram positive bacteria, yeast and mould. It is also used as a solvent and, because of its properties as a solvent, it is used in many blends and mixtures with other preservatives.
2-Phenoxyethanol is not registered as a food additive in the EU.
Scognamiglio et al. (ref. 105) reported that 2-phenoxyethanol is a fragrance ingredient used in many fragrance mixtures (see discussion). An ester of 2-Phenoxyethanol, 2-Phenoxyethyl isobutyrate and 2-Phenoxyacetic acid, the main metabolite of 2-Phenoxyethanol, were mentioned in a WHO publication where 43 flavouring agents in food were evaluated (WHO 2003, AR4), however at intakes assessed to be very low in Europe (around 1 μg/kg bw/day).
Contact allergens
Phenoxyethanol is an aromatic ether-alcohol used
mainly as a preservative, mostly with methyldibromoglutaronitrile
(in Euxyl? K 400) or with parabens.
Sensitization to this molecule is very rare.
Safety Profile
Moderately toxic by ingestion and skin contact. A skin and severe eye irritant. Mutation data reported. Some glycol ethers have dangerous human reproductive effects. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes. To fight fEe, use CO2, dry chemical. Used as a solvent for ester-type resins. See also GLYCOL ETHERS.
Safety
Phenoxyethanol produces a local anesthetic effect on the lips, tongue, and other mucous membranes. The pure material is a moderate irritant to the skin and eyes. In animal studies, a 10% v/v solution was not irritant to rabbit skin and a 2% v/v solution was not irritant to the rabbit eye.Long-term exposure to phenoxyethanol may result in CNS toxic effects similar to other organic solvents.Safety issues related to preservatives used in vaccines, including 2-phenoxyethanol have been reviewed.Contact urticaria has been reported upon exposure to 2-phenoxyethanol-containing cosmetics.
The US FDA has recommended avoiding at least one topical product containing phenoxyethanol due to concerns over inadvertant exposure to nursing infants.
LD50 (rabbit, skin): 5 g/kg
LD50 (rat, oral): 1.26 g/kg
storage
Aqueous phenoxyethanol solutions are stable and may be sterilized
by autoclaving. The bulk material is also stable and should be stored
in a well-closed container in a cool, dry place.
Incompatibilities
The antimicrobial activity of phenoxyethanol may be reduced by
interaction with nonionic surfactants and possibly by absorption by
polyvinyl chloride.The antimicrobial activity of phenoxyethanol
against Pseudomonas aeruginosa may be reduced in the presence of
cellulose derivatives (methylcellulose, sodium carboxymethylcellulose,
and hypromellose (hydroxypropylmethylcellulose)).
Regulatory Status
Included in the FDA Inactive Ingredients Database (topical
preparations). Included in nonparenteral medicines licensed in the
UK. Included in the Canadian List of Acceptable Non-medicinal
Ingredients.
Under European regulations for cosmetics (76/768/EEC), the
maximum authorized concentration (MAC) of 2-phenoxyethanol is
1.0%.
Check Digit Verification of cas no
The CAS Registry Mumber 122-99-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 122-99:
(5*1)+(4*2)+(3*2)+(2*9)+(1*9)=46
46 % 10 = 6
So 122-99-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2
122-99-6Relevant articles and documents
Zirconium complexes with pendant aryloxy groups attached to the metallocene moiety by ethyl or hexyl spacers
Cho, Won Seok,Kim, So Han,Kim, Da Jung,Mun, Sang-Deok,Kim, Ran,Go, Min Jeong,Park, Myung Hwan,Kim, Min,Lee, Junseong,Kim, Youngjo
, p. 205 - 212 (2014)
Four zirconium complexes with pendant aryloxy groups attached to the metallocene moiety by ethyl or hexyl spacers have been synthesized and characterized by spectroscopic methods and HR-MS or elemental analysis. The solid state structure of bis[{6-(2,6-dimethylphenoxy)hexyl}cyclopentadienyl] zirconium dichloride was determined by single crystal X-ray diffraction. The prepared complexes were tested as catalyst precursors in the polymerization of ethylene upon activation with MAO. The results showed a marked effect of the spacer length on the catalytic activity, while only a minor effect of the substitution on the aryl group, which affected its steric properties.
2-(1-naphthyloxy)ethylamines with enhanced affinity for human 5-HT(1Dβ) (h5-HT(1B)) serotonin receptors
Ismaiel,Dukat,Law,Kamboj,Fan,Lee,Mazzocco,Buekschkens,Teitler,Pierson,Glennon
, p. 4415 - 4419 (1997)
Although the β-adrenergic antagonist propanolol (1) binds at rodent 5- HT(1B) serotonin receptors, it displays low affinity (K(i) > 10 000 nM) for its species homologue 5-HT(1DB) (i.e., h5-HT(1B)) receptors. The structure of propanolol was systematically modified in an attempt to enhance its affinity for the latter population of receptors. Removal of the alkyl hydroxyl group, shortening of the O-alkyl chain from three to two methylene groups, and variation of the terminal amine substituent resulted in compounds, such as N- monomethyl-2-(1-naphthyloxy)-ethylamine (11; K(i) = 26 nM), that display significantly higher h5-HT(1B) affinity than propanolol. Compound 11 was shown to bind equally well at human 5-HT(1Dα) (h5-HT(1D) receptors (K(i) = 34 nM) and was further demonstrated to possess h5-HT(1B) agonist character in an adenylate cyclase assay. It would appear that such (aryloxy)alkylamines may represent a novel class of 5-HT(1D) receptor agonists.
