4-OHE
Based on 1 Customer Validation
4-OHE ((E)-4-Oxo-2-hexenal) is a mutagen formed by omega-3 lipid peroxidation. 4-OHE reacts with deoxyguanosine, deoxycytidine and 5-methyldeoxycytidine to form covalent adducts. 4-OHE induces apoptosis and exhibits genotoxicity. 4-OHE inhibits the growth of Gram-positive and Gram-negative bacteria, which correlates with its electrophilic reactivity towards nucleophilic biomolecules. 4-OHE is a chemical defense component of Dolycoris baccarum (sloe bug), and acts as a deterrent and toxin against insect predators.
Nos produits utilisent uniquement pour la recherche. Nous ne vendons pas aux patients.
- Pureté : 98.97%
- CAS No.: 2492-43-5
- Formule: C6H8O2
- Masse moléculaire:112.13
-
Stockage:
-20°C, protect from light, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
-
Activité biologique
-
Chemical Information
-
Solvant et solubilité
- Protocole
- Pureté et documentation
- Références
-
Help & FAQs
Activité biologique
Description
In Vitro
4-OHE induces mutagenicity in Salmonella typhimurium TA100 and Salmonella typhimurium TA104[1].
4-OHE induces apoptosis in human HL-60 cells[1].
4-OHE forms three types of DNA adducts with double-stranded calf thymus DNA[1].
4-OHE is a substance formed by peroxidation of ω-3 polyunsaturated fatty acid (methyl linolenate) in the presence of heme, and it can react with deoxyguanosine (dG) to form adducts[1].
4-OHE (10-1000 μg/disc; 24 h) exhibits concentration-dependent antimicrobial activity against Micrococcus luteus APU4a, Methylophilus sp. APU211a, Pseudomonas sp. APU3a, and Spirosoma sp. APU1a[2].
4-OHE (1.25-10 mg/plate; 60 min) exhibits dose-dependent mutagenic activity against Salmonella typhimurium strains TA100 (78 revertants/mg) and TA104 (67 revertants/mg) in in vitro assays without metabolic activation[3].
4-OHE forms adducts with dG, dC and 5-Me-dC in vitro, and the amount of dC adducts generated upon reaction with double-stranded calf thymus DNA is significantly higher than that of dG adducts[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
Chemical Information
-
CAS No. 2492-43-5
-
Appearance Liquid (Density: 0.969±0.06 g/cm3)
-
Masse moléculaire 112.13
-
Formule C6H8O2
-
Color Light yellow to brown
-
SMILES
O=C/C=C/C(CC)=O
-
Synonyms
(E)-4-Oxo-2-hexenal
-
Structure Classification
-
Initial Source
Dolycoris baccarum
-
Livraison
Room temperature in continental US; may vary elsewhere.
-
Stockage
-20°C, protect from light, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)
Solvant et solubilité
In Vitro:
DMSO : 100 mg/mL (891.82 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (22.30 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
-
-
-
-
Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
-
%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
-
%+
-
+%Tween-80 + +
-
%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocole
-
Detection of Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
-
TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
-
Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
-
Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
-
Ferroptosis Solutions
Ferroptosis is an iron-dependent, non-apoptotic form of regulated cell death characterized by lethal lipid peroxidation and sensitivity to suppression by iron chelators or lipophilic radical-trapping antioxidants. The core pathway links cystine uptake through system Xc−, glutathione availability, GPX4-dependent detoxification of phospholipid hydroperoxides, iron-dependent oxidative reactions, and polyunsaturated-phospholipid metabolism into a cell-death program that is biochemically and morphologically distinct from apoptosis, necrosis, and autophagy. The ferroptosis pathway is experimentally linked to phenotype through chemical and genetic perturbation. Erastin induces ferroptosis by inhibiting cystine uptake through system Xc− and weakening antioxidant defenses, while GPX4 inhibition or depletion causes lipid peroxide accumulation and ferroptotic cancer-cell death. ACSL4 and oxidizable arachidonoyl- or adrenoyl-containing phosphatidylethanolamines shape ferroptosis sensitivity by con
-
Gram Staining of Tissue Sections
Gram staining of tissue sections is a histochemical technique used to differentiate Gram-positive and Gram-negative bacteria within histological specimens based on differences in bacterial cell wall structure and dye retention, adapted from classical bacteriological Gram staining into tissue-compatible “histological Gram stain” variants. In tissue applications, modifications of the Brown-Hopps and Brown-Brenn methods are commonly used to improve differentiation of microorganisms embedded within host connective tissue and to reduce overstaining or loss of Gram-negative signal, which are known limitations of earlier approaches. The principle relies on crystal violet-iodine complex retention in Gram-positive organisms and subsequent decolorization and counterstaining steps that allow contrast visualization of Gram-negative organisms against tissue background.
-
Genotoxicity/Mutagenicity Study
The bacterial reverse mutation assay detects point mutations that restore amino-acid prototrophy in auxotrophic Salmonella typhimurium or Escherichia coli tester strains; after exposure to a test article, mutagenic activity is read out as an increased number of revertant colonies on minimal agar compared with the vehicle control. The assay uses tester strains with different mutation targets so that base-substitution and frameshift mutagens can be detected, and testing is performed with and without exogenous mammalian metabolic activation because some chemicals require biotransformation to become mutagenic.
Pureté et documentation
-
Fiche technique (271 KB)
-
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
-
Instruction de manipulation (2659 KB)
Références
[1]. Kasai H, et al. 4-oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation, causes DNA adduct formation in mouse organs. Ind Health. 2005;43(4):699-701. [Content Brief]
[2]. Noge K, et al. Antibacterial activity of 4-oxo-(E)-2-hexenal from adults and nymphs of the heteropteran, Dolycoris baccarum (Heteroptera: Pentatomidae). Biosci Biotechnol Biochem. 2012;76(10):1975-1978. [Content Brief]
[3]. Kasai H, et al. 4-oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation: occurrence, detection and adduct formation. Mutat Res. 2008;659(1-2):56-59. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 8.9182 mL | 44.5911 mL | 89.1822 mL | 222.9555 mL |
| 5 mM | 1.7836 mL | 8.9182 mL | 17.8364 mL | 44.5911 mL | |
| 10 mM | 0.8918 mL | 4.4591 mL | 8.9182 mL | 22.2956 mL | |
| 15 mM | 0.5945 mL | 2.9727 mL | 5.9455 mL | 14.8637 mL | |
| 20 mM | 0.4459 mL | 2.2296 mL | 4.4591 mL | 11.1478 mL | |
| 25 mM | 0.3567 mL | 1.7836 mL | 3.5673 mL | 8.9182 mL | |
| 30 mM | 0.2973 mL | 1.4864 mL | 2.9727 mL | 7.4319 mL | |
| 40 mM | 0.2230 mL | 1.1148 mL | 2.2296 mL | 5.5739 mL | |
| 50 mM | 0.1784 mL | 0.8918 mL | 1.7836 mL | 4.4591 mL | |
| 60 mM | 0.1486 mL | 0.7432 mL | 1.4864 mL | 3.7159 mL | |
| 80 mM | 0.1115 mL | 0.5574 mL | 1.1148 mL | 2.7869 mL | |
| 100 mM | 0.0892 mL | 0.4459 mL | 0.8918 mL | 2.2296 mL |
4-OHE Related Classifications
HY-N12851 Related Classifications
Powered by Bioz