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PubMed1999

Extractive fermentation of aroma with supercritical CO2

This work deals with the feasibility of achieving an extractive fermentation of 2-phenylethyl alcohol, the rose aroma, coupling fermentation with Kluyveromyces marxianus and supercritical carbon dioxide (SCCO2) extraction. The extractive process is, in this case, of special interest due to the strong yeast inhibition by 2-phenylethyl alcohol. First results confirmed that direct SCCO2 extraction is not possible, due to a drastic CO2 effect on cell viability. It is therefore necessary to perform cell separation prior to the extraction. Aroma extraction conditions from a synthetic mixture were then optimized, a pressure of 200 bar and a temperature in the range 35-45 degrees C being chosen. Under these conditions, the distribution coefficient Kd is 2 times higher than during the extraction using a conventional organic solvent, n-hexane. Using a simple model of aroma partition between aqueous and SCCO2 phases, the parameters of a continuous extraction from a synthetic broth were defined. The two substrates, glucose and phenylalanine, are not extracted whatever the conditions. As predicted by the model, more than 90% of 2-phenylethyl alcohol can be extracted, while the extraction of ethanol, the second main product, can be easily tuned with respect to operating conditions, as a function of its influence on the fermentation. Finally, the feasibility of the aroma recovery using two depressurization steps at the outflow of the extraction vessel was demonstrated; 97% of the extracted aroma was recovered, and a mass purity of 91% was achieved. Copyright 1999 John Wiley & Sons, Inc.

Journal Article↗

PubMed1995

Electrocortical and autonomic alteration by administration of a pleasant and an unpleasant odor.

The present study was designed to investigate whether there is a consistent response in ongoing EEG due to repetitive olfactory stimulation. Two odors of different hedonic quality were presented bilaterally to five male subjects at suprathreshold levels. A room-air blank served as the control stimulus. Each odor was presented six times to each subject in each of three sessions. Electrocortical activity, heart rate, skin conductance and breathing cycle were recorded continuously. EEG variables assessed were difference scores of absolute power in the frequency bands theta, alpha 1, alpha 2 and beta 1 at eight locations. Phenylethyl alcohol was rated pleasant, while valeric acid was judged unpleasant. Within 8 s after stimulus release, valeric acid increased alpha 2 power, whereas phenylethyl alcohol did not. No further frequency bands were affected by olfactory stimulation. These findings suggest that smelling an unpleasant odor leads to a cortical deactivation.

Adult↗

PubMed2000

Investigation of charge localization and charge delocalization in model molecules by multiphoton ionization photoelectron spectroscopy and DFT calculations.

In this work we focus on the question to which degree a surplus charge is localized or delocalized in extended molecular systems. Molecules consisting of a flexible tail and the benzene chromophore, such as n-propylbenzene, 2-phenylethyl alcohol and 2-phenylethylamine, are used as model molecules. Their S0-S1 resonance enhanced multiphoton ionization (MPI) spectra containing origin transitions of different conformers appear at similar wavelengths. This shows, that in the neutral the electronic excitation is localized at the benzene chromophore. Geometry differences between the neutral and the cation can be qualitatively derived from intensities of vibrational transitions or the onset behavior in MPI high-resolution photoelectron (MPI-PE) spectra. We identify two possible reasons for structural changes: Charge-dipole interaction and charge delocalization. Whereas both effects can be active for the folded gauche conformers, the charge-dipole interaction is expected to be small for the extended anti conformers and geometry changes are attributed to charge delocalization. Density functional calculations of structures and energies qualitatively confirm the experimental results for all molecules and their conformers. They predict charge delocalization into the end group of below 20% for n-propylbenzene and 2-phenylethyl alcohol. In the case of 2-phenylethylamine the charge is equally shared by the near-isoenergetic charge sites of the benzene chromophore and the amine group.

Benzene Derivatives↗

PubMed2006

Generation of phenylpropanoid pathway-derived volatiles in transgenic plants: rose alcohol acetyltransferase produces phenylethyl acetate and benzyl acetate in petunia flowers.

