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Usage

Uses

Used in Environmental Monitoring:
ACROLEIN 2,4-DINITROPHENYLHYDRAZONE is used as a chemical marker for the presence of acrolein in cigarette smoke. Its formation as a DNPH derivative enables the detection and quantification of acrolein levels, which is important for assessing the environmental impact and potential health risks associated with cigarette smoke exposure.
Used in Analytical Chemistry:
In the field of analytical chemistry, ACROLEIN 2,4-DINITROPHENYLHYDRAZONE serves as a valuable reagent for the identification and measurement of aliphatic aldehydes, such as acrolein. Its unique chemical properties allow for the selective reaction with aldehydes, facilitating their detection and analysis in complex samples.
Used in Toxicological Research:
ACROLEIN 2,4-DINITROPHENYLHYDRAZONE is utilized in toxicological research to study the effects of acrolein exposure. As a stable derivative of acrolein, it can be used to investigate the mechanisms of acrolein toxicity and its potential role in various health issues, including respiratory and cardiovascular diseases.
Used in Pharmaceutical Development:
In the pharmaceutical industry, ACROLEIN 2,4-DINITROPHENYLHYDRAZONE may be employed as a starting material or intermediate in the synthesis of drugs targeting aldehyde-metabolizing enzymes or pathways. Its unique structure and reactivity can be leveraged to develop novel therapeutic agents with potential applications in treating conditions related to aldehyde exposure or metabolism.

InChI:InChI=1/C9H8N4O4/c1-2-5-10-11-8-4-3-7(12(14)15)6-9(8)13(16)17/h2-6,11H,1H2

Upstream product

• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 107-02-8 acrolein 
• 93734-97-5 3-Benzolsulfonyl-propionaldehyd-<2.4-dinitro-phenylhydrazon> 
• 36986-33-1 2-(2-hydroxyethyl)-4-hydroxy-1,3-dioxane 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 500349-34-8 1,1,3-triacetoxy-propane 
• 108-90-7 chlorobenzene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 40964-63-4 1-phenyl-4-penten-1-yn-3-ol 
• 107-18-6 allyl alcohol 

Downstream Products

• 79348-65-5 C₉H₇BrN₄O₄ 

Relevant academic research and scientific papers

Removal of acrolein from active pharmaceutical ingredients using aldehyde scavengers

A variety of chemical compounds, intermediates, and reagents are used during the process of synthesizing active pharmaceutical ingredients (APIs). Some of these chemicals, intermediates, and reagents, as well as byproducts of synthetic processes, can have toxic properties and be present as impurities at low levels in the API or final drug formulation. If present at high concentrations, the toxic impurities could cause adverse health effects in humans. This paper describes a simple and rapid approach for selective removal of acrolein from APIs using iodixanol as a model API. Several scavengers were tested, and the resins which showed highest binding efficiency and selectivity were chosen for further evaluations. The kinetics of acrolein scavenging in the presence of the API iodixanol and the scavenging capacity of resins were demonstrated in this paper. The most complete scavenging is obtained with PS-NH2 which removes 97.8% of acrolein without any substantial removal of the API during 20 min of reaction time.

Scavenging of Acrolein by Food-Grade Antioxidant Propyl Gallate in a Model Reaction System and Cakes

Reactive carbonyl species (RCS), such as acrolein (ACR), glyoxal (GO), and methylglyoxal (MGO), have received extensive attention recently as a result of their high activity and toxicity in vitro and in vivo. In the present study, propyl gallate (PG), a common food antioxidant, was found to effectively trap more ACR than butylated hydroxytoluene and butylated hydroxyanisole through the formation of mono-ACR adducts (PG-ACR) and di-ACR adducts (PG-2ACR). The two adducts were successfully purified, and their structures were elucidated on the basis of their high-resolution mass spectrometry and1H,13C, and two-dimensional nuclear magnetic resonance data. We further identified that PG-ACR had the ability to continue to trap GO and MGO to form PG-ACR-GO and PG-ACR-MGO, respectively, by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Furthermore, we verified that PG could inhibit the production of ACR, GO, and MGO via trapping these RCS simultaneously to form the corresponding adducts in pound cakes using LC-MS/MS.

