hexanols

Summary

Summary: Isomeric forms and derivatives of hexanol (C6H11OH).

Top Publications

  1. Kessler A, Baldwin I. Defensive function of herbivore-induced plant volatile emissions in nature. Science. 2001;291:2141-4 pubmed
    ..As a consequence, a plant could reduce the number of herbivores by more than 90% by releasing volatiles. These results confirm that indirect defenses can operate in nature...
  2. Bate N, Rothstein S. C6-volatiles derived from the lipoxygenase pathway induce a subset of defense-related genes. Plant J. 1998;16:561-9 pubmed
    ..These results suggest that C6-volatiles of the LOX pathway act as a wound signal in plants, but result in a moderate plant response relative to MeJA at both the physiological and molecular level...
  3. Norback D, Wieslander G, Nordstrom K, Wålinder R. Asthma symptoms in relation to measured building dampness in upper concrete floor construction, and 2-ethyl-1-hexanol in indoor air. Int J Tuberc Lung Dis. 2000;4:1016-25 pubmed
    ..Asthma symptoms in adults in relation to the indoor environment...
  4. Ruther J, Kleier S. Plant-plant signaling: ethylene synergizes volatile emission in Zea mays induced by exposure to (Z)-3-hexen-1-ol. J Chem Ecol. 2005;31:2217-22 pubmed
    ..We suggest that ethylene plays a synergistic role in plant-plant signaling mediated by green leaf volatiles...
  5. McGinty D, Scognamiglio J, Letizia C, Api A. Fragrance material review on 2-ethyl-1-hexanol. Food Chem Toxicol. 2010;48 Suppl 4:S115-29 pubmed publisher
    ..2010) for an overall assessment of the safe use of this material and all other branched chain saturated alcohols in fragrances...
  6. Minato K, Miyake Y, Fukumoto S, Yamamoto K, Kato Y, Shimomura Y, et al. Lemon flavonoid, eriocitrin, suppresses exercise-induced oxidative damage in rat liver. Life Sci. 2003;72:1609-16 pubmed
    ..These findings showed that eriocitrin was effective in the prevention of oxidative damages caused by acute exercise-induced oxidative stress...
  7. Sato A, Kawai S, Hiramoto A, Morita M, Tanigawa N, Nakase Y, et al. Antimalarial activity of 6-(1,2,6,7-tetraoxaspiro[7.11]nonadec-4-yl)hexan-1-ol (N-251) and its carboxylic acid derivatives. Parasitol Int. 2011;60:488-92 pubmed publisher
    ..The reactions of N-89 and its derivatives with Fe(II) demonstrated a highly efficient formation of the corresponding carbon radical which may be suspected as a key for the antiparasitic activity...
  8. Zhang S, Kawakami K. One-step preparation of chitosan solid nanoparticles by electrospray deposition. Int J Pharm. 2010;397:211-7 pubmed publisher
  9. Turner S, Ray A. Modification of CO2 avoidance behaviour in Drosophila by inhibitory odorants. Nature. 2009;461:277-81 pubmed publisher
    ..Our findings have broader implications in highlighting the important role of inhibitory odorants in olfactory coding, and in their potential to disrupt CO(2)-mediated host-seeking behaviour in disease-carrying insects like mosquitoes...

More Information

Publications61

  1. Cisko Anić B, Hamersak Z. Desymmetrization of cyclic anhydrides mediated by cinchona alkaloids: synthesis and olfactory properties of new fragrances based on (R)- and (S)-2-ethylhexanol. Chirality. 2009;21:894-904 pubmed publisher
    ..Enantiomerically pure alcohols were prepared by lipase-catalyzed kinetic resolution of 2-ethylhexanol using vinyl laurate as acyl donor...
  2. Voegtle H, Jones T, Davidson D, Snelling R. E-2-ethylhexenal, E-2-ethyl-2-hexenol, mellein, and 4-hydroxymellein in Camponotus species from Brunei. J Chem Ecol. 2008;34:215-9 pubmed publisher
  3. Ulland S, Ian E, Mozuraitis R, Borg Karlson A, Meadow R, Mustaparta H. Methyl salicylate, identified as primary odorant of a specific receptor neuron type, inhibits oviposition by the moth Mamestra brassicae L. (Lepidoptera, noctuidae). Chem Senses. 2008;33:35-46 pubmed
    ..brassicae females avoid plants with dispensers emitting MeS. As it is induced by caterpillar feeding, this compound may mediate a message to mated M. brassicae females that the plant is already occupied...