Esters are important contributors to the aroma of numerous flowers and fruits. Acetate esters such as geranyl acetate, phenylethyl acetate and benzyl acetate are generated as a result of the action of alcohol acetyltransferases (AATs). Numerous homologous AATs from various plants have been characterized using in-vitro assays. To study the function of rose alcohol acetyltransferase (RhAAT) in planta, we generated transgenic petunia plants expressing the rose gene under the control of a CaMV-35S promoter. Although the preferred substrate of RhAAT in vitro is geraniol, in transgenic petunia flowers, it used phenylethyl alcohol and benzyl alcohol to produce the corresponding acetate esters, not generated by control flowers. The level of benzyl alcohol emitted by the flowers of different transgenic lines was ca. three times higher than that of phenylethyl alcohol, which corresponded to the ratio between the respective products, i.e. ca. three times more benzyl acetate than phenylethyl acetate. Feeding of transgenic petunia tissues with geraniol or octanol led to the production of their respective acetates, suggesting the dependence of volatile production on substrate availability.

Acetates↗

PubMed2003

Individual differences in sensitivity to the odor of 4,16-androstadien-3-one.

Individual differences in sensitivity to the putative human pheromone androstadienone were investigated in three experiments. In experiment 1, the absolute detection threshold for androstadienone was determined to be 211 micro M using the method of constant stimuli. Detection for the related compound estratetraenol was also investigated but a threshold could not be determined. In experiment 2, using an adaptive threshold test on 100 participants, the sensitivity distribution for androstadienone, but not for the reference odor phenylethyl alcohol, was bimodal, with a smaller group of individuals with a high sensitivity to androstadienone (supersmellers). A lack of correlation between thresholds for androstadienone and phenylethyl alcohol further suggested that the bimodality for androstadienone was not due to individuals with a high general olfactory sensitivity. In line with an earlier observation, there was a statistical tendency for women to be more sensitive to androstadienone than men. Results of experiment 3 preclude the possibility that the bimodal sensitivity distribution for androstadienone would depend on individual differences in trigeminal activation. Altogether, the current study suggests that olfactory sensitivity to androstadienone is bimodally distributed in the population with a subgroup consisting of highly sensitive people.

Adult↗

PubMed2002

Germination and growth inhibitors from wheat (Triticum aestivum L.) husks.

On the basis of our findings that the germination of intact wheat seeds (with husks) belonging to dormancy varieties was restrained as compared with that of the dehusked seeds (grains), the germination inhibitors in the husks were explored. The water-soluble extracts from the husks were separated by the aid of inhibition assay experiments, resulting in the characterization of 2-phenylethyl alcohol 1, 4-vinylphenol 2 and its 2-methoxy derivative 3, and dihydroactinidiolide 4, all of which showed clear inhibition of germination at 500 ppm in aqueous solution. The related compounds 1-phenylethyl alcohol 5 and tetrahydroactinidiolide 6 were as active as 1 and 4, while no noticeable difference in activity was detected among both enantiomers and the DL-form of compounds 4-6. Clear synergistic relations were observed between 4 and 1 and also 4 and 3. Since the present inhibitors have been isolated from various kinds of seed plants, they may be responsible for the general germination inhibition in the seed plants.

Drug Synergism↗

PubMed2001

Antioxidative activity of volatile chemicals extracted from beer.

Volatile chemicals obtained from a commercial beer by liquid-liquid continuous extraction were evaluated for antioxidant activity. The inhibitory ability of this extract toward the conversion of hexanal to hexanoic acid was monitored over a 35-day period. The volatile extract demonstrated >99% effectiveness at inhibiting hexanal oxidation at 50 microg/mL, comparable to that of the natural antioxidant alpha-tocopherol (vitamin E). Volatile compounds contained in the extract were isolated and identified by gas chromatography-mass spectrometry (GC-MS). From the volatile constituents identified in beer extract, phenylethyl alcohol, maltol, and 2-furanmethanol were examined for antioxidative activities. At a concentration of 500 microg/mL, maltol and 2-furanmethanol demonstrated approximately 95 and 100% inhibition of hexanal oxidation over 35 days, respectively. Phenylethyl alcohol did not show any appreciable level of inhibition of hexanal oxidation. Heterocyclic compounds, some of which are known to possess antioxidative activities, were also identified in the volatile extract.

Aldehydes↗

PubMedDate not supplied

Cerebral chemosensory evoked potentials elicited by chemical stimulation of the human olfactory and respiratory nasal mucosa.

