Summary: Derivatives of butanone, also known as methyl ethyl ketone (with structural formula CH3COC2H5).

Top Publications

  1. Kumpulainen H, Mähönen N, Laitinen M, Jaurakkajärvi M, Raunio H, Juvonen R, et al. Evaluation of hydroxyimine as cytochrome P450-selective prodrug structure. J Med Chem. 2006;49:1207-11 pubmed
    ..Results indicate that hydroxyimine is a useful intermediate prodrug structure for ketone drugs. ..
  2. Demir H, Soygun K, Dogan A, Keskin S, Dogan O, Bolayir G. Effect of maleic anhydride pretreatment on tensile bond strength of a silicone soft liner to a denture base polymer. J Adhes Dent. 2011;13:481-7 pubmed publisher
    ..The treatment of resin surfaces with maleic anhydride added to Primo adhesive effectively increased bond strength between silicone soft liner and denture base resin. ..
  3. Bokhari T, Mushtaq A, Khan I. Concentration of 68Ga via solvent extraction. Appl Radiat Isot. 2009;67:100-2 pubmed publisher
    ..The (68)Ga eluate (1M HCl) is extracted in methyl ethyl ketone, which is evaporated and taken in a small volume of buffer. ..
  4. Tani A, Tobe S, Shimizu S. Uptake of methacrolein and methyl vinyl ketone by tree saplings and implications for forest atmosphere. Environ Sci Technol. 2010;44:7096-101 pubmed publisher
    ..The loss rate by tree uptake was the highest, followed by the reaction with OH radicals, even at a high OH concentration (0.15 pptv) both for MACR and MVK, suggesting that tree uptake provides a significant sink. ..
  5. McDermott C, Allshire A, van Pelt F, Heffron J. Sub-chronic toxicity of low concentrations of industrial volatile organic pollutants in vitro. Toxicol Appl Pharmacol. 2007;219:85-94 pubmed
    ..The lowest-observed-adverse-effect-levels (LOAELs) measured in vitro were close to blood solvent concentrations reported for individuals exposed to the agents at levels at or below their individual threshold limit values (TLVs). ..
  6. Wang H, Yan J, Song X, Fan L, Xu J, Zhou G, et al. Synthesis and antidiabetic performance of ?-amino ketone containing nabumetone moiety. Bioorg Med Chem. 2012;20:2119-30 pubmed publisher
  7. Cai Q, You S. Organocatalyzed enantioselective formal [4 + 2] cycloaddition of 2,3-disubstituted indole and methyl vinyl ketone. Org Lett. 2012;14:3040-3 pubmed publisher
    ..This method provides bridged-ring indoline scaffolds containing two quaternary carbon centers with excellent yields and enantioselectivity (up to 98% yield and 98% ee). ..
  8. Noya Y, Seki K, Asano H, Mai Y, Horinouchi T, Higashi T, et al. Identification of stable cytotoxic factors in the gas phase extract of cigarette smoke and pharmacological characterization of their cytotoxicity. Toxicology. 2013;314:1-10 pubmed publisher
  9. Krishnan S, Hvastkovs E, Bajrami B, Schenkman J, Rusling J. Human cyt P450 mediated metabolic toxicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) evaluated using electrochemiluminescent arrays. Mol Biosyst. 2009;5:163-9 pubmed publisher
    ..Chemical screening in this fashion allows rapid clarification of enzymes responsible for genotoxic activation as well as offering insight into cyt P450-related toxicity and mechanisms. ..

More Information


  1. Prieto A, de Barrio M, Martin E, Fernández Bohórquez M, de Castro F, Ruiz F, et al. Tolerability to nabumetone and meloxicam in patients with nonsteroidal anti-inflammatory drug intolerance. J Allergy Clin Immunol. 2007;119:960-4 pubmed
    ..Nabumetone and meloxicam are safe alternatives in NSAID-intolerant patients. ..
  2. Chang C, Cho I, Li Q. Insecticidal activity of basil oil, trans-anethole, estragole, and linalool to adult fruit flies of Ceratitis capitata, Bactrocera dorsalis, and Bactrocera cucurbitae. J Econ Entomol. 2009;102:203-9 pubmed
    ..Methyl eugenol also may play a physiological role on the toxicity reduction. ..
