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PubMed1999

Involvement of manganese in conversion of phenylalanine to benzaldehyde by lactic acid bacteria.

We examined the involvement of Mn(II) in the conversion of phenylalanine to benzaldehyde in cell extracts of lactic acid bacteria. Experiments performed with Lactobacillus plantarum demonstrated that Mn(II), present at high levels in this strain, is involved in benzaldehyde formation by catalyzing the conversion of phenylpyruvic acid. Experiments performed with various lactic acid bacterial strains belonging to different genera revealed that benzaldehyde formation in a strain was related to a high Mn(II) level.

Benzaldehydes↗
PubMed1980

Biodistribution and excretion of [11C]benzaldehyde by the rat after two-minute inhalation exposures.

1. Based on the decay characteristics of short-lived gamma-emitting radioisotopes a new acute exposure method was developed for studying the kinetics and biodistribution of inhaled toxic agents. Such body-penetrating radiation allows direct, non-invasive determination of the radiation in the animal at any time. 2. Rats exposed to 11C-labelled benzaldehyde for 2 min accumulated an average of 2.5 micrograms of this aldehyde. 3. Inhaled benzaldehyde was rapidly absorbed and at 1.5 min after exposure only 0.8% of the administered dose was resident in the lungs. This aldehyde was quickly distributed with the peak radioactivity in the organs occurring at 1.5 min after exposure. Subsequent loss of radiolabel from tissues was rapid and paralleled the removal from the blood. The adipose tissue cleared most slowly. 4. Benzaldehyde was rapidly excreted via the renal system with the kidneys containing 17% of the total administered activity at 5 min. The excreted radiolabelled compound co-chromatographed with hippuric acid on t.l.c.

Adipose Tissue↗
PubMed1978

[Investigations on the antimicrobial activity of amin-aldehyde-condensates. 5. Communication: azomethins of benzaldehyde (author's transl)].

In the scope of our research about the antimicrobial activity of amin-aldehyde-condensates a number of benzylidene-amines (azomethins of benzyldehyde) was synthesized by condensation of primary amines with benzaldehyde. Structures and physical constants are shown in table 1 and 2. The antimicrobial activity of these benzylidene-amines is demonstrated by the results of the disk-test (table 3), of the minimal inhibition concentration test (MIC, table 4) and the suspension test (table 5) following the method of the DGHM. The different hydrophilic behaviour was equalized by using the standard solution described earlier with 3% dioxane. The results show, that the germistatic activity of the benzylideneamines resembles or exceeds in some cases that of benzaldehyde (table 4). Some compounds show good fungistatic activity versus Trichophyton mentagrophytes (table 3). The bactericidal power versus Klebsiella pneumoniae, Pseudomonas aeruginosa and Proteus vulgaris is remarkable and quiet stronger than that of the benzaldehyde.

Azo Compounds↗
PubMed2006

Factors mediating activity, selectivity, and substrate specificity for the thiamin diphosphate-dependent enzymes benzaldehyde lyase and benzoylformate decarboxylase.

Benzaldehyde lyase from Pseudomonas fluorescens and benzoylformate decarboxylase from Pseudomonas putida are homologous thiamin diphosphate-dependent enzymes that catalyze carboligase and carbolyase reactions. Both enzymes catalyze the formation of chiral 2-hydroxy ketones from aldehydes. However, the reverse reaction has only been observed with benzaldehyde lyase. Whereas benzaldehyde lyase is strictly R specific, the stereoselectivity of benzoylformate decarboxylase from P. putida is dependent on the structure and orientation of the substrate aldehydes. In this study, the binding sites of both enzymes were investigated by using molecular modelling studies to explain the experimentally observed differences in the activity, stereo- and enantioselectivity and substrate specificity of both enzymes. We designed a detailed illustration that describes the shape of the binding site of both enzymes and sufficiently explains the experimental effects observed with the wild-type enzymes and different variants. These findings demonstrate that steric reasons are predominantly responsible for the differences observed in the (R)-benzoin cleavage and in the formation of chiral 2-hydroxy ketones.

Aldehyde-Lyases↗
PubMed2005

Mechanism of oxidation of benzaldehyde by polypyridyl oxo complexes of Ru(IV).

