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Food and Chemical Toxicology : An... Oct 2015The use of this material under current use conditions is supported by the existing information. This material was evaluated for genotoxicity, repeated dose toxicity,... (Review)
Review
The use of this material under current use conditions is supported by the existing information. This material was evaluated for genotoxicity, repeated dose toxicity, developmental toxicity, reproductive toxicity, local respiratory toxicity, phototoxicity, skin sensitization potential, as well as, environmental safety. Repeated dose toxicity was determined to have the most conservative systemic exposure derived NO[A]EL of 29.9 mg/kg/day. A dietary 14-week subchronic toxicity study conducted in rats on a suitable read across analog resulted in a MOE of 3784810 while considering 9.54% absorption from skin contact and 100% from inhalation. A MOE of > 100 is deemed acceptable.
Topics: Acrolein; Animals; Consumer Product Safety; DNA Damage; Dose-Response Relationship, Drug; Drug Evaluation, Preclinical; Endpoint Determination; Humans; No-Observed-Adverse-Effect Level; Perfume; Rats; Risk Assessment; Toxicity Tests
PubMed: 26364876
DOI: 10.1016/j.fct.2015.09.006 -
Methods in Molecular Biology (Clifton,... 2008Acrolein is an alpha,beta-unsaturated aldehyde with enormous capacity of reaction, occurs in the air like a pollutant, but it is (we know now) an important lipid...
Acrolein is an alpha,beta-unsaturated aldehyde with enormous capacity of reaction, occurs in the air like a pollutant, but it is (we know now) an important lipid peroxidation product as well. The compound is one of the several aldehydes produced from fatty acid oxidation, although it is particularly important because it constitutes the major electrophyle aldehyde derived from lipid oxidation. Acrolein can be formed actively from oxidized fatty acids and undergo aldolic condensation in alkaline pH; this is a particular characteristic that we have used in its process of separation with capillary electrophoresis. We have shown that the oxidation of unsaturated fatty acids forms acrolein, and that the use of capillary electrophoresis to be a powerful, sensitive, and attractive method for separation, identification, and quantization of this and other aldehydes from in vitro lipid peroxidation.
Topics: Acrolein; Adult; Chemical Fractionation; Electrophoresis, Capillary; Erythrocyte Membrane; Fatty Acids; Humans; Malondialdehyde; Oxidation-Reduction; Ozone; Reference Standards; Thiobarbiturates
PubMed: 19082946
DOI: 10.1007/978-1-60327-517-0_13 -
British Dental Journal Nov 2006
Topics: Acrolein; Flavoring Agents; Humans; Stomatitis
PubMed: 17099643
DOI: 10.1038/sj.bdj.4814224 -
Zeitschrift Fur Naturforschung. C,... Jan 2018While the chemical composition of leaf and stem bark essential oils of the Chinese cinnamon, Cinnamomum cassia (L.) J. Presl, has been well investigated, little is known...
While the chemical composition of leaf and stem bark essential oils of the Chinese cinnamon, Cinnamomum cassia (L.) J. Presl, has been well investigated, little is known about the volatilom of its buds, which appeared recently on German markets. Soxhlet extracts of the commercial samples were prepared, fractionated using silica gel and characterised by gas chromatography-flame ionisation detector (GC-FID) for semi-quantification, by gas chromatography-mass spectrometry (GC-MS) for identification and by GC-FID/olfactometry for sensory evaluation. Cinnamaldehyde was the most abundant compound with concentrations up to 40 mg/g sample. In total, 36 compounds were identified and 30 were semi-quantified. The extracts contained mostly phenylpropanoids, mono- and sesquiterpene hydrocarbons and oxygenated derivatives. Because of the high abundance of cinnamaldehyde, the aldehyde fraction was removed from the extracts by adding hydrogen sulphite to improve both the detection of trace compounds and column chromatography. The aldehyde fraction was analysed by GC-MS separately. The highest flavour dilution factor of 316 was calculated for cinnamaldehyde. Other main sensory contributors were 2-phenylethanol and cinnamyl alcohol. This report provides the first GC-olfactometry data of a plant part of a Cinnamomum species. The strongly lignified C. cassia buds combine a high abundance of cinnamaldehyde with comparably low coumarin concentrations (<0.48 mg/g), and provide a large cinnamaldehyde depot for slow release applications.
