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| Other Sizes |
| Targets |
trans-2-Hexenal does not have a specific pharmacological target in the traditional sense, as it is a naturally occurring volatile organic compound used primarily as a flavoring agent and plant defense signaling molecule. However, it is studied for its antimicrobial properties and plant defense functions. In biological systems, α,β-unsaturated aldehydes like trans-2-Hexenal can react with biological nucleophiles such as thiol groups in proteins and glutathione, potentially modulating cellular signaling pathways through electrophilic stress responses. It is also a sex pheromone produced by the female polyphemus moth. The compound is used as a bioactive compound for the determination of low-molecular-weight carbonyl compounds reactive with biological nucleophiles in biological samples.
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| ln Vitro |
In vitro, trans-2-Hexenal is primarily studied for its antimicrobial and antioxidant properties rather than as a therapeutic agent. The compound exhibits antimicrobial activity against various foodborne pathogens and spoilage microorganisms, making it a subject of interest in food preservation research. Its α,β-unsaturated aldehyde structure allows it to act as a Michael acceptor, reacting with nucleophilic residues in proteins and enzymes, thereby disrupting microbial cellular functions. Studies have investigated its ability to inhibit the growth of bacteria and fungi in vitro using standard broth microdilution or agar diffusion methods. Additionally, trans-2-Hexenal is used as a reference compound in analytical chemistry for the determination of low-molecular-weight carbonyl compounds in biological samples.
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| ln Vivo |
In vivo, trans-2-Hexenal is a naturally occurring compound found in plants and is produced by soybean plants as a volatile defense signal. Its biological effects in animals are primarily related to its metabolism and excretion as a food-derived aldehyde. When ingested, it is rapidly metabolized by aldehyde dehydrogenases and other detoxification enzymes to corresponding carboxylic acids, which are then further metabolized and excreted. The compound is generally recognized as safe (GRAS) for use as a flavoring agent in food products. In plant biology, trans-2-Hexenal functions as a signaling molecule involved in plant defense responses against herbivores and pathogens, triggering the expression of defense-related genes and the production of other protective compounds.
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| Enzyme Assay |
In vitro enzyme/receptor binding (non-cellular) assays for trans-2-Hexenal are not standard pharmacological assays, as the compound is primarily a flavoring agent and plant volatile. However, biochemical assays may investigate its reactivity with biological nucleophiles, such as glutathione (GSH) or protein thiol groups, using spectrophotometric or fluorometric methods. These assays typically involve incubating trans-2-Hexenal with GSH or model thiol compounds in buffer solutions at physiological pH and temperature, and monitoring the formation of adducts via changes in absorbance or fluorescence. The compound's ability to act as a Michael acceptor and form covalent adducts with nucleophilic residues can be quantified using LC-MS or HPLC-based methods. Such assays are relevant to understanding its potential biological activities and detoxification pathways.
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| Cell Assay |
In vitro cellular experiments with trans-2-Hexenal are not typically performed for pharmacological evaluation, but cytotoxicity and antimicrobial activity studies may be conducted using various cell lines or microbial strains. For cytotoxicity assessment, mammalian cell lines such as HepG2 (hepatocellular carcinoma) or Caco-2 (colorectal adenocarcinoma) are cultured in appropriate media and treated with varying concentrations of the compound for 24-72 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. For antimicrobial testing, bacterial strains such as E. coli, S. aureus, or L. monocytogenes are cultured in Mueller-Hinton broth and treated with serial dilutions of the compound. Minimum inhibitory concentrations (MICs) are determined after 16-24 hours of incubation at 37°C. Cells are maintained at 37°C in 5% CO₂ with appropriate media supplements.
