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PubMed1979

Quantitative comparison of physical dependence on tertiary butanol and ethanol in mice: correlation with lipid solubility.

Mice were made physically dependent on t-butanol and the withdrawal reaction was compared quantitatively with that produced by ethanol. The mice inhaled t-butanol vapor (50-140 mumol/1 of air) continuously for 1, 3, 6 or 9 days. Daily t-butanol blood levels were determined by gas chromatography, using ethanol as internal standard. After t-butanol exposure the mice were removed from the vapor chamber and the withdrawal reaction was quantitated by hourly scoring of convulsions elicited by handling. The peak of the withdrawal reaction occurred 3 to 5 hr after the mice were removed from the t-butanol vapor. The intensity of the withdrawal reaction increased with the duration of inhalation, and with the t-butanol blood levels maintained during the intoxication period. The withdrawal syndrome was qualitatively similar to that produced by ethanol. Quantitatively, t-butanol was 4 to 5 times more potent than ethanol in producing physical dependence. Since t-butanol is about 4 to 5 times more lipid soluble than ethanol, the data are consistent with a cell membrane site for alcohols in producing physical dependence.

Alcoholism↗
PubMed1988

Enhancement of Butanol Formation by Clostridium acetobutylicum in the Presence of Decanol-Oleyl Alcohol Mixed Extractants.

Extractive fermentation has been proposed to enhance the productivity of fermentations that are end product inhibited. Unfortunately, good extractants for butanol, such as decanol, are toxic to Clostridium acetobutylicum. The use of mixed extractants, namely, mixtures of toxic and nontoxic coextractants, was proposed to circumvent this toxicity. Decanol appeared to inhibit butanol formation by C. acetobutylicum when present in a mixed extractant that also contained oleyl alcohol. However, maintenance of the pH at 4.5 alleviated the inhibition of butanol production and the consumption of butyrate during solventogenesis. A mixed extractant that contained 20% decanol in oleyl alcohol enhanced butanol formation by 72% under pH-controlled conditions. The production of acetone and acetoin was also increased, even though these two products were not extractable. The enhancement of butanol formation was not limited by the toxicity of decanol. Supplementation of glucose and butyrate in the extractive fermentation yielded a 47% increase in butanol. The enhancement of butanol formation appeared to be dependent on the presence of dissolved decanol in the broth but was not observed unless an organic phase was present to extract butanol. A mechanism for the effects of decanol on product formation is proposed.

Journal Article↗
PubMed2004

Butanol fermentation research: upstream and downstream manipulations.

An overview of advances in acetone-butanol fermentation research is presented with specific reference to the history of acetone-butanol fermentation, genetic manipulation of the butanol-producing Clostridium beijerinckii NCIMB 8052, as well as upstream and downstream processing. Specific reference is made to the development of the hyperamylolytic, hyper-"butanolagenic" C. beijerinckii BA101 strain. Amylolytic enzyme production by C. beijerinckii BA101 was 1.8- and 2.5-fold greater than that of the C. beijerinckii NCIMB 8052 strain grown in starch and glucose, respectively. We confirmed the presence of a phosphoenolpyruvate (PEP)-dependent phosphotransferase system (PTS) associated with cell extracts of C. beijerinckii BA101 by glucose phosphorylation by PEP and ATP-dependent glucose phosphorylation. It was found that C. beijerinckii BA101 was defective in PTS activity and that it compensates for this defect with enhanced glucokinase activity, resulting in an ability to transport and utilize glucose during the solventogenic stage. The principal problem associated with acetone-butanol fermentation by C. beijerinckii or C. acetobutylicum is butanol toxicity/inhibition to the culture. To solve this problem, we have attempted various alternative in situ/online techniques of butanol removal including membrane-based systems such as pervaporation, liquid-liquid extraction, and gas stripping. We found that gas stripping and pervaporation appear to be the most promising of the in situ acetone-butanol fermentation and recovery techniques but, in terms of cost-effective industrial applications, gas stripping appears to be the most promising.

Acetone↗
PubMed1995

One-step extraction and concentration of pigments and acyl lipids by sec-butanol from in vitro and in vivo samples.