The oxidation of benzaldehyde and several of its derivatives to their carboxylic acids by cis-[Ru(IV)(bpy)2(py)(O)]2+ (Ru(IV)=O2+; bpy is 2,2'-bipyridine, py is pyridine), cis-[Ru(III)(bpy)2(py)(OH)]2+ (Ru(III)-OH2+), and [Ru(IV)(tpy)(bpy)(O)]2+ (tpy is 2,2':6',2''-terpyridine) in acetonitrile and water has been investigated using a variety of techniques. Several lines of evidence support a one-electron hydrogen-atom transfer (HAT) mechanism for the redox step in the oxidation of benzaldehyde. They include (i) moderate k(C-H)/k(C-D) kinetic isotope effects of 8.1 +/- 0.3 in CH3CN, 9.4 +/- 0.4 in H2O, and 7.2 +/- 0.8 in D2O; (ii) a low k(H2O/D2O) kinetic isotope effect of 1.2 +/- 0.1; (iii) a decrease in rate constant by a factor of only approximately 5 in CH3CN and approximately 8 in H2O for the oxidation of benzaldehyde by cis-[Ru(III)(bpy)2(py)(OH)]2+ compared to cis-[Ru(IV)(bpy)2(py)(O)]2+; (iv) the appearance of cis-[Ru(III)(bpy)2(py)(OH)]2+ rather than cis-[Ru(II)(bpy)2(py)(OH2)]2+ as the initial product; and (v) the small rho value of -0.65 +/- 0.03 in a Hammett plot of log k vs sigma in the oxidation of a series of aldehydes. A mechanism is proposed for the process occurring in the absence of O2 involving (i) preassociation of the reactants, (ii) H-atom transfer to Ru(IV)=O2+ to give Ru(III)-OH2+ and PhCO, (iii) capture of PhCO by Ru(III)-OH2+ to give Ru(II)-OC(O)Ph+ and H+, and (iv) solvolysis to give cis-[Ru(II)(bpy)2(py)(NCCH3)]2+ or the aqua complex and the carboxylic acid as products.

Journal Article↗
PubMed2003

Kinetic study of the phthalimide N-oxyl radical in acetic acid. Hydrogen abstraction from substituted toluenes, benzaldehydes, and benzyl alcohols.

The phthalimide N-oxyl (PINO) radical was generated by the oxidation of N-hydroxyphthalimide (NHPI) with Pb(OAc)4 in acetic acid. The molar absorptivity of PINO* is 1.36 x 10(3) L mol(-1) cm(-1) at lambda(max) 382 nm. The PINO radical decomposes slowly with a second-order rate constant of 0.6 +/- 0.1 L mol(-1) s(-1) at 25 degrees C. The reactions of PINO(*) with substituted toluenes, benzaldehydes, and benzyl alcohols were investigated under an argon atmosphere. The second-order rate constants were correlated by means of a Hammett analysis. The reactions with toluenes and benzyl alcohols have better correlations with sigma+ (rho = -1.3 and -0.41), and the reaction with benzaldehydes correlates better with sigma (rho = -0.91). The kinetic isotope effect was also studied and significantly large values of k(H)/k(D) were obtained: 25.0 (p-xylene), 27.1 (toluene), 27.5 (benzaldehyde), and 16.9 (benzyl alcohol) at 25 degrees C. From the Arrhenius plot for the reactions with p-xylene and p-xylene-d(10), the difference of the activation energies, E(a)(D) - E(a)(H), was 12.6 +/- 0.8 kJ mol(-1) and the ratio of preexponential factors, A(H)/A(D), was 0.17 +/- 0.05. These findings indicate that quantum mechanical tunneling plays an important role in these reactions.

Journal Article↗
PubMed2006

Effect of structure in benzaldehyde oximes on the formation of aldehydes and nitriles under photoinduced electron-transfer conditions.