A stimulation method was employed by which chemosensory evoked potentials were recorded without tactile somatosensory contamination. The purpose of the study was to determine whether potential components evoked by stimulation of the chemoreceptors of the trigeminal nerve can be distinguished from those of the olfactory nerve. The stimulants (vanillin, phenylethyl alcohol, limonene, menthol, anethol, benzaldehyde, carbon dioxide and a mixture of vanillin and carbon dioxide) were presented in a randomized order to 13 volunteers. Chemosensory evoked potentials to substances which anosmics are unable to perceive (vanillin, phenylethyl alcohol) were termed olfactory evoked potentials; potentials to CO2, which effected no olfactory sensations were termed chemo-somatosensory potentials. Analysis of variance revealed that the different substances resulted in statistically significant changes in the amplitudes and latencies of the evoked potentials, and also in the subjective estimates of intensity. An increased excitation of the somatosensory system resulted in reduced latencies and enhanced amplitudes of the evoked potentials. Responses to the mixture of carbon dioxide and vanillin appeared significantly earlier (50-150 msec) than responses to either substance alone.

Adult↗

PubMed2005

Chlorogenate hydrolase-catalyzed synthesis of hydroxycinnamic acid ester derivatives by transesterification, substitution of bromine, and condensation reactions.

A chlorogenate hydrolase (EC 3.1.1.42) synthesized 2-phenylethyl caffeate (2-CAPE) from 5-chlorogenic acid (5-CQA) and 2-phenylethyl alcohol (2-PA) (by transesterification), from 5-CQA and 2-phenylethyl bromide (2-PBr) (by substitution of bromine), and from caffeic acid (CA) and 2-PA or 2-PBr (by condensation) as well as hydrolysis of 5-CQA. Some reaction conditions including pH, temperature, substrate and solvent concentrates, and reaction time were optimized for the production of 2-CAPE. A maximal molar yield of 50% was achieved by transesterification, 4.7% by substitution of bromine, and 13% by condensation. Among the parameters studied for optimization, the pH of the buffer solution and concentration of 2-PA or 2-PBr affected the production of 2-CAPE. The optimum pH for the hydrolysis reaction was within the neutral range (pH 6.5), whereas the residual three reactions were only catalyzed within the acidic range (pH 3.0-4.0). The optimum concentrations of 2-PA and 2-PBr for three reactions were 5-70 vol% and no 2-CAPE was produced in the 2-PA or 2-PBr solutions containing powdered enzyme. The enzyme may bind to the caffeoyl moiety of 5-CQA or CA to form an enzyme-substrate complex. It then catalyzes four different reactions corresponding to the reaction conditions.

Aspergillus↗

PubMed2004

[Studies on the chemical constituents of the volatiles of Clerodendron bungei].

OBJECTIVE: To analyse chemical constituents of the volatiles of Clerodendron bungei. METHOD: The volatiles of C. bungei were extracted through steam distillation, and then the constituents were separated by GC and identified by MS. RESULT AND CONCLUSION: 33 Compounds were identified. The principal chemical constituents of the volatiles of C. bungei are ethanol, acetone, 1-penten-3-ol,2-pentanol, (Z)-2-penten-1-ol, 3-furaldehyde, 3-hexen-1-ol, 4-hexen-1-ol, 1-hexanol, 1-octen-3-ol, 3-octanol, benzenemethanol, linal-ool oxide, trans-Linalool oxide, linalool,2,5-dimethylcyclohexanol, phenylethyl alcohol, etc.

Acetone↗

PubMed1991

Synthesis and biological activity of 2-phenylethyl ester analogues of C-terminal heptapeptide of cholecystokinin modified in Trp 30 region.

We have tried to evaluate the significance of the tryptophan side chain residue and of the surrounding peptide bonds in the antagonist activity of cholecystokinin analogues lacking the C-terminal amide function and having a D-tryptophan. In order to perform this study, analogues of the C-terminal heptapeptide of cholecystokinin were synthesized by replacing the C-terminal phenylalanine residue with 2-phenylethyl alcohol and by either replacing the tryptophan residue with an alanine, a norleucine and a phenylalanine residue, or introducing a "reduced peptide bond" in the tryptophan 30 region. Most of these compounds were able to reproduce only part of the response of cholecystokinin in stimulating amylase release from rat pancreatic acini, as was already observed for 2-phenylethyl ester analogues of CCK. These results point out the key role of tryptophan 30 in the biological response of cholecystokinin.

