Names | |
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Systematic IUPAC name acetyloxy(phenyl)mercury | |
Identifiers | |
3D model (JSmol) | |
3662930 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.000.484 |
EC Number |
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83357 | |
KEGG | |
MeSH | Phenylmercuric+acetate |
PubChem CID | |
RTECS number |
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UNII | |
UN number | 1674 |
CompTox Dashboard (EPA) | |
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Properties | |
C8H8HgO2 | |
Molar mass | 336.742 g·mol−1 |
Melting point | 148 to 151 °C (298 to 304 °F; 421 to 424 K) |
Hazards | |
GHS labelling: | |
Danger | |
H301, H314, H372, H410 | |
P260, P264, P270, P273, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P314, P321, P330, P363, P391, P405, P501 | |
Safety data sheet (SDS) | Oxford MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Phenylmercuric acetate is an organomercury compound used as a preservative, disinfectant, and antitranspirant.
Phenylmercuric acetate forms colorless, lustrous crystals, and is soluble in ethanol, benzene, acetic acid, and sparingly in water. [1]
Phenylmercuric acetate has been used as a preservative in eyedrops and paint, disinfectant, former fungicide in agriculture, and a potential fungicide in leather processing. [1] [2] [3] It kills crabgrass, the seedlings of which are especially vulnerable, but leaves most lawn grasses intact. [4] It exhibits anti-fungal activity against a broad range of ocular pathogenic fungi, with the greatest activity against Fusarium spp, and has been investigated as a potential treatment for keratomycosis. [3]
Phenylmercuric acetate was used for disinfecting mucous membranes, but due to toxicological and ecotoxicological reasons, is no longer used. [5] Phenylmercuric acetate was once used commercially as a catalyst in 3M Tartan brand polyurethane flexible floors, a common flooring used in public buildings, especially in school gymnasiums, in the 1950's through 1970's. [6] In 2006, PMA was discovered to slowly leach from the 3M Tartan flooring in several Idaho public schools and was detectible using analytical methods of air monitoring via NIOSH 6009 Carulite Tubes and the Ohio-Lumex mercury vapor direct-reading analyzer. [6]
Contact with phenylmercuric acetate can cause allergic reactions. [2] , such as erythema and contact urticaria syndrome. [7] [8] IgE plays a crucial role in contact urticaria syndrome pathogenesis. [8]
A rare side effect of phenylmercuric acetate in eye drops is mercurialentis, the buildup of pigment on the anterior capsule of the lens. This has been estimated to affect 18 of 500 patients who have used eye drops containing phenylmercuric acetate two to four times a day for more than six years. The pigmentation is not associated with visual impairment nor any ocular abnormalities. [3]
Benzalkonium chloride, also known as alkyldimethylbenzylammonium chloride (ADBAC) and by the trade name Zephiran, is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. ADBACs have three main categories of use: as a biocide, a cationic surfactant, and a phase transfer agent. ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.
p-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna.
In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed acetate esters or simply acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.
In chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.
Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels. The D-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common L-isomer has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants.
The oligodynamic effect is a biocidal effect of metals, especially heavy metals, that occurs even in low concentrations.
Bronopol is an organic compound that is used as an antimicrobial. It is a white solid although commercial samples appear yellow.
Isethionic acid is an organosulfur compound containing an alkylsulfonic acid located beta to a hydroxy group. Its discovery is generally attributed to Heinrich Gustav Magnus, who prepared it by the action of solid sulfur trioxide on ethanol in 1833. It is a white water-soluble solid used in the manufacture of certain surfactants and in the industrial production of taurine. It is most commonly available in the form of its sodium salt.
Sodium dichloroisocyanurate is a chemical compound widely used as a cleansing agent and disinfectant. It is a colorless, water-soluble solid, produced as a result of reaction of cyanuric acid with chlorine. The dihydrate is also known as is the potassium salt.
2-Phenylphenol, or o-phenylphenol, is an organic compound. In terms of structure, it is one of the monohydroxylated isomers of biphenyl. It is a white solid. It is a biocide used as a preservative with E number E231 and under the trade names Dowicide, Torsite, Fungal, Preventol, Nipacide and many others.
Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ethylmercury(II) cation, C2H5Hg+; dimethylmercury, (CH3)2Hg, diethylmercury and merbromin ("Mercurochrome"). Thiomersal is used as a preservative for vaccines and intravenous drugs.
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.
1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This 3-carbon diol is a colorless viscous liquid that is miscible with water.
Phenethyl alcohol, or 2-phenylethanol, is an organic compound with the chemical formula C6H5CH2CH2OH. It is a colourless liquid with a pleasant floral odor. It occurs widely in nature, being found in a variety of essential oils. It is slightly soluble in water, but miscible with most organic solvents. The molecule of phenethyl alcohol consists of a phenethyl group attached to a hydroxyl group.
2,4,6-Trichlorophenol, also known as TCP, phenaclor, Dowicide 2S, Dowcide 2S, omal, is a chlorinated phenol that has been used as a fungicide, herbicide, insecticide, antiseptic, defoliant, and glue preservative. It is a clear to yellowish crystalline solid with a strong, phenolic odor. It decomposes on heating to produce toxic and corrosive fumes including hydrogen chloride and chlorine.
A formaldehyde releaser, formaldehyde donor or formaldehyde-releasing preservative is a chemical compound that slowly releases formaldehyde. Formaldehyde-releasers are added to prevent microbial growth and extend shelf life. The intent of these compounds is that they release formaldehyde at levels that suppress microbial growth but sufficiently low to not threaten humans. The use of these chemicals in cosmetics has elicited controversy.
DMDM hydantoin is an antimicrobial formaldehyde releaser preservative with the trade name Glydant. DMDM hydantoin is an organic compound belonging to a class of compounds known as hydantoins. It is used in the cosmetics industry and found in products like shampoos, hair conditioners, hair gels, and skin care products.
In industrial chemistry, carboalkoxylation is a process for converting alkenes to esters. This reaction is a form of carbonylation. A closely related reaction is hydrocarboxylation, which employs water in place of alcohols
Benzoguanamine is an organic compound with the chemical formula (CNH2)2(CC6H5)N3. It is related to melamine but with one amino group replaced by phenyl. Benzoguanamine is used in the manufacturing of melamine resins. Unlike melamine ((CNH2)3N3), benzoguanamine is not a crosslinker. The "benzo" prefix is historical, as the compound contains phenyl, not a benzo group. A related compound is acetoguanamine.
Phenylmercuric nitrate is an organomercury compound with powerful antiseptic and antifungal effects. It was once commonly used as a topical solution for disinfecting wounds, but as with all organomercury compounds it is highly toxic, especially to the kidneys, and is no longer used in this application. However it is still used in low concentrations as a preservative in eye drops for ophthalmic use, making it one of the few organomercury derivatives remaining in current medical use.