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Journal of Applied Toxicology : JAT 1996The metabolism and disposition of [2,3-14C]acrolein was studied in Sprague-Dawley rats after oral or intravenous dosing. Four groups of ten rats (five male and five...
The metabolism and disposition of [2,3-14C]acrolein was studied in Sprague-Dawley rats after oral or intravenous dosing. Four groups of ten rats (five male and five female) were dosed with radiolabeled acrolein intravenously at 2.5 mg kg-1 (Group 2), orally by gavage at 2.5 mg kg-1, either as a single dose (Group 3) or after 14 daily doses of unlabeled acrolein (Group 4), or orally by gavage at 15 mg kg-1 (Group 5). Urine, feces, expired air and organic volatiles were collected for 7 days, after which the animals were sacrificed and tissues collected. All samples were analyzed for total radioactivity. After 7 days, the excretory patterns of male and female rats were almost identical. Urinary excretion was highest in the intravenously dosed animals (66-69%) and lowest in the Group 5 animals (36-40%), whereas the reverse was true for feces (< 2% for i.v. Group 2 animals and 28-30% for the Group 5 animals). Carbon dioxide expiration was comparable (26-31%) across all groups. Tissue concentrations of radioactivity were minimal in all groups (< 1.2%), but concentrations of radioactivity were highest in the intravenous Group 2 animals. The time course of excretion for all groups was similar with the exception of the high-dose animal group, which showed a pronounced delay in excretion during the first 12 h.
Topics: Acrolein; Administration, Oral; Analysis of Variance; Animals; Carbon Dioxide; Carbon Radioisotopes; Feces; Female; Injections, Intravenous; Isotope Labeling; Male; Rats; Rats, Sprague-Dawley; Sex Factors; Tissue Distribution
PubMed: 8889798
DOI: 10.1002/(SICI)1099-1263(199609)16:5<449::AID-JAT369>3.0.CO;2-9 -
Journal of Agricultural and Food... Mar 2001The metabolism and distribution of [2,3-(14)C]acrolein were studied in a lactating goat orally administered 0.82 mg/kg of body weight/day for 5 days. Milk, urine, feces,...
The metabolism and distribution of [2,3-(14)C]acrolein were studied in a lactating goat orally administered 0.82 mg/kg of body weight/day for 5 days. Milk, urine, feces, and expired air were collected. The goat was killed 12 h after the last dose, and edible tissues were collected. The nature of the radioactive residues was determined in milk and tissues. All of the identified metabolites were the result of the incorporation of acrolein into the normal, natural products of intermediary metabolism. There was evidence that the three-carbon unit of acrolein was incorporated intact into glucose, and subsequently lactose, and into glycerol. In the case of other natural products, the incorporation of radioactivity appeared to result from the metabolism of acrolein to smaller molecules followed by incorporation of these metabolites into the normal biosynthetic pathways.
Topics: Acrolein; Administration, Oral; Animals; Biotransformation; Breath Tests; Carbon Radioisotopes; Feces; Female; Goats; Lactation; Milk; Tissue Distribution
PubMed: 11312907
DOI: 10.1021/jf000078z -
Spectrochimica Acta. Part A, Molecular... Aug 2009The geometrical structure, conformer energy differences, and conformational and vibrational dynamics of acrolein in (1,3)(pi,pi(*)) electronic states were investigated...
The geometrical structure, conformer energy differences, and conformational and vibrational dynamics of acrolein in (1,3)(pi,pi(*)) electronic states were investigated using a number of single- and multi-reference quantum-chemical methods. Peculiarities of acrolein in the (1)(pi,pi(*)) state were described with both conformers being significantly non-planar. A Valence Focal-Point Analysis of the conformer energy difference in the (3)(pi,pi(*)) state was performed. The coupling of the internal rotation about C-C and C=C bonds with large amplitude molecular motions, such as non-planar distortions of carbonyl, methylene, and methyne fragments was also investigated. The corresponding two-dimensional PES sections were constructed.