  4. Lyandres O, Shah N, Yonzon C, Walsh J, Glucksberg M, Van Duyne R. Real-time glucose sensing by surface-enhanced Raman spectroscopy in bovine plasma facilitated by a mixed decanethiol/mercaptohexanol partition layer. Anal Chem. 2005;77:6134-9 pubmed
    ..The time constant is 28 s for partitioning and 25 s for departitioning, indicating the rapid interaction between the SAM and glucose that is essential for continuous sensing...
  5. Starkenmann C, Niclass Y, Troccaz M, Clark A. Identification of the precursor of (S)-3-methyl-3-sulfanylhexan-1-ol, the sulfury malodour of human axilla sweat. Chem Biodivers. 2005;2:705-16 pubmed
    ..epidermidis were less efficient in cleaving Cys-Gly-(S)-conjugate 12 to form the corresponding thiol 3. Incubation of glutathione-(S)-conjugate 11 never led to the formation of 3 under the experimental conditions employed...
  6. Xu F, Wang Q, Haji A. [Analysis of essential oil extracted from Lactuca sativa seeds growing in Xinjiang by GC-MS]. Zhong Yao Cai. 2011;34:1887-91 pubmed
    ..To analyze the components of essential oil from Lactuca sativa seeds growing in Xinjiang...
  7. Noble R, Dobrovin Pennington A, Hobbs P, Pederby J, Rodger A. Volatile C8 compounds and pseudomonads influence primordium formation of Agaricus bisporus. Mycologia. 2009;101:583-91 pubmed
    ..Monitoring and controlling the levels of these inhibitory VOC in mushroom culture should enable primordium formation of A. bisporus to be more efficiently and precisely controlled...
  8. Getz W. A kinetic model of the transient phase in the response of olfactory receptor neurons. Chem Senses. 1999;24:497-508 pubmed
    ..The sensitivity of model output to various model parameters is investigated and changes to parameters are discussed that would improve the ability of ORNs to follow rapidly pulsed stimuli...
  9. Nalli S, Horn O, Grochowalski A, Cooper D, Nicell J. Origin of 2-ethylhexanol as a VOC. Environ Pollut. 2006;140:181-5 pubmed
    ..Thus, the microbial degradation of plasticizers is the most likely source of 2-ethylhexanol in indoor air...
  10. Hu D, Feng J, Wang Z, Wu H, Zhang X. Effect of nine plant volatiles in the field on the sex pheromones of Leguminivora glycinivorella. Nat Prod Commun. 2013;8:393-6 pubmed
    ..These results suggest that efficacy of pheromone-baited traps for survey and monitoring of L. glycinivorella male moths may be enhanced by the addition of specific plant volatiles and that the relative dose is critical...
  11. Streiff J, Warner D, Klimtchuk E, Perkins W, Jones K, Jones K. The effects of hexanol on Galpha(i) subunits of heterotrimeric G proteins. Anesth Analg. 2004;98:660-7, table of contents pubmed
  12. Liu Y, Dong X, Sun Y. Effect of hexanol on the reversed micelles of Span 85 modified with Cibacron Blue F-3GA for protein solubilization. J Colloid Interface Sci. 2006;297:805-12 pubmed
  13. Dong J, Jia Z. [Study on the chemical constituents in herb of Hypericum attenuatum]. Zhongguo Zhong Yao Za Zhi. 2005;30:1595-7 pubmed
    ..To study the constituents of Hypericum attenatum...
  14. Harsch M, Benkwitz F, Frost A, Colonna Ceccaldi B, Gardner R, Salmon J. New precursor of 3-mercaptohexan-1-ol in grape juice: thiol-forming potential and kinetics during early stages of must fermentation. J Agric Food Chem. 2013;61:3703-13 pubmed publisher
  15. Nalli S, Cooper D, Nicell J. Interaction of metabolites with R. rhodochrous during the biodegradation of di-ester plasticizers. Chemosphere. 2006;65:1510-7 pubmed
    ..The most hydrophobic of the plasticizers, DEHP, was particularly sensitive to this effect...
  16. Farag M, Fokar M, Abd H, Zhang H, Allen R, Pare P. (Z)-3-Hexenol induces defense genes and downstream metabolites in maize. Planta. 2005;220:900-9 pubmed
    ..These data indicate that (Z)-3-hexenol can serve as a signaling molecule that triggers defense responses in maize and can rapidly be turned over in planta...
  17. Samy M, Khalil H, Sugimoto S, Matsunami K, Otsuka H, Kamel M. Three new flavonoid glycosides, byzantionoside B 6'-O-sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula. Chem Pharm Bull (Tokyo). 2011;59:725-9 pubmed
    ..Their structures were elucidated by means of spectroscopic analyses...
