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|SystematicName = Phenylmercurio acetate{{citation needed|date=January 2011}}
| SystematicName = acetyloxy(phenyl)mercury
|Section1={{Chembox Identifiers
| Section1 = {{Chembox Identifiers
|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
|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
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|ExternalSDS= [http://msds.chem.ox.ac.uk/PH/phenylmercuric_acetate.html Oxford MSDS]
|ExternalSDS= [http://msds.chem.ox.ac.uk/PH/phenylmercuric_acetate.html Oxford MSDS]
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'''Phenylmercuric acetate''' is an [[organomercury compound]] used as a [[preservative]], [[disinfectant]], and [[antitranspirant]].
'''Phenylmercuric acetate''' is an [[organomercury compound]]. This compound was formerly used as a preservative in paints,<ref>{{cite book |doi=10.1002/14356007.a16_269.pub2 |chapter=Mercury, Mercury Alloys, and Mercury Compounds |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2006 |last1=Simon |first1=Matthias |last2=Jönk |first2=Peter |last3=Wühl-Couturier |first3=Gabriele |last4=Halbach |first4=Stefan |isbn=978-3-527-30673-2}}</ref> and as a disinfectant.<ref>{{cite book |doi=10.1002/14356007.a08_551.pub2 |chapter=Disinfectants |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2009 |last1=Siebert |first1=Jörg |last2=Harke |first2=Hans-Peter |isbn=978-3-527-30673-2}}</ref> When applied to the leaves of most plants, it is an [[antitranspirant]].<ref>{{cite journal |first1=S. |last1=Moreshet |year=1975 |title=Effects of Phenyl-Mercuric Acetate on Stomatal and Cuticular Resistance to Transpiration |journal=New Phytologist |volume=75 |issue=1 |pages=47–52 |jstor=2431139 |doi=10.1111/j.1469-8137.1975.tb01369.x|doi-access=free}}</ref>It kills [[crabgrass]], the seedlings of which are especially vulnerable, but leaves most lawn grasses intact.<ref>Sunset Western Garden Book (1954), p.69</ref>

== Properties ==
Phenylmercuric acetate forms colorless, lustrous crystals, and is soluble in ethanol, benzene, acetic acid, and sparingly in water.<ref name=":0">{{cite book |last1=Simon |first1=Matthias |title=Ullmann's Encyclopedia of Industrial Chemistry |last2=Jönk |first2=Peter |last3=Wühl-Couturier |first3=Gabriele |last4=Halbach |first4=Stefan |year=2006 |isbn=978-3-527-30673-2 |chapter=Mercury, Mercury Alloys, and Mercury Compounds |doi=10.1002/14356007.a16_269.pub2}}</ref>


==Applications==
==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.<ref>{{cite journal |doi=10.1111/j.0105-1873.2005.0650d.x |title=Patch testing with phenylmercuric acetate |year=2005 |last1=Geier |first1=J. |last2=Lessmann |first2=H. |last3=Uter |first3=W. |last4=Schnuch |first4=A. |journal=Contact Dermatitis |volume=53 |issue=2 |pages=117–8 |pmid=16033409|s2cid=42906373 }}</ref><ref name="pmid18365889" /> 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.<ref name=pmid18365889>{{cite journal |doi=10.1080/15459620802017425 |title=Phenyl Mercuric Acetate (PMA): Mercury-Bearing Flexible Gymnasium Floors in Schools — Evaluation of Hazards and Controlled Abatement |year=2008 |last1=Beaulieu |first1=Harry J. |last2=Beaulieu |first2=Serrita |last3=Brown |first3=Chris |journal=Journal of Occupational and Environmental Hygiene |volume=5 |issue=6 |pages=360–6 |pmid=18365889|s2cid=43701302}}</ref> 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.
Phenylmercuric acetate has been used as a preservative in eyedrops and paint, disinfectant, former fungicide in agriculture, and a potential fungicide in leather processing.<ref name=":0" /><ref name=":2">{{cite journal |last1=Geier |first1=J. |last2=Lessmann |first2=H. |last3=Uter |first3=W. |last4=Schnuch |first4=A. |year=2005 |title=Patch testing with phenylmercuric acetate |journal=Contact Dermatitis |volume=53 |issue=2 |pages=117–8 |doi=10.1111/j.0105-1873.2005.0650d.x |pmid=16033409 |s2cid=42906373}}</ref><ref name="Pmid2">{{cite journal |last1=Xu |first1=Y. |last2=Zhao |first2=D. |last3=Gao |first3=C. |last4=Zhou |first4=L. |last5=Pang |first5=G. |last6=Sun |first6=S. |year=2012 |title=In vitro activity of phenylmercuric acetate against ocular pathogenic fungi |journal=[[Journal of Antimicrobial Chemotherapy]] |volume=67 |issue=8 |pages=1941–4 |doi=10.1093/jac/dks133 |pmid=22514262 |doi-access=free}}</ref> It kills [[crabgrass]], the seedlings of which are especially vulnerable, but leaves most lawn grasses intact.<ref>Sunset Western Garden Book (1954), p.69</ref> 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 [[Fungal keratitis|keratomycosis]].<ref name="Pmid2" />


