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Chemical Compound Review

ANISOLE     methoxybenzene

Synonyms: Anisloe, Anisol, Anizol, Methoxybenzene, Phenoxymethane, ...
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Disease relevance of anisole


Psychiatry related information on anisole

  • With more reactive and/or nonvolatile reagents (anisole, xylenes, mesitylene) expeditious conditions (short reaction time at constant MW power without control of the temperature) were used [2].

High impact information on anisole

  • Biomimetic model high-valent porphyrins showed reduction rates with variously 4-substituted N,N-dialkylanilines that were consistent with a positively charged intermediate; such relationships were not seen for anisole O-demethylation with P450 2B1 [3].
  • The fluorescence of one of the derivatives can be efficiently quenched by the presence of electron-rich compounds such as triphenylamines, phenol or anisole, which make them very promising compounds for sensor applications [4].
  • It is also shown that the product distribution for the alkylation of anisole shows significant pressure dependence with substitution at the ortho-position being favored at lower pressures, which is ascribed to hydrogen bonding [5].
  • The hydrogenation of arenes containing functional groups, such as anisole, by the [Ir(0)](n) nanoparticles occurs with concomitant hydrogenolysis of the C-O bond, suggesting that these nanoparticles behave as "heterogeneous catalysts" rather than "homogeneous catalysts" [6].
  • A mechanistic study of the FeO+-mediated decomposition pathways of phenol, anisol, and their thio analogues [7].

Biological context of anisole


Anatomical context of anisole

  • Effect of oxygen concentration on the metabolic pathway of anisole in rat liver microsomes [13].
  • Some odors (e.g., amyl acetate and anisole) produced increased responses in the epithelium of the lateral recesses when flow rates or sniff durations were high [14].
  • The effect of the antioxidant, butylated hydroxy anisole, on peroxide-induced and spontaneous activity of the uterus from the pregnant rat [15].

Associations of anisole with other chemical compounds

  • Kinetic studies in dioxane-water (4:1, v/v) at 60-90 degrees C have revealed that the folded backbone of the oligomers was, like the rigidified spherand, able to complex Li+, Na+, and K+ and, consequently, accelerated the hydrolysis of the nitro-appended anisole unit of the foldamers [10].
  • Palladium-catalyzed coupling of the dibromo derivative afforded the disubstituted phenyl, anisole, and acetylene derivatives, while reduction of the dinitro derivative and acetylation provided amino-dione and amide-hydroxyl derivatives [16].
  • On the other hand, tert-butyl methyl ether and anisole fail to form stable boron trichloride adducts and the corresponding ether-cleaved products are obtained [17].
  • The present polyoxoanion-stabilized Rh(0) nanoclusters also display a record, albeit modest, 30% selectivity for the partial hydrogenation of anisole to 1-methoxycyclohexene with an overall yield of up to 8% at higher temperatures [18].
  • Oxidation was monitored using HPLC and the fluorescence properties of Triton N-101 and other alkylphenol ethoxylate detergents, which are similar to those of anisole [19].

Gene context of anisole

  • N-(4-Methoxyphenylazoformyl)-L-phenylalanine is efficiently cleaved by the enzyme bovine carboxypeptidase A into fragments anisole, molecular nitrogen, carbonate, and phenylalanine, in the course of which an intense spectral absorption of the substrate (epsilon350 = 19,000 M-1 cm-1) disappears completely [20].
  • Subsequent resin cleavage and deprotection of the phosphorylated peptide resins was effected by treatment with 5% anisole: TFA and gave the seven phosphopeptides in high yield and purity [21].
  • Modulatory influence of arecanut on antioxidant 2(3)-tert-butyl-4-hydroxy anisole-induced hepatic detoxification system and antioxidant defence mechanism in mice [22].
  • Synthetic procedures for CKII substrate peptides often result in anisole adducts and dehydrated forms [23].
  • The use of anisole as an additive in the HF resin/peptide cleavage was rejected because anisole was found to undergo electrophilic substitution of the dibromoindole nucleus; a modified HF deprotection/cleavage procedure was developed and used instead [24].

