142-83-6

Usage

Uses

Used in Flavor and Fragrance Industry:
(E,E)-2,4-Hexadienal is used as a flavoring agent for its sweet, green, waxy, aldehydic taste with fresh melon nuances. It is particularly useful in the food industry to enhance the taste of various products.
Used in Chemical Synthesis:
(E,E)-2,4-Hexadienal serves as a chemical intermediate in various organic synthetic reactions, contributing to the production of different compounds.
Used in Manufacturing Sorbic Acid:
(E,E)-2,4-Hexadienal is used as a raw material in the manufacture of sorbic acid, which is a widely used preservative in the food and pharmaceutical industries.
Used in Pharmaceutical Industry:
(E,E)-2,4-Hexadienal is used as a pharmaceutical intermediate in the manufacture of mitomycins and antihypercholesteraemics, highlighting its importance in the development of various medications.
Used in Corrosion Inhibition:
(E,E)-2,4-Hexadienal acts as an inhibitor of corrosion for steel used in oil field operations, playing a crucial role in maintaining the integrity of equipment and infrastructure.
Used in Polymer Production:
(E,E)-2,4-Hexadienal is used as a monomer in reactions with silane comonomers for the manufacture of polyalkenyloxysilane polymer, which has potential applications in various industries.
Used in Pest Control:
(E,E)-2,4-Hexadienal is used as a fumigant against larvae of the Caribbean fruit fly, demonstrating its utility in agricultural and pest management practices.
Used in Synthesis of Chiral Cycloadducts:
(E,E)-2,4-Hexadienal is also used in the synthesis of chiral cycloadducts, which are important in the development of enantiomerically pure compounds for various applications, including pharmaceuticals and agrochemicals.

Preparation

Can be obtained by slowly heating crotonaldehyde with acetaldehyde in the presence of pyridine at 85 to 90°C.

InChI:InChI=1/C6H8O/c1-2-3-4-5-6-7/h2-6H,1H3/b3-2+,5-4+

Upstream product

• 110-89-4 piperidine 
• 64-17-5 ethanol 
• 75-07-0 acetaldehyde 
• 64-19-7 acetic acid 
• 123-73-9 crotonaldehyde 
• 821-42-1 pentenedial 
• 25724-11-2 1.1.3.5-tetramethoxy-hexane 
• 1593-50-6 pentenedial; sodium enolate 
• 107-89-1 acetaldol 
• 127-09-3 sodium acetate 
• 123-73-9 trans-Crotonaldehyde 
• 7422-90-4 acetaldehydedimethylhydrazone 
• 17102-64-6 Sorbyl alcohol 
• 6044-68-4 3,3-dimethoxyprop-1-ene 

Downstream Products

• 94088-28-5 1,1-Diethoxyhexa-2,4-diene 
• 105540-72-5 3-ethoxy-2-ethyl-octa-4t,6t-dienal 
• 5205-32-3 octa-2,4,6-trienoic acid 
• 58927-78-9 (2E,4E)-1-phenyl-2,4-hexadien-1-ol 
• 110-44-1 sorbic Acid 
• 111-28-4 2,4-hexadiene-1-ol 
• 17102-64-6 Sorbyl alcohol 
• 928-92-7 (E)-hex-4-en-1-ol 
• 110-44-1 hexa-2,4-dienoic acid 
• 66-25-1 hexanal 
• 111-27-3 hexan-1-ol 
• 5963-20-2 2-oxo-nona-3,5,7-trienoic acid 
• 29179-34-8 1-phenylocta-2,4,6-trien-1-one 
• 42022-66-2 hexa-2t,4t-dienal-(2,4-dinitro-phenylhydrazone) 

Relevant academic research and scientific papers

A Diels-Alder macrocyclization enables an efficient asymmetric synthesis of the antibacterial natural product abyssomicin C

An efficient and highly diastereoselective intramolecular Diels-Alder reaction is the basis of a concise asymmetric synthesis of the potent antibacterial natural product abyssomicin C (see formula). The complexity of the target structure was reduced to three fragments and required two carbonyl addition reactions to achieve key bond formations. (Figure Presented).

Palladium-Catalyzed Three Carbon Chain Extension Reactions with Acrolein Acetals. A Convenient Synthesis of Conjugated Dienals

A variety of vinylic halides has been found to react with acrolein or methacrolein acetals and amines with palladium catalysts to form 5-amino 3-enal acetals and/or dienal acetals.The reaction products yield 2,4-dienals on treatment with aqueous acids, in moderate to good yields.Crotonaldehyde dimethyl acetal also undergoes the reaction, but only in low yields. 3-Buten-2-one ethylene ketal reacted well under the same conditions, however, and Hofmann elimination and hydrolysis of the product amine gave (E,E)-3,5-heptadien-2-one in 90percent yield.

Cu(II)-catalyzed selective aerobic oxidation of alcohols under mild conditions

Aerobic Alcohol Oxidation. An efficient four-component system consisting of acetamido-TEMPO/Cu(ClO4)2/TMDP/DABCO in DMSO has been developed for room-temperature aerobic alcohol oxidation. Under the optimal conditions, various alcohols could be converted into their corresponding aldehydes or ketones in good to excellent yields. The newly developed catalytic system could also be recycled and reused for three runs without any significant loss of catalytic activity.

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.

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.

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.

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.

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).

CONVERSION OF ALCOHOLS TO LINEAR AND BRANCHED FUNCTIONALIZED ALKANES

Embodiments herein concerns the eco-friendly conversion of simple alcohols to linear or branched functionalized alkanes, by integrated catalysis. The alcohols are firstlyoxidized either chemically or enzymatically to the corresponding aldehydes or ketones, followed by aldol condensations using a catalyst to give the corresponding enals or enones. The enals or enones are subsequently and selectively hydrogenated using a recyclable heterogeneous metal catalyst, organocatalyst or an enzyme to provide linear or branched functionalized alkanes with an aldehyde, keto- or alcohol functionality. The process is also iterative and can be further extended by repeating the above integrated catalysis for producing long-chain functionalized alkanes from simple alcohols.

Synthesis of trans-Configured Enol Ethers by a Sequence of syn-Selective Glycolate Aldol Addition, Hydrolysis, and Grob Fragmentation

A trans-selective access to enol ethers with a disubstituted C=C bond was developed. It consists of a diastereoselective glycolate aldol addition, a hydrolysis, and a Grob fragmentation. Aldol additions of N-[(benzyloxy)acetyl]oxazolidinones furnished syn-aldols selectively. Hydrolytic removal of the auxiliaries gave α-benzyloxy-β-hydroxycarboxylic acids. Exposure to DMF dineopentylacetal induced Grob fragmentations, which delivered trans-configured enol ethers. Applying our 3-step sequence in a bidirectional synthesis led to bis(enol ethers) trans,trans-selectively, i.e., to a motif rarely encountered in the literature. A modified precursor synthesis allowed for the first time to access both the E- and the Z-isomer of an enol ether with a trisubstituted C=C bond stereoselectively using a Grob fragmentation route. The Ar–Br and C≡C–SiMe2tBu motifs of appropriate enol ethers engaged in follow-up reactions via organometallics. These provided more elaborated enol ethers.