The mechanistic aspects of the photosensitized reactions of a series of benzaldehyde oximes (1a-o) were studied by steady-state (product studies) and laser flash photolysis methods. Nanosecond laser flash photolysis studies have shown that the reaction of the oxime with triplet chloranil (3CA) proceeds via an electron-transfer mechanism provided the free energy for electron transfer (DeltaG(ET)) is favorable; typically, the oxidation potential of the oxime should be below 2.0 V. Substituted benzaldehyde oximes with oxidation potentials greater than 2.0 V quench 3CA at rates that are independent of the substituent and the oxidation potential. The most likely mechanism under these conditions is a hydrogen atom transfer mechanism as this reaction should be dependent on the O-H bond strength only, which is virtually the same for all oximes. Product studies have shown that aldoximes react to give both the corresponding aldehyde and the nitrile. The important intermediate in the aldehyde pathway is the iminoxyl radical, which is formed via an electron transfer-proton transfer (ET-PT) sequence (for oximes with low oxidation potentials) or via a hydrogen atom transfer (HAT) pathway (for oximes with larger oxidation potentials). The nitriles are proposed to result from intermediate iminoyl radicals, which can be formed via direct hydrogen atom abstraction or via an electron-transfer-proton-transfer sequence. The experimental data seems to support the direct hydrogen atom abstraction as evidenced by the break in linearity in the plot of the quenching rates against the oxidation potential, which suggests a change in mechanism. The nitrile product is favored when electron-accepting substituents are present on the benzene ring of the benzaldehyde oximes or when the hydroxyl hydrogen atom is unavailable for abstraction. The latter is the case in pyridine-2-carboxaldoxime (2), where a strong intramolecular hydrogen bond is formed. Other molecules that form weaker intramolecular hydrogen bonds such as 2-furaldehyde oxime (3) and thiophene-2-carboxaldoxime (4) tend to yield increasing amounts of aldehyde.

Journal Article↗
PubMed2005

Structure and mechanism of the ThDP-dependent benzaldehyde lyase from Pseudomonas fluorescens.

Pseudomonas fluorescens is able to grow on R-benzoin as the sole carbon and energy source because it harbours the enzyme benzaldehyde lyase that cleaves the acyloin linkage using thiamine diphosphate (ThDP) as a cofactor. In the reverse reaction, this lyase catalyses the carboligation of two aldehydes with high substrate and stereospecificity. The enzyme structure was determined by X-ray diffraction at 2.6 A resolution. A structure-based comparison with other proteins showed that benzaldehyde lyase belongs to a group of closely related ThDP-dependent enzymes. The ThDP cofactors of these enzymes are fixed at their two ends in separate domains, suspending a comparatively mobile thiazolium ring between them. While the residues binding the two ends of ThDP are well conserved, the lining of the active centre pocket around the thiazolium moiety varies greatly within the group. Accounting for the known reaction chemistry, the natural substrate R-benzoin was modelled unambiguously into the active centre of the reported benzaldehyde lyase. Due to its substrate spectrum and stereospecificity, the enzyme extends the synthetic potential for carboligations appreciably.

Aldehyde-Lyases↗
PubMed1991

Comparative subcellular distribution of benzaldehyde and acetaldehyde dehydrogenase activities in two hepatoma cell lines and in normal hepatocytes.

The NAD- and NADP-dependent aldehyde dehydrogenase (ALDH) activities were evaluated in two rat hepatoma cell lines, namely the well-differentiated MH1C1 line and the less differentiated HTC line. Each activity was determined in parallel in isolated rat hepatocytes, for comparison. The aliphatic aldehyde acetaldehyde (ACA) and the aromatic aldehyde benzaldehyde (BA) were used as substrates. With the first substrate the ALDH activities found in the crude cytoplasmic extracts were lower in hepatoma cells than in normal hepatocytes, especially when measured with NADP as coenzyme (ACA/NADP). Otherwise, with benzaldehyde as substrate the NAD-dependent enzyme activity (BA/NAD) was increased about 9-fold in HTC cells over hepatocytes and decreased in MH1C1 cells, while the NADP-dependent (BA/NADP) activity was increased 38- and 2.5-fold in HTC and MH1C1 cell lines, respectively. Studies on the subcellular distribution of these enzyme activities showed that the activity measured with acetaldehyde and NAD (ACA/NAD) was almost equally distributed between the cytosol and the subcellular particles in the three cell populations, but the ACA/NADP activity was shifted towards the cytosolic compartment in hepatomas, especially in HTC cells. The BA/NAD and BA/NADP ALDH activities found in the organelles of hepatoma cells were markedly reduced in comparison with hepatocytes, in favour of the cytosol. The most striking difference between the normal and the transformed cells was the 94-fold increase over hepatocytes of the BA/NADP activity, found in the cytosolic fractions of HTC cells. MH1C1 cells showed a less pronounced (7.5-fold) enhancement of this tumour-associated specific activity.(ABSTRACT TRUNCATED AT 250 WORDS)

Acetaldehyde↗
PubMed1976

Antioxidant efficiency of polyhydric phenols in photooxidation of benzaldehyde.

