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| Other Sizes |
| Targets |
The primary chemical target of ethyl (triphenylphosphoranylidene) acetate is the carbonyl group (C=O) of aldehydes and ketones in the Wittig reaction. The phosphorus ylide attacks the carbonyl carbon, forming a four-membered oxaphosphetane intermediate, which decomposes to yield an alkene (specifically, an alpha,beta-unsaturated ester) and triphenylphosphine oxide. As a cholinesterase inhibitor, it targets the active site serine residue of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), forming a covalent or reversible complex. This is a secondary activity, and potency is not the primary use of this reagent.
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| ln Vitro |
Ethyl (triphenylphosphoranylidene) acetate can be used as a cholinesterase inhibitor that inhibits AChE and BChE.
In vitro, as a Wittig reagent, ethyl (triphenylphosphoranylidene) acetate is used to synthesize alpha,beta-unsaturated esters from aldehydes. For example, benzaldehyde reacts with the ylide to produce ethyl cinnamate (E-isomer predominantly). The reaction proceeds in refluxing toluene or THF for 4-12 hours, yielding 80-95% product. As a cholinesterase inhibitor, the compound may inhibit AChE and BChE, which are enzymes that hydrolyze acetylcholine in the synaptic cleft. However, the biological activity is not the primary use. When used in cell culture, any unreacted ylide or byproducts would be removed during purification of the synthetic product. The compound itself is not typically added to cells. |
| ln Vivo |
No dedicated in vivo pharmacological studies have been conducted for ethyl (triphenylphosphoranylidene) acetate as a therapeutic agent. It is not administered to animals for pharmacodynamic evaluation. In drug discovery, the compound is used as a building block to synthesize drug candidates. For example, alpha,beta-unsaturated esters synthesized by Wittig reactions are key intermediates for COX-2 inhibitors, anticancer agents, and anti-inflammatory compounds. These final drug candidates are then tested in animal models. The cholinesterase inhibitory activity might suggest potential use in Alzheimer's disease research, but no in vivo efficacy studies for the ylide itself have been published.
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| Enzyme Assay |
No dedicated cell-free receptor binding or enzyme activity protocols exist for ethyl (triphenylphosphoranylidene) acetate. For cholinesterase inhibition assays: Recombinant human AChE (1-10 ng/well) or BChE (1-10 ng/well) is incubated in 96-well plates with 50 uL of assay buffer (50 mM Tris-HCl, pH 8.0, 0.1% BSA). Test compound (1 nM to 100 uM) is added and incubated for 10-30 minutes at 25degC. Then 150 uL of substrate solution (1 mM acetylthiocholine for AChE or butyrylthiocholine for BChE, plus 0.5 mM DTNB in buffer) is added. Absorbance at 412 nm is measured kinetically for 10 minutes using a microplate reader. Enzyme activity is calculated relative to control (no inhibitor). IC₅0 values are determined by nonlinear regression. For Wittig reaction protocols, see field 5.
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| Cell Assay |
No cell-based assay protocols exist for ethyl (triphenylphosphoranylidene) acetate as a test compound. For cholinesterase inhibition in cell-based systems: SH-SY5Y neuroblastoma cells (1×10⁴ cells/well in 96-well plates) are cultured in DMEM/F12 with 10% FBS. Cells are treated with test compound (0.1-100 uM) for 24-48 hours. After treatment, cells are washed with PBS, lysed, and AChE/BChE activity in cell lysates is measured using the Ellman assay (as in field 5). Cellular viability is assessed by MTT assay. Neuroprotection studies: Cells are exposed to amyloid-beta (1-10 uM) or H2O2 (100-500 uM) to induce oxidative stress. Test compound is added before or after stress. However, ethyl (triphenylphosphoranylidene) acetate is rarely used for this purpose, as its cholinesterase inhibition potency is not well characterized.