  3. Vargas R, Miller N, Stark J. Field trials of spinosad as a replacement for naled, DDVP, and malathion in methyl eugenol and cue-lure bucket traps to attract and kill male oriental fruit flies and melon flies (Diptera: Tephritidae) in Hawaii. J Econ Entomol. 2003;96:1780-5 pubmed
    ..dorsalis and B. cucurbitae areawide integrated pest management programs in Hawaii. ..
  4. Márquez Sillero I, Cárdenas S, Sielemann S, Valcarcel M. On-line headspace-multicapillary column-ion mobility spectrometry hyphenation as a tool for the determination of off-flavours in foods. J Chromatogr A. 2014;1333:99-105 pubmed publisher
    ..After the degradation study, it can be concluded that the stability of the milk samples during storage is more affected by the light while temperature was more critical for oil samples. ..
  5. Pastor J, del Nozal M, Zamarrón E, Garcia M. Solubility of triamcinolone acetonide and other anti-inflammatory drugs in silicone oil: implications for Therapeutic Efficacy. Retina. 2008;28:1247-50 pubmed publisher
  6. Bennett J, Marlow D, Nourian F, Breay J, Hammond D. Hexavalent chromium and isocyanate exposures during military aircraft painting under crossflow ventilation. J Occup Environ Hyg. 2016;13:356-71 pubmed publisher
    ..Smoke releases showing more effective ventilation here than in other aircraft painting facilities carries technical feasibility relevance. ..
  7. Yoshida T, Park J, Yokosuka K, Jimbo K, Yamada K, Sato K, et al. Effect of a nonprotein bioactive agent on the reduction of cyclooxygenase-2 and tumor necrosis factor-alpha in human intervertebral disc cells in vitro. J Neurosurg Spine. 2008;9:411-8 pubmed publisher
    ..Thus, Neurotropin could decrease pain by blocking the central pain pathway or increasing focal antiinflammatory effects. ..
  8. Kerola M, Vuolteenaho K, Kosonen O, Kankaanranta H, Sarna S, Moilanen E. Effects of nimesulide, acetylsalicylic acid, ibuprofen and nabumetone on cyclooxygenase-1- and cyclooxygenase-2-mediated prostanoid production in healthy volunteers ex vivo. Basic Clin Pharmacol Toxicol. 2009;104:17-21 pubmed publisher
    ..Nabumetone showed only a slight inhibitory effect on COX-1 and COX-2. Nimesulide caused almost complete suppression of COX-2 activity and a partial reduction of COX-1 activity. This confirms the relative COX-2 selectivity of nimesulide. ..
  9. Yan Y, Bornscheuer U, Schmid R. Efficient water removal in lipase-catalyzed esterifications using a low-boiling-point azeotrope. Biotechnol Bioeng. 2002;78:31-4 pubmed
    ..In addition, immobilization of CAL-B on a magnetic polypropylene carrier (EP 100) facilitated separation of the biocatalyst. ..
  10. Ablordeppey S, Lyles Eggleston M, Bricker B, Zhang W, Zhu X, Goodman C, et al. Evaluation of the eutomer of 4-{3-(4-chlorophenyl)-3-hydroxypyrrolidin-1-yl}-1-(4-fluorophenyl)butan-1-one, {(+)-SYA 09}, a pyrrolidine analog of haloperidol. Bioorg Med Chem Lett. 2006;16:3219-23 pubmed
    ..2 (D2Ki/D4Ki ratio = 14.2). In an animal model of antipsychotic efficacy, the (+)-SYA 09 was efficacious with an ED50 value of 1.6 mg/kg, i.p., and at twice this value, (+)-SYA 09 did not induce significant catalepsy in rats. ..
  11. Hrazdina G. Aroma production by tissue cultures. J Agric Food Chem. 2006;54:1116-23 pubmed
    ..In this paper the results of experiments for the use of tissue cultures in the production of vanilla, raspberry, strawberry garlic, and onion aromas is discussed. ..
