4488-48-6

Usage

Uses

Used in Food Industry:
2,4-HEXADIENAL is used as a flavoring agent for its ability to enhance the taste and aroma of various food products, making it an essential component in the creation of natural and artificial flavors.
Used in Fragrance Industry:
In the fragrance industry, 2,4-HEXADIENAL is utilized as an ingredient in perfumes, leveraging its strong odor to contribute to the overall scent profile of different fragrances.
Used in Industrial Applications:
2,4-HEXADIENAL is studied for its potential antioxidant properties, which could make it a valuable additive in various industrial processes where oxidation resistance is required.
Used in Medical Applications:
2,4-HEXADIENAL is also of interest in the medical field due to its antimicrobial properties, suggesting potential uses in the development of new treatments or preventative measures against microbial infections.

Upstream product

• 110-89-4 piperidine 
• 64-17-5 ethanol 
• 75-07-0 acetaldehyde 
• 64-19-7 acetic acid 
• 123-73-9 crotonaldehyde 
• 107-89-1 acetaldol 
• 127-09-3 sodium acetate 
• 123-73-9 trans-Crotonaldehyde 
• 7422-90-4 acetaldehydedimethylhydrazone 
• 17102-64-6 Sorbyl alcohol 
• 64724-29-4 tributyl-((Z)-2-ethoxy-vinyl)-stannane 
• 7664-41-7 ammonia 
• 7732-18-5 water 
• 25724-11-2 1.1.3.5-tetramethoxy-hexane 

Downstream Products

• 5205-32-3 octa-2,4,6-trienoic acid 
• 58927-78-9 (2E,4E)-1-phenyl-2,4-hexadien-1-ol 
• 150197-74-3 (3S,6S)-6-((2S,4S,5R)-3,4-Dimethyl-5-phenyl-oxazolidin-2-yl)-3-methyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester 
• 5941-49-1 2E,4E,6E-octatrienoic acid ethyl ester 
• 86590-03-6 2-(2E,4E-hexadienylamino)phenol 
• 134962-98-4 4-Methyl-6-((1E,3E)-penta-1,3-dienyl)-5,6-dihydro-2H-pyran-2-ol 
• 1334144-90-9 methyl (1R,2S,6R)-1-benzamido-2-(3,3-dibromoallyl)-6-(pyridin-3-yl)cyclohex-3-enecarboxylate 
• 1334144-86-3 methyl (1S,2R,6S)-1-benzamido-2-(3,3-dibromoallyl)-6-phenylcyclohex-3-enecarboxylate 
• 1334144-87-4 methyl (1S,2R,6S)-1-benzamido-2-(3,3-dibromoallyl)-6-p-tolylcyclohex-3-enecarboxylate 
• 1334144-88-5 methyl (1S,2R,6S)-1-benzamido-2-(3,3-dibromoallyl)-6-(4-methoxyphenyl)cyclohex-3-enecarboxylate 
• 1334144-89-6 methyl (1S,2R,6S)-1-benzamido-6-(2-bromophenyl)-2-(3,3-dibromoallyl)cyclohex-3-enecarboxylate 
• 1334144-91-0 methyl (1R,2S,6S)-1-benzamido-2-(3,3-dibromoallyl)-6-(thiophen-2-yl)cyclohex-3-enecarboxylate 
• 54716-12-0 (2Z,4E)-hexa-2,4-dienal 
• 127717-91-3 3,6-dimethyl-7-methoxy-9H-pyrrolo<1,2-a>indol-9-ol 

Relevant academic research and scientific papers

Ambruticins: tetrahydropyran ring formation and total synthesis

The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.