Disease-associated acrolein: A possible diagnostic and therapeutic substrate for in vivo synthetic chemistry

Acrolein, a highly reactive α,β-unsaturated aldehyde, is a compound to which humans are exposed in many different situations and often causes various human diseases. This paper summarizes the reports over the past twenty-five years regarding disease-associated acrolein detected in clinical patients and the role acrolein plays in various diseases. In several diseases, it was found that the increased acrolein acts as a pathogenetic factor. Thus, we propose the utility of over-produced acrolein as a substrate for a promising therapeutic or diagnostic method applicable to a wide range of diseases based on an in vivo synthetic chemistry strategy.

Application of screening experimental designs to assess chromatographic isotope effect upon isotope-coded derivatization for quantitative liquid chromatography-mass spectrometry

Isotope effect may cause partial chromatographic separation of labeled (heavy) and unlabeled (light) isotopologue pairs. Together with a simultaneous matrix effect, this could lead to unacceptable accuracy in quantitative liquid chromatography-mass spectrometry assays, especially when electrospray ionization is used. Four biologically relevant reactive aldehydes (acrolein, malondialdehyde, 4-hydroxy-2-nonenal, and 4-oxo-2-nonenal) were derivatized with light or heavy (d3-, 13C6-, 15N2-, or 15N4-labeled) 2,4-dinitrophenylhydrazine and used as model compounds to evaluate chromatographic isotope effects. For comprehensive assessment of retention time differences between light/heavy pairs under various gradient reversed-phase liquid chromatography conditions, major chromatographic parameters (stationary phase, mobile phase pH, temperature, organic solvent, and gradient slope) and different isotope labelings were addressed by multiple-factor screening using experimental designs that included both asymmetrical (Addelman) and Plackett-Burman schemes followed by statistical evaluations. Results confirmed that the most effective approach to avoid chromatographic isotope effect is the use of 15N or 13C labeling instead of deuterium labeling, while chromatographic parameters had no general influence. Comparison of the alternate isotope-coded derivatization assay (AIDA) using deuterium versus 15N labeling gave unacceptable differences (>15%) upon quantifying some of the model aldehydes from biological matrixes. On the basis of our results, we recommend the modification of the AIDA protocol by replacing d 3-2,4-dinitrophenylhydrazine with 15N- or 13C-labeled derivatizing reagent to avoid possible unfavorable consequences of chromatographic isotope effects.

Ammonium chlorochromate adsorbed on alumina: A new reagent for the oxidation of alcohols and benzoins to the corresponding carbonyl compounds

A new reagent, ammonium chlorochromate adsorbed on alumina, suitable for the oxidation of alcohols and benzoins to the corresponding carbonyl compounds is described.

AUTOOXIDATION OF ACETYLENES AND THEIR DERIVATIVES. XXV. 1-PHENYL-4-PENTEN-1-YN-3-0L AND 1-PHENYL-4-HEXEN-1-YN-3-OL

During the autooxidation of secondary enynyl alcohols attack by oxygen takes place at the C-H bonds at the α position to the triple and double bonds and the hydroxyl group.The initially formed unstable hydroxyhydroperoxides dissociate under the oxidation conditions into the corresponding enynyl ketones, acetylenic keto epoxydes, and products from degradation of the carbon skeleton.

KINETICS OF THE FORMATION OF 2,4-DINITROPHENYLHYDRAZONES IN HYDROCARBONS

The kinetics of the formation of 2,4-dinitrophenylhydrazones in a hydrocarbon medium were studied.By an integral method it was found that the reaction of carbonyl compounds with 2,4-dinitrophenylhydrazine is reversible, and the forward and reverse reactio

KINETICS AND MECHANISM OF THE REDOX REACTION OF THALLIC SULPHATE WITH ACROLEINE

The stoichiometry, kinetics and mechanism of the redox reaction of thallic sulphate with acroleine in aqueous sulphuric acid or in aqueous dioxane solutions were studied.The acroleine molecule is oxidised with Tl(III) ions in two consecutive one-electron step to glyceraldehyde.The corresponding rate equation is -d/dt = kn , where n = 0-2.The zeroth reaction order with respect to thallic ions is attributed to a slow enolization of the hydrated acroleine, which is the rate-determining step preceding the redox reaction proper.