Photosynthetic pigments and acyl lipids were simultaneously extracted and concentrated by sec-butanol. Pigments extracted with sec-butanol were indistinguishable from those extracted using acetone as determined by quantitative and qualitative HPLC. Use of sec-butanol has several advantages over conventional extraction solvents: (1) pigments are extracted directly from polyacrylamide gel slices without an elution step; (2) pigments in dilute, isolated pigment-protein complexes are extracted and concentrated without first concentrating the sample; (3) when necessary, the concentration factor is readily increased by addition of water; (4) sec-butanol extracts acyl lipids and vitamin K1 as effectively, but much quicker, than chloroform:methanol; (5) sec-butanol rapidly extracts and concentrates pigments from thylakoids of all plant species tested and even directly from many algal/higher plant cells, facilitating analysis of pigment biosynthetic pathways using radioactive substrates; and (6) pigments are stable in sec-butanol for several days at room temperature in the dark or for many weeks if stored at -20 degrees C in darkness. Finally, sec-butanol is preferable to ether for concentrating pigments extracted with acetone.

Butanols↗
PubMed2005

Evaluation of developmental toxicity of 1-butanol given to rats in drinking water throughout pregnancy.

The objective of this study was to evaluate the developmental toxicity of 1-butanol in rats. Pregnant rats were given drinking water containing 1-butanol at 0.2%, 1.0% or 5.0% (316, 1454 or 5654 mg/kg/day) on days 0-20 of pregnancy. A significant decrease in maternal body weight gain accompanied by reduced food and water consumption was found at 5.0%. No significant increase in the incidence of pre- and postimplantation embryonic loss was observed in any groups treated with 1-butanol. Fetal weight was significantly lowered at 5.0%. Although a significant increase in the incidence of fetuses with skeletal variations and decreased degree of ossification was found at 5.0%, no increase in the incidence of fetuses with external, skeletal and internal abnormalities was detected in any groups treated with 1-butanol. The data demonstrate that 1-butanol is developmental toxic only at maternal toxic doses. No evidence for teratogenicity of 1-butanol was noted in rats. Based on the significant decreases in maternal body weight gain and fetal weight, it is concluded that the no observed adverse effect levels (NOAELs) of 1-butanol for both dams and fetuses are 1.0% (1454 mg/kg/day) in rats.

1-Butanol↗
PubMed1993

Effect of pyridine on the hepatic and pulmonary metabolism of 2-butanol in rat and rabbit.

Pyridine has been shown to be an effective inducer of the ethanol-inducible cytochrome P-450IIE1 in both liver and lung. The oxidation of 2-butanol by rat liver is inducible by chronic ethanol consumption. The purpose of this study was to determine the effect of pyridine on the hepatic and pulmonary metabolism of butanol. Comparisons were made between rat and rabbit. Acute pyridine treatment (200 mg/kg, ip) increased hepatic metabolism of 2-butanol in the rat twofold and in the rabbit threefold. The effect of pyridine on hepatic butanol oxidase is similar to the effect reported by other investigators for ethanol administered in the drinking water for 3 wk. Control rabbit pulmonary butanol oxidase activity was 10-fold higher than that in the rat. Pyridine decreased pulmonary butanol oxidase activity in the rabbit. The effect was demonstrated both in vitro and in the isolated perfused rabbit lung. Pyridine had no effect on pulmonary butanol oxidase activity in the rat.

Animals↗
PubMed2003

The effects of the phospholipase D-antagonist 1-butanol on seedling development and microtubule organisation in Arabidopsis.

The organisation of plant microtubules into distinct arrays during the cell cycle requires interactions with partner proteins. Having recently identified a 90-kDa phospholipase D (PLD) that associates with microtubules and the plasma membrane [Gardiner et al. (2001) Plant Cell 13: 2143], we exposed seeds and young seedlings of Arabidopsis to 1-butanol, a specific inhibitor of PLD-dependent production of the signalling molecule phosphatidic acid (PA). When added to agar growth media, 0.2% 1-butanol strongly inhibited the emergence of the radicle and cotyledons, while 0.4% 1-butanol effectively blocked germination. When normal seedlings were transferred onto media containing 0.2% and 0.4% 1-butanol, the inhibitor retarded root growth by about 40% and 90%, respectively, by reducing cell elongation. Inhibited plants showed significant swelling in the root elongation zone, bulbous or branched root hairs, and modified cotyledon morphology. Confocal immunofluorescence microscopy of root tips revealed that 1-butanol disrupted the organisation of interphase cortical microtubules. Butanol isomers that do not inhibit PLD-dependent PA production, 2- and 3-butanol, had no effect on seed germination, seedling growth, or microtubule organisation. We propose that production of PA by PLD may be required for normal microtubule organisation and hence normal growth in Arabidopsis.

1-Butanol↗
PubMed2006

n-Butanol induces depolymerization of microtubules in vivo and in vitro.