Synthesis of α,β- and β-Unsaturated Acids and Hydroxy Acids by Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol Derivatives

We report a reaction platform for the synthesis of three different high-value specialty chemical building blocks starting from bio-ethanol, which might have an important impact in the implementation of biorefineries. First, oxidative dehydrogenation of ethanol to acetaldehyde generates an aldehyde-containing stream active for the production of C4 aldehydes via base-catalyzed aldol-condensation. Then, the resulting C4 adduct is selectively converted into crotonic acid via catalytic aerobic oxidation (62 % yield). Using a sequential epoxidation and hydrogenation of crotonic acid leads to 29 % yield of β-hydroxy acid (3-hydroxybutanoic acid). By controlling the pH of the reaction media, it is possible to hydrolyze the oxirane moiety leading to 21 % yield of α,β-dihydroxy acid (2,3-dihydroxybutanoic acid). Crotonic acid, 3-hydroxybutanoic acid, and 2,3-dihydroxybutanoic acid are archetypal specialty chemicals used in the synthesis of polyvinyl-co-unsaturated acids resins, pharmaceutics, and bio-degradable/ -compatible polymers, respectively.

Step-Economic Synthesis of Biomimetic β-Ketopolyene Thioesters and Demonstration of Their Usefulness in Enzymatic Biosynthesis Studies

Studies on the biosynthetic processing of polyene thioester intermediates are complicated by limited access to appropriate substrate surrogates. We present a step-economic synthetic access to biomimetic β-ketopolyene thioesters that is based on an Ir-catalyzed reductive Horner-Wadsworth-Emmons olefination. New β-ketotriene and pentaenethioates of pantetheine and N-acetylcysteamine were exemplarily synthesized via short and concise routes. The usefulness of these compounds was demonstrated in an in vitro assay with the ketoreductase domain MycKRB from mycolactone biosynthesis.

An Engineered Alcohol Oxidase for the Oxidation of Primary Alcohols

Structure-guided directed evolution of choline oxidase has been carried out by using the oxidation of hexan-1-ol to hexanal as the target reaction. A six-amino-acid variant was identified with a 20-fold increased kcat compared to that of the wild-type enzyme. This variant enabled the oxidation of 10 mm hexanol to hexanal in less than 24 h with 100 % conversion. Furthermore, this variant showed a marked increase in thermostability with a corresponding increase in Tm of 20 °C. Improved solvent tolerance was demonstrated with organic solvents including ethyl acetate, heptane and cyclohexane, thereby enabling improved conversions to the aldehyde by up to 30 % above conversion for the solvent-free system. Despite the evolution of choline oxidase towards hexan-1-ol, this new variant also showed increased specific activities (by up to 100-fold) for around 50 primary aliphatic, unsaturated, branched, cyclic, benzylic and halogenated alcohols.

Structure-Guided Evolution of Aryl Alcohol Oxidase from Pleurotus eryngii for the Selective Oxidation of Secondary Benzyl Alcohols

Aryl alcohol oxidase (AAO) is a fungal flavoenzyme capable of oxidizing aromatic primary alcohols into their correspondent aldehydes through a stereoselective hydride abstraction. Unfortunately, this enzyme does not act on secondary benzyl alcohols in racemic mixtures due to the strict control of substrate diffusion and positioning at the active site restricted to primary benzyl alcohols. Here we describe the engineering of AAO from Pleurotus eryngii to oxidize chiral benzyl alcohols with high enantioselectivity. The secondary benzyl alcohol oxidase was remodeled at the active site through four cycles of structure-guided evolution, including a final step of in vivo site-directed recombination to address the positive epistatic interactions between mutations. The final variant, with five substitutions and a renovated active site, was characterized at biochemical and computational level. The mutational sculpting helped position the bulkier (S)-1-(p-methoxyphenyl)-ethanol, improving the mutant's catalytic efficiency by three orders of magnitude relative to the native enzyme while showing a high enantioselectivity (ee >99%). As a promising candidate for racemic resolution, this evolved secondary benzyl alcohol oxidase maintained its natural stereoselective mechanism while displaying activity on several secondary benzyl alcohols. (Figure presented.).