  18. Ziółkowska N, Bujacz A, Randad R, Erickson J, Skalova T, Hasek J, et al. New active HIV-1 protease inhibitors derived from 3-hexanol: conformation study of the free inhibitors in crystalline state and in complex with the enzyme. Chem Biol Drug Des. 2012;79:798-809 pubmed publisher
    ..High conformational flexibility and low conformational stress in the molecules of these inhibitors most likely increase their biological activity in comparison with more rigid compounds...
  19. Hansen K, Kristensen C, Tattersall D, Jones P, Olsen C, Bak S, et al. The in vitro substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from Sorghum bicolor. Phytochemistry. 2003;64:143-51 pubmed
    ..g. as part of a cyanohydrin function, as a primary alcohol or as a phenolic hydroxyl group and being influenced by the stereochemistry and/or interactive chemistry of the substituents on the hydroxyl-bearing carbon atom...
  20. Granvil C, Sharkawi M, Plaa G. Metabolic fate of methyl n-butyl ketone, methyl isobutyl ketone and their metabolites in mice. Toxicol Lett. 1994;70:263-7 pubmed
    ..The administration of HMP did not result in the appearance of MiBK or 4-MPOL. These results indicate that the metabolic fate of MnBK and MiBK is similar to that reported in other species...
  21. Aubery C, Solans C, Prévost S, Gradzielski M, Sanchez Dominguez M. Microemulsions as reaction media for the synthesis of mixed oxide nanoparticles: relationships between microemulsion structure, reactivity, and nanoparticle characteristics. Langmuir. 2013;29:1779-89 pubmed publisher
    ..The latter effect of constant size is attributed to the fact that the water present is dominantly bound to the EO units of the surfactant...
  22. Varlet V, Knockaert C, Prost C, Serot T. Comparison of odor-active volatile compounds of fresh and smoked salmon. J Agric Food Chem. 2006;54:3391-401 pubmed
    ..For smoked salmon, phenolic compounds, such as cresol or guaiacol, and furanic compounds seem to be responsible for the smoked odor...
  23. Zhang X, Zhou L, Luo H, Li N. A sensitive and label-free impedimetric biosensor based on an adjunct probe. Anal Chim Acta. 2013;776:11-6 pubmed publisher
    ..1 nM to 0.5 ?M with a good linearity (R=0.9988) and a low detection limit of 6.3 pM. This impedimetric biosensor has the advantages of simplicity, sensitivity, good selectivity, and large dynamic range...
  24. Shahriari S, Mandanici A, Wang L, Richert R. Dynamics of glass-forming liquids. VIII. Dielectric signature of probe rotation and bulk dynamics in branched alkanes. J Chem Phys. 2004;121:8960-7 pubmed
    ..For the alcohol guest molecules, the large relative rotational time scales and small effective dipole moments are indicative of hydrogen bonded clusters instead of individual molecules...
  25. Paterson A, Kassim A, McCallum S, Woodhead M, Smith K, Zait D, et al. Environmental and seasonal influences on red raspberry flavour volatiles and identification of quantitative trait loci (QTL) and candidate genes. Theor Appl Genet. 2013;126:33-48 pubmed publisher
    ..Quantitative trait loci were determined and mapped to six of the seven linkage groups, as were candidate genes in the volatiles pathways...
  26. Seto T, Firestone L. Effects of normal alcohols and isoflurane on lipid headgroup dynamics in nicotinic acetylcholine receptor-rich lipid vesicles. Biochim Biophys Acta. 2000;1509:111-22 pubmed
  27. Almagro L, García Pérez P, Belchí Navarro S, Sánchez Pujante P, Pedreño M. New strategies for the use of Linum usitatissimum cell factories for the production of bioactive compounds. Plant Physiol Biochem. 2016;99:73-8 pubmed publisher
    ..usitatissimum can provide an alternative system, which is at the same time more sustainable, economical and ecological for their production. ..
  28. Piesik D, Pańka D, Delaney K, Skoczek A, Lamparski R, Weaver D. Cereal crop volatile organic compound induction after mechanical injury, beetle herbivory (Oulema spp.), or fungal infection (Fusarium spp.). J Plant Physiol. 2011;168:878-86 pubmed publisher
    ..Also, our work suggests large qualitative and quantitative overlap of VOC induction from plants of all three cereals having beetle herbivory injury when compared to infection injury from necrotrophic fungal pathogens...
  29. Nasef H, Ozalp V, Beni V, O Sullivan C. Melting temperature of surface-tethered DNA. Anal Biochem. 2010;406:34-40 pubmed publisher
    ..The approach has application in optimization of assay conditions for biosensors that use gold substrates as well as in melting curve analysis...