Analytical, diagnostic and therapeutic context of anisole


  1. Dermatitis from butylated hydroxy anisole. Turner, T.W. Contact Derm. (1977) [Pubmed]
  2. Acylation and related reactions under microwaves. 4. Sulfonylation reactions of aromatics. Marquié, J., Laporterie, A., Dubac, J., Roques, N., Desmurs, J.R. J. Org. Chem. (2001) [Pubmed]
  3. Evidence for a 1-electron oxidation mechanism in N-dealkylation of N,N-dialkylanilines by cytochrome P450 2B1. Kinetic hydrogen isotope effects, linear free energy relationships, comparisons with horseradish peroxidase, and studies with oxygen surrogates. Guengerich, F.P., Yun, C.H., Macdonald, T.L. J. Biol. Chem. (1996) [Pubmed]
  4. Synthesis and properties of new tetrazines substituted by heteroatoms: towards the world's smallest organic fluorophores. Audebert, P., Miomandre, F., Clavier, G., Vernières, M.C., Badré, S., Méallet-Renault, R. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  5. Pressure effects on Friedel-Crafts alkylation reactions in supercritical difluoromethane. Abbott, A.P., Corr, S., Durling, N.E., Hope, E.G. Chemphyschem : a European journal of chemical physics and physical chemistry. (2005) [Pubmed]
  6. The use of imidazolium ionic liquids for the formation and stabilization of ir0 and rh0 nanoparticles: efficient catalysts for the hydrogenation of arenes. Fonseca, G.S., Umpierre, A.P., Fichtner, P.F., Teixeira, S.R., Dupont, J. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  7. A mechanistic study of the FeO+-mediated decomposition pathways of phenol, anisol, and their thio analogues. Brönstrup, M., Schröder, D., Schwarz, H. Chemistry (Weinheim an der Bergstrasse, Germany) (2000) [Pubmed]
  8. UDP-glucuronosyltransferase (UGT1A1*28 and UGT1A6*2) polymorphisms in Caucasians and Asians: relationships to serum bilirubin concentrations. Lampe, J.W., Bigler, J., Horner, N.K., Potter, J.D. Pharmacogenetics (1999) [Pubmed]
  9. Reactions on a solid surface. A simple, economical and efficient Friedel-Crafts acylation reaction over zinc oxide (ZnO) as a new catalyst. Sarvari, M.H., Sharghi, H. J. Org. Chem. (2004) [Pubmed]
  10. Hydrogen bonding-induced aromatic oligoamide foldamers as spherand analogues to accelerate the hydrolysis of nitro-substituted anisole in aqueous media. Yi, H.P., Wu, J., Ding, K.L., Jiang, X.K., Li, Z.T. J. Org. Chem. (2007) [Pubmed]
  11. An anion-induced regio- and chemoselective acylation and its application to the synthesis of an anticancer agent. Poirier, M., Chen, F., Bernard, C., Wong, Y.S., Wu, G.G. Org. Lett. (2001) [Pubmed]
  12. Increased longevity, reduced fecundity, and delayed development in fruitfly (Zaprionus paravittiger) fed on butylated hydroxy anisole. Bains, J.S., Kakkar, R., Sharma, S.P. Proc. Soc. Exp. Biol. Med. (1997) [Pubmed]
  13. Effect of oxygen concentration on the metabolic pathway of anisole in rat liver microsomes. Takahara, E., Ohta, S., Hirobe, M. Biochem. Pharmacol. (1986) [Pubmed]
  14. Regional distribution of rat electroolfactogram. Ezeh, P.I., Davis, L.M., Scott, J.W. J. Neurophysiol. (1995) [Pubmed]
  15. The effect of the antioxidant, butylated hydroxy anisole, on peroxide-induced and spontaneous activity of the uterus from the pregnant rat. Cherouny, P.H., Ghodgaonkar, R.B., Gurtner, G.H., Dubin, N.H. Biol. Reprod. (1989) [Pubmed]
  16. Synthesis of functionalized chiral carbocyclic cleft molecules complementary to Tröger's base derivatives. Kimber, M.C., Try, A.C., Painter, L., Harding, M.M., Turner, P. J. Org. Chem. (2000) [Pubmed]
  17. Hydroboration. 97. Synthesis of new exceptional chloroborane--Lewis base adducts for hydroboration. Dioxane--monochloroborane as a superior reagent for the selective hydroboration of terminal alkenes. Kanth, J.V., Brown, H.C. J. Org. Chem. (2001) [Pubmed]
  18. Anisole hydrogenation with well-characterized polyoxoanion- and tetrabutylammonium-stabilized Rh(0) nanoclusters: effects of added water and acid, plus enhanced catalytic rate, lifetime, and partial hydrogenation selectivity. Widegren, J.A., Finke, R.G. Inorganic chemistry. (2002) [Pubmed]
  19. Oxidation of nonionic detergents by cytochrome P450 enzymes. Hosea, N.A., Guengerich, F.P. Arch. Biochem. Biophys. (1998) [Pubmed]
  20. Arazoformyl peptide surrogates as spectrophotometric kinetic assay substrates for carboxypeptidase A. Mock, W.L., Liu, Y., Stanford, D.J. Anal. Biochem. (1996) [Pubmed]
  21. Solid phase synthesis of pp60src-related phosphopeptides via 'global' phosphorylation and their use as substrates for enzymatic phosphorylation by casein kinase-2. Perich, J.W., Meggio, F., Pinna, L.A. Bioorg. Med. Chem. (1996) [Pubmed]
  22. Modulatory influence of arecanut on antioxidant 2(3)-tert-butyl-4-hydroxy anisole-induced hepatic detoxification system and antioxidant defence mechanism in mice. Singh, A., Rao, A.R. Cancer Lett. (1995) [Pubmed]
  23. Synthetic peptide substrates for casein kinase II. Marshak, D.R., Carroll, D. Meth. Enzymol. (1991) [Pubmed]
  24. Synthesis of a tritiated human growth hormone releasing peptide. Shu, A.Y., Heys, J.R. Int. J. Pept. Protein Res. (1993) [Pubmed]
  25. Isolation of liver microsomal anisole O-demethylase and aniline hydroxylase from laboratory animals by Sepharose gel filtration. Pitout, M.J., Thiel, P.G. Int. J. Biochem. (1978) [Pubmed]
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