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Chemical Compound Review

Isoamylazetat     3-methylbutyl ethanoate

Synonyms: Bananan Oil, Banana oil, pear essence, CHEMBL42013, NSC-9260, ...
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Disease relevance of isopentyl acetate

  • Enhanced isoamyl acetate production upon manipulation of the acetyl-CoA node in Escherichia coli [1].
  • Behavioral assays from three colonies each of Africanized and European bees showed that 3M2BA recruited worker bees from hives of both Africanized bees and European bees at least as efficiently as isopentyl acetate IPA, a compound widely reported to have the highest activity for releasing alarm and stinging behavior in honeybees [2].
  • The first-episode-psychosis patients had significantly higher sensitivity to isoamyl acetate and to androstenone, but the incidence of anosmia to androstenone was not higher in the first episode patient group as compared to the control group [3].

Psychiatry related information on isopentyl acetate


High impact information on isopentyl acetate

  • Dynamic blood oxygenation level-dependent functional MRI was applied at 7 T in the rat olfactory bulb (OB) with pulsed delivery of iso-amyl acetate (IAA) and limonene [6].
  • On an intrasubject basis, short IAA exposures of 0.6 min separated by 3.5-min intervals induced reproducible spatial activity patterns (SAPs) in the olfactory nerve layer, glomerular layer, and external plexiform layer [6].
  • In addition, the onset and recovery kinetics following isoamyl acetate stimulation are prolonged in the null mice [7].
  • In MDD patients, a significant increase in the sensitivity to isoamyl acetate was observed 6 weeks after initiation of treatment, compared to controls [5].
  • Analysis of the fermentation products confirmed that the expression levels of ATF1 and ATF2 greatly affect the production of ethyl acetate and isoamyl acetate [8].

Chemical compound and disease context of isopentyl acetate


Biological context of isopentyl acetate


Anatomical context of isopentyl acetate


Associations of isopentyl acetate with other chemical compounds


Gene context of isopentyl acetate


Analytical, diagnostic and therapeutic context of isopentyl acetate

  • Isoamyl-acetate synthase was solubilized and extensively purified to apparent homogeneity by successive chromatographies on various columns [26].
  • The experimental paradigm involves subjects sniffing pairs of bottles, one containing an odorant (e.g. isoamyl acetate) dissolved in an odorless solvent (water or liquid silicone), the other containing just the solvent, while 19 channels of EEG are continuously recorded [27].
  • Atomic force microscopy and electrochemical impedance spectroscopy were used to characterize mixed Langmuir-Blodgett (LB) films before and after contact with a specific odorant molecule, isoamyl acetate [28].
  • In the aversive context of electrical stimulation, significant differences between isopentyl acetate and 2-heptanone were found [29].
  • The basic procedure consists of the collection of air samples using sampling cartridges containing XAD-2 resin, extraction of the resin with isoamyl acetate, and an analysis of the extract using gas chromatography with electron capture detection [30].


