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Chemical Compound Review

Hexanon     cyclohexanone

Synonyms: Hytrolo, Sextone, hexanoe, Nadone, Anone, ...
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Disease relevance of cyclohexanone


Psychiatry related information on cyclohexanone


High impact information on cyclohexanone


Chemical compound and disease context of cyclohexanone


Biological context of cyclohexanone

  • The inhibitors are based upon a cyclohexanone nucleus and are designed to probe binding interactions in the S2 and S2' binding sites [13].
  • Whereas one ORF showed high homology to cyclohexanone monooxygenase from Acinetobacter sp. strain NCIB 9871, most of the ORFs showed only moderate homology to proteins in GenBank [14].
  • These unusual kinetics are followed by 2,2'-methylene-bis(4-methyl-6-tert-butylphenol), BIS, in five solvents (acetonitrile, benzonitrile, acetone, cyclohexanone, and DMSO) [15].
  • The diastereoselective Michael alkylation of alpha-substituted and alpha,alpha'-disubstituted cyclohexanone benzylimines with ethylidenemalonate diesters was carried out for mechanistic and synthetic purposes [16].
  • The catalytic activity of 2-8a,b in transfer hydrogenation of cyclohexanone, as well as theoretical calculations on the models [Ru(eta(6)-C(6)H(6))Cl(kappa(2)-P,N-H(2)PCH(2)P[=NP(=O)(OH)(2)]H(2))]+ and [Ru(eta(6)-C(6)H(6))Cl(kappa(2)-P,O-H(2)PCH(2)P[=NP(=O)(OH)(2)]H(2))]+, has been also studied [17].

Anatomical context of cyclohexanone


Associations of cyclohexanone with other chemical compounds

  • The kinetic 15N isotope effect for LADH catalysis was 0.9989 +/- 0.0006 for cyclohexanol oxidation and 0.997 +/- 0.002 for cyclohexanone reduction [22].
  • Both the quantum-chemical results and the kinetic study indicate that the reaction follows mechanism 1, and that the catalyst active site consists of two centers: the Lewis acid Sn atom to which cyclohexanone has to coordinate, and the oxygen atom of the Sn-OH group that interacts with H(2)O(2) forming a hydrogen bond [23].
  • The requirement in catalysis of the deprotonated flavin C4a-peroxide, a nucleophile, is consistent with a Baeyer-Villiger rearrangement mechanism for the enzymatic oxygenation of cyclohexanone [24].
  • The reaction catalyzed involves the four-electron reduction of O2 at the expense of a two-electron oxidation of NADPH and a two-electron oxidation of cyclohexanone to form epsilon-caprolactone [24].
  • Conformational analysis of the Diels-Alder adducts based on both (1)H NMR spectrometry and X-ray diffraction data indicates that the newly created cyclohexene and cyclohexanone rings adopt a pseudoboat conformation [25].

Gene context of cyclohexanone

  • Multiple forms of cyclohexanone oxygenase from Nocardia globerula CL1 [26].
  • Furthermore, the high stability of the "derivatizing" reagent, cyclohexanone, compared with acyl and TMS derivatizing reagents, is a useful property in method development [27].
  • Enantioselective synthesis of tert-butyl tert-butanethiosulfinate catalyzed by cyclohexanone monooxygenase [28].
  • This highly specific reaction of carcinogen with alcohol dehydrogenase lowers its Vmax and increases its Km with cyclohexanone thereby reducing its catalytic efficiency for this substrate [29].
  • The crystal structure of cyclohexanone oxime, C(6)H(11)NO, was reported as severely disordered in the trigonal non-centrosymmetric space group P3 [Olivato, Ribeiro, Zukerman-Schpector & Bombieri (2001). Acta Cryst. B57, 705-713] [30].