The effects of butanol on microtubules (MTs) were examined by immunofluorescence microscopy. Fragmentation of cortical MTs was induced by n-butanol, but not by s- and t-butanols, in cultured tobacco BY-2 cells. Taxol prevented n-butanol-induced MT fragmentation. Fragmented cortical MTs were still attached to the inner face of the plasma membrane when n-butanol-treated protoplasts were ruptured on the slide glass. Moreover, MTs were depolymerized in the presence of n-butanol in vitro. Therefore, n-butanol is not only an activator of phospholipase D but also an effective MT-depolymerizing agent.

1-Butanol↗
PubMed1999

Butanol is superior to water for performing positron emission tomography activation studies.

[15(O)]Butanol has been shown to be superior to [15(O)]water for measuring cerebral blood flow with positron emission tomography. This work demonstrates that it is also superior for performing activation studies. Data were collected under three conditions: a visual confrontation animal-naming task, nonsense figure size discrimination, and a nonvisual darkroom control task. Time-activity curves (TAC) were obtained for regions known to be activated by the confrontation naming task to compare absolute uptake and the different kinetics of the two tracers. Also, t statistic maps were calculated from the data of 10 subjects for both tracers and compared for magnitude of change and size of activated regions. Peak uptake in the whole-brain TAC were similar for the two tracers. For all regions and conditions, the washout rate of [15(O)]butanol was 41% greater than that of [15(O)]water. At a threshold of 0, the [15(O)]water and [15(O)]butanol percent difference (nonnormalized) and t statistic (global normalization) images are nearly identical, indicating that the same property is being measured with both tracers. The [15(O)]butanol parametric images displayed at a threshold of /t/ = 5 look similar to the [15(O)]water parametric maps displayed at a threshold of /t/ = 4, which is consistent with the observation that t statistic values in [15(O)]butanol images are generally greater. The t statistic values were equal when the [15(O)]butanol parametric map was created from any subset of 6 subjects and the [15(O)]water parametric map was created from all 10 subjects. Fewer subjects need to be studied with [15(O)]butanol to reach the same statistical power as an [15(O)]water-based study.

Adult↗
PubMed1978

Butanol extraction of serum and urinary gamma-glutamyltransferase and its application in clinical diagnosis.

Gamma-glutamyltransferase (gamma-GT) activity was measured in serum and urine before and after extraction with n-butanol. Residual gamma-GT activity after extraction of normal serum with butanol was more than 75%, whereas for normal urine the figure was less than 68%. The loss of activity from urine was not affected by prior dialysis, and the stabilisation which resulted from adding bovine serum albumin at a concentration of 40 g/l did not approach the residual activity with normal serum. In patients with a variety of renal diseases, residual gamma-GT activity in the urine after butanol extraction was inversely correlated with the creatinine clearance. Butanol extraction was performed on serum samples from 182 patients with a variety of diseases. Eighty-one per cent of patients with elevated gamma-GT activities caused by hepatobiliary disease had an increased loss of activity after butanol extraction. By contrast, only 34% of patients with increases gamma-GT activities in whom there was no clinical or other biochemical evidence of hepatic disease, had increased loss of gamma-GT activity after butanol. The reasons for differences between urinary and serum gamma-GT in response to butanol, and the implications in interpreting serum gamma-GT activities are discussed.

Butanols↗
PubMed2002

Butanol production by Clostridium beijerinckii BA101 in an immobilized cell biofilm reactor: increase in sugar utilization.

Acetone butanol ethanol was produced in a continuous immobilized cell (biofilm) plug-flow reactor inoculated with Clostridium beijerinckii BA101. To achieve high reactor productivity, C. beijerinckii BA101 cells were immobilized by adsorption onto clay brick. The continuous plug-flow reactor offers high productivities owing to reduced butanol inhibition and increased cell concentration. Although high productivity was achieved, it was at the expense of low sugar utilization (30.3%). To increase sugar utilization, the reactor effluent was recycled. However, this approach is complicated by butanol toxicity. The effluent was recycled after removal of butanol by pervaporation to reduce butanol toxicity in the reactor. Recycling of butanol-free effluent resulted in a sugar utilization of 100.7% in addition to high productivity of 10.2 g/(L x h) at a dilution rate of 1.5 h(-1). A dilution rate of 2.0 h(-1) resulted in a reactor productivity of 16.2 g/(L x h) and sugar utilization of 101.4%. It is anticipated that this reactor-recovery system would be economical for butanol production when using C. beijerinckii BA101.

