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| Other Sizes |
| Targets |
15-Crown-5 does not have a defined biological target as it is a chemical reagent and phase transfer catalyst rather than a pharmacologically active compound. Its function is physicochemical—it selectively binds metal ions (particularly Na⁺ and K⁺) through coordination with its five oxygen atoms in the crown ether cavity. This ion-binding property enables phase transfer catalysis, where the crown ether encapsulates a metal cation and transports it into organic solvents. In biological systems, crown ethers can affect ion homeostasis and membrane permeability, but these are non-specific effects. The compound is not designed for therapeutic use.
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| ln Vitro |
15-Crown-5 is a very effective complexing agent and phase transfer catalyst. Oxonium ions (H7O3)+ salts are separated using it, particularly from solutions containing tetrachloroauric acid. In the penicillin and cephalosporin series, it catalyzes the O-alkylation of carboxylic acid sodium salts, facilitating esterification reactions without the need for acid. Additionally, it is employed to facilitate the Williamson synthesis of sodium hydride and ethers with hindered alcohols. utilized in reduction reactions in hydrogen solvents in conjunction with lithium aluminum hydride. It also takes part in the Horner-Wadsworth-Emmons reaction, which is used to convert aldehydes into stilbenes.
In vitro, 15-crown-5 exhibits no pharmacological activity as it is a chemical reagent. Its utility is demonstrated as an efficient phase transfer catalyst and complexing agent. It is used to isolate oxonium ion salts and to complex various metal salts, ammonium salts, and organic cationic compounds. The compound has been reported to induce cytotoxicity and oxidative stress markers in WI38 cells. In cell-based assays, crown ethers can cause concentration-dependent cytotoxicity due to membrane disruption and ion imbalance. However, 15-crown-5 is not used as a therapeutic agent. Its role is primarily chemical—providing ion complexation and phase transfer properties. |
| ln Vivo |
15-Crown-5 is not a pharmacologically active agent and does not exhibit in vivo therapeutic activity. It is used as a phase transfer catalyst and complexing agent in chemical reactions. The compound is not intended for human or animal exposure. It is used exclusively in laboratory and industrial settings. No therapeutic efficacy has been reported for this compound. The compound is not administered to animals in pharmacological studies and has no known physiological effects beyond its ion-binding properties.
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| Enzyme Assay |
In vitro assays for 15-crown-5 focus on its ion-binding and phase transfer properties rather than receptor binding. A standard protocol involves measuring the binding affinity of the crown ether for various metal ions (Na⁺, K⁺, etc.) using conductometry, potentiometry, or UV-Vis spectroscopy. Stability constants (log K) are determined by titration methods. For phase transfer catalysis applications, the compound is dissolved in organic solvents and used to facilitate reactions between aqueous and organic phases. For cytotoxicity studies, WI38 cells are treated with the compound at varying concentrations and cell viability is assessed using MTT assays.
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| Cell Assay |
In vitro cell culture experiments with 15-crown-5 typically involve cytotoxicity studies. A standard protocol involves culturing mammalian cells (e.g., WI38 fibroblasts) in 96-well plates until 70-80% confluence. The compound is serially diluted in culture medium (typically 0-1000 µg/mL) and added to cells for 24-48 hours. Cell viability is assessed using MTT or resazurin reduction assays. Oxidative stress markers (e.g., ROS, glutathione levels) are measured using fluorescent probes. IC₅₀ values are calculated from dose-response curves. Positive controls and vehicle controls are included in each experiment.
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| Animal Protocol |
In vivo animal studies with 15-crown-5 are limited to toxicological evaluations. Standard protocols for oral toxicity testing in rodents follow OECD guidelines. The compound is administered by gavage at doses ranging from 100-2000 mg/kg, and animals are monitored for 14 days for mortality, body weight changes, and clinical signs. Histopathological examination of major organs is performed at study termination. The compound is not used in efficacy studies as it is not a therapeutic agent. Crown ethers are known to have low oral bioavailability due to their hydrophilic nature.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 15-crown-5 are not well characterized as it is not a drug substance. Based on its physicochemical properties (molecular weight 220.26, logP 0.083, moderate water solubility), the compound would be expected to have low oral bioavailability due to limited membrane permeability. It would likely be distributed primarily in extracellular fluid and rapidly cleared via renal excretion. The compound is not significantly metabolized. However, the compound is not intended for human exposure and has not been evaluated in formal pharmacokinetic studies.
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| Toxicity/Toxicokinetics |
Toxicological data for 15-crown-5 indicate that it is stable but incompatible with oxidizing agents and strong acids. The compound should be protected from exposure to water or moist air. Standard laboratory safety precautions should be followed when handling this compound, including the use of gloves, safety glasses, and working in a fume hood. The compound should be stored in a cool, dry place away from incompatible materials. No acute toxicity data are available. The compound is not intended for drug, household, or other uses.
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| Additional Infomation |
15-Crown ether-5 is a saturated organic heterocyclic monocyclic parent compound. It is a derivative of cyclopentadecane in which carbon atoms at positions 1, 4, 7, 10, and 13 are replaced by oxygen atoms to form a crown ether. It is both a crown ether and a saturated organic heterocyclic monocyclic parent compound.
15-Crown-5 is a crown ether used as an efficient phase transfer catalyst and complexing agent. It selectively binds metal ions through coordination with its five oxygen atoms and is used to isolate oxonium ion salts. The compound can induce cytotoxicity and oxidative stress in WI38 cells. It is also known as 1,4,7,10,13-pentaoxacyclopentadecane. It has not undergone clinical trials and is not approved as a pharmaceutical. Its mechanism of action is physicochemical—binding metal ions and facilitating phase transfer in chemical reactions. |
| Molecular Formula |
C10H20O5
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|---|---|
| Molecular Weight |
220.26
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| Exact Mass |
220.131
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| CAS # |
33100-27-5
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| PubChem CID |
36336
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| Appearance |
Colorless to light yellow liquid（Density：1.324 g/cm3）
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
350.9±0.0 °C at 760 mmHg
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| Melting Point |
-20ºC
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| Flash Point |
139.1±25.0 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.404
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| LogP |
-0.68
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
15
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| Complexity |
86.2
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1COCCOCCOCCOCCO1
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| InChi Key |
VFTFKUDGYRBSAL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
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| Chemical Name |
1,4,7,10,13-pentaoxacyclopentadecane
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.5401 mL | 22.7004 mL | 45.4009 mL | |
| 5 mM | 0.9080 mL | 4.5401 mL | 9.0802 mL | |
| 10 mM | 0.4540 mL | 2.2700 mL | 4.5401 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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