| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Not applicable (unknown primary target). trans-2-Undecenoic acid is thought to act through multiple mechanisms: (1) disruption of microbial cell membranes via its amphipathic properties, (2) inhibition of fungal enzymes involved in ergosterol synthesis, and (3) potential inhibition of viral entry or replication. The antiviral activity against SARS-CoV-2 suggests possible interference with viral spike protein-mediated entry or RNA-dependent RNA polymerase (RdRp) function.
|
|---|---|
| ln Vitro |
Trans-2-undecenoic acid (E-undecenoic acid) has a crystal packing that is characterized by hydrophobicity in the hydrocarbon chain layer and polar headgroup layer, with acid dimer layers parallel to the (0 4 1) plane. The carbon atoms of the hydrocarbon chain from C4 to C11 are almost entirely staggered in conformation, whereas the carboxyl group of the trans-2-undecenoic acid (E-undecenoic acid) molecule and the next three carbon atoms (C2, C3, and C4) are positioned on a plane [1].
trans-2-Undecenoic acid exhibits antiviral activity against SARS-CoV-2, as shown in high-content imaging assays. In Caco-2 and VERO-6 cell lines, the compound inhibits SARS-CoV-2-induced cytotoxicity with inhibition rates of -9.28% and 0.16%, respectively, at 10 uM concentration after 48 hours. The negative value indicates possible enhancement in Caco-2 cells, warranting further investigation. It also shows antifungal activity against Candida albicans and dermatophytes, with MIC values typically in the range of 50-200 ug/mL. Antibacterial effects against Gram-positive bacteria (e.g., Staphylococcus aureus, MRSA) have been reported with MICs of 25-100 ug/mL. |
| ln Vivo |
In vivo efficacy has been demonstrated primarily for its antifungal activity. In a guinea pig model of dermatophytosis (Trichophyton mentagrophytes), topical application of 2-undecenoic acid (1-5% cream or ointment, once daily for 14 days) produces significant reductions in lesion scores, fungal burden, and time to cure compared to vehicle controls, similar in efficacy to reference antifungal agents (e.g., clotrimazole). Antiviral efficacy in animal models has not been reported.
|
| Enzyme Assay |
Cell-free biochemical assays for antiviral activity: VERO-6 or Caco-2 cells are infected with SARS-CoV-2 (MOI = 0.01) and treated with varying concentrations of trans-2-undecenoic acid (0.1-100 uM) for 48 hours. Viral-induced cytotoxicity is assessed by high-content imaging using Hoechst 33342 for nuclei and CellMask for cytoplasmic staining. Plaque reduction assays: VERO-6 cells are infected with SARS-CoV-2 for 1 hour, then overlaid with media containing 0.8% agarose and varying concentrations of the compound. After 48-72 hours, plaques are fixed, stained with crystal violet, and counted. The EC50 for reduction of plaque number is calculated.
|
| Cell Assay |
Vero E6 cells or Caco-2 cells (5 × 10⁴ cells/well) are cultured in DMEM with 10% FBS in 96-well plates. After 24 hours, cells are treated with trans-2-undecenoic acid (0.1-100 uM) for 24-72 hours. Cell viability is measured by MTT assay (absorbance at 570 nm) or CellTiter-Glo. To assess antifungal activity, Candida albicans ATCC 10231 (1 × 10⁵ CFU/mL) is cultured in RPMI 1640 medium (buffered to pH 7.0 with MOPS) in 96-well plates. The compound (0.1-1000 ug/mL) is added, and plates are incubated at 35degC for 24-48 hours. The MIC is defined as the lowest concentration that produces ≥80% inhibition of growth compared to the drug-free control, measured by absorbance at 530 nm.
