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PubMed1984

Urinalysis of minor metabolites of ethylbenzene and m-xylene.

Gas chromatographic methods have been developed for the urinalysis of metabolic products of ethylbenzene. "Minor" metabolites were emphasized in this process. The methods were worked out so that simultaneous determination of several compounds could be achieved with one method. On the whole, four assays are described, which together allow 12 different compounds to be measured. Since one of the methods presented can be applied to determine "minor" metabolites of xylene as well, methodological data for these are also reported. The methods described have successfully been used in metabolic studies of ethylbenzene in rat and man.

Acetophenones↗
PubMed1978

The interaction of short-chain aralkyl alcohols and amines with the erythrocyte membrane.

Erythrocytes in isotonic saline are hemolyzed by benzyl alcohol and by 2-phenylethanol, but not by the corresponding amines nor by the ring-or side-chain-hydroxylated analogs. All these compounds could however interact with the erythrocyte membrane since: a) they facilitated the hemolytic effect of benzyl alcohol and/or of phenylelytic effect of benzyl alcohol and/or of phenylethanol; b) they exerted a protective effect against controlled hypotonic hemolysis.

Alcohols↗
PubMed2005

Controlled formation of volatile components in cider making using a combination of Saccharomyces cerevisiae and Hanseniaspora valbyensis yeast species.

The effect of pure and mixed fermentation by Saccharomyces cerevisiae and Hanseniaspora valbyensis on the formation of major volatile components in cider was investigated. When the interaction between yeast strains of S. cerevisiae and H. valbyensis was studied, it was found that the two strains each affected the cell growth of the other upon inoculation of S. cerevisiae during growth of H. valbyensis. The effects of pure and mixed cultures of S. cerevisiae and H. valbyensis on alcohol fermentation and major volatile compound formation in cider were assessed. S. cerevisiae showed a conversion of sugar to alcohol of 11.5%, while H. valbyensis produced alcohol with a conversion not exceeding 6%. Higher concentrations of ethyl acetate and phenethyl acetate were obtained with H. valbyensis, and higher concentrations of isoamyl alcohol and isobutyl were formed by S. cerevisiae. Consequently, a combination of these two yeast species in sequential fermentation was used to increase the concentration of ethyl esters by 7.41-20.96%, and to decrease the alcohol concentration by 25.06-51.38%. Efficient control of the formation of volatile compounds was achieved by adjusting the inoculation time of the two yeasts.

Acetates↗
PubMed1986

Human class I alcohol dehydrogenases catalyze the interconversion of alcohols and aldehydes in the metabolism of dopamine.

The class I human liver alcohol dehydrogenases (ADHs) catalyze the interconversion of the intermediary alcohols and aldehydes of dopamine metabolism in vitro, whereas those of the class II and class III do not. The individual, homogeneous class I isozymes oxidize (3,4-dihydroxyphenyl)ethanol and (4-hydroxy-3-methoxyphenyl)ethanol (HMPE) and ethanol with kcat/Km values in the range from 16 to 240 mM-1 min-1 and from 16 to 66 mM-1 min-1, respectively. They reduce the corresponding dopamine aldehydes (3,4-dihydroxyphenyl)acetaldehyde and (4-hydroxy-3-methoxyphenyl)acetaldehyde (HMPAL) with kcat/Km values varying from 7800 to 190,000 mM-1 min-1, considerably more efficient than the reduction of acetaldehyde with kcat/Km values from 780 to 4900 mM-1 min-1. For beta 1 gamma 2 ADH, ethanol competes with HMPE oxidation with a Ki of 23 microM. In addition, 1,10-phenanthroline inhibits HMPE oxidation and HMPAL reduction with Ki values of 20 microM and 12 microM, respectively, both quite similar to that for ethanol, Ki = 22 microM. Thus, both ethanol/acetaldehyde and the dopamine intermediates compete for the same site of ADH, a basis for the ethanol-induced in vivo alterations of dopamine metabolism.

3,4-Dihydroxyphenylacetic Acid↗
PubMed1990

Stereochemical aspects of the oxidation of 4-ethylphenol by the bacterial enzyme 4-ethylphenol methylenehydroxylase.

The O2-independent hydroxylase 4-ethylphenol methylenehydroxylase (4EPMH) from Pseudomonas putida JD1 catalysed the complete conversion of 4-ethylphenol into 1-(4-hydroxyphenyl)ethanol together with a small amount of 4-hydroxyacetophenone, but with no formation of the side product 4-vinylphenol reported to be formed when the similar enzyme p-cresol methylhydroxylase (PCMH) catalyses this reaction. The enantiomer of 1-(4-hydroxyphenyl)ethanol produced by 4EPMH was R(+) when horse heart cytochrome c or azurin was used as electron acceptor for the enzyme. PCMHs from various bacterial strains produced the S(-)-alcohol. Both enantiomers of 1-(4-hydroxyphenyl)ethanol were substrates for conversion into 4-hydroxyacetophenone by 4EPMH, but the S(-)-isomer was preferred. The Km and kcat. were 1.2 mM and 41 s-1 respectively for the S(-)-alcohol and 4.7 mM and 22 s-1 for the R(+)-alcohol. In addition to the 1-(4-hydroxyphenyl)ethanol dehydrogenase activity of 4-EPMH, NAD(+)-linked dehydrogenase activity for both enantiomers of the alcohol was found in extracts of Ps. putida JD1.