  12. Bozdemir M, Yildiz M, Seyhanli E, Gürbüz S, Kilicaslan I, Karlidag T. Narrowing of airway caused by ingestion of methyl ethyl ketone peroxide. Hum Exp Toxicol. 2011;30:2002-6 pubmed publisher
    ..Therefore, these containers should be kept in safe places. In addition, the priority following the ingestion of MEKP should be given to maintain open and adequate airway in the ED. ..
  13. Stevens A, Guan L, Bebenek K, Kunkel T, Greenberg M. DNA polymerase ? inactivation by oxidized abasic sites. Biochemistry. 2013;52:975-83 pubmed publisher
    ..The ability of DOB and pC4-AP to inactivate Pol ? provides additional evidence that these lesions are significant sources of the cytotoxicity of DNA-damaging agents that produce them. ..
  14. Ashokkumar S, Nair A, Saravanan V, Rajasimman M, Rajamohan N. Kinetics studies on the removal of Methyl ethyl ketone using cornstack based biofilter. Ecotoxicol Environ Saf. 2016;134:377-382 pubmed publisher
    ..The critical inlet concentration, critical inlet load and biofilm thickness were estimated using the model predictions. ..
  15. Kang K, Kan C, Du Y, Liu D. The generation of void morphology inside soap-free P(MMA-EA-MAA) particles prepared by seeded emulsion polymerization. J Colloid Interface Sci. 2006;297:505-12 pubmed
    ..The void structure disappeared completely as the initial pH was higher than 12.0. The generation mechanism of the void morphology was discussed. ..
  16. Catz P, Shinn W, Kapetanovic I, Kim H, Kim M, Jacobson E, et al. Simultaneous determination of myristyl nicotinate, nicotinic acid, and nicotinamide in rabbit plasma by liquid chromatography-tandem mass spectrometry using methyl ethyl ketone as a deproteinization solvent. J Chromatogr B Analyt Technol Biomed Life Sci. 2005;829:123-35 pubmed
  17. Torayama I, Ishihara T, Katsura I. Caenorhabditis elegans integrates the signals of butanone and food to enhance chemotaxis to butanone. J Neurosci. 2007;27:741-50 pubmed
  18. Yamagami C, Motohashi N, Emoto T, Hamasaki A, Tanahashi T, Nagakura N, et al. Quantitative structure-activity relationship analyses of antioxidant and free radical scavenging activities for hydroxybenzalacetones. Bioorg Med Chem Lett. 2004;14:5629-33 pubmed
  19. Beekwilder J, van der Meer I, Sibbesen O, Broekgaarden M, Qvist I, Mikkelsen J, et al. Microbial production of natural raspberry ketone. Biotechnol J. 2007;2:1270-9 pubmed
    ..These results therefore lay a strong foundation for a potentially renewable source of "natural" flavour compounds making use of plant genes. ..
  20. Hahin R, Larsen J, Gasser K. Predictions of the EC50 for action potential block for aliphatic solutes. J Membr Biol. 2008;221:73-85 pubmed publisher
    ..The results are consistent with the hypothesis that the solutes bind to channel crevices to cause Na(+) channel and AP block. ..
  21. Kim M, Baek H, Lee M, Park H, Shin S, Choi D, et al. Rhododenol and raspberry ketone impair the normal proliferation of melanocytes through reactive oxygen species-dependent activation of GADD45. Toxicol In Vitro. 2016;32:339-46 pubmed publisher
    ..Consistently, up-regulation of GADD45 and GADD153 was significantly attenuated by NAC, suggesting that increased ROS and the resultant growth arrest of melanocytes may contribute to RD and RK-induced leukoderma. ..
  22. Yang C, Lopez C, Rana T. Discovery of nonsteroidal anti-inflammatory drug and anticancer drug enhancing reprogramming and induced pluripotent stem cell generation. Stem Cells. 2011;29:1528-36 pubmed publisher
    ..This hypothesis-driven approach provides an alternative to shot-gun screening and accelerates understanding of molecular mechanisms underlying iPSC induction. ..