Phenylmercuric acetate was used for disinfecting mucous membranes, but due to toxicological and ecotoxicological reasons, is no longer used.<ref name=":1">{{cite book |last1=Siebert |first1=Jörg |title=Ullmann's Encyclopedia of Industrial Chemistry |last2=Harke |first2=Hans-Peter |year=2009 |isbn=978-3-527-30673-2 |chapter=Disinfectants |doi=10.1002/14356007.a08_551.pub2}}</ref> In the 1950s, phenylmercuric acetate was used as a catalyst in 3M Tartan brand polyurethane flexible floors, a common flooring used public buildings, especially in school gymnasiums, but due to concerns about mercury vapors, is not used.<ref name="pmid183658892">{{cite journal |last1=Beaulieu |first1=Harry J. |last2=Beaulieu |first2=Serrita |last3=Brown |first3=Chris |year=2008 |title=Phenyl Mercuric Acetate (PMA): Mercury-Bearing Flexible Gymnasium Floors in Schools — Evaluation of Hazards and Controlled Abatement |journal=Journal of Occupational and Environmental Hygiene |volume=5 |issue=6 |pages=360–6 |doi=10.1080/15459620802017425 |pmid=18365889 |s2cid=43701302}}</ref>
==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 more{{fact|date=October 2022}}<sup>anti- and increases?</sup> 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.<ref name="Pmid">{{cite journal |doi=10.1093/jac/dks133 |title=In vitro activity of phenylmercuric acetate against ocular pathogenic fungi |year=2012 |last1=Xu |first1=Y. |last2=Zhao |first2=D. |last3=Gao |first3=C. |last4=Zhou |first4=L. |last5=Pang |first5=G. |last6=Sun |first6=S. |journal=[[Journal of Antimicrobial Chemotherapy]] |volume=67 |issue=8 |pages=1941–4 |pmid=22514262|doi-access=free}}</ref> 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.<ref name="Pmid" />


==Hazards==
==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.<ref>{{cite journal |doi=10.1001/archderm.1975.01630180054004 |title=Contact Urticaria Syndrome: Contact Urticaria to Diethyltoluamide (Immediate-Type Hypersensitivity) |year=1975 |last1=Maibach |first1=H. I. |last2=Johnson |first2=H. L. |journal=Archives of Dermatology |volume=111 |issue=6 |pages=726–30 |pmid=1137416}}</ref> CUS has been categorized as an immediate hypersensitivity reaction with IgE (a type of antibody) playing a crucial role in its pathogenesis.<ref name=pmid8112079>{{cite journal |doi=10.1111/j.1600-0536.1993.tb03574.x |title=Contact urticaria syndrome due to phyenylmercuric acetate |year=1993 |last1=Torresani |first1=Claudio |last2=Caprari |first2=Elisabetta |last3=Manara |first3=Gian Carlo |journal=Contact Dermatitis |volume=29 |issue=5 |pages=282–3 |pmid=8112079|s2cid=46255307}}</ref> Investigations dealing with CUS seem to suggest that a percentage of urticarias encompass a contact mechanism.<ref name=pmid8112079/>
Contact with phenylmercuric acetate can cause allergic reactions.<ref name=":2" />, such as [[erythema]] and contact [[Hives|urticaria]] syndrome.<ref>{{cite journal |last1=Maibach |first1=H. I. |last2=Johnson |first2=H. L. |year=1975 |title=Contact Urticaria Syndrome: Contact Urticaria to Diethyltoluamide (Immediate-Type Hypersensitivity) |journal=Archives of Dermatology |volume=111 |issue=6 |pages=726–30 |doi=10.1001/archderm.1975.01630180054004 |pmid=1137416}}</ref><ref name="pmid81120792">{{cite journal |last1=Torresani |first1=Claudio |last2=Caprari |first2=Elisabetta |last3=Manara |first3=Gian Carlo |year=1993 |title=Contact urticaria syndrome due to phyenylmercuric acetate |journal=Contact Dermatitis |volume=29 |issue=5 |pages=282–3 |doi=10.1111/j.1600-0536.1993.tb03574.x |pmid=8112079 |s2cid=46255307}}</ref> [[Immunoglobulin E|IgE]] plays a crucial role in contact urticaria syndrome pathogenesis.<ref name="pmid81120792" />

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.<ref name="Pmid2" />


==See also==
==See also==

Revision as of 20:33, 30 December 2022

Phenylmercury acetate
Skeletal formula of phenylmercury acetate
Ball and stick model of the phenylmercury acetate molecule
Names
Systematic IUPAC name
acetyloxy(phenyl)mercury
Identifiers
3D model (JSmol)
3662930
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.484 Edit this at Wikidata
EC Number
  • 200-532-5
83357
KEGG
MeSH Phenylmercuric+acetate
RTECS number
  • OV6475000
UNII
UN number 1674
  • 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 checkY
    Key: XEBWQGVWTUSTLN-UHFFFAOYSA-M checkY
  • 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
  • CC(=O)O[Hg]C1=CC=CC=C1
  • CC(=O)O[Hg]c1ccccc1
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:
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
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).
☒N verify (what is checkY☒N ?)

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

Properties

Phenylmercuric acetate forms colorless, lustrous crystals, and is soluble in ethanol, benzene, acetic acid, and sparingly in water.[1]

Applications

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] In the 1950s, phenylmercuric acetate was used as a catalyst in 3M Tartan brand polyurethane flexible floors, a common flooring used public buildings, especially in school gymnasiums, but due to concerns about mercury vapors, is not used.[6]

Hazards

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]

See also

References

  1. ^ a b 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. ^ a b 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.
  3. ^ a b c 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.
  4. ^ Sunset Western Garden Book (1954), p.69
  5. ^ 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.
  6. ^ 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.
  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. ^ a b 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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