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2-Acetylpyrrole

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Takayuki Shibamoto – One of the best experts on this subject based on the ideXlab platform.

  • Antioxidant activities of extracts from teas prepared from medicinal plants, Morus alba L., Camellia sinensis L., and Cudrania tricuspidata , and their volatile components.
    Journal of agricultural and food chemistry, 2012
    Co-Authors: Sanghae Nam, Hae Won Jang, Takayuki Shibamoto
    Abstract:

    The antioxidant activity of essences of teas prepared from mulberry ( Morus alba L.), Camellia sinensis L., and Cudrania tricuspidata (Carr.) Burea plant was examined using two antioxidant assays. Selected volatile chemicals identified in these plants were also tested for antioxidant activity. All extracts exhibited antioxidant activity with a clear dose response in the aldehyde/carboxylic acid and the malonaldehyde/gas chromatography (MA/GC) assays. Antioxidant activity of extracts at the level of 500 μg/mL ranged from 77.02 ± 0.51% (stems of Burea plant) to 52.57 ± 0.92% (fermented tea of Camellia and stems of Mulberry tea) in the aldehydes/carboxylic acid assay. Their antioxidant activity at the level of 160 μg/mL ranged from 76.17 ± 0.27% (roots of Burea plant) to 59.32 ± 0.27% (stems of Mulberry tea) in the MA/GC assay. Among the positively identified compounds (11 terpenes and terpenoids, 15 alkyl compounds, 26 nitrogen containing heterocyclic compounds, 9 oxygen containing heterocyclic compounds, 18 aromatic compounds, 7 lactones, 6 acids, and 4 miscellaneous compounds), eugenol, 2,5-dihydroxyl acetophenone, and isoeugenol exhibited antioxidant activity comparable to that of BHT in both assays. Vanillin and 2-Acetylpyrrole showed potent antioxidant activity in the aldehydes/carboxylic acid assay but only moderate activity in the MA/GC assay. These results suggest that consumption of antioxidant-rich beverages prepared from these plants may be beneficial to human health.

  • role of roasting conditions in the profile of volatile flavor chemicals formed from coffee beans
    Journal of Agricultural and Food Chemistry, 2009
    Co-Authors: Joonkwan Moon, Takayuki Shibamoto
    Abstract:

    The volatile chemicals in dichloromethane extracts from green coffee beans, roasted at 230 degrees C for 12 min (light), at 240 degrees C for 14 min (medium), at 250 degrees C for 17 min (city), or at 250 degrees C for 21 min (French), were analyzed by gas chromatography and gas chromatography-mass spectrometry. Among the 52 volatile compounds identified, the major compounds were 5-hydroxymethylfurfural, furfuryl alcohol, and 6-methyl-3,5-dihydroxy-4H-pyran-4-one in light-roasted beans; furfuryl alcohol, 5-hydroxymethylfurfural, and gamma-butyrolactone in medium-roasted beans; furfuryl alcohol, gamma-butyrolactone, and 2-Acetylpyrrole in city-raosted beans; and gamma-butyrolactone, furfuryl alcohol, and catechol in French-roasted beans. Furfural derivatives and furanones were yielded in relatively high concentrations under mild roasting conditions and then reduced at higher roasting intensities. More pyridines and pyrroles were formed by high roasting intensities than by mild roasting intensities. Chlorogenic acid degradation products, phenols, and a lactone were produced more by high roasting intensities than by low roasting intensities. The results of the present study suggest that controlling the roasting conditions according to the formation of particular chemicals can prepare a roasted coffee with preferable flavor.

  • Antioxidative Activity of Heterocyclic Compounds Found in Coffee Volatiles Produced by Maillard Reaction
    Journal of agricultural and food chemistry, 2002
    Co-Authors: Kenichi Yanagimoto, Hirotomo Ochi, Kwang-geun Lee, Takayuki Shibamoto
    Abstract:

    Typical heterocyclic compounds substituted with various functional groups found in Maillard reacreaction products were examined for antioxidant activity. Pyrroles exhibited the greatest antioxidant activity among all heterocyclic compounds tested. All pyrroles inhibited hexanal oxidation by almost 100% at a concentration of 50 microg/mL over 40 days. Addition of formyl and acetyl groups to a pyrrole ring enhanced antioxidative activity remarkably. Pyrrole-2-carboxaldehyde, 2-Acetylpyrrole, 1-methyl-2-pyrrolecarboxaldehyde, and 2-acetyl1-methylpyrrole inhibited hexanal oxidation by >80% at 10 microg/mL. Unsubstituted furan exhibited the greatest antioxidant activity among furans tested. Addition of all functional groups used in this study to furan decreased antioxidative activity. The antioxidant activity of thiophene increased with the addition of methyl and ethyl groups, but the addition of formyl or acetyl groups to thiophene decreased antioxidant activity. Thiazoles and pyrazines were ineffective antioxidants at all concentrations tested. Reaction of all heterocyclic compounds with hydrogen peroxide resulted in the formation of various oxidized products.

Teresa Pérez – One of the best experts on this subject based on the ideXlab platform.

