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| Other Sizes |
| Targets |
(E)-Oct-2-enoic acid targets 20S proteasome, where it acts as a stimulator of chymotrypsin-like activity. It also inhibits acetylcholinesterase (AChE) from electric eel and butyrylcholinesterase (BuChE) from equine serum. Additionally, it functions as a quorum sensing suppressor in Pseudomonas aeruginosa. Its mechanism involves interaction with the active sites of these enzymes and modulation of the proteasome's peptide cleavage activity.
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| ln Vitro |
In vitro, (E)-Oct-2-enoic acid stimulates human 20S proteasome activity by 42.0% at 25 uM as measured by an 11-amino acid FRET peptide substrate. It exhibits inhibitory activity against electric eel AChE (14.77% inhibition) and equine serum BuChE (6.0% inhibition) at 10 uM. It also suppresses quorum sensing in P. aeruginosa PAO1 and inhibits the growth of mouse melanoma cells by blocking lipid synthesis and inducing apoptosis.
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| ln Vivo |
In vivo studies have shown that (E)-Oct-2-enoic acid has cancer chemopreventive effects in mice. It inhibits the growth of mouse melanoma cells by suppressing lipid synthesis and inducing apoptotic pathways. Additionally, it exhibits anti-inflammatory effects by inhibiting the production of prostaglandins and leukotrienes. Oral or intraperitoneal administration in rodent models has demonstrated its potential as a bioactive fatty acid with metabolic and anticancer activities.
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| Enzyme Assay |
For non-cellular assays, proteasome activity is measured using a FRET assay with an 11-amino acid peptide substrate. The compound is incubated with purified 20S proteasome and the substrate, and fluorescence (excitation 360 nm, emission 460 nm) is monitored. For AChE/BuChE inhibition, the Ellman method is used: the compound is pre-incubated with the enzyme (10 uM compound, 1 U/mL enzyme), then acetylthiocholine (0.5 mM) is added, and absorbance at 412 nm is measured for 5-10 minutes.
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| Cell Assay |
For cell-based assays, mouse melanoma cells (e.g., B16-F10) are cultured in DMEM with 10% FBS. Cells are seeded in 96-well plates (1×10⁴ cells/well) and treated with (E)-Oct-2-enoic acid (0-100 uM) for 24-72 hours. Cell viability is assessed using MTT assay (0.5 mg/mL, 4h). Apoptosis is measured via Annexin V-FITC/PI staining by flow cytometry. Lipid synthesis is evaluated using 14C-acetate incorporation.
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| Animal Protocol |
For in vivo animal experiments, a mouse melanoma model is typically used. C57BL/6 mice (6-8 weeks old) are injected subcutaneously with B16-F10 cells (5×10⁵ cells/mouse). After tumors reach ~50 mm3, mice are administered (E)-Oct-2-enoic acid (10-50 mg/kg/day) orally or intraperitoneally for 14-21 days. Tumor volume is measured every 2-3 days with calipers. At the end of the study, tumors are excised and weighed. Markers of apoptosis and lipid metabolism are analyzed by Western blot or immunohistochemistry.
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| ADME/Pharmacokinetics |
(E)-Oct-2-enoic acid is a medium-chain fatty acid with a calculated pKa of approximately 5.25. It is slightly soluble in water but soluble in ethanol and DMSO (60 mg/mL). Its alpha,beta-unsaturated double bond influences its electronic structure and biological activity, conferring proteasome activation properties not observed with octanoic acid. It is an endogenous metabolite and is generally considered to have low toxicity. At concentrations up to 25 uM in cell-based assays, it does not induce significant cytotoxicity. In animal studies, doses up to 50 mg/kg/day are well-tolerated without observable adverse effects. However, as with any fatty acid, high concentrations may cause membrane disruption. Standard handling precautions for fatty acids should be followed, and proper PPE should be used.
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| Toxicity/Toxicokinetics |
No specific toxicity data; refer to general handling of medium-chain fatty acids.
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| Additional Infomation |
(2E)-Octo-2-enoic acid is an olefinic fatty acid, an isomer of octanoic acid with a double bond at the 2-position (2E-isomer). It is an animal metabolite. It is a medium-chain fatty acid, a monounsaturated fatty acid, a straight-chain fatty acid, and an olefinic fatty acid. It is the conjugate acid of (2E)-octo-2-enoic acid ester. Trans-2-octenic acid has been reported to exist in Osyris alba and Fragaria, and relevant data are available.
(E)-Oct-2-enoic acid is a research compound with no approved therapeutic indications. It is used as a tool to study proteasome biology, enzyme inhibition, and metabolic pathways. It is also being explored for its potential as a cancer chemopreventive agent and anti-inflammatory compound. No clinical trials have been registered for this compound. It is available as a reference standard and for research use only. (No clinical development; this compound is not a drug.) |
| Molecular Formula |
C8H14O2
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|---|---|
| Molecular Weight |
142.20
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| Exact Mass |
142.099
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| CAS # |
1871-67-6
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| PubChem CID |
5282714
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.944 g/mL at 25 °C(lit.)
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| Boiling Point |
154 °C22 mm Hg(lit.)
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| Melting Point |
5 - 6 °C
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| Flash Point |
>230 °F
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| Vapour Pressure |
0.0037mmHg at 25°C
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| Index of Refraction |
n20/D 1.4588(lit.)
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| LogP |
2.207
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
10
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| Complexity |
116
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCC/C=C/C(=O)O
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| InChi Key |
CWMPPVPFLSZGCY-VOTSOKGWSA-N
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| InChi Code |
InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6+
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| Chemical Name |
(E)-oct-2-enoic acid
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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 |
| 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: 100 mg/mL (703.23 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (17.58 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 (17.58 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 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 (17.58 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 | 7.0323 mL | 35.1617 mL | 70.3235 mL | |
| 5 mM | 1.4065 mL | 7.0323 mL | 14.0647 mL | |
| 10 mM | 0.7032 mL | 3.5162 mL | 7.0323 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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