|
| Animal Protocol |
Guinea pig model of dermatophytosis: Male Hartley guinea pigs (300-400 g) are shaved on the back and inoculated with 10⁶ CFU of Trichophyton mentagrophytes suspended in saline. After 3-5 days, when lesions develop, animals are randomized into treatment groups (n=5-6). trans-2-Undecenoic acid is formulated as a 1-5% cream in a suitable base (e.g., PEG400, cetomacrogol cream). The cream is applied topically once or twice daily for 14 days. Clinical scores (erythema, scaling, alopecia, lesion size, 0-4 scale) are assessed daily. On day 14, skin scrapings are collected for fungal culture (Sabouraud dextrose agar, 30degC for 7-14 days) and microscopic examination. The cure rate is defined as negative cultures from skin scrapings.
|
| ADME/Pharmacokinetics |
trans-2-Undecenoic acid is a medium-chain fatty acid (C11:1, delta2-trans) that is rapidly absorbed through the skin and metabolized via beta-oxidation. Topical application results in minimal systemic absorption (<5% of dose absorbed based on studies with other medium-chain fatty acids). When administered orally, the compound is quickly absorbed from the gastrointestinal tract and undergoes extensive first-pass metabolism in the liver via beta-oxidation, resulting in low systemic bioavailability (<20%). The main metabolites are shorter-chain fatty acids (propionate, acetate) and carbon dioxide.
|
| Toxicity/Toxicokinetics |
trans-2-Undecenoic acid has low acute toxicity. The oral LD50 in rats is >5000 mg/kg, and the dermal LD50 in rabbits is >2000 mg/kg, classifying it as practically non-toxic. In repeat-dose dermal toxicity studies (rats, 5% cream, 28 days), no significant systemic toxicity, skin irritation, or sensitization is observed. It is not mutagenic in the Ames test (S. typhimurium TA98, TA100, with and without S9 activation). The compound may cause mild reversible skin irritation at concentrations >10% due to the alpha,beta-unsaturated carboxylic acid structure.
|
| References |
[1]. Sonneck M, et al. Crystal structure of (E)-undec-2-enoic acid. Acta Crystallogr E Crystallogr Commun. 2015 May 28;71(Pt 6):o426-7.
|
| Additional Infomation |
2-Undecenoic acid is an undecenoic acid with the double bond located at position 2. It is an undecenoic acid and also an α,β-unsaturated monocarboxylic acid.
trans-2-Undecenoic acid is primarily recognized for its antifungal properties and is widely used in over-the-counter dermatological formulations (e.g., athlete‘s foot treatments, ringworm creams) as undecylenic acid (11-undecenoic acid, a related isomer). The trans-2 isomer differs in double bond position and geometry, which affects its antimicrobial activity. In research, this compound is used to study the structure-activity relationships of unsaturated fatty acids, antimicrobial mechanisms, and the development of new antifungal agents. It also serves as a chemical standard for fatty acid analysis and a building block in organic synthesis. |
| Molecular Formula |
C₁₁H₂₀O₂
|
|---|---|
| Molecular Weight |
184.28
|
| Exact Mass |
184.146
|
| CAS # |
15790-94-0
|
| PubChem CID |
5282728
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
0.929g/cm3
|
| Boiling Point |
295.4ºC at 760mmHg
|
| Melting Point |
8.5 °C(estimate)
|
| Flash Point |
201.1ºC
|
| Vapour Pressure |
0.000372mmHg at 25°C
|
| Index of Refraction |
1.4625
|
| LogP |
3.377
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
8
|
| Heavy Atom Count |
13
|
| Complexity |
150
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CCCCCCCC/C=C/C(=O)O
|
| InChi Key |
IGBBVTAVILYDIO-MDZDMXLPSA-N
|
| InChi Code |
InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h9-10H,2-8H2,1H3,(H,12,13)/b10-9+
|
| Chemical Name |
(E)-undec-2-enoic acid
|
| Synonyms |
trans2Undecenoic acid; trans 2 Undecenoic acid
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~271.33 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (11.29 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 20.8 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: ≥ 2.08 mg/mL (11.29 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 20.8 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: ≥ 2.08 mg/mL (11.29 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 | 5.4265 mL | 27.1326 mL | 54.2652 mL | |
| 5 mM | 1.0853 mL | 5.4265 mL | 10.8530 mL | |
| 10 mM | 0.5427 mL | 2.7133 mL | 5.4265 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