  30. Schupp P, Charlton T, Taylor M, Kjelleberg S, Steinberg P. Use of solid-phase extraction to enable enhanced detection of acyl homoserine lactones (AHLs) in environmental samples. Anal Bioanal Chem. 2005;383:132-7 pubmed
    ..01 ppm for 3-oxo-hexanoyl homoserine lactone (3-oxo C6-HSL) and 1 ppm for hexanoyl homoserine lactone (C6-HSL). Compared with liquid extraction methods use of SPE resulted in twofold and tenfold improvements in sensitivity, respectively...
  31. Criswell H, Ming Z, Pleasant N, Griffith B, Mueller R, Breese G. Macrokinetic analysis of blockade of NMDA-gated currents by substituted alcohols, alkanes and ethers. Brain Res. 2004;1015:107-13 pubmed
    ..These data indicate that a wide variety of volatile hydrocarbon based CNS depressants produce a similar inhibition of NMDA-gated currents and that the kinetics for these agents are inconsistent with an open channel block...
  32. Yoshida Y, Kimura Y, Kadota M, Tsuno T, Adachi S. Continuous synthesis of alkyl ferulate by immobilized Candida antarctica lipase at high temperature. Biotechnol Lett. 2006;28:1471-4 pubmed
    ..Conversions greater than 0.9 were achieved for the synthesis of the 1-hexyl and 1-heptyl ferulates at 90 degrees C. The system could be stably operated for the 1-heptyl ferulate synthesis at 90 degrees C for at least two weeks...
  33. Inoue K, Okumura H, Higuchi T, Oka H, Yoshimura Y, Nakazawa H. Characterization of estrogenic compounds in medical polyvinyl chloride tubing by gas chromatography-mass spectrometry and estrogen receptor binding assay. Clin Chim Acta. 2002;325:157-63 pubmed
    ..This study aims to investigate the harmful effects of estrogenic compounds in medical PVC tubing by two approaches of gas chromatography-mass spectrometry (GC-MS) and estrogen receptor (ER) binding assay...
  34. Luisier J, Buettner H, Völker S, Rausis T, Frey U. Quantification of cysteine S-conjugate of 3-sulfanylhexan-1-ol in must and wine of petite arvine vine by stable isotope dilution analysis. J Agric Food Chem. 2008;56:2883-7 pubmed publisher
    ..The method has limits of detection and quantification of 3 and 10 microg/L, respectively. A correlation between the increase of the precursor concentration and the increase of the degree of rot has been established...
  35. Na Z. [Study on the chemical constituents of the volatile oil from aerial parts of Isodon eriocalyx var. laxiflora]. Zhongguo Zhong Yao Za Zhi. 2005;30:1268-70 pubmed
    ..To study the chemical constituents of the volatile oil from the aerial parts of Isodon eriocalyx var. laxiflora...
  36. Holmberg M, Kuhle A, Garnaes J, Boisen A. Hybridisation of short DNA molecules investigated with in situ atomic force microscopy. Ultramicroscopy. 2003;97:257-61 pubmed
    ..Both the increase in order and thickness of the molecular layer can be expected if hybridisation occurs, since double stranded DNA molecules have a more rigid and elongated structure than ssDNA molecules...
  37. Ervin R, Boroumand A, Abriola L, Ramsburg C. Kinetic limitations on tracer partitioning in ganglia dominated source zones. J Contam Hydrol. 2011;126:195-207 pubmed publisher
  38. Lee L, Schaller R, Haber L, Saykally R. High spatial resolution imaging with near-field scanning optical microscopy in liquids. Anal Chem. 2001;73:5015-9 pubmed
    ..e., buffer) solutions. Images of MEH-PPV were obtained with comparable spatial resolution in both air and water. High optical resolution (approximately160 nm fwhm) was observed...
  39. Jeon Y, Fong J, Riyanti E, Neilan B, Rogers P, Svenson C. Heterologous expression of the alcohol dehydrogenase (adhI) gene from Geobacillus thermoglucosidasius strain M10EXG. J Biotechnol. 2008;135:127-33 pubmed publisher
    ..In silico analysis, including phylogenetic reconstruction and protein modeling, confirmed that the thermostable enzyme from G. thermoglucosidasius is likely to belong to the NAD-Zn-dependent family of alcohol dehydrogenases...
