| Size | Price | Stock | Qty |
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| 50g |
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| 100g |
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| Other Sizes |
| Targets |
(R)-4-Benzyl-2-oxazolidinone does not have a specific primary biological target, as it functions primarily as a chiral auxiliary in asymmetric synthesis rather than a direct pharmacological agent. However, it is an impurity of Zolmitriptan, which is a serotonin 5-HT1B and D receptor agonist used for the treatment of migraine. The compound's role as a chiral auxiliary means that it is used to synthesize enantiomerically pure drug candidates that target various biological pathways. For example, HIV protease inhibitors synthesized using this compound target the HIV protease enzyme, blocking viral replication. Antitumor and anesthetic agents synthesized using this compound may target various cellular processes. The compound's defined stereochemistry is critical for the biological activity of the final drug molecules.
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| ln Vitro |
In vitro, (R)-4-benzyl-2-oxazolidinone is used as a chiral auxiliary in the enantioselective synthesis of beta-lactams and alpha-amino acids. It is used in the synthesis of HIV protease inhibitors and as a starting material in the synthesis of enantiopure carbocyclic nucleosides. It is also used as a chiral auxiliary in the enantioselective synthesis of (2R,2′S)-erythro-methylphenidate. The compound is utilized in the total synthesis of natural products and pharmaceutical compounds. End products can include asymmetric single isomeric drugs with antitumor and anesthetic properties. In medicinal chemistry, it serves as a valuable tool for constructing enantiomerically pure drug candidates. Its use in asymmetric synthesis enables the production of single isomers with enhanced efficacy and reduced side effects.
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| ln Vivo |
In vivo activity is mediated through the derivatives of (R)-4-benzyl-2-oxazolidinone rather than the parent compound itself. For example, HIV protease inhibitors synthesized using this compound are evaluated in animal models of HIV infection. Antitumor agents synthesized using this compound are evaluated in animal models of cancer. Anesthetic agents synthesized using this compound are evaluated in animal models for anesthetic efficacy. Zolmitriptan, for which this compound is an impurity, is evaluated in animal models of migraine. However, specific in vivo studies on the parent compound are not documented, as it is a synthetic intermediate rather than a pharmacological agent.
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| Enzyme Assay |
Cell-free assays involving (R)-4-benzyl-2-oxazolidinone are focused on its use as a chiral auxiliary in asymmetric synthesis. Standard protocols involve deprotonating the compound with n-butyllithium, reacting with an acyl chloride to form an acyl oxazolidinone, performing a diastereoselective alkylation or aldol reaction, and then cleaving the auxiliary. The reaction progress is monitored by TLC or HPLC, and the products are purified by column chromatography. The compound's chiral nature allows for the synthesis of enantiomerically pure compounds, and its use in asymmetric synthesis is well-established. Its reactivity can be studied using various analytical techniques, including NMR spectroscopy and polarimetry.
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| Cell Assay |
Cellular assays are not performed with the parent compound (R)-4-benzyl-2-oxazolidinone. Instead, its derivatives, such as HIV protease inhibitors, antitumor agents, and anesthetics, are evaluated in cell-based systems. For HIV protease inhibitors, viral replication assays are performed using HIV-infected cells. For antitumor agents, cancer cell lines are treated with the derivatives, and cell viability and proliferation are measured. For anesthetics, neuronal cell cultures may be used to assess effects on ion channels or neurotransmitter release. The parent compound itself is not used as a test article in cell-based experiments.
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| Animal Protocol |
Animal studies are not conducted with the parent compound (R)-4-benzyl-2-oxazolidinone. Its derivatives, such as HIV protease inhibitors, antitumor agents, and anesthetics, are evaluated in animal models. For HIV protease inhibitors, animal models of HIV infection are used, and viral load and immune function are assessed. For antitumor agents, xenograft or orthotopic mouse models of cancer are used, and tumor growth and survival are assessed. For anesthetics, animal models are used to assess anesthetic efficacy and safety. The parent compound itself is not administered to animals.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for the parent compound (R)-4-benzyl-2-oxazolidinone are not available. As a small polar molecule with a molecular weight of 177.20 g/mol, it is expected to have moderate bioavailability if administered, but it is not intended for therapeutic use. Comprehensive pharmacokinetic studies have not been performed, as the compound is not intended for systemic administration. For research purposes, the compound is typically handled as a neat chemical and not administered to living organisms for pharmacokinetic profiling.
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| Toxicity/Toxicokinetics |
Toxicological data for (R)-4-benzyl-2-oxazolidinone are limited. Standard safety precautions for handling chiral auxiliaries apply, including the use of personal protective equipment such as gloves and safety goggles. The compound should be handled in a well-ventilated area, and contact with skin and eyes should be avoided. In case of exposure, affected areas should be rinsed thoroughly with water. The compound is not classified as a carcinogen or mutagen based on available data, but comprehensive toxicological evaluation has not been performed. As with all research chemicals, it should be handled with care and used only in accordance with safety guidelines.
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| Additional Infomation |
(R)-4-Benzyl-2-oxazolidinone is a research chemical, not an approved drug. It has no clinical trial or marketing approval status for therapeutic use. The compound is a chiral oxazolidinone auxiliary used in the enantioselective synthesis of beta-lactams and alpha-amino acids. It is used in the synthesis of HIV protease inhibitors and as a starting material in the synthesis of enantiopure carbocyclic nucleosides. It is also used as a chiral auxiliary in the enantioselective synthesis of (2R,2′S)-erythro-methylphenidate. The compound is utilized in the total synthesis of natural products and pharmaceutical compounds. End products can include asymmetric single isomeric drugs with antitumor and anesthetic properties. The compound is an impurity of Zolmitriptan. It is supplied with a purity of ≥99% and should be stored in a cool, dry place.
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| Molecular Formula |
C10H11NO2
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| Molecular Weight |
177.20
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| Exact Mass |
177.078
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| CAS # |
102029-44-7
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| PubChem CID |
2734969
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
398.8±9.0 °C at 760 mmHg
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| Melting Point |
88-90 °C
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| Flash Point |
195.0±18.7 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.552
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| LogP |
1.8
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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 |
2
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| Heavy Atom Count |
13
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| Complexity |
187
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O1C(N([H])[C@@]([H])(C1([H])[H])C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])=O
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| InChi Key |
OJOFMLDBXPDXLQ-SECBINFHSA-N
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| InChi Code |
InChI=1S/C10H11NO2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m1/s1
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| Chemical Name |
(4R)-4-benzyl-1,3-oxazolidin-2-one
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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 | 5.6433 mL | 28.2167 mL | 56.4334 mL | |
| 5 mM | 1.1287 mL | 5.6433 mL | 11.2867 mL | |
| 10 mM | 0.5643 mL | 2.8217 mL | 5.6433 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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