Topics: Acrolein; Models, Molecular; Molecular Conformation; Quantum Theory
PubMed: 19419904
DOI: 10.1016/j.saa.2009.03.008 -
Cancer Treatment Reports Apr 19763-Hydroxypropylmercapturic acid (MCA) has been quantitatively determined in the urine of rats given cyclophosphamide (CP), related antineoplastic agents, allyl alcohol,...
3-Hydroxypropylmercapturic acid (MCA) has been quantitatively determined in the urine of rats given cyclophosphamide (CP), related antineoplastic agents, allyl alcohol, or acrolein, with a simple procedure involving the use of an amino-acid analyzer. Male rats (300-400 g) injected with CP (50mg [179.1 mumols]/kg of body weight) excreted 16.7 mumols of MCA/kg in their 24-hour urine. Equivalent amounts of isophosphamide produced 9.0; triphosphamide, 16.1; ASTA-5607, 7.2; ASTA-5122, 4.1; and cytoxyl alcohol, 0.4mumols of MCA/kg. From allyl alcohol and acrolein, 26.3 and 19.7 mumols of MCA/kg were obtained respectively. MCA values were directly proportional to drug dose levels. Since acrolein and phosphorodiamidic acid mustard are the toxic decomposition products of aldophosphamide, and acrolein conjugation appears to be the first step for MCA formation values for MCA would reflect active CP levels. The in vitro interaction of acrolein with glutathione, other sulfhydryl compounds, and a few amino acids at concentrations of 0.15 mumols/ml was also studied. The decrease of acrolein's main absorption peak at 209 nm was used to follow its reaction rate. The faster interactions observed were with the sulfhydryl compounds, where a 50% decrease of absorption in interactions with glutathione and cysteine (at pH 7.4 and 23 degrees C) took place in 111 and 30 seconds respectively. Incubation of these adducts at 37 degrees C and 100 degrees C generated acrolein with a maximum recovery yield of 83% at 100 degrees C. Five patients given 1 g of CP iv excreted 6.4-50 mumols of MCA in their urine in 6 hours.
Topics: Acetylcysteine; Acrolein; Aldehydes; Alkylation; Animals; Chemical Phenomena; Chemistry; Cyclophosphamide; Glutathione; Humans; In Vitro Techniques; Male; Microsomes, Liver; Rats; Sulfhydryl Compounds
PubMed: 1277208
DOI: No ID Found -
The Journal of Chemical Physics Sep 2014The vibrational branching ratios in the photoionization of acrolein for ionization leading to the X̃²A' ion state were studied. Computed logarithmic derivatives of the...
The vibrational branching ratios in the photoionization of acrolein for ionization leading to the X̃²A' ion state were studied. Computed logarithmic derivatives of the cross section and the corresponding experimental data derived from measured vibrational branching ratios for several normal modes (ν9, ν10, ν11, and ν12) were found to be in relatively good agreement, particularly for the lower half of the 11-100 eV photon energy range considered. Two shape resonances have been found near photon energies of 15.5 and 23 eV in the photoionization cross section and have been demonstrated to originate from the partial cross section of the A' scattering symmetry. The wave functions computed at the resonance complex energies are delocalized over the whole molecule. By looking at the dependence of the cross section on the different normal mode displacements together with the wave function at the resonant energy, a qualitative explanation is given for the change of the cross sections with respect to changing geometry.
Topics: Acrolein; Ions; Photochemical Processes; Photons
PubMed: 25194366
DOI: 10.1063/1.4893702 -
The Analyst Jun 1987
Topics: Acrolein; Aldehydes; Electrochemistry; Gas Chromatography-Mass Spectrometry; Vehicle Emissions
PubMed: 2441624
DOI: 10.1039/an9871200859 -
Journal of Applied Toxicology : JAT Dec 1984Cinnamic acid is a compound of low toxicity, but its molecular structure and the known toxicity of similar molecules, such as styrene, have brought it to the... (Review)
Review
Cinnamic acid is a compound of low toxicity, but its molecular structure and the known toxicity of similar molecules, such as styrene, have brought it to the toxicologist's attention. Commercially, its use is permitted as flavouring and it is ubiquitous in products containing cinnamon oil and to a lesser extent in all plants. The related aldehyde, alcohol and esters are all more toxic than cinnamic acid. Certain substituted cinnamates containing cyano and fluoro moieties are of particular interest because they inhibit mitochondrial pyruvate transport. The literature about this whole group of commercially important compounds is diverse and many key studies are in languages other than English. This review looks at the history and legal constraints, as well as the results of metabolism and toxicology studies.