Amino Acid Sequence↗

PubMed1979

Autoregulation of germ tube formation by Candida albicans.

Germ tube formation by Candida albicans is at least partially controlled by a product(s) of the yeast phase of the organism which is released from cells upon incubation at 37 degrees C in tissue culture medium or fetal calf serum. This germination regulatory substance is stable under conditions of lyophilization and heating of 70 degrees C, but becomes inactivated at pH values of 4.0 and 9.5. A germination regulatory substance was produced by both strains of C. albicans tested and by a strain of C. tropicalis. Production does not appear to be a universal characteristic of yeasts because the factor could not be recovered from either Cryptococcus laurentii or Candida parapsilosis. Previously described C. albicans germination inhibitors such as cysteine, tryptophol, and phenylethyl alcohol appear not to be the substance described here. Because of the ability of the factor to influence C. albicans morphology, we have designated it morphogenic autoregulatory substance.

Candida albicans↗

PubMed1996

Odorants activate the human superior temporal sulcus.

The human olfactory pathways are well defined up to the level of the prepiriform cortex but the neocortical projections and their functional organization are still largely unknown. We recorded whole-scalp neuromagnetic signals to olfactory stimulation with boluses of phenylethyl alcohol, hydrogen sulphide, and vanillin. The main magnetic response peaked about 700 ms after the stimulus onset. The three odorants activated overlapping cortical areas around the superior temporal sulci of both hemispheres, revealing a neocortical area involved in olfactory processing.

Adult↗

PubMed1995

Enhanced sensitivity to androstenone following regular exposure to pemenone.

The responses elicited by olfactory stimuli may be modified throughout an organism's life. For example, Wysocki et al. found that regular presentations of 5a-androst-16-en-3-one (androstenone) to anosmic subjects resulted in a graded increase in the perceived intensity of this substance in about half of their subjects (Wysocki et al., 1989). The increased sensitivity they observed appeared to be specific to the exposed odorant and was presumed to occur only in anosmic subjects. Here, we continue our explorations of the individual differences in olfactory capabilities among subjects initially classified by their ability to detect and identify the odor of the diastereoisomeric ketone, cis-4-(4'-t-butylcyclo-hexyl)-4-methyl-2-pentanone (pemenone) which shares with androstenone a pronounced urine-sweaty odor. We asked if regular pemenone exposure enhances the sensitivity of human subjects to pemenone, androstenone, isovaleric acid, or phenylethyl alcohol and, if shifts in threshold occurred, were they specific to particular odorants and classes of subject? Detection thresholds for the four substances were determined before and after 7-8 weeks of regular, biweekly, exposure to pemenone (n = 18 subjects) or a control substance (22 subjects). Significant decreases in threshold were seen in the experimental group, relative to the control group, for androstenone, but not for the other compounds evaluated. Neither gender nor initial pemenone osmicity significantly affected the frequency of subjects with enhanced sensitivity. These findings show that a subject's sensitivity to one odorant can be enhanced by exposure to another, chemically distinct compound.(ABSTRACT TRUNCATED AT 250 WORDS)

Adult↗

PubMed1997

Perceived odor, irritation, and health symptoms following short-term exposure to acetone.

The subjectivity of irritancy judgments can bias attempts to establish exposure guidelines that protect individuals from the sensory irritation produced by volatile chemicals. At low to moderate chemical concentrations, naive and occupationally exposed individuals often show considerable variation in the reported levels of perceived irritation. Such variation could result from differences in exposure history, differences in the perceived odor of a chemical, or differences in generalized response tendencies to report irritation, or response bias. Thus, experimental evaluation of sensory irritancy must dissociate sensory irritation from response bias. To this end, judgments of perceived irritation from 800 ppm acetone were obtained from acetone-exposed workers and age- and gender-matched naive controls. To assess the role of response bias during exposure to odorants, subjects were also exposed to phenylethyl alcohol (PEA), an odorant that does not produce sensory irritation. Following exposure, subjects completed a subjective symptom survey that included symptoms that have been associated with long-term solvent exposures and symptoms that have not. Acetone-exposed workers and naive controls reported large differences in the perceived intensity of odor and irritation from acetone, yet no differences in the perception of PEA. However, for both groups, the most significant factors mediating reported irritancy and health symptoms from acetone were the perceived intensity of its odor and an individual's bias to report irritation from PEA. The perception of odor intensity and degree of response bias will differ between and within groups of exposed and naive individuals; hence, an assessment of the influence of these factors in experimental and workplace studies of chemical irritancy is warranted.