An experimental system is described for the observation of the kinetics of photochemically initiated oxidation reactions; this system is based on the measurement of oxygen consumption with a polarographic oxygen electrode. The photooxidation of benzaldehyde in dilute aqueous solution was examined and appears to conform to a free radical chain mechanism. The antioxidant efficiency of some polyhydric phenols was determined kinetically and found to be catechol greather than pyrogallol greater than hydroquinone greather than resorcinol greater than n-propyl gallate for the benzaldehyde photooxidation.

Antioxidants↗
PubMed2004

Synthesis of prenylated benzaldehydes and their use in the synthesis of analogues of licochalcone A.

In this paper, a general applicable synthesis of prenylated aromatic compounds exemplified by prenylated benzaldehydes starting from readily available acetophenones is described. The synthesized benzaldehydes are used to prepare a number of novel analogues of Licochalcone A, a known antibacterial compound, and for the exploration of the pharmacophoric elements that are essential for the antibacterial activity. It is shown that the hydroxyl group in the A ring is essential for the activity and that the hydroxyl group in the B ring has no influence on the antibacterial effect of Licochalcone A. Furthermore, it is shown that the prenyl group at the position 5 of the B ring also has a dominating influence on the activity. This aliphatic group can be replaced by other lipophilic long chained substituents in order to maintain the activity.

Acetophenones↗
PubMed2005

Contamination in HPLC quantified benzaldehyde is from polypropylene microtubes.

Semicarbazide-sensitive amine oxidase (SSAO; EC 1.4.3.6) is a copper-containing enzyme predominantly expressed by vascular smooth muscle cells. SSAO deaminates primary amines to produce aldehydes and oxygen peroxides, and may thus play a role in vascular damage. SSAO activity can be quantified by assaying benzaldehyde production using fluorescent derivatisation and separation by HPLC. We performed the derivatisation step in polypropylene or borosilicate glass tubes over 45 min at 95 degrees C. High and obstructing background levels of benzaldehyde were found in one batch of polypropylene vials, as opposed to its alternatives. Treatment and handling of product shipment into the country did not account for introduction of contaminant into packaged vials nor did any reagent used in the assay. We conclude that the source of contamination was most likely due to variation in the commercial production process. Use of borosilicate vials for assays based on aldehyde production and derivatisation is recommended.

Amine Oxidase (Copper-Containing)↗
PubMed2001

Ozone reaction with n-aldehydes (n=4-10), benzaldehyde, ethanol, isopropanol, and n-propanol adsorbed on a dual-bed graphitized carbon-carbon molecular sieve adsorbent cartridge.

Ozone reacts with n-aldehydes (n=4-10), benzaldehyde, ethanol, isopropanol and n-propanol adsorbed on a dual-bed graphitized carbon-carbon molecular sieve adsorbent cartridge. Destruction of n-aldehydes increases with n number and with ozone concentration. In some sampling experiments both generation and destruction of n-aldehydes by ozone are observed. In field experiments the results of sample analysis for n-aldehydes and benzaldehyde are frequently not proportional to sample volume whereas results for toluene and isoprene, and sometimes for total carbon, are. A simple theory is developed to simulate the net result of three processes: the adsorption of compounds from an air stream onto a solid adsorbent, the generation of compounds by reaction of ozone with materials upstream of or on the adsorbent, and the destruction by ozone of pre-existing compounds and compounds adsorbed from the sample stream. The use of distributed volume pairs is recommended as a way to identify loss of sample integrity during air monitoring experiments.

1-Propanol↗
PubMed1990

Determination of hydrazine in hydralazine by capillary gas chromatography with nitrogen-selective detection after benzaldehyde derivatization.

A method for the determination of hydralazine substance is described. Hydrazine is derivatized in aqueous media with benzaldehyde to benzalazine. After extraction to an organic phase containing a homologue as marker, the sample is subjected to capillary column gas chromatography with nitrogen-selective detection. A prolonged reaction with 0.1 M benzaldehyde of 20 min or more led to an increased level of benzalazine when hydralazine was analysed. An increase was also observed if the aqueous hydralazine sample had been allowed to stand for some time before analysis. The final method involved the use of a 5-min reaction time, fresh solutions and the standard addition principle. The levels of hydrazine found in hydralazine hydrochloride were below 1 ppm (as bases, 1 ng/mg).