Topics: Acrolein; Animals; Chemical Phenomena; Chemistry; Cinnamates; Hippurates; Humans; Oxidation-Reduction
PubMed: 6394637
DOI: 10.1002/jat.2550040602 -
Chemistry (Weinheim An Der Bergstrasse,... Jul 2013
Topics: Acrolein; Catalysis; Imines; Nitriles; Stereoisomerism
PubMed: 23740616
DOI: 10.1002/chem.201301558 -
Chemical Research in Toxicology 1993The products of the reaction of the mutagenic aldehydes, acrolein and 2-bromoacrolein, with 2'-deoxycytidine and 2'-deoxyuridine have been determined. These products,...
The products of the reaction of the mutagenic aldehydes, acrolein and 2-bromoacrolein, with 2'-deoxycytidine and 2'-deoxyuridine have been determined. These products, formed at physiological conditions, were isolated by reverse-phase HPLC and characterized by UV, 1H NMR, fast atom bombardment MS, electrospray MS, and chemical transformation. The reaction of 2'-deoxycytidine with acrolein and 2-bromoacrolein produced the exocyclic compounds 3-(2'-deoxyribosyl)-7,8,9-trihydro-7-hydroxypyrimido[3,4- c]pyrimidin-2-one and 3-(2'-deoxyribosyl)-7,8,9-trihydro-7-hydroxy-8-bromopyrimido [3,4-c] pyrimidin-2-one, respectively. In addition to the chiral centers of deoxyribose, one new chiral center was formed from C-1 of acrolein and two new chiral centers were formed from C-1 and C-2 of 2-bromoacrolein, creating a mixture of diastereomers for each product. These compounds are not stable in basic solution and undergo ring opening and hydrolytic deamination, resulting in 2'-deoxyuridine adducts. The N3-alkylated 2'-deoxyuridines were also synthesized by permitting 2'-deoxyuridine to react with 2-bromoacrolein and acrolein. An unstable intermediate, N3-(2"-bromo-3"-oxopropyl)-2'-deoxyuridine, was also isolated and characterized from the reaction with 2-bromoacrolein. The reaction of 2'-deoxyuridine with acrolein gave N3-(3"-oxopropyl)-2'-deoxyuridine as the major product, which was reduced to its corresponding alcohol with NaBH4. Reactions of 2'-deoxycytidine with 2-bromoacrolein and acrolein proceed most rapidly at acidic or neutral pH; however, 2'-deoxyuridine reacts most rapidly at neutral or basic pH.
Topics: Acrolein; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Deoxycytidine; Deoxyuridine; Hydrolysis; Mass Spectrometry; Spectrometry, Mass, Fast Atom Bombardment; Spectrophotometry, Ultraviolet
PubMed: 8318647
DOI: 10.1021/tx00033a003 -
Food & Function Jun 2024Cinnamaldehyde (CA) is the main bioactive component extracted from the internal bark of cinnamon trees with many health benefits. In this paper, the bioavailability and... (Review)
Review
Cinnamaldehyde (CA) is the main bioactive component extracted from the internal bark of cinnamon trees with many health benefits. In this paper, the bioavailability and biological activities of cinnamaldehyde, and the underlying molecular mechanism are reviewed and discussed, including antioxidant, cardioprotective, anti-inflammatory, anti-obesity, anticancer, and antibacterial properties. Common delivery systems that could improve the stability and bioavailability of CA are also summarized and evaluated, such as micelles, microcapsules, liposomes, nanoparticles, and nanoemulsions. This work provides a comprehensive understanding of the beneficial functions and delivery strategies of CA, which is useful for the future application of CA in the functional food industry.
Topics: Acrolein; Humans; Drug Delivery Systems; Animals; Administration, Oral; Biological Availability; Nanoparticles; Antioxidants; Cinnamomum zeylanicum
PubMed: 38767618
DOI: 10.1039/d4fo00614c