  23. Bednar I, Tscheliessnig R, Berger E, Podgornik A, Jungbauer A. Surface energies of hydrophobic interaction chromatography media by inverse liquid chromatography. J Chromatogr A. 2012;1220:115-21 pubmed publisher
    ..The media with polymethacrylate backbone had a higher surface energy (? ? 200 mJ/m(2)) and Lifshitz-van-der-Waals contribution (?(LW) ? 140 mJ/m(2)) than the agarose-based media (? ? 90-180 mJ/m(2) and ?(LW) ? 50-160 mJ/m(2)). ..
  24. Guan L, Greenberg M. Irreversible inhibition of DNA polymerase beta by an oxidized abasic lesion. J Am Chem Soc. 2010;132:5004-5 pubmed publisher
    ..Finally, these observations provide the impetus for the design of a new family of inhibitors of Pol beta. ..
  25. Hashimoto H, Itadani A, Kudoh T, Fukui S, Kuroda Y, Seno M, et al. Nano-micrometer-architectural acidic silica prepared from iron oxide of Leptothrix ochracea origin. ACS Appl Mater Interfaces. 2013;5:5194-200 pubmed publisher
    ..The acidity of this new silica material was confirmed through representative two catalytic reactions: ring-opening reaction and Friedel-Crafts-type reaction, both of which are known to require acid catalysts...
  26. Horiyama S, Kunitomo M, Yoshikawa N, Nakamura K. Mass Spectrometric Approaches to the Identification of Potential Ingredients in Cigarette Smoke Causing Cytotoxicity. Biol Pharm Bull. 2016;39:903-8 pubmed publisher
    ..These ?,?-unsaturated carbonyl compounds may have a key role in CSE-induced cell death. ..
  27. Szántó G, Bombicz P, Grün A, Kádas I. Highly enantioselective organocatalytic conjugate addition of nitromethane to benzylidene acetones. Chirality. 2008;20:1120-6 pubmed publisher
    ..The ee ratio of the products were between 67 and 100%, determined by HPLC with Chiracel OD. Molecular and crystal structure of 3,4-methylenedioxy-phenyl-5-nitro-pentan-2-one has been studied by single crystal X-ray diffraction. ..
  28. Myers S, Ali M. Haemoglobin adducts as biomarkers of exposure to tobacco-related nitrosamines. Biomarkers. 2008;13:145-59 pubmed
  29. Barshteyn N, Elfarra A. Formation of mono- and bis-Michael adducts by the reaction of nucleophilic amino acids with hydroxymethylvinyl ketone, a reactive metabolite of 1,3-butadiene. Chem Res Toxicol. 2009;22:918-25 pubmed publisher
  30. Pathak R, Pant C, Shaw A, Bhaduri A, Gaikwad A, Sinha S, et al. Baylis-Hillman reaction: convenient ascending syntheses and biological evaluation of acyclic deoxy monosaccharides as potential antimycobacterial agents. Bioorg Med Chem. 2002;10:3187-96 pubmed
    ..Among the compounds evaluated for their antimycobacterial activity, compound (10) showed the desired activity in the range of 3.125 microg/mL. ..
  31. Abe I, Sano Y, Takahashi Y, Noguchi H. Site-directed mutagenesis of benzalacetone synthase. The role of the Phe215 in plant type III polyketide synthases. J Biol Chem. 2003;278:25218-26 pubmed
    ..These results confirmed the critical role of Phe-215 in the polyketide formation reactions and provided structural basis for understanding the structure-function relationship of the plant type III PKSs. ..
  32. von Stedingk H, Davies R, Rydberg P, Törnqvist M. Methyl vinyl ketone--identification and quantification of adducts to N-terminal valine in human hemoglobin. J Chromatogr B Analyt Technol Biomed Life Sci. 2010;878:2491-6 pubmed publisher
    ..Analysis of an Hb adduct from MVK in humans has to our knowledge not been described before. ..
  33. Park K. Raspberry ketone increases both lipolysis and fatty acid oxidation in 3T3-L1 adipocytes. Planta Med. 2010;76:1654-8 pubmed publisher
    ..These findings suggest that RK holds great promise as an herbal medicine since its biological activities alter the lipid metabolism in 3T3-L1 adipocytes. ..