  40. Blom D, Fabbri C, Connor E, Schiestl F, Klauser D, Boller T, et al. Production of plant growth modulating volatiles is widespread among rhizosphere bacteria and strongly depends on culture conditions. Environ Microbiol. 2011;13:3047-58 pubmed publisher
  41. Wu J, Yan H, Zhang X, Wei L, Liu X, Xu B. Magnesium hydroxide nanoparticles synthesized in water-in-oil microemulsions. J Colloid Interface Sci. 2008;324:167-71 pubmed publisher
    ..The compatibility and dispersibility of nanoparticles obtained from reverse micelles were improved in the organic phase...
  42. Vergara Fernández A, Van Haaren B, Revah S. Phase partition of gaseous hexane and surface hydrophobicity of Fusarium solani when grown in liquid and solid media with hexanol and hexane. Biotechnol Lett. 2006;28:2011-7 pubmed
    ..The fungus thus adapts to hydrophobic conditions and these changes may explain the higher uptake of gaseous hydrophobic substances by fungi in biofilters...
  43. Fujiwara T, Mohammadzai I, Kojima M, Kumamaru T. An improved method for the flow-injection determination of iodine using the luminol chemiluminescence reaction in a reversed micellar medium of cetyltrimethylammonium chloride in 1-hexanol-cyclohexane. Anal Sci. 2006;22:67-71 pubmed
    ..5%. The improved FI method is rapid and equally sensitive like the original one and was found to be suitable for the determination of trace iodine...
  44. French K, Rock D, Rock D, Manchester J, Goldstein B, Jones J. Active site mutations of cytochrome p450cam alter the binding, coupling, and oxidation of the foreign substrates (R)- and (s)-2-ethylhexanol. Arch Biochem Biophys. 2002;398:188-97 pubmed
    ..The L244A mutation altered the stereoselectivity of 2-ethylhexanoic acid production. These results indicate that active site mutations of P450cam can alter catalysis of 2-ethylhexanol...
  45. Kadi N, Belloy L, Chalier P, Crouzet J. Enzymatic synthesis of aroma compound xylosides using transfer reaction by Trichoderma longibrachiatum xylanase. J Agric Food Chem. 2002;50:5552-7 pubmed
    ..5 mg/L for citronellyl xylosides. No synthesis occurred when menthol, linalool, and eugenol were used as acceptors...
  46. Cao Z, Xiao Z, Zhang L, Luo D, Kamahori M, Shimoda M. Molecule counting with alkanethiol and DNA immobilized on gold microplates for extended gate FET. Mater Sci Eng C Mater Biol Appl. 2013;33:1481-90 pubmed publisher
    ..36 molecules per 100 nm(2), showing that the EGFET is a promising sensing biochip for DNA molecule counting...
  47. Chang G, Bao Z, Zhang Z, Xing H, Su B, Yang Y, et al. Salt-enhanced removal of 2-ethyl-1-hexanol from aqueous solutions by adsorption on activated carbon. J Colloid Interface Sci. 2013;412:7-12 pubmed publisher
    ..3mg/g in the deionized water to 309.5mg/g in a salt lake brine. The Tomas model was well applied to predict the breakthrough curves and determine the characteristics parameters of the adsorption column...
  48. Ackerman M, Shortle D. Molecular alignment of denatured states of staphylococcal nuclease with strained polyacrylamide gels and surfactant liquid crystalline phases. Biochemistry. 2002;41:3089-95 pubmed
    ..Although SDS/nuclease complexes give sharp and disperse (1)H-(15)N correlation spectra, only small couplings are observed in strained polyacrylamide gels...
  49. Azcarate C, Barringer S. Effect of enzyme activity and frozen storage on jalapeño pepper volatiles by selected ion flow tube-mass spectrometry. J Food Sci. 2010;75:C710-21 pubmed publisher
    ..The compounds (E,Z)-2,6-nonadienal, n-propyl aldehyde, 2-isobutyl-3-methoxypyrazine, and a mixture of terpenes decreased in unblanched and blanched frozen samples, while nonanal and methylbutanal increased only in unblanched samples...
  50. Braasch J, Wimp G, Kaplan I. Testing for phytochemical synergism: arthropod community responses to induced plant volatile blends across crops. J Chem Ecol. 2012;38:1264-75 pubmed publisher
  51. Yamaguchi H, Kojima H, Takezawa T. Vitrigel-eye irritancy test method using HCE-T cells. Toxicol Sci. 2013;135:347-55 pubmed publisher
  52. Carrascosa L, Martínez L, Huttel Y, Román E, Lechuga L. Understanding the role of thiol and disulfide self-assembled DNA receptor monolayers for biosensing applications. Eur Biophys J. 2010;39:1433-44 pubmed publisher
    ..It is demonstrated that -SH derivatization is the most suitable for biosensing purposes as it results in densely packed monolayers with the lowest ratio of physisorbed probes...