| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
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| Other Sizes |
| Targets |
Thyroid peroxidase (TPO); hepatic trimethylamine oxidase. 1,3-Oxazolidine-2-thione is a goitrogen that interferes with thyroid hormone synthesis by inhibiting iodine uptake and thyroid peroxidase activity. Thyroid peroxidase is the key enzyme responsible for the iodination of thyroglobulin and the coupling of iodotyrosines to form the thyroid hormones T₃ and T₄. By inhibiting this enzyme, the compound reduces thyroid hormone production, leading to increased thyroid-stimulating hormone (TSH) secretion via the hypothalamic-pituitary-thyroid axis and subsequent thyroid gland enlargement (goiter). The compound also severely depresses hepatic trimethylamine oxidase activity, an enzyme involved in the metabolism of trimethylamine derived from dietary choline and carnitine.
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| ln Vitro |
1,3-Oxazolidine-2-thione increases thyroid size and severely depresses hepatic trimethylamine oxidase activity in brown-egg laying hens. The goitrogenic effect is attributed to the compound's ability to inhibit iodine uptake and thyroid peroxidase activity, leading to reduced thyroid hormone synthesis and compensatory thyroid enlargement. The depression of hepatic trimethylamine oxidase activity suggests that the compound may affect flavin-containing monooxygenase (FMO) enzymes, which are responsible for the oxidation of trimethylamine to trimethylamine N-oxide. These activities indicate that the compound can modulate both endocrine and metabolic pathways