2-Acetylpyrrole, a Hepatoprotective Compound from<i>Streptomyces</i>sp. A-5071

Ito, Mayumi; Shimura, Hitoshi; Watanabe, Naoharu; Tamai, Masamitsu; Takahashi, Akiko; Tanaka, Yoshitaka; Arai, Iwao; Hanada, Kazunori

doi:10.1080/00021369.1991.10870903

Cited by 3 publications

(3 citation statements)

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“…5 With respect to applications of acetylpyrroles, 2-acetylpyrrole possesses hepatoprotective properties, showing liverfunction-facilitating activity. 6 Moreover, it is a volatile compound naturally occurring in foods, like vegetables, bread, meat, and alcoholic and roasted products. It has a sweet, nutty, and tea-like odor and flavor, being applied in baked, fried, and roasted flavorings, 7 and its aroma is included in tobacco smoke 8 and in Japanese green tea.…”

Section: Introductionmentioning

confidence: 99%

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2- and 3-Acetylpyrroles: A Combined Calorimetric and Computational Study

2009

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A combined experimental and computational study on the thermochemistry of 2- and 3-acetylpyrroles was performed. The enthalpies of combustion and sublimation were measured by static bomb combustion calorimetry and Knudsen effusion mass-loss technique, respectively, and the standard (p(o) = 0.1 MPa) molar enthalpies of formation, in the gaseous phase, at T = 298.15 K, were determined. Additionally, the gas-phase enthalpies of formation were estimated by G3(MP2)//B3LYP calculations, using several gas-phase working reactions, and were compared with the experimental ones. N-H bond dissociation enthalpies, gas-phase acidities and basicities, proton and electron affinities and ionization enthalpies were also calculated. Experimental and theoretical results are in good agreement and show that 2-acetylpyrrole is thermodynamically more stable than the 3-isomer. The substituent effects of the acetyl group in pyrrole, thiophene and pyridine rings were also analyzed.

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Section: Introductionmentioning

confidence: 99%

“…With respect to applications of acetylpyrroles, 2-acetylpyrrole possesses hepatoprotective properties, showing liver-function-facilitating activity . Moreover, it is a volatile compound naturally occurring in foods, like vegetables, bread, meat, and alcoholic and roasted products.…”

Section: Introductionmentioning

confidence: 99%

2- and 3-Acetylpyrroles: A Combined Calorimetric and Computational Study

2009

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“…Its current applications include roasted food and tobacco. Compound (I) has also been claimed to possess hepatoprotective properties (Ito et al, 1991). The corresponding anion, 2-acetylpyrrolate, has been used, although to a limited extent, as a ligand in transition metal complexes (e.g.…”

Section: Commentmentioning

confidence: 99%