Analytical, diagnostic and therapeutic context of cyclohexanone


  1. Chronic toxicity study of cyclohexanone in rats and mice. Lijinsky, W., Kovatch, R.M. J. Natl. Cancer Inst. (1986) [Pubmed]
  2. To the core of autocatalysis in cyclohexane autoxidation. Hermans, I., Jacobs, P.A., Peeters, J. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  3. Influence of cyclohexanone carboxymethoxime on behaviour and electroshock susceptibility of young chicks [proceedings]. Osuide, G., Stansfield, F., Lahan, G.D. West African journal of pharmacology and drug research. (1977) [Pubmed]
  4. The relationship of hemoglobin synthesis to erythroid colony and burst formation. Eliason, J.F., Van Zant, G., Goldwasser, E. Blood (1979) [Pubmed]
  5. Nuclear type II sites and malignant cell proliferation: inhibition by 2,6-bis-benzylidenecyclohexanones. Markaverich, B.M., Schauweker, T.H., Gregory, R.R., Varma, M., Kittrell, F.S., Medina, D., Varma, R.S. Cancer Res. (1992) [Pubmed]
  6. Oxidation of ammonia by Nitrosomonas europaea. Definite 18O-tracer evidence that hydroxylamine formation involves a monooxygenase. Hollocher, T.C., Tate, M.E., Nicholas, D.J. J. Biol. Chem. (1981) [Pubmed]
  7. Group 6 heteroatom- and non-heteroatom-stabilized carbene complexes. beta,beta'- and alpha,beta,beta'-annulation reactions of cyclic enamines. Barluenga, J., Ballesteros, A., Bernardo De La Rúa, R., Santamaría, J., Rubio, E., Tomás, M. J. Am. Chem. Soc. (2003) [Pubmed]
  8. Studies on the chirality of sulfoxidation catalyzed by bacterial flavoenzyme cyclohexanone monooxygenase and hog liver flavin adenine dinucleotide containing monooxygenase. Light, D.R., Waxman, D.J., Walsh, C. Biochemistry (1982) [Pubmed]
  9. Conversion of 4-hydroxyacetophenone into 4-phenyl acetate by a flavin adenine dinucleotide-containing Baeyer-Villiger-type monooxygenase. Tanner, A., Hopper, D.J. J. Bacteriol. (2000) [Pubmed]
  10. Identification of two gene clusters involved in cyclohexanone oxidation in Brevibacterium epidermidis strain HCU. Brzostowicz, P.C., Blasko, M.S., Rouvière, P.E. Appl. Microbiol. Biotechnol. (2002) [Pubmed]
  11. Occupational contact dermatitis from cyclohexanone as a PVC adhesive. Sanmartín, O., de la Cuadra, J. Contact Derm. (1992) [Pubmed]
  12. Understanding and improving NADPH-dependent reactions by nongrowing Escherichia coli cells. Walton, A.Z., Stewart, J.D. Biotechnol. Prog. (2004) [Pubmed]
  13. Combinatorial library of serine and cysteine protease inhibitors that interact with both the S and S' binding sites. Abato, P., Conroy, J.L., Seto, C.T. J. Med. Chem. (1999) [Pubmed]
  14. Genetic analysis of a gene cluster for cyclohexanol oxidation in Acinetobacter sp. Strain SE19 by in vitro transposition. Cheng, Q., Thomas, S.M., Kostichka, K., Valentine, J.R., Nagarajan, V. J. Bacteriol. (2000) [Pubmed]
  15. Abnormal solvent effects on hydrogen atom abstraction. 3. Novel kinetics in sequential proton loss electron transfer chemistry. Litwinienko, G., Ingold, K.U. J. Org. Chem. (2005) [Pubmed]
  16. Reaction of cyclohexanone benzylimines with ethylidenemalonate diesters. Diphenyl 2-ethylidenemalonate: a highly electrophilic synthetic equivalent of crotonic esters. Jabin, I., Revial, G., Monnier-Benoit, N., Netchitaïlo, P. J. Org. Chem. (2001) [Pubmed]
  17. Ruthenium(II) and ruthenium(IV) complexes containing kappa1-P-, kappa2-P,O-, and kappa3-P,N,O-iminophosphorane-phosphine ligands Ph2PCH2P[=NP(=O)(OR)2]Ph2 (R = Et, Ph): synthesis, reactivity, theoretical studies, and catalytic activity in transfer hydrogenation of cyclohexanone. Cadierno, V., Crochet, P., Díez, J., García-Alvarez, J., García-Garrido, S.E., Gimeno, J., García-Granda, S., Rodríguez, M.A. Inorganic chemistry. (2003) [Pubmed]