Ethanol to Butanol Conversion over Bifunctional Zeotype Catalysts Containing Palladium and Zirconium

Abstract: A study of the kinetics of ethanol conversion in the presence of Zr-containing zeolites BEA doped with palladium particles has revealed the order of formation of the main reaction products. It has been shown that the primary processes are ethanol dehydrogenation to acetaldehyde on Pd sites and ethanol dehydration to diethyl ether on the acid sites of the catalyst. After that, acetaldehyde undergoes the aldol–croton condensation reaction to form crotonal, which is hydrogenated to butanol on the metal sites. Butanol, in turn, is dehydrated into butenes, which undergo hydrogenation to butane. The presence of hydrogen in the gas phase leads to the displacement of ethanol from the metal surface and prevents the formation of surface carbonates and acetates. It has been found that hydrogen significantly accelerates ethanol dehydration owing to a decrease in the activation energy, which can be attributed to hydrogen spillover to the zeolite. The addition of water inhibits all acid-catalyzed reactions owing to competitive adsorption on acid sites and thereby decreases the butanol yield and the ethanol conversion.

Length-Selective Synthesis of Acylglycerol-Phosphates through Energy-Dissipative Cycling

The main aim of origins of life research is to find a plausible sequence of transitions from prebiotic chemistry to nascent biology. In this context, understanding how and when phospholipid membranes appeared on early Earth is critical to elucidating the prebiotic pathways that led to the emergence of primitive cells. Here we show that exposing glycerol-2-phosphate to acylating agents leads to the formation of a library of acylglycerol-phosphates. Medium-chain acylglycerol-phosphates were found to self-assemble into vesicles stable across a wide range of conditions and capable of retaining mono- and oligonucleotides. Starting with a mixture of activated carboxylic acids of different lengths, iterative cycling of acylation and hydrolysis steps allowed for the selection of longer-chain acylglycerol-phosphates. Our results suggest that a selection pathway based on energy-dissipative cycling could have driven the selective synthesis of phospholipids on early Earth.

Synthesis of Tetradecapentaenoic Acid Derivatives

A 12-stage method for the stereoselective synthesis of tetradecapentaenoic acid derivatives using phosphoric reagents was developed. The key step in the synthesis is the Z-selective Wittig reaction between sorbaldehyde and triphenylphosphonium (6-methoxycarbonyl)hexanilide, as well as the Ramirez-Corey-Fuchs reaction and the Trost-Kazmaier rearrangement. The synthesized (2E,4E,8Z,10E,12E)-N-isobutyltetradeca-2,4,8,10,12-pentaenamide corresponds to a natural compound called γ-Sansho?l.

Catalytic Reactions of Homo- and Cross-Condensation of Ethanal and Propanal

Abstract: Processes of catalytic homocondensation of propanal and its cross-condensation with ethanal and methanal in the presence of aniline and amino acids have been studied. The dependence of the conversion of the reactants and selectivity of the homo/heterocondensation process on the catalyst nature and temperature has been revealed. It has been shown that the maximum acrolein selectivity is reached in the case of using benzoyl-substituted derivatives in water, with the proportion of the products of further condensation decreasing. The selectivity for the ethanal homocondensation product 2-butenal decreases simultaneously as a result of the formation of linear and branched oligomers of successive condensation.

METHOD FOR PRODUCING 2,4-DIENAL ACETAL COMPOUND AND 2,4-DIENAL COMPOUND

Methods of producing a 2,4-dienal acetal compound and a 2,4-dienal compound useful as synthesis intermediates of a sex pheromone compound having a conjugated diene structure or a conjugated triene structure. More specifically, a method produces a 2,4-dienal acetal compound of Formula (2): R1CH═CH—CH═CH—CH(OR2)(OR3), including a step of subjecting a 2-enal acetal compound having a leaving group X at position C5 and being expressed by Formula (1): R1CHX—CH2—CH═CH—CH(OR2)(OR3) to an elimination reaction in the presence of a base to obtain the 2,4-dienal acetal compound (2); and a method for producing a 2,4-dienal compound of Formula (3): R1CH═CH—CH═CH—CHO, further including a step of deprotecting the 2,4-dienal acetal compound (2) to obtain the 2,4-dienal compound (3).