  34. Shimoda K, Harada T, Hamada H, Nakajima N, Hamada H. Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana. Phytochemistry. 2007;68:487-92 pubmed
    ..Cultured cells of P. americana can reduce, and regioselectively hydroxylate and glucosylate, these food ingredients to their beta-glycosides...
  35. Gao K, Song Q, Wei D. Coupling of enantioselective biooxidation of DL-1,2-propanediol and bioreduction of pinacolone via regeneration cycle of coenzyme. Appl Microbiol Biotechnol. 2006;71:819-23 pubmed
    ..In the article, the bioreduction of pinacolone was coupled to the enantioselective oxidation. Yield of the acid was increased by 36% and e.e. value of the product approached 99%...
  36. Ashworth N, Peloso P, Muhajarine N, Stang M. Risk of hospitalization with peptic ulcer disease or gastrointestinal hemorrhage associated with nabumetone, Arthrotec, diclofenac, and naproxen in a population based cohort study. J Rheumatol. 2005;32:2212-7 pubmed
    ..It appears that inherent gastroprotective strategies with Arthrotec and to a lesser extent with nabumetone do translate into decreased serious GI side effects at the population level in the short term. ..
  37. Yildirim E, Sağıroğlu O, Kilic F, Erol K. Effects of nabumetone and dipyrone on experimentally induced gastric ulcers in rats. Inflammation. 2013;36:476-81 pubmed publisher
    ..These effects may be attributed to their non-acidic structures and weak inhibitory effects on gastric mucosal cyclooxygenases. ..
  38. Fiorentini F, Romero E, Fraaije M, Faber K, Hall M, Mattevi A. Baeyer-Villiger Monooxygenase FMO5 as Entry Point in Drug Metabolism. ACS Chem Biol. 2017;12:2379-2387 pubmed publisher
    ..This protocol can potentially be extended to other FMO5 candidate substrates as it represents an effective and robust bench-ready platform applicable to API screening and metabolite synthesis. ..
  39. Zhang Q, Pan L. A one-dimensional coordination polymer formed from the reaction of 1,1-diphenyl-3,3'-[(1R,2R)-cyclohexane-1,2-diylbis(azanediyl)]dibut-2-en-1-one with MnCl2·4H2O. Acta Crystallogr C Struct Chem. 2014;70:16-8 pubmed publisher
    ..The ligand is in the zwitterionic enol form and displays intramolecular ionic N(+)-H...O(-) hydrogen bonding and ?-? interactions between pairs of phenyl rings which strengthen the chains. ..
  40. Nobilis M, Holcapek M, Kolarova L, Kopecky J, Kunes M, Svoboda Z, et al. Identification and determination of phase II nabumetone metabolites by high-performance liquid chromatography with photodiode array and mass spectrometric detection. J Chromatogr A. 2004;1031:229-36 pubmed
  41. Kivitz A, Greenwald M, Cohen S, Polis A, Najarian D, Dixon M, et al. Efficacy and safety of rofecoxib 12.5 mg versus nabumetone 1,000 mg in patients with osteoarthritis of the knee: a randomized controlled trial. J Am Geriatr Soc. 2004;52:666-74 pubmed
    ..Rofecoxib 12.5 mg daily demonstrated better efficacy over 6 weeks of treatment and quicker onset of OA efficacy over the first 6 days than nabumetone 1,000 mg daily. Both therapies were generally well tolerated. ..
  42. Hedner T, Samulesson O, Wahrborg P, Wadenvik H, Ung K, Ekbom A. Nabumetone: therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis. Drugs. 2004;64:2315-43; discussion 2344-5 pubmed
    ..Compared with COX-2 selective inhibitors, nabumetone exhibits similar anti-inflammatory and analgesic properties in patients with arthritis and there is no evidence of excess GI or other forms of complications to date. ..
  43. Skopp G, Schmitt G, Pötsch L. Plasma-to-blood ratios of congener analytes. J Anal Toxicol. 2005;29:145-7 pubmed
  44. Canudas N, Zamora D, Villamizar J, Fuentes J, Castelli C, Taddei A. Photosensitizing properties of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic non-steroidal anti-inflammatory and analgesic drug nabumetone. Pharmazie. 2005;60:604-8 pubmed
    ..6-MNAA was phototoxic to C. albicans, C. lipolytica and C. tropicalis. A mechanism involving singlet oxygen, radicals, and electron transfer reactions is suggested for the observed phototoxicity. ..