Topics: Acrolein; Cinnamates; Cinnamomum aromaticum; Flowers; Plant Extracts; Sesquiterpenes; Volatile Organic Compounds
PubMed: 29145172
DOI: 10.1515/znc-2017-0087 -
Chemical Research in Toxicology Nov 2007The smoke-borne electrophile acrolein reacts extensively with proteins, forming carbonyl-retaining Michael adducts that may be attacked by adjacent protein nucleophiles...
The smoke-borne electrophile acrolein reacts extensively with proteins, forming carbonyl-retaining Michael adducts that may be attacked by adjacent protein nucleophiles to form cross-links. Because little information is available concerning the extent of intermolecular protein cross-linking during acrolein toxicity in cells, we used an antibody against a known target for toxic carbonyls, the chaperone protein Hsp90, to detect the formation of high-mass protein complexes in acrolein-exposed A549 cells. A 3 h exposure to acrolein (0 to 200 microM) resulted in concentration-dependent formation of a single high-mass band (approx. 180 kDa). This species was detected in cells exposed to just 50 microM acrolein, a concentration that did not elicit acute cell death as assessed by measurements of cell ATP levels. The formation of cross-linked Hsp90 coincided with a rapid loss of carbonyl adducts within cells that had been subjected to a brief "pulse" exposure to a subtoxic concentration of acrolein, suggesting Michael adducts are short-lived within cells due in part to consumption during reactions with protein nucleophiles. Cross-linked Hsp90 persisted following an overnight recovery incubation, suggesting the cellular ability to repair or degrade these species is limited. Two known carbonyl scavengers, hydralazine and bisulfite, strongly protected against the ATP depletion accompanying acrolein exposure, but only the latter suppressed protein adduction and Hsp90 cross-linking. As previously shown for hydralazine, mass spectrometry studies using a model peptide indicated that bisulfite traps carbonyl groups possessed by Michael addition adducts, and such adduct-trapping reactivity appeared to contribute to the blockade of Hsp90 cross-linking in acrolein-preloaded cells. Collectively, these findings establish that formation of stable intermolecular protein cross-links accompanies exposure to acrolein. Future clarification of the chemistry underlying this damage may provide novel biomarkers of acrolein exposure.
Topics: Acrolein; Adenosine Triphosphate; Blotting, Western; Cell Line, Tumor; Cross-Linking Reagents; Cytoprotection; HSP90 Heat-Shock Proteins; Humans; Hydralazine; Lung; Mass Spectrometry; Protein Carbonylation; Sulfites
PubMed: 17907782
DOI: 10.1021/tx700192e -
BioMed Research International 2020Neurodegenerative diseases are devastating and incurable disorders characterized by neuronal dysfunction. The major focus of experimental and clinical studies are... (Review)
Review
Neurodegenerative diseases are devastating and incurable disorders characterized by neuronal dysfunction. The major focus of experimental and clinical studies are conducted on the effects of natural products and their active components on neurodegenerative diseases. This review will discuss an herbal constituent known as cinnamaldehyde (CA) with the neuroprotective potential to treat neurodegenerative disorders, such as Alzheimer's disease (AD) and Parkinson's disease (PD). Accumulating evidence supports the notion that CA displays neuroprotective effects in AD and PD animal models by modulating neuroinflammation, suppressing oxidative stress, and improving the synaptic connection. CA exerts these effects through its action on multiple signaling pathways, including TLR4/NF-B, NLRP3, ERK1/2-MEK, NO, and Nrf2 pathways. To summarize, CA and its derivatives have been shown to improve pathological changes in AD and PD animal models, which may provide a new therapeutic option for neurodegenerative interventions. To this end, further experimental and clinical studies are required to prove the neuroprotective effects of CA and its derivatives.
Topics: Acrolein; Animals; Disease Models, Animal; Disease Progression; Humans; Inflammation; Neurodegenerative Diseases; Neuroprotective Agents
PubMed: 33274192
DOI: 10.1155/2020/1034325 -
Zeitschrift Fur... Feb 1951
Topics: Acrolein; Alcoholic Beverages; Flavoring Agents; Fruit; Humans; Wine
PubMed: 14837079
DOI: 10.1007/BF02033277 -
Molecules (Basel, Switzerland) Mar 2017The antioxidant activity of ferulic acid (), ferulic acid (), coniferyl aldehyde (), methyl ferulate (), and ethyl ferulate () were investigated using...