  • Group 12 Metal Complexes of 2-Formylpyrrole-(4PL1) and 2-Acetylpyrrole-N(4)-phenylthiosemicarbazone (4Pl2), as Examples form Different Donor Modes. Crystal and Molecular Structures of [Hg(4PL1- H)Br]2 and [Zn(4PL2)2Br2] · 2 EtOH
    Zeitschrift für Naturforschung B, 2001
    Co-Authors: Rosa Carballo, Alfonso Castiñeiras, Teresa Pérez
    Abstract:

    Abstract The reactions of 4N-phenyl-2-[ 1 -(pyrrol-2-yl)methylidene]-hydrazine carbothioamide (4PL1) and 4N-phenyl-2-[l-(pyrrol-2-yl)ethylidene]-hydrazine carbothioamide (4PL2) with Group 12 metal halides afford complexes of types [M(L)2X2] [M = Zn, L = 4PL1 or 4PL2, X = Cl, Br or I; M = Cd, L = 4PL1, and X = Cl, or L = 4PL2 and X = Cl, Br or I] and [M(L)X2] [M = Cd, L = 4PL1, X = Br or I; M = Hg, L = 4PL1 or 4PL2, X = Cl, Br or I]. The new compounds were characterized by elemental analysis, FAB mass spectrometry, IR specspectroscopy, and, in the case of sufficiently soluble compounds, 1H, 13C and, when appropriate, 113Cd or 199Hg NMR spectrometry. The structures of [Hg(4PL1-H)Br] and [Zn(4PL2)2Br2] · 2 EtOH were also studied by single-crystal X-ray diffdiffractometry. In [Hg(4PL1-H)Br] crystallized from the mother liquor of its synthesis, 4PL1 behaves as a monodeprotonated S,N-bidentate ligand. Otherwise, with Hg(II), Zn(II) and Cd(II), 4PL1 and 4PL2 both behave as neutral S-monodentate ligands.

  • Synthesis and structural characterization of complexes of Zn(II), Cd(II) and Hg(II) halides with 2-formylpyrrole thiosemicarbazone and 2-Acetylpyrrole thiosemicarbazone
    Polyhedron, 2001
    Co-Authors: Alfonso Castiñeiras, Rosa Carballo, Teresa Pérez
    Abstract:

    Abstract Reaction of 2-[1-(pyrrol-2-yl)methylidene]hidrazine carbothioamide (L1) and 2-[1-(pyrrol-2-yl)ethylidene]hidrazine carbothioamide (L2) with zinc(II) cadmium(II) and mercury(II) halides afforded complexes with formulae [M(L1)X2] [M, X=Zn, Cl (1); Cd, Cl (4); Hg, Cl (7); Hg, Br (8); Hg, I (9)], [M(L1)2X2] [M, X=Zn, Br (2); Zn, I (3); Cd, Br (5); Cd, I (6)], [M(L2)X2] [M, X=Cd, Cl (13); Hg, Cl (16); Hg, Br (17); Hg, I (18)] and [M(L2)2X2] [M, X=Zn, Cl (10); Zn, Br (11); Zn, I (12); Cd, Br (14); Cd, I (15)]. Crystals of 5, 18 and 15·CH3CN were studied by X-ray diffdiffractometry, and all the new compounds were characterized by elemental analysis, mass spectrometry, IR and 1H and 13C NMR specspectroscopy and, when pertinent and allowed by the solubility of the compounds, 113Cd or 199Hg NMR spectroscopy. In these complexes, the metal atoms are tetra-coordinate and the ligands are neutral and S-monodentate.

Holger Zorn – One of the best experts on this subject based on the ideXlab platform.

  • Identification of potent odorants in a novel nonalcoholic beverage produced by fermentation of wort with shiitake (Lentinula edodes).
    Journal of agricultural and food chemistry, 2014
    Co-Authors: Yanyan Zhang, Marco A. Fraatz, Felix Horlamus, Hendrich Quitmann, Holger Zorn
    Abstract:

    Novel refreshments with pleasant flavors were developed by fermentation of wort with basidiomycetes. Among 31 screened fungi, shiitake (Lentinula edodes) produced the most pleasant flavor. It was perceived as fruity, slightly sour, and plum-like. Flavor compounds were isolated by liquid–liquid extraction (LLE) and by headspace solid phase microextraction (HS-SPME). The key odor-active compounds were analyzed by a gas chromatography system equipped with a tandem mass spectrometry detector and an olfactory detection port (GC-MS/MS-O) and aroma extract dilution analysis (AEDA). For HS-SPME, a revised method of increasing the GC inlet split ratio was used. Most of the key odor-active compounds (e.g., 2-Acetylpyrrole, β-damascenone, (E)-2-nonenal, and 2-phenylethanol) were detected with both extraction techniques. However, distinct differences between these two methods were observed.

  • Identification of Potent Odorants in a Novel Nonalcoholic Beverage Produced by Fermentation of Wort with Shiitake (Lentinula edodes)
    , 2014
    Co-Authors: Yanyan Zhang, Marco A. Fraatz, Felix Horlamus, Hendrich Quitmann, Holger Zorn
    Abstract:

    Novel refreshments with pleasant flavors were developed by fermentation of wort with basidiomycetes. Among 31 screened fungi, shiitake (Lentinula edodes) produced the most pleasant flavor. It was perceived as fruity, slightly sour, and plum-like. Flavor compounds were isolated by liquid–liquid extraction (LLE) and by headspace solid phase microextraction (HS-SPME). The key odor-active compounds were analyzed by a gas chromatography system equipped with a tandem mass spectrometry detector and an olfactory detection port (GC-MS/MS-O) and aroma extract dilution analysis (AEDA). For HS-SPME, a revised method of increasing the GC inlet split ratio was used. Most of the key odor-active compounds (e.g., 2-Acetylpyrrole, β-damascenone, (E)-2-nonenal, and 2-phenylethanol) were detected with both extraction techniques. However, distinct differences between these two methods were observed