Adsorption↗
PubMed2004

Variability and repeatability of olfactometric results of n-butanol, pig odour and a synthetic gas mixture.

For the purposes of a research project for the Flemish authorities, olfactometric measurements were carried out at six closed pig farms and six fattener farms. The results of these olfactometric measurements were compared with the olfactometric results of n-butanol samples and samples of a synthetic gas mixture of ethanethiol, methylacetate and 2-propanol in nitrogen, both analysed on the same days as the air samples from the pig farms. The results of the n-butanol tests for all panellists showed that nobody was qualified according to the CEN criteria, and that, consequently, these criteria are rather stringent. Comparing the variability of the results for the three different odours showed that the mean and standard deviation of the mean variance were not significantly different for the three odour types, which means that the repeatability of the panellist results was equal for the examined odour types. The principle of traceability was checked by comparing the variance of the n-butanol, pig odour and synthetic mixture ratio. For the complete dataset, the principle of traceability could not been proven for n-butanol. For the restricted dataset, the principle of traceability was more valid for n-butanol than for the mixture, but differences were small. Finally, normalization was looked for with regard to olfactometric measurements of air samples from pig arms based either on n-butanol or on the synthetic mixture. Both models had low determination coefficients, but the model based on the synthetic mixture gave better results than the one based on n-butanol.

1-Butanol↗
PubMed1977

Mechanism of protection from alloxan diabetes provided by n-butanol.

Pretreatment with n-butanol (10 mmol/kg i.p.) 30 minutes before alloxan (100 mg/kg) protects mice from the permanent hyperglycemic effects (measured at 72 hours) of the diabetogenic agent. This dose of n-butanol caused an elevation of serum glucose at 30 minutes, the time of alloxan administration. Since glucose administration can protect animals from alloxan, the possibility that alcohol-induced hyperglycemia protected mice from alloxan was investigated. Mannoheptulose, an antagonist of glucose action at the pancreatic beta-cell, when given 24 minutes after n-butanol and 6 minutes before alloxan, eliminated the alcohol-induced protection. Fasted mice did not exhibit n-butanol-induced hyperglycemia at 30 minutes and alloxan given at that time produced diabetes. No protection was observed in fed animals when n-butanol was given 5 minutes before alloxan. The high serum levels of butanol and normal serum glucose which were observed at 5 minutes after alcohol administration indicated that the lack of protection was not due to a lack of circulating alcohol but resulted from an absence of hyperglycemia. The results indicate that pretreatment with n-butanol protects mice from alloxan-induced diabetes by the indirect mechanism of producing hyperglycemia at the time of alloxan administration.

Animals↗
PubMed2000

Light Scattering Study of the Effect of n-Butanol on the Micellar Properties of Undecylammonium Chloride in Aqueous Electrolyte Solutions.

Light scattering measurements have been performed on aqueous solutions of undecylammonium chloride in the presence of 0 to 0.2 mol dm(-3) NaCl and 0 to 0.5 mol dm(-3) n-butanol at 25 degrees C. The critical micelle concentration (CMC), aggregation number, and degree of dissociation of the micelles have been determined. The observed decrease of the CMC with the increase of the n-butanol concentration was explained by the effect of the n-butanol on water structure and by the selective solvation of the micelles with n-butanol, which counteract the decrease of the polar character of the solvent caused by n-butanol addition. An observed increase in the degree of dissociation of the micelles and a decrease in the aggregation number following alcohol addition have been explained by considering the effect of this additive on the electrostatic and other interactions involved in free energy of micellization. Our results support the concept of opposing effects between n-butanol and NaCl on the cooperativity in the micellization process of this surfactant, with the n-butanol disfavoring micellar growth. Copyright 2000 Academic Press.

Journal Article↗
PubMed1997

Enhanced Butanol Production by Clostridium beijerinckii BA101 Grown in Semidefined P2 Medium Containing 6 Percent Maltodextrin or Glucose.