Acetone↗

PubMed2003

Olfactory function in workers exposed to styrene in the reinforced-plastics industry.

BACKGROUND: Impairment of olfactory function in humans has been associated with occupational exposure to volatile chemicals. To investigate whether exposure to styrene was associated with olfactory impairment, olfactory function was examined in workers with a minimum of 4 years exposure to styrene in the reinforced-plastics industry (current mean exposure: 26 ppm, range: 10-60 ppm; historic mean dose: 156 ppm-years, range: 13.8-328 ppm-years) and in a group of age- and gender-matched, unexposed controls. METHODS: Olfactory function was assessed using a standardized battery that included tests of threshold sensitivity for phenylethyl alcohol (PEA), odor identification ability, and retronasal odor perception. Odor detection thresholds for styrene were also obtained as a measure of specific adaptation to the work environment. RESULTS: No differences were observed between exposed workers and controls on tests of olfactory function. Elevation of styrene odor detection thresholds among exposed workers indicated exposure-induced adaptation. CONCLUSIONS: The present study found no evidence among a cross-section of reinforced-plastics industry workers that current or historical exposure to styrene was associated with impairment of olfactory function. Taken together with anatomical differences between rodent and human airways and the lack of evidence for styrene metabolism in human nasal tissue, the results strongly suggest that at these concentrations, styrene is not an olfactory toxicant in humans.

Adaptation, Physiological↗

PubMed2006

[Subjective and objectifying olfactometry by means of flow-olfactometer].

BACKGROUND: Is the flow-olfactometer OM2S suitable for subjective and objectifying screening of olfactory function, additional to its use for chemosensory evoked potentials? METHODS: 53 normosmics were challenged prenasally and synchronously with inspiration by two short weak, moderate and strong hydrogen sulfide (H (2)S)- and phenylethyl alcohol (PEA)-stimuli. The subject pressed a button if there was an olfactory perception. The respiratory nasal pressure changes were recorded continuously via a differential pressure transducer. The alterations of breathing pattern during olfactory stimulation were calculated using a custom made LabView software. The interstimulus interval was at least 3 minutes, the respiration had to be regular. RESULTS: The detection-rate (79 - 98 %) was dependent on quality of odor and its concentration during stimulation. H (2)S-stimuli were detected more frequently than PEA-stimuli. The frequency of detection with simultaneous alteration of breathing pattern was independent of quality of odor and strength of odor concentration. 64 % of the subjects detected both weak H (2)S as well as changed synchronously their first poststimulatory breath. CONCLUSION: The H (2)S-detection threshold was estimated both by subjective data and by data of olfactory evoked respiration changes. The flow-olfactometer by Kobal is very well suitable for subjective and respiration-olfactometry, too.

Adult↗

PubMed1994

Laboratory evaluation of urinary tract infections in an ambulatory clinic.

A 4-month evaluation of ambulatory patients with a suspicion of a urinary tract infection was performed. Specific objectives included assessment of five urinary screening methods, reevaluation of the necessity of the phenylethyl alcohol plate (PEA), and cost-effectiveness of screening for low colony count bacteriuria. Urine samples were collected as midstream, clean-caught specimens. A total of 142 samples, 87 from 79 symptomatic patients and 55 negative controls, were evaluated. All urine specimens were cultured using a 0.01 mL loop and a 0.001 mL loop onto Columbia sheep blood agar, MacConkey agar, and PEA agar. Twenty-four specimens (17%) were sterile, 64 (45%) were contaminated, and 54 (38%) were infected. Five urine screening methods were performed. These tests and their associated sensitivity and specificity are as follows. The Chemstrip 9 (Behring, Inc., Somerville, NJ) for leukocyte esterase and nitrate, 67%, 98%; microscopic analysis on spun urine, 79%, 93%; methylene blue stain for pyuria, 60%, 99%; Gram stain for pyuria, 45%, 93%; Gram stain for bacteriuria, 65%, 75%; and the URISCREEN (Analytab Products, Plainview, NY), 92%, 89%. Inclusion of a PEA plate for isolation of gram-positive organisms provided no additional information. Routine culture of urine samples at 10(-2) mL increased the contamination rate by 19%.

Ambulatory Care↗