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Chemical Compound Review

phenolate     phenoxide

Synonyms: Phenoxy ion, Phenol ion, CHEBI:50526, AR-1L0353, AC1L3O3Z, ...
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Disease relevance of phenol


High impact information on phenol

  • Myeloperoxidase (MPO)-catalyzed one-electron oxidation of the etoposide phenolic ring and/or interaction of this phenolic moiety with reactive radicals yields its phenoxyl radical, whose reactivity may determine the pro- or antioxidant effects of this molecule in cells [3].
  • Combined optical and conductimetric measurements in aqueous solution indicate that at high pH (greater than or equal to 10).OH radicals react with the phenoxide form of 2,4-dihydroxybenzoic acid to form transiently phenoxyl radicals and a small amount of hydroxyeyclohexadienyl (HCHD) radicals by 150 ns [4].
  • This reaction results in the complete reduction of the free radical of acetaminophen, whereas the glutathione reduction of the phenoxyl radical of acetaminophen was not complete on the fast-flow ESR time scale of milliseconds [5].
  • A selectivity of 230:20:1 was determined for alkylation of phenol at oxygen, C-4 and C-2 to form 1-OPh and biphenyls 1-(4-C6H4OH) and 1-(2-C6H4OH), respectively, and of 2:2:1 for alkylation of the corresponding nucleophilic sites of phenoxide ion in diffusion-limited reactions [6].
  • Coenzyme Q (CoQ) was previously demonstrated in vitro to indirectly act as an antioxidant in respiring mitochondria by regenerating alpha-tocopherol from its phenoxyl radical [7].

Biological context of phenol


Anatomical context of phenol


Associations of phenol with other chemical compounds


Gene context of phenol

  • All phenolics were substrates for the enzymes, but MPx only weakly activated 4OHTAM to its phenoxyl radical [23].
  • Spectroscopic analyses indicated that paracetamol, similar to tyrosine, could undergo peroxidase-induced phenoxyl radical formation, which was inhibited by the radical scavenger ascorbic acid as well as by heme poisons and catalase [24].
  • The semidehydroascorbyl radical ESR signal preceded the quenching of the VP-16 phenoxyl radical by GSH and metallothionein [22].
  • Formation of 4 was also specific for peroxidase activation that is known to oxidize PCP into the phenoxyl radical [25].
  • The results reveal that imidazole substitution lowers the pK(a) of phenol and increases the E degrees of phenoxide due to its sigma-electron withdrawing ability (sigma(p)(-) = +0.21, sigma(m)(-) = +0.45) but decreases the O-H BDE and E degrees of phenol due to its pi-electron-donating ability (sigma(p)(+) = -0.45) [26].