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| Animal Protocol |
No animal protocols exist for ethyl (triphenylphosphoranylidene) acetate. For cholinesterase inhibitor studies in Alzheimer‘s disease models, typical protocols involve other compounds (e.g., donepezil, rivastigmine). For a novel cholinesterase inhibitor synthesized using the Wittig reaction, a typical protocol is: Male Sprague-Dawley rats or C57BL/6 mice (8-12 weeks) are used. For scopolamine-induced amnesia: scopolamine (1-3 mg/kg, IP) is administered 30 minutes before behavioral testing. Test compound (0.1-30 mg/kg, oral or IP) is given 30-60 minutes before scopolamine. Cognitive function is assessed by Morris water maze (escape latency, probe trial) or passive avoidance test (step-through latency). After behavior testing, animals are euthanized, brains are collected, and cholinesterase activity and acetylcholine levels are measured in brain homogenates. No dedicated studies for ethyl (triphenylphosphoranylidene) acetate are available.
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| ADME/Pharmacokinetics |
No pharmacokinetic data exist for ethyl (triphenylphosphoranylidene) acetate. The compound is highly lipophilic (logP estimated 4-5) due to the three phenyl groups. It is insoluble in water (<0.01 mg/mL) but soluble in organic solvents (DMSO, DMF, ethanol). Oral absorption is expected to be moderate, but the compound is a chemical reagent, not a drug candidate. Metabolism likely involves oxidative N-demethylation? Not applicable. Cholinesterase inhibitor activity suggests some systemic exposure might occur, but no PK studies have been performed. The compound is not administered therapeutically. As a Wittig reagent, its fate in biological systems is not relevant. It degrades to triphenylphosphine oxide (TPPO) in the presence of water and oxygen, which is excreted in urine.
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| Toxicity/Toxicokinetics |
No dedicated toxicology data for ethyl (triphenylphosphoranylidene) acetate are available. Based on its similarity to other phosphonium salts and Wittig reagents, this compound is expected to be an irritant. GHS hazard statements (not specifically for this compound but for the class) may include: H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation). Precautions: avoid inhalation, ingestion, and skin contact. Wear PPE (gloves, lab coat, safety goggles). In case of contact, wash with soap and water. The compound is not classified as a carcinogen based on available data. Storage: 4degC, under nitrogen, protected from moisture. The compound should be handled with care in a well-ventilated fume hood. Not for human use.
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| Additional Infomation |
Ethyl (triphenylphosphoranylidene) acetate is a research-use only reagent, not approved for diagnostic or therapeutic use. It has not been evaluated in clinical trials. Its primary application is as a Wittig reagent in organic synthesis for the construction of alpha,beta-unsaturated esters from aldehydes and ketones. It is a stabilized ylide, making it easier to handle and less reactive than non-stabilized ylides, and the E-alkene is typically formed preferentially. Applications include: (1) Synthesis of cinnamate derivatives for pharmaceutical and natural product synthesis, (2) Preparation of conjugated esters for materials science, (3) Key intermediate in the synthesis of COX-2 inhibitors, retinoids, and other bioactive molecules, (4) Potential (but not primary) use as a cholinesterase inhibitor in Alzheimer's disease research, (5) Method development in organic chemistry education. Unlabeled compound is widely used.
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| Molecular Formula |
C22H21O2P
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|---|---|
| Molecular Weight |
348.37
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| Exact Mass |
348.127
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| CAS # |
1099-45-2
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| PubChem CID |
70670
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| Appearance |
Solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
490.4±28.0 °C at 760 mmHg
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| Melting Point |
128-131 °C
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| Flash Point |
263.5±44.3 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.601
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| LogP |
4.21
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
25
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| Complexity |
414
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| Defined Atom Stereocenter Count |
0
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| SMILES |
P(=C([H])C(=O)OC([H])([H])C([H])([H])[H])(C1C([H])=C([H])C([H])=C([H])C=1[H])(C1C([H])=C([H])C([H])=C([H])C=1[H])C1C([H])=C([H])C([H])=C([H])C=1[H]
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| InChi Key |
IIHPVYJPDKJYOU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C22H21O2P/c1-2-24-22(23)18-25(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21/h3-18H,2H2,1H3
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| Chemical Name |
ethyl 2-(triphenyl-λ5-phosphanylidene)acetate
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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) |
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 | 2.8705 mL | 14.3526 mL | 28.7051 mL | |
| 5 mM | 0.5741 mL | 2.8705 mL | 5.7410 mL | |
| 10 mM | 0.2871 mL | 1.4353 mL | 2.8705 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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