Alcohol Oxidoreductases↗
PubMed2005

Main compounds responsible for off-odour of strawberries infected by Phytophthora cactorum.

AIMS: Volatile compounds present in strawberries infected with Phytophthora cactorum, especially those responsible for the characteristic off-odour of such fruits were the subject of this study. METHODS AND RESULTS: Six strawberry varieties (Redgauntlet, Selva, Korona, Tenira, Real, Pegasus) inoculated with P. cactorum strain (PC-5), isolated from naturally infected fruit and one variety inoculated with 15 strains of P. cactorum in the laboratory were analysed. All the samples had a distinct, to a various degree, off-odour reminiscent of watercolour paint with phenolic notes. Volatile compounds were isolated by solid phase microextraction and simultaneous distillation extraction methods. To detect compounds responsible for the characteristic off-odour, gas chromatography-olfactometry was used. Two compounds were found to be responsible for the characteristic off-odour of strawberries infected by P. cactorum: 4-ethyl phenol and 4-ethyl-2-metoxy phenol (4-ethyl guaiacol). The content of these compounds in infected varieties ranged from 1.12 to 22.56 mg kg(-1) and 0.14-1.05 mg kg(-1) respectively. Other volatile compounds, not detected in noninoculated sound strawberries, were also identified: camphene, 1-octene-3-ol, 3-octanone, o-cymene, phenyl methanol, cis-linaloloxide, nonanal, phenyl ethyl alcohol, 2-undecanone and alpha-muurolene. SIGNIFICANCE AND IMPACT OF THE STUDY: Volatile compounds responsible for the characteristic off-odour of strawberries infected with P. cactorum were identified. Also compounds produced as a result of P. cactorum growth on strawberry fruit were characterized.

Aldehydes↗
PubMed1994

Antioxidant actions of thymol, carvacrol, 6-gingerol, zingerone and hydroxytyrosol.

Antioxidants minimize oxidation of the lipid components in foods. There is an increasing interest in the use of natural and/or synthetic antioxidants in food preservation, but it is important to evaluate such compounds fully for both antioxidant and pro-oxidant properties. The properties of thymol, carvacrol, 6-ginerol, hydroxytyrosol and zingerone were characterized in detail. Thymol, carvacrol, 6-gingerol and hydroxytyrosol decreased peroxidation of phospholipid liposomes in the presence of iron(III) and ascorbate, but zingerone had only a weak inhibitory effect on the system. The compounds were good scavengers of peroxyl radicals (CCl3O2; calculated rate constants > 10(6) M-1 sec-1) generated by pulse radiolysis. Thymol, carvacrol, 6-gingerol and zingerone were not able to accelerate DNA damage in the bleomycin-Fe(III) system. Hydroxytyrosol promoted deoxyribose damage in the deoxyribose assay and also promoted DNA damage in the bleomycin-Fe(III) system. This promotion was inhibited strongly in the deoxyribose assay by the addition of bovine serum albumin to the reaction mixtures. Our data suggest that thymol, carvacrol and 6-gingerol possess useful antioxidant properties and may become important in the search for 'natural' replacements for 'synthetic' antioxidant food additives.

Antioxidants↗
PubMed2005

Combined ruthenium(II) and lipase catalysis for efficient dynamic kinetic resolution of secondary alcohols. Insight into the racemization mechanism.

Pentaphenylcyclopentadienyl ruthenium complexes (3) are excellent catalysts for the racemization of secondary alcohols at ambient temperature. The combination of this process with enzymatic resolution of the alcohols results in a highly efficient synthesis of enantiomerically pure acetates at room temperature with short reaction times for most substrates. This new reaction was applied to a wide range of functionalized alcohols including heteroaromatic alcohols, and for many of the latter, enantiopure acetates were efficiently prepared for the first time via dynamic kinetic resolution (DKR). Different substituted cyclopentadienyl ruthenium complexes were prepared and studied as catalysts for racemization of alcohols. Pentaaryl-substituted cyclopentadienyl complexes were found to be highly efficient catalysts for the racemization. Substitution of one of the aryl groups by an alkyl group considerably slows down the racemization process. A study of the racemization of (S)-1-phenylethanol catalyzed by ruthenium hydride eta(5)-Ph(5)CpRu(CO)(2)H (8) indicates that the racemization takes place within the coordination sphere of the ruthenium catalyst. This conclusion was supported by the lack of ketone exchange in the racemization of (S)-1-phenylethanol performed in the presence of p-tolyl methyl ketone (1 equiv), which gave <1% of 1-(p-tolyl)ethanol. The structures of ruthenium chloride and iodide complexes 3a and 3c and of ruthenium hydride complex 8 were confirmed by X-ray analysis.