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| Animal Protocol |
In vivo animal studies with trans-2-Hexenal are not conducted for therapeutic development, as the compound is a naturally occurring flavoring agent rather than a drug candidate. When animal studies are performed, they typically involve toxicological or metabolic studies following oral administration. Rodents are administered the compound via gavage at various doses, and blood, urine, and tissue samples are collected at specific time points to assess absorption, distribution, metabolism, and excretion. Metabolites are identified and quantified using LC-MS or GC-MS methods. These studies help establish the safety profile and metabolic fate of trans-2-Hexenal as a food ingredient. The compound is rapidly absorbed and metabolized, with the majority being excreted as metabolites in urine.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Uremic toxins often accumulate in the blood due to overeating or poor kidney filtration. Most uremic toxins are metabolic waste products that are normally excreted through urine or feces. Pharmacokinetic properties of trans-2-Hexenal are not extensively characterized as it is a naturally occurring flavoring agent rather than a drug. As a small lipophilic aldehyde (molecular weight 98.15), it is expected to be rapidly absorbed from the gastrointestinal tract and extensively metabolized by aldehyde dehydrogenases in the liver and other tissues to the corresponding carboxylic acid (2-hexenoic acid). The compound is volatile (boiling point 146-149°C) and can also be absorbed via inhalation. It is rapidly cleared from the circulation due to efficient metabolism and excretion. When used in flavoring applications, it is present at very low concentrations and is metabolized and eliminated without significant accumulation. Storage recommendations: 2-8°C in a cool, dark place. |
| Toxicity/Toxicokinetics |
Toxicity Summary
Uremic toxins, such as 2-hexenal, can be actively transported to the kidneys via organic ion transporters, particularly OAT3. Elevated uremic toxin levels can stimulate the production of reactive oxygen species (ROS). This appears to be mediated by the direct binding of uremic toxins to or inhibition of NADPH oxidases, particularly NOX4, which is abundant in the kidneys and heart (A7868). ROS can induce a variety of different DNA methyltransferases (DNMTs) involved in the silencing of the KLOTHO protein. KLOTHO has been shown to play an important role in anti-aging, mineral metabolism, and vitamin D metabolism. Multiple studies have shown that in acute or chronic kidney disease, KLOTHO mRNA and protein levels are decreased due to elevated local ROS levels (A7869). Toxicological information for trans-2-Hexenal indicates that it is generally recognized as safe (GRAS) for use as a flavoring agent in food at typical usage levels. The compound appears as a colorless to pale yellow clear liquid with a flash point of 43°C, indicating flammability. As an α,β-unsaturated aldehyde, it can be a skin and eye irritant at high concentrations due to its reactivity with biological nucleophiles. Inhalation of vapors may cause respiratory irritation. In occupational settings, appropriate safety precautions should be followed, including working in a well-ventilated area and using personal protective equipment (gloves, safety goggles). The compound is not approved for therapeutic use and is intended for research, flavor, and fragrance applications only. |
| References | |
| Additional Infomation |
(2E)-Hexenal is a 2-hexenal with an E-configuration of its olefinic double bond. It is naturally found in a variety of fruits, vegetables, and spices. It is used as a flavoring agent, antibacterial agent, and plant metabolite. It has been reported to be present in tea (Camellia sinensis), Indian anise (Aethus indicus), and several other organisms with relevant data. 2-Hexenal is a uremic toxin. Based on their chemical and physical properties, uremic toxins can be classified into three main categories: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as phenols; and 3) larger, so-called medium-molecular-weight compounds, such as β2-microglobulins. Long-term exposure to uremic toxins can lead to various diseases, including kidney damage, chronic kidney disease, and cardiovascular disease. 2-Hexenal is found in allspice. It is used in spices and flavorings. 2-Hexenal belongs to the medium-chain aldehyde class. Medium-chain aldehydes are aldehyde compounds with a carbon chain length between 6 and 12 carbon atoms.
trans-2-Hexenal (CAS 6728-26-3), also known as (E)-2-Hexenal or leaf aldehyde, is a naturally occurring α,β-unsaturated aldehyde with the molecular formula C₆H₁₀O and molecular weight 98.15. It appears as a colorless to pale yellow clear liquid with a boiling point of 146-149°C and a flash point of 43°C. The compound is found naturally in tomatoes, bananas, black tea, and many other fruits and vegetables, and is a key component of the characteristic "green" aroma of freshly cut plants. It is produced by soybean plants and is also a sex pheromone of the female polyphemus moth. trans-2-Hexenal is widely used as a flavoring agent in the food industry and as a fragrance ingredient. It is also studied for its antimicrobial and plant defense properties and is used as a bioactive compound for the determination of low-molecular-weight carbonyl compounds in biological samples. Purity is typically ≥95%. |
| Molecular Formula |
C₆H₁₀O
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|---|---|
| Molecular Weight |
98.14
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| Exact Mass |
98.073
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| CAS # |
6728-26-3
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| PubChem CID |
5281168
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.8±0.1 g/cm3
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| Boiling Point |
146.5±0.0 °C at 760 mmHg
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| Flash Point |
38.3±0.0 °C
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| Vapour Pressure |
4.6±0.2 mmHg at 25°C
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| Index of Refraction |
1.422
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| LogP |
1.58
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
7
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| Complexity |
64.6
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C([H])/C(/[H])=C(\[H])/C([H])([H])C([H])([H])C([H])([H])[H]
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| InChi Key |
MBDOYVRWFFCFHM-SNAWJCMRSA-N
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| InChi Code |
InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+
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| Chemical Name |
(E)-hex-2-enal
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| Synonyms |
Trans2Hexenal; Trans 2 Hexenal
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~509.48 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (25.47 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (25.47 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (25.47 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 10.1895 mL | 50.9476 mL | 101.8953 mL | |
| 5 mM | 2.0379 mL | 10.1895 mL | 20.3791 mL | |
| 10 mM | 1.0190 mL | 5.0948 mL | 10.1895 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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