Carbonates as reactants for the production of fine chemicals: The synthesis of 2-phenoxyethanol
Ziosi,Tabanelli,Fornasari,Cocchi,Cavani,Righi
, p. 4386 - 4395 (2014)
The solventless and heterogeneously catalysed synthesis of 2-phenoxyethanol (ethylene glycol monophenyl ether) via the reaction between phenol and ethylene carbonate was investigated using Na-mordenite catalysts as an alternative to the industrial process using ethylene oxide and homogeneous basic conditions. Under specific reaction conditions, it was possible to obtain total selectivity to phenoxyethanol at up to 75% phenol conversion and 82% selectivity at total phenol conversion in 5-7 hours of reaction time and using a moderate excess of ethylene carbonate. The main by-product was the linear carbonate of phenoxyethanol, bis(2-phenoxyethyl)carbonate (selectivity 15%), which could then be converted to phenoxyethanol by reacting with phenol in basic medium with 100% yield; so overall, the phenoxyethanol yield was as high as 97%. With a stoichiometric feed of phenol and ethylene carbonate, the maximum conversion of phenol was just 60%, still with 100% selectivity to phenoxyethanol. An autocatalytic phenomenon was also observed due to the higher basicity of 2-phenoxyethanol compared to phenol, which overlapped the Na-catalyzed activation of phenol. Starting from a commercial Na-mordenite, which showed significant deactivation, and by applying a post-treatment aimed at the reduction of microporosity, it was possible to minimize both the deactivation and Na leaching while keeping the selectivity enhancement effect shown by the mordenite structure.
Preparation and structure investigation of novel Schiff bases using spectroscopic, thermal analyses and molecular orbital calculations and studying their biological activities
Zayed, Ehab M.,Zayed,El-Desawy
, p. 155 - 164 (2015)
Two novel Schiff's bases (EB1 and L1) as new macrocyclic compounds were prepared via condensation reactions between bisaldehyde (2,2′-(ethane-1,2- diylbis(oxy))dibenzaldehyde): firstly with hydrazine carbothioamide to give (EB1), secondly with 4,6-diaminopyrimidine-2-thiol to give (L1). EB1 has a general formula C18H20N6O2S 2 of mole mass = 416.520, and IUPAC name ((N,N′Z,N,N′E)- N,N′-(((ethane1,2diylbis(oxy))bis(2,1phenylene))bis(methanylylidene)) bis(1hydrazinylmethanethioamide). L1 has a general formula C20H 16N4O2S of mole mass = 376.10; and IUPAC name 1,2-bis(2-vinylphenoxy)ethane4,6-diaminopyrimidine-2-thiol). The structures of the compounds obtained were characterized based on elemental analysis, FT-IR and 1H NMR spectra, mass, and thermogravimetric analysis (TG, DTG). The activation thermodynamic parameters, such as, ΔE*, ΔH*, ΔS* and ΔG * were calculated from the TG curves using Coats-Redfern method. It is important to investigate their structures to know the active groups and weak bond responsible for their biological activities. The obtained thermal (TA) and mass (MS) practical results are confirmed by semi-empirical MO-calculation using PM3 procedure, on the neutral and positively charged forms of these novel Schiff bases. Therefore, comparison between MS and TA helps in selection of the proper pathway representing the decomposition of these compounds to give indication about their structures and consequently their biological activities. Their biological activities have been tested in vitro against Escherichia coli, Proteus vulgaris, Bacillissubtilies and Staphylococcus aurous bacteria in order to assess their antimicrobial potential.
Olefin oxidative cleavage and dioxetane formation using triethylsilyl hydrotrioxide: Applications to preparation of potent antimalarial 1,2,4-trioxanes
Posner,Oh,Milhous
, p. 4235 - 4238 (1991)
Oxidative cleavage of alkenyl esters and ethers using Et3SiOOOH was found to be easier than oxidative cleavage of hydrocarbon alkenes, and Et3SiOOOH was successfully applied to very short syntheses of new, simple, and potent antimalarial trioxanes 6 and 8.
Novel Bis[N-alkyl-N-(2-diphenylphosphinylethyl)]diglycolamides: Synthesis and NMR Spectroscopy Studies
Bondarenko,Tcarkova,Belus’,Artyushin,Peregudov
, p. 181 - 189 (2021/03/20)
Abstract: Pentadentate bis[N-alkyl-N-(2-diphenylphosphinylethyl)]diglycolamides [Ph2P(O)CH2CH2N(R)· C(O)CH2]2O, where R Me, Bu, Oct, were synthesized by reaction of diglycolyl chloride with N-alkyl-N-(2-diphenylphosphinylethyl)amines Ph2P(O)CH2CH2NHR obtained by reacting diphenyl(2-phenoxyethyl)phosphine oxide with primary alkylamines in DMSO in the presence of an aqueous alkali. Structure of the prepared compounds was studied by 1H, 13C, and 31P NMR spectroscopy.
Me3SI-promoted chemoselective deacetylation: a general and mild protocol
Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj
, p. 19310 - 19315 (2021/06/03)
A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.