Alcohols↗
PubMed1964

PHYSIOLOGICAL STATE OF ESCHERICHIA COLI AND THE INHIBITION OF DEOXYRIBONUCLEIC ACID SYNTHESIS BY PHENETHYL ALCOHOL.

Treick, R. W. (Indiana University, Bloomington), and W. A. Konetzka. Physiological state of Escherichia coli and the inhibition of deoxyribonucleic acid synthesis by phenethyl alcohol. J. Bacteriol. 88:1580-1584. 1964.-The effects of concentration of phenethyl alcohol (PEA) and the physiological state of the cells on inhibition of macromolecular synthesis in Escherichia coli were investigated. Deoxyribonucleic acid (DNA) synthesis by cells of E. coli from the maximum stationary phase is completely inhibited by 0.32% (v/v) PEA immediately upon addition of the inhibitor, although there is a net increase in the synthesis of ribonucleic acid (RNA) and protein. However, DNA synthesis in cells from the exponential phase is inhibited only after an increase which corresponds to 1.4 to 1.6 times the amount of DNA present at the time of PEA addition. In a randomly dividing culture, this increment of DNA synthesis presumably represents completion of the DNA replication cycle initiated at the time of PEA addition. By programming the addition and removal of PEA, DNA synthesis can be made to proceed in stepwise increments corresponding to doublings of the DNA. The data indicate that the DNA being replicated at the time of PEA addition completes the replication cycle and, although there is net synthesis of RNA and protein, no initiation of a second cycle of DNA replication occurs until the removal of the inhibitor.

Alcohols↗
PubMed2005

Kinetic modeling of acetophenone reduction catalyzed by alcohol dehydrogenase from Thermoanaerobacter sp.

NADPH-dependent alcohol dehydrogenase (ADH) from Thermoanaerobacter sp. was kinetically characterized using reduction of acetophenone as a model. To achieve 98% conversion of acetophenone, cofactor regeneration by oxidation of 2-propanol with the same enzyme was used. The enzyme was stable in the batch reactor. It was enantioselective towards (S)-1-phenylethanol (ee>99.5%). Due to its high deactivation in continuously operated stirred tank reactor (kd=0.0141 min-1) there was no way to keep high conversion of acetophenone at 98%. The deactivation occurred in the repetitive batch as well. A mathematical model for the acetophenone reduction with cofactor regeneration describing the behaviour in a batch, repetitive-batch and continuously stirred tank reactor was developed.

2-Propanol↗
PubMed1964

PHENETHYL ALCOHOL SYNERGISM WITH MITOMYCIN C, PORFIROMYCIN, AND STREPTONIGRIN.

Cyanide and phenethyl alcohol greatly enhance the lethal action of mitomycin C, porfiromycin, and streptonigrin on an exponentially growing culture of Escherichia coli. Dinitrophenol similarly enhances the lethal action of mitomycin C and porfiromycin, but only slightly that of streptonigrin. Phenethyl alcohol may be functioning in these experiments as an inhibitor of electron transport.

Alcohols↗
PubMed1984

Potentiation of carbon tetrachloride hepatotoxicity by beta-phenethyl alcohol.

Carbon tetrachloride (CCl4)-induced hepatotoxicity was potentiated by pretreatment with beta-phenethyl alcohol, abundantly present in sake. The injury was determined by serum GPT levels and histological examination. Similar results were observed in ethanol- and phenobarbital-pretreated rats. Acetaminophen-induced hepatotoxicity was not accentuated by beta-phenethyl alcohol or ethanol pretreatment. The activities of liver microsomal enzymes, such as cytochrome P-450, cytochrome b5 reductase, aniline hydroxylase and aminopyrine demethylase, were not altered in beta-phenethyl alcohol-pretreated rats. Thus, CCl4-induced hepatotoxicity potentiation by beta-phenethyl alcohol administration is postulated to be due to a mechanism other than increased free radical generation.

Acetaminophen↗
PubMed2006

Recycling of distillery effluents in alcoholic fermentation: role in inhibition of 10 organic molecules.

In beet distilleries, condensates arising from stillage concentration could be recycled as dilution water for the fermentation step, thus preserving groundwater resources and ensuring a quality-controlled water supply. However, the recycling of condensates has been found to cause a significant reduction in fermentation activity. This study aimed to verify that condensates are toxic to alcoholic fermentation. Ten compounds found in condensates (formic, acetic, propionic, butyric, valeric, and hexanoic acids; 2,3-butanediol, furfuryl alcohol, furfural, and 2-phenyl-ethyl-alcohol) were tested. With the exception of 2,3-butanediol, they all proved to be inhibitors. At the same molar concentration, the longer the carbonaceous chain, the stronger the inhibition by fatty acids. An experimental design was used to study the inhibitory characteristics of the 10 compounds at the concentrations found in condensates. Synergistic effects were also confirmed. In real effluents, acetic acid was so highly concentrated that it became the strongest inhibitor. It is therefore necessary to eliminate it before recycling, as well as less concentrated compounds that may accumulate, as illustrated by the simulation.

Acids, Acyclic↗