Phenylmercury acetate

Phenylmercuric acetate is an organomercury compound. This compound was formerly used as a preservative in paints,[1] and as a disinfectant.[2] When applied to the leaves of plants, it is an antitranspirant.[3]

Phenylmercury acetate
Names
Systematic IUPAC name
Phenylmercurio acetate
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 3662930
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.484
EC Number
  • 200-532-5
Gmelin Reference
 83357
KEGG
MeSH Phenylmercuric+acetate
PubChem CID
RTECS number
  • OV6475000
UNII
UN number 1674
InChI
  • InChI=1S/C6H5.C2H4O2.Hg/c1-2-4-6-5-3-1;1-2(3)4;/h1-5H;1H3,(H,3,4);/q;;+1/p-1 Y
    Key: XEBWQGVWTUSTLN-UHFFFAOYSA-M Y
  • InChI=1S/C6H5.C2H4O2.Hg/c1-2-4-6-5-3-1;1-2(3)4;/h1-5H;1H3,(H,3,4);/q;;+1/p-1
  • Key: XEBWQGVWTUSTLN-UHFFFAOYSA-M
SMILES
  • CC(=O)O[Hg]C1=CC=CC=C1
  • CC(=O)O[Hg]c1ccccc1
Properties
Chemical formula
 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:
Pictograms
Signal word
 Danger
Hazard statements
 H301, H314, H372, H410
Precautionary statements
 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).
N verify (what is YN ?)
Infobox references

Applications

Phenylmercuric acetate (PMA) has been used against fungal activity in agriculture and in leather processing and has been known to work well. PMA has also been used as an additive in eye-drops and paint in order to preserve them, as a disinfectant, and as a catalyst in polyurethane systems.[4][5] In the 1950s–1970s, PMA was used as a catalyst in the 3M Tartan brand polyurethane flexible floors that were commonly found in school gymnasiums.[5] School officials worried that mercury vapor was being released into air above the surface of these floors. They had to be carefully removed since mercury is such a toxic heavy metal.

Findings

The study on PMA as an antifungal is the most studied topic for this compound. It has been found that plants treated with PMA transpired moreanti- and increases? due to the retarded stomatal closure in the plants. Day-time reductions in transpiration by PMA greatly exceed night-time increases in water loss. PMA stunts stomatal closures as well as openings.[6] Research has found that PMA may plausibly decrease the absorbency of guard cell membranes to solutes, thereby retarding all stomatal movements that are osmotically prompted.[6]

Hazards

PMA can cause contact urticaria syndrome (CUS). Contact urticaria refers to a wheal-and-flare response occurring on the application of chemicals to intact skin. A wheal-and-flare response is a skin eruption that may follow injury or injection of an antigen. It is characterized by swelling and redness caused by a release of histamine. The reaction usually occurs in three stages, beginning with the appearance of an erythematous area at the site of injury, followed by development of a flare surrounding the site; finally a wheal forms at the site as fluid leaks under the skin from surrounding capillaries.[7] CUS has been categorized as an immediate hypersensitivity reaction with IgE (a type of antibody) playing a crucial role in its pathogenesis.[8] Investigations dealing with CUS seem to suggest that a percentage of urticarias encompass a contact mechanism.[8]

See also

References
  1. Simon, Matthias; Jönk, Peter; Wühl-Couturier, Gabriele; Halbach, Stefan (2006). "Mercury, Mercury Alloys, and Mercury Compounds". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_269.pub2. ISBN 978-3-527-30673-2.
  2. Siebert, Jörg; Harke, Hans-Peter (2009). "Disinfectants". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_551.pub2. ISBN 978-3-527-30673-2.
  3. Moreshet, S. (1975). "Effects of Phenyl-Mercuric Acetate on Stomatal and Cuticular Resistance to Transpiration". New Phytologist. 75 (1): 47–52. doi:10.1111/j.1469-8137.1975.tb01369.x. JSTOR 2431139.
  4. Geier, J.; Lessmann, H.; Uter, W.; Schnuch, A. (2005). "Patch testing with phenylmercuric acetate". Contact Dermatitis. 53 (2): 117–8. doi:10.1111/j.0105-1873.2005.0650d.x. PMID 16033409. S2CID 42906373.
  5. Beaulieu, Harry J.; Beaulieu, Serrita; Brown, Chris (2008). "Phenyl Mercuric Acetate (PMA): Mercury-Bearing Flexible Gymnasium Floors in Schools — Evaluation of Hazards and Controlled Abatement". Journal of Occupational and Environmental Hygiene. 5 (6): 360–6. doi:10.1080/15459620802017425. PMID 18365889. S2CID 43701302.
  6. Xu, Y.; Zhao, D.; Gao, C.; Zhou, L.; Pang, G.; Sun, S. (2012). "In vitro activity of phenylmercuric acetate against ocular pathogenic fungi". Journal of Antimicrobial Chemotherapy. 67 (8): 1941–4. doi:10.1093/jac/dks133. PMID 22514262.
  7. Maibach, H. I.; Johnson, H. L. (1975). "Contact Urticaria Syndrome: Contact Urticaria to Diethyltoluamide (Immediate-Type Hypersensitivity)". Archives of Dermatology. 111 (6): 726–30. doi:10.1001/archderm.1975.01630180054004. PMID 1137416.
  8. Torresani, Claudio; Caprari, Elisabetta; Manara, Gian Carlo (1993). "Contact urticaria syndrome due to phyenylmercuric acetate". Contact Dermatitis. 29 (5): 282–3. doi:10.1111/j.1600-0536.1993.tb03574.x. PMID 8112079. S2CID 46255307.
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