Analytical, diagnostic and therapeutic context of phenol


  1. Myeloperoxidase-catalyzed metabolism of etoposide to its quinone and glutathione adduct forms in HL60 cells. Fan, Y., Schreiber, E.M., Giorgianni, A., Yalowich, J.C., Day, B.W. Chem. Res. Toxicol. (2006) [Pubmed]
  2. Phenoxyl radical-induced thiol-dependent generation of reactive oxygen species: implications for benzene toxicity. Stoyanovsky, D.A., Goldman, R., Claycamp, H.G., Kagan, V.E. Arch. Biochem. Biophys. (1995) [Pubmed]
  3. Pro-oxidant and antioxidant mechanisms of etoposide in HL-60 cells: role of myeloperoxidase. Kagan, V.E., Kuzmenko, A.I., Tyurina, Y.Y., Shvedova, A.A., Matsura, T., Yalowich, J.C. Cancer Res. (2001) [Pubmed]
  4. Absorption spectra of radical forms of 2,4-dihydroxybenzoic acid, a substrate for p-hydroxybenzoate hydroxylase. Anderson, R.F., Patel, K.B., Vojnovic, B. J. Biol. Chem. (1991) [Pubmed]
  5. Glutathione and ascorbate reduction of the acetaminophen radical formed by peroxidase. Detection of the glutathione disulfide radical anion and the ascorbyl radical. Ramakrishna Rao, D.N., Fischer, V., Mason, R.P. J. Biol. Chem. (1990) [Pubmed]
  6. Kinetic and thermodynamic barriers to carbon and oxygen alkylation of phenol and phenoxide ion by the 1-(4-methoxyphenyl)ethyl carbocation. Tsuji, Y., Toteva, M.M., Garth, H.A., Richard, J.P. J. Am. Chem. Soc. (2003) [Pubmed]
  7. Effects of coenzyme Q10 and alpha-tocopherol administration on their tissue levels in the mouse: elevation of mitochondrial alpha-tocopherol by coenzyme Q10. Lass, A., Forster, M.J., Sohal, R.S. Free Radic. Biol. Med. (1999) [Pubmed]
  8. Antihydrophobic cosolvent effects for alkylation reactions in water solution, particularly oxygen versus carbon alkylations of phenoxide ions. Breslow, R., Groves, K., Mayer, M.U. J. Am. Chem. Soc. (2002) [Pubmed]
  9. Crystallographic structure of a phosphonate derivative of the Enterobacter cloacae P99 cephalosporinase: mechanistic interpretation of a beta-lactamase transition-state analog. Lobkovsky, E., Billings, E.M., Moews, P.C., Rahil, J., Pratt, R.F., Knox, J.R. Biochemistry (1994) [Pubmed]
  10. Atmospheric pressure ionization (API) mass spectrometry: formation of phenoxide ions from chlorinated aromatic compounds. Dzidic, I., Carroll, D.I., Stillwell, R.N., Horning, E.C. Anal. Chem. (1975) [Pubmed]
  11. Kinetic study of the phenolysis of bis(4-nitrophenyl) carbonate, bis(4-nitrophenyl) thionocarbonate, and methyl 4-nitrophenyl thionocarbonate. Castro, E.A., Angel, M., Arellano, D., Santos, J.G. J. Org. Chem. (2001) [Pubmed]
  12. A theoretical study on the metabolic activation of paracetamol by cytochrome P-450: indications for a uniform oxidation mechanism. Koymans, L., van Lenthe, J.H., van de Straat, R., Donné-Op den Kelder, G.M., Vermeulen, N.P. Chem. Res. Toxicol. (1989) [Pubmed]
  13. Evidence for covalent DNA adduction by ochratoxin A following chronic exposure to rat and subacute exposure to pig. Faucet, V., Pfohl-Leszkowicz, A., Dai, J., Castegnaro, M., Manderville, R.A. Chem. Res. Toxicol. (2004) [Pubmed]
  14. Involvement of phenoxyl radical intermediates in lipid antioxidant action of myricetin in iron-treated rat hepatocyte culture. Morel, I., Abaléa, V., Sergent, O., Cillard, P., Cillard, J. Biochem. Pharmacol. (1998) [Pubmed]
  15. Antioxidant paradoxes of phenolic compounds: peroxyl radical scavenger and lipid antioxidant, etoposide (VP-16), inhibits sarcoplasmic reticulum Ca(2+)-ATPase via thiol oxidation by its phenoxyl radical. Ritov, V.B., Goldman, R., Stoyanovsky, D.A., Menshikova, E.V., Kagan, V.E. Arch. Biochem. Biophys. (1995) [Pubmed]
  16. Generation and recycling of radicals from phenolic antioxidants. Kagan, V.E., Serbinova, E.A., Packer, L. Arch. Biochem. Biophys. (1990) [Pubmed]
  17. Identification of initiating agents in myoglobin-induced lipid peroxidation. Newman, E.S., Rice-Evans, C.A., Davies, M.J. Biochem. Biophys. Res. Commun. (1991) [Pubmed]
  18. The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization. Hunter, E.P., Desrosiers, M.F., Simic, M.G. Free Radic. Biol. Med. (1989) [Pubmed]
  19. Quenching of reactive oxidative species by probucol and comparison with other antioxidants. Bisby, R.H., Johnson, S.A., Parker, A.W. Free Radic. Biol. Med. (1996) [Pubmed]
  20. Depolymerization of poly(2,6-dimethyl-1,4-phenylene oxide) under oxidative conditions. Saito, K., Masuyama, T., Oyaizu, K., Nishide, H. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  21. Reactions of phenoxyl radicals with NADPH-cytochrome P-450 oxidoreductase and NADPH: reduction of the radicals and inhibition of the enzyme. Goldman, R., Tsyrlov, I.B., Grogan, J., Kagan, V.E. Biochemistry (1997) [Pubmed]
  22. Ascorbate is the primary reductant of the phenoxyl radical of etoposide in the presence of thiols both in cell homogenates and in model systems. Kagan, V.E., Yalowich, J.C., Day, B.W., Goldman, R., Gantchev, T.G., Stoyanovsky, D.A. Biochemistry (1994) [Pubmed]
  23. Peroxidase-catalyzed pro- versus antioxidant effects of 4-hydroxytamoxifen: enzyme specificity and biochemical sequelae. Day, B.W., Tyurin, V.A., Tyurina, Y.Y., Liu, M., Facey, J.A., Carta, G., Kisin, E.R., Dubey, R.K., Kagan, V.E. Chem. Res. Toxicol. (1999) [Pubmed]
  24. Paracetamol catalyzes myeloperoxidase-initiated lipid oxidation in LDL. Kapiotis, S., Sengoelge, G., Hermann, M., Held, I., Seelos, C., Gmeiner, B.M. Arterioscler. Thromb. Vasc. Biol. (1997) [Pubmed]
  25. An oxygen-bonded c8-deoxyguanosine nucleoside adduct of pentachlorophenol by peroxidase activation: evidence for ambident c8 reactivity by phenoxyl radicals. Dai, J., Wright, M.W., Manderville, R.A. Chem. Res. Toxicol. (2003) [Pubmed]
  26. Model studies of the histidine-tyrosine cross-link in cytochrome C oxidase reveal the flexible substituent effect of the imidazole moiety. Pratt, D.A., Pesavento, R.P., van der Donk, W.A. Org. Lett. (2005) [Pubmed]
  27. Singlet oxygen quenching and the redox properties of hydroxycinnamic acids. Foley, S., Navaratnam, S., McGarvey, D.J., Land, E.J., Truscott, T.G., Rice-Evans, C.A. Free Radic. Biol. Med. (1999) [Pubmed]
  28. Multi-frequency ESR study of the polycrystalline phenoxyl radical of alpha-(3,5-di-tert-butyl-4-hydroxyphenyl)-N-tert-butylnitrone in the diamagnetic matrix. Yamaji, T., Noda, Y., Yamauchi, S., Yamauchi, J. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  29. Interactions of phenoxyl radical of antitumor drug, etoposide, with reductants in solution and in cell and nuclear homogenates: electron spin resonance and high-performance liquid chromatography. Gantchev, T.G., van Lier, J.E., Stoyanovsky, D.A., Yalowich, J.C., Kagan, V.E. Meth. Enzymol. (1994) [Pubmed]
  30. Comparison of structurally analogous Zn2, Co2, and Mg2 catalysts for the polymerization of cyclic esters. Breyfogle, L.E., Williams, C.K., Young, V.G., Hillmyer, M.A., Tolman, W.B. Dalton transactions (Cambridge, England : 2003) (2006) [Pubmed]
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