  45. Xia X, Liu C, Yuan W, Wang X, Meng X, Zhang M, et al. [The secondary metabolites of the mangrove endophytic fungi ZZF13 and Guignardia sp. 4382 from the South China Sea]. Zhong Yao Cai. 2009;32:1385-7 pubmed
    ..Their structures were identified as Bacillpsporin C (1), 5-carboxymellein (2), 5-methylmellein (3) and 1-(2,6-dihydroxyphenyl) butanone (4). The compounds 2 - 4 are isolated from the Guignardia sp. of Marine fungi for the first time. ..
  46. Bunkoed O, Thavarungkul P, Thammakhet C, Kanatharana P. A simple and high collection efficiency sampling method for monitoring of carbonyl compounds in a workplace environment. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2012;47:167-75 pubmed publisher
    ..The sampling of air directly into the absorbing solution was compared with the conventional method of using an adsorbent cartridge, and the results were in good agreement (P > 0.05). ..
  47. Zhu L, Chen Z. [Ozonolysis of methacrolein and methyl vinyl ketone in aqueous solutions]. Huan Jing Ke Xue. 2005;26:83-6 pubmed
    ..9, 26.6 +/- 3.9, 4.6 +/- 0.4 and 10.0 +/- 0.8 respectively for MAC; 40.8+/- 2.2, 40.7 +/- 3.5, 6.8 +/- 0.5 and 10.4 +/- 0.8 respectively for MVK. Finally, the reaction mechanisms are deduced to explain the formation of products observed. ..
  48. Arai Y, Tanaka K, Ushijima H, Tomisato W, Tsutsumi S, Aburaya M, et al. Low direct cytotoxicity of nabumetone on gastric mucosal cells. Dig Dis Sci. 2005;50:1641-6 pubmed
    ..We thus propose that the low direct cytotoxicity of nabumetone observed in vitro is maintained in vivo, and that the use of nabumetone does not harm the gastric mucosa. ..
  49. Nobilis M, Kopecky J, Kvetina J, Svoboda Z, Pour M, Kunes J, et al. Comparative biotransformation and disposition studies of nabumetone in humans and minipigs using high-performance liquid chromatography with ultraviolet, fluorescence and mass spectrometric detection. J Pharm Biomed Anal. 2003;32:641-56 pubmed
    ..The concentration levels of nabumetone metabolites in urine, bile and synovial fluid were also evaluated. ..
  50. Sathishkumar K, Rangan V, Gao X, Uppu R. Methyl vinyl ketone induces apoptosis in murine GT1-7 hypothalamic neurons through glutathione depletion and the generation of reactive oxygen species. Free Radic Res. 2007;41:469-77 pubmed
    ..The suggested sequence of events in the MVK-induced apoptosis in neuronal cells involves the depletion of cellular glutathione followed by an increased generation of ROS and finally the loss of mitochondrial function. ..
  51. Lee S, Lee G. Development of apoptosis-resistant dihydrofolate reductase-deficient Chinese hamster ovary cell line. Biotechnol Bioeng. 2003;82:872-6 pubmed
  52. Chiang H, Chiang P, Huang C. Ozonation of activated carbon and its effects on the adsorption of VOCs exemplified by methylethylketone and benzene. Chemosphere. 2002;47:267-75 pubmed
    ..Results of factorial analysis indicate that physical characteristics, namely, micropore, BET surface area, pore diameter (PD), micropore volume (MV) play an important role on benzene and MEK adsorption. ..
  53. Rius Solé M, Garcia Regueiro J. Role of 4-phenyl-3-buten-2-one in boar taint: identification of new compounds related to sensorial descriptors in pig fat. J Agric Food Chem. 2001;49:5303-9 pubmed
    ..The sensorial analysis of 4-phenyl-3-buten-2-one showed its possible contribution to boar taint. The possible contribution of phenol derivatives and short-chain fatty acids was also evaluated. ..