  1. Enhanced isoamyl acetate production upon manipulation of the acetyl-CoA node in Escherichia coli. Vadali, R.V., Bennett, G.N., San, K.Y. Biotechnol. Prog. (2004) [Pubmed]
  2. Discovery of 3-methyl-2-buten-1-yl acetate, a new alarm component in the sting apparatus of Africanized honeybees. Hunt, G.J., Wood, K.V., Guzmán-Novoa, E., Lee, H.D., Rothwell, A.P., Bonham, C.C. J. Chem. Ecol. (2003) [Pubmed]
  3. Increased olfactory sensitivity in first episode psychosis and the effect of neuroleptic treatment on olfactory sensitivity in schizophrenia. Sirota, P., Davidson, B., Mosheva, T., Benhatov, R., Zohar, J., Gross-Isseroff, R. Psychiatry research. (1999) [Pubmed]
  4. Olfactory pathways and the sense of smell. Slotnick, B.M., Schoonover, F.W. Neuroscience and biobehavioral reviews. (1992) [Pubmed]
  5. Olfactory sensitivity in major depressive disorder and obsessive compulsive disorder. Gross-Isseroff, R., Luca-Haimovici, K., Sasson, Y., Kindler, S., Kotler, M., Zohar, J. Biol. Psychiatry (1994) [Pubmed]
  6. Assessment and discrimination of odor stimuli in rat olfactory bulb by dynamic functional MRI. Xu, F., Kida, I., Hyder, F., Shulman, R.G. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  7. Olfactory marker protein (OMP) gene deletion causes altered physiological activity of olfactory sensory neurons. Buiakova, O.I., Baker, H., Scott, J.W., Farbman, A., Kream, R., Grillo, M., Franzen, L., Richman, M., Davis, L.M., Abbondanzo, S., Stewart, C.L., Margolis, F.L. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  8. Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters. Verstrepen, K.J., Van Laere, S.D., Vanderhaegen, B.M., Derdelinckx, G., Dufour, J.P., Pretorius, I.S., Winderickx, J., Thevelein, J.M., Delvaux, F.R. Appl. Environ. Microbiol. (2003) [Pubmed]
  9. Production of isoamyl acetate in ackA-pta and/or ldh mutants of Escherichia coli with overexpression of yeast ATF2. Vadali, R.V., Horton, C.E., Rudolph, F.B., Bennett, G.N., San, K.Y. Appl. Microbiol. Biotechnol. (2004) [Pubmed]
  10. Patterns of intracellular potentials in salamander mitral/tufted cells in response to odor stimulation. Hamilton, K.A., Kauer, J.S. J. Neurophysiol. (1989) [Pubmed]
  11. Evidence for genetic determination in human twins of olfactory thresholds for a standard odorant. Gross-Isseroff, R., Ophir, D., Bartana, A., Voet, H., Lancet, D. Neurosci. Lett. (1992) [Pubmed]
  12. Autonomic nervous system responses to odours: the role of pleasantness and arousal. Bensafi, M., Rouby, C., Farget, V., Bertrand, B., Vigouroux, M., Holley, A. Chem. Senses (2002) [Pubmed]
  13. Normal aging and odor intensity effects on the olfactory event-related potential. Covington, J.W., Geisler, M.W., Polich, J., Murphy, C. International journal of psychophysiology : official journal of the International Organization of Psychophysiology. (1999) [Pubmed]
  14. Enzymatic synthesis of isoamyl acetate using immobilized lipase from Rhizomucor miehei. Hari Krishna, S., Divakar, S., Prapulla, S.G., Karanth, N.G. J. Biotechnol. (2001) [Pubmed]
  15. Outward currents in olfactory receptor neurons activated by odorants and by elevation of cyclic AMP. Pun, R.Y., Kleene, S.J. Cell Biochem. Biophys. (2002) [Pubmed]
  16. Uptake of barbituric acid derivatives in small intestinal brush border membrane vesicles from retinyl palmitate-treated rats. Tanii, H., Horie, T. Pharmacol. Toxicol. (2000) [Pubmed]
  17. Odorant specificity of three oscillations and the DC signal in the turtle olfactory bulb. Lam, Y.W., Cohen, L.B., Zochowski, M.R. Eur. J. Neurosci. (2003) [Pubmed]
  18. Olfactory experience decreases responsiveness of the olfactory bulb in the adult rat. Buonviso, N., Chaput, M. Neuroscience (2000) [Pubmed]
  19. Olfactory discrimination ability for aliphatic esters in squirrel monkeys and humans. Laska, M., Freyer, D. Chem. Senses (1997) [Pubmed]
  20. The effect of increased yeast alcohol acetyltransferase and esterase activity on the flavour profiles of wine and distillates. Lilly, M., Bauer, F.F., Lambrechts, M.G., Swiegers, J.H., Cozzolino, D., Pretorius, I.S. Yeast (2006) [Pubmed]
  21. Genetic and physiological analysis of branched-chain alcohols and isoamyl acetate production in Saccharomyces cerevisiae. Yoshimoto, H., Fukushige, T., Yonezawa, T., Sone, H. Appl. Microbiol. Biotechnol. (2002) [Pubmed]
  22. Redistribution of metabolic fluxes in the central aerobic metabolic pathway of E. coli mutant strains with deletion of the ackA-pta and poxB pathways for the synthesis of isoamyl acetate. Dittrich, C.R., Vadali, R.V., Bennett, G.N., San, K.Y. Biotechnol. Prog. (2005) [Pubmed]
  23. Purification and characterization of isoamyl acetate-hydrolyzing esterase encoded by the IAH1 gene of Saccharomyces cerevisiae from a recombinant Escherichia coli. Fukuda, K., Kiyokawa, Y., Yanagiuchi, T., Wakai, Y., Kitamoto, K., Inoue, Y., Kimura, A. Appl. Microbiol. Biotechnol. (2000) [Pubmed]
  24. Construction of a self-cloning sake yeast that overexpresses alcohol acetyltransferase gene by a two-step gene replacement protocol. Hirosawa, I., Aritomi, K., Hoshida, H., Kashiwagi, S., Nishizawa, Y., Akada, R. Appl. Microbiol. Biotechnol. (2004) [Pubmed]
  25. Applicability of CoA/acetyl-CoA manipulation system to enhance isoamyl acetate production in Escherichia coli. Vadali, R.V., Bennett, G.N., San, K.Y. Metab. Eng. (2004) [Pubmed]
  26. Short-chain and medium-chain aliphatic-ester synthesis in Saccharomyces cerevisiae. Malcorps, P., Dufour, J.P. Eur. J. Biochem. (1992) [Pubmed]
  27. EEG responses to low-level chemicals in normals and cacosmics. Schwartz, G.E., Bell, I.R., Dikman, Z.V., Fernandez, M., Kline, J.P., Peterson, J.M., Wright, K.P. Toxicology and industrial health. (1994) [Pubmed]
  28. Study of Langmuir and Langmuir-Blodgett films of odorant-binding protein/amphiphile for odorant biosensors. Hou, Y., Jaffrezic-Renault, N., Martelet, C., Tlili, C., Zhang, A., Pernollet, J.C., Briand, L., Gomila, G., Errachid, A., Samitier, J., Salvagnac, L., Torbiéro, B., Temple-Boyer, P. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  29. Different functions of two alarm substances in the honeybee. Balderrama, N., Núñez, J., Guerrieri, F., Giurfa, M. Journal of comparative physiology. A, Neuroethology, sensory, neural, and behavioral physiology. (2002) [Pubmed]
  30. A procedure for sampling and analysis of air for energetics and related compounds. Hable, M.A., Sutphin, J.B., Oliver, C.G., McKenzie, R.M., Gordon, E.F., Bishop, R.W. Journal of chromatographic science. (2002) [Pubmed]
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