  18. Effect of ethanol on the redox state of the coenzyme bound to alcohol dehydrogenase studied in isolated hepatocytes. Cronholm, T. Biochem. J. (1987) [Pubmed]
  19. Odorants presented to the rat nasal cavity increase cortical blood flow. Major, D.A., Silver, W.L. Chem. Senses (1999) [Pubmed]
  20. Spine density on olfactory granule cell dendrites is reduced in rats reared in a restricted olfactory environment. Rehn, B., Panhuber, H., Laing, D.G., Breipohl, W. Brain Res. (1988) [Pubmed]
  21. TRPV1 Receptors and Nasal Trigeminal Chemesthesis. Silver, W.L., Clapp, T.R., Stone, L.M., Kinnamon, S.C. Chem. Senses (2006) [Pubmed]
  22. Secondary 15N isotope effects on the reactions catalyzed by alcohol and formate dehydrogenases. Rotberg, N.S., Cleland, W.W. Biochemistry (1991) [Pubmed]
  23. A multisite molecular mechanism forBaeyer-Villiger oxidations on solid catalysts using environmentally friendly H2O2 as oxidant. Boronat, M., Corma, A., Renz, M., Sastre, G., Viruela, P.M. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  24. Mechanistic studies of cyclohexanone monooxygenase: chemical properties of intermediates involved in catalysis. Sheng, D., Ballou, D.P., Massey, V. Biochemistry (2001) [Pubmed]
  25. Complete and remarkable reversal of chemoselectivity in [4 + 2] cycloadditions involving electron-poor indoles as dienophiles. Diels-Alder versus hetero-Diels-Alder processes. Chrétien, A., Chataigner, I., L'Hélias, N., Piettre, S.R. J. Org. Chem. (2003) [Pubmed]
  26. Multiple forms of cyclohexanone oxygenase from Nocardia globerula CL1. Norris, D.B., Trudgill, P.W. Eur. J. Biochem. (1976) [Pubmed]
  27. The use of cyclohexanone as a "derivatizing" reagent for the GC-MS detection of amphetamines and ephedrines in seizures and the urine. El-Haj, B.M., Al-Amri, A.M., Hassan, M.H., Ali, H.S., Bin Khadem, R.K. Forensic Sci. Int. (2003) [Pubmed]
  28. Enantioselective synthesis of tert-butyl tert-butanethiosulfinate catalyzed by cyclohexanone monooxygenase. Colonna, S., Gaggero, N., Carrea, G., Pasta, P., Alphand, V., Furstoss, R. Chirality. (2001) [Pubmed]
  29. The binding of an aminoazo dye carcinogen to a specific methionine residue in rat liver alcohol dehydrogenase in vivo. Coles, B., Beale, D., Miller, D., Lay, J., Kadlubar, F., Aitken, A., Ketterer, B. Chem. Biol. Interact. (1987) [Pubmed]
  30. Twinning by merohedry in cyclohexanone oxime: a revised structure. Lutz, M., Spek, A.L., Dabirian, R., van Walree, C.A., Jenneskens, L.W. Acta crystallographica. Section C, Crystal structure communications. (2004) [Pubmed]
  31. mRNA differential display in a microbial enrichment culture: simultaneous identification of three cyclohexanone monooxygenases from three species. Brzostowicz, P.C., Walters, D.M., Thomas, S.M., Nagarajan, V., Rouvière, P.E. Appl. Environ. Microbiol. (2003) [Pubmed]
  32. Acinetobacter cyclohexanone monooxygenase: gene cloning and sequence determination. Chen, Y.C., Peoples, O.P., Walsh, C.T. J. Bacteriol. (1988) [Pubmed]
  33. High-performance liquid chromatography of cyclohexanone oxime in urine and plasma. Unger, P.D., McMahon, F.J. J. Chromatogr. (1981) [Pubmed]
  34. Determination of cyclohexanone in intravenous solutions stored in PVC bags by gas chromatography. Ulsaker, G.A., Korsnes, R.M. The Analyst. (1977) [Pubmed]
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