Benzaldehydes↗
PubMed2002

A radiolabelling study of radicals derived from benzene, toluene and benzaldehyde sorbed in model environmental carbon.

Radiolabelled free radicals were formed by the addition of muonium--a radioactive hydrogen atom with a positive muon as its nucleus--to benzene, toluene and benzaldehyde, as sorbed in porous carbon. The activation parameters associated with their reorientational motion were measured using longitudinal-field muon spin relaxation (LF-MuSRx). Two distinct sorbed fractions were detected in each sample, characterised by molecular reorientational activation energies of 5.9/25.8 kJ/mol for benzene, 2.5/5.9 kJ/mol for toluene and 2.9/11.5 kJ/mol for benzaldehyde.

Benzaldehydes↗
PubMed2006

Rhodium assisted C-H activation of benzaldehyde thiosemicarbazones and their oxidation via activation of molecular oxygen.

The benzaldehyde thiosemicarbazones are found to undergo oxidation at the sulfur center upon reaction with [Rh(PPh3)3Cl] in refluxing ethanol in the presence of a base (NEt3). A group of organorhodium complexes are obtained from such reactions, in which the oxidized thiosemicarbazones are coordinated to rhodium as tridentate CNS donors, along with two triphenylphosphines and a hydride. From the reaction with para-nitrobenzaldehyde thiosemicarbazone, a second organometallic complex is obtained, in which the thiosemicarbazone is coordinated to rhodium as a tridentate CNS donor, along with two triphenylphosphines and a hydride. Reaction of the benzaldehyde thiosemicarbazones with [Rh(PPh3)3Cl] in refluxing ethanol in the absence of NEt3 affords another group of organorhodium complexes, in which the thiosemicarbazones are coordinated to rhodium as tridentate CNS donors, along with two triphenylphosphines and a chloride. Structures of representative complexes of each type of complexes have been determined by X-ray crystallography. In all of the complexes, the two PPh3 ligands are trans. All of the complexes show intense MLCT transitions in the visible region. Cyclic voltammetry on these complexes shows a Rh(III)-Rh(IV) oxidation on the positive side of SCE. Redox responses of the coordinated thiosemicarbazones are also displayed by all of the complexes.

Benzaldehydes↗
PubMed1999

2,4-Nonadienal and benzaldehyde bioantimutagens in Fushimi sweet pepper (Fushimi-togarashi).

Fushimi sweet pepper, "Fushimi-togarashi", is one of the "Kyo-yasai", traditional vegetables, in Kyoto, Japan. The chloroform fraction of Fushimi sweet pepper showed bioantimutagenicity on UV induced mutation in Escherichia coli B/r WP2. The bioantimutagen was purified with silica gel chromatography and identified as 2, 4-nonadienal (ID(50) = 20 microg/plate) on the basis of GC retention time and EI-MS spectrum of authentic 2,4-nonadienal. The sweet pepper also contained a known bioantimutagen, benzaldehyde (ID(50) = 2 mg/plate). Additive bioantimutagenicity was also observed by 2, 4-nonadienal with benzaldehyde. 2,4-Nonadienal did not show bioantimutagenicity in an UV excision repair deficient strain, E. coli B/r WP2s uvrA(-)(). Furthermore no delay of the first cell division after UV irradiation was observed in E. coli B/r WP2. These results indicate that the bioantimutagenic activity of 2, 4-nonadienal on UV mutagenesis might depend on the excision repair system in E. coli B/r WP2.

Aldehydes↗
PubMed2002

Asymmetric synthesis of beta-amino alcohols by reductive cross-coupling of benzylideneamine with planar chiral benzaldehydes.

[reaction: see text] Samarium iodide mediated reductive cross-coupling of N-tosyl benzylideneamine with benzaldehydes or the corresponding chromium complexes gave syn-beta-amino alcohol derivatives. A dynamic kinetic resolution of a configurationally equilibrated reactive species occurred in the cross-coupling with planar chiral benzaldehyde chromium complexes.

Amines↗