The antioxidant activity of ferulic acid (), ferulic acid (), coniferyl aldehyde (), methyl ferulate (), and ethyl ferulate () were investigated using 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and ferric-reducing antioxidant power (FRAP) assays and autoxidation of triacylglycerols of commercially available sunflower oil (TGSO). The compounds tested for ability to scavenge ABTS radical cations was in the order of ferulic acid > coniferyl aldehyde ≈ ferulic acid > ethyl ferulate ≈ methyl ferulate. The results of the FRAP assay for ferulic acid, ferulic acid, and coniferyl aldehyde were similar to and higher than those of methyl ferulate and ethyl ferulate. In the lipid system, ferulic acid showed weak antioxidant activity. The other ferulates exhibited much stronger, yet similar, activities.
Topics: Acrolein; Antioxidants; Caffeic Acids; Coumaric Acids; Molecular Structure; Oxidation-Reduction; Structure-Activity Relationship
PubMed: 28346342
DOI: 10.3390/molecules22040527 -
Mutation Research Jun 1999The reduced form of glutathione (GSH) is a well-known antioxidant, while there have been few reports indicating the contribution of glutathione to protection of...
The reduced form of glutathione (GSH) is a well-known antioxidant, while there have been few reports indicating the contribution of glutathione to protection of Escherichia coli cells from the lethal effect of oxidative damage. Here, we report that depletion of glutathione causes hypersensitivity of E. coli to acrolein, the structurally simplest alpha, beta-unsaturated aldehyde derived from lipid peroxide-degradation, and that GSH can chemically react with acrolein in vitro thus reducing its toxicity. We further demonstrated that acrolein inactivates glutathione oxidoreductase followed by depletion of glutathione, probably as a part of the toxic effect of acrolein. These results suggested that GSH contributes to cellular defense against the toxic effects.
Topics: Acrolein; Escherichia coli; Glutathione; Glutathione Reductase; Hydrogen Peroxide; Kinetics; Mutagens; Oxidative Stress
PubMed: 10366767
DOI: 10.1016/s1383-5718(99)00052-2 -
Chemical Research in Toxicology Apr 1998The structures and conformations of adducts formed by reaction of guanosine with several mutagenic alpha,beta-unsaturated carbonyl compounds have been investigated by... (Comparative Study)
Comparative Study
The structures and conformations of adducts formed by reaction of guanosine with several mutagenic alpha,beta-unsaturated carbonyl compounds have been investigated by semi-empirical molecular orbital calculations and compared with NMR spectral results. Two cyclization processes taking place on the pyrimidine ring of guanine leading to two sets of regioisomers, 11-hydroxy- and 13-hydroxytetrahydropyrimidinoguanines (THPG), were considered. Relative stabilities and geometries of all configurations and conformations of adducts with acrolein, crotonaldehyde, and alpha-chloroacrolein were calculated by PM3, AM1, and MNDO methods. PM3 results were the most compatible with experimental structures based on 400-MHz 1H NMR spectroscopy. The most stable structures for the 11-hydroxy and 13-hydroxy THPG isomers from acrolein are predicted to have chair-like structures for the tetrahydropyrimidine ring and axial hydroxyl groups, as suggested by the NMR spectra of the isolated adducts. Of the possible isomers from guanine and crotonaldehyde, cis-11-hydroxy-13-methyl THPG with methyl and hydroxyl groups axial is predicted to be the most stable. The only isolated adduct is the trans-13-hydroxy-11-methyl THPG with methyl shown to be equatorial and hydroxyl axial by 1H NMR. This is completely consistent with the geometry predicted by PM3 for the 13-hydroxy regioisomer of crotonaldehyde. In the case of adducts of alpha-chloroacrolein, one stereoisomer predominates for each of the two possible regioisomers. For the 12-chloro-11-hydroxy isomer, the cis configuration with chlorine axial and hydroxyl quasi-axial is calculated to have the most stable geometry. In contrast, the 1H NMR spectrum supports a trans diaxial orientation, although the cis computed structure could also be accommodated by the spectrum. The 12-chloro-13-hydroxy regioisomer is unambiguously assigned as trans diaxial by PM3 calculations and 1H NMR spectroscopy.
Topics: Acrolein; Aldehydes; DNA Adducts; Guanine; Magnetic Resonance Spectroscopy; Mutagens
PubMed: 9548798
DOI: 10.1021/tx970152g