Dramatically elevated levels of butanol and acetone resulted in higher butanol and total solvent yields for hyperamylolytic Clostridium beijerinckii BA101 relative to the NCIMB 8052 parent strain grown in semidefined P2 medium containing either 6% glucose or STAR-DRI 5 maltodextrin. C. beijerinckii BA101 consistently produced on the order of 19 g of butanol per liter in 20-liter batch fermentations. This represents a greater than 100% increase in butanol concentration by the BA101 strain compared to the parent NCIMB 8052 strain. The kinetics of butanol production over time also indicate a more rapid rate of butanol production by BA101 in semidefined P2 medium containing glucose or maltodextrin. The lower levels of butyric and acetic acids produced over the course of the fermentation carried out by BA101 are consistent with an enhanced capacity for uptake and recycling of these acids. C. beijerinckii BA101 appears to more completely utilize carbohydrate compared to the 8052 strain. Carbon balance following fermentation by C. beijerinckii 8052 and BA101 indicates that sufficient carbon is available for the twofold increase in butanol concentration observed during BA101 fermentations. C. beijerinckii BA101 also has superior solvent production capacity during continuous culture fermentation in P2 medium containing 6% glucose. Volumetric solvent yields of 0.78 and 1.74 g/liter/h for BA101 and 0.34 and 1.17 g/liter/h for NCIMB 8052 were obtained at dilution rates of 0.05 and 0.20 h(sup-1), respectively. No drift towards acid synthesis (strain degeneration) was observed for up to 200 h (d = 0.05 h(sup-1)) and 100 h (d = 0.20 h(sup-1)).

Journal Article↗
PubMed2006

[EQCM and in situ FTIR studies on the adsorption and oxidation of 1-butanol at a platinum electrode in alkaline media].

The adsorption and oxidation of 1-butanol in alkaline media on a platinum electrode were investigated mainly by EQCM and in situ FTIR spectroscopy. The experimental results demonstrate that the electrooxidation of 1-butanol is closely relative to solution acidity. Since no chemically adsorbed species, such as CO, were evidenced by in situ FTIR spectroscopy, the adsorption of 1-butanol or its dissociative products on Pt surface is suggested by EQCM and CV data. Only one current peak of 1-butanol oxidation in PGPS was detected at -0.23 V/SCE, which illustrated the disappearance of the second current peak due to Pt electrode passivation in alkaline media. The final product of 1-butanol oxidation is only butyric acid anion under experimental condition. It may therefore be suggested that the main reaction occurring at the electrode is the oxidation of 1-butanol to butyric acid anion. The EQCM studies provide quantitative results of surface mass variation and have shed light on elucidating 1-butanol oxidation.

English Abstract↗
PubMed1980

Initial membrane reaction in peptidoglycan synthesis: perturbation of lipid-phospho-N-acetylmuramyl-pentapeptide translocase interactions by n-butanol.

Phospho-N-acetylmuramyl-pentapeptide translocase, the initial membrane enzyme in the biosynthesis of peptidoglycan, requires a lipid microenvironment for function. n-Butanol was reversibly intercalated into membranes to perturb the hydrophobic interactions in this microenvironment in order to define further the role of lipid. In the concentration range for maximal stimulation of enzymic activity (0.12-0.18 M), n-butanol causes a 40% decrease in the fluorescence emission of the dansylated product, undecaprenyl diphosphate-(N epsilon-dansyl)pentapeptide. Since no change in emission maximum occurs below 22 degrees C in the presence of 0.12 M n-butanol, it is concluded that intercalation of this alkanol causes an increase in fluidity. Above 22 degrees C this concentration of n-butanol causes both a decrease in the fluorescence emission and a red shift in the emission maximum. It is concluded that a polarity change as well as fluidity change occurs above 22 degrees C. n-Butanol also causes a significant change in the phase transition experienced by the dansylated lipid product. Thus, it is possible with n-alkanols, e.g. n-butanol, to perturb lipid-translocase interactions resulting in an increase in fluidity in the microenvironment of the enzyme. This change in fluidity correlates with a stimulation of enzymic activity.

1-Butanol↗
PubMed1990

Extraction of diquat with 1-butanol from biological materials.

Diquat can be extracted with 1-butanol from high pH solution in the presence of several moderate reductants. The red colored reduced compound of diquat in water turns to a purple compound in 1-butanol. The absorption of the purple compound is 0.105 at 383 nm and 0.119 at 520 nm in 1 microgram diquat/ml 1-butanol. The latter value is a little higher than that of the red compound at 495 nm in water. The purple compound is much more stable than the red compound in water. More than 80% of 10 ppm diquat added can be extracted from serum, blood, tissues, urine and some drinks. The extraction with 1-butanol is useful for concentration of diquat contained in large volume. The lower limit of detection is 0.1 microgram/ml 1-butanol. Paraquat is insoluble in 1-butanol under the same condition. Therefore, this method is applicable for the determination of diquat when paraquat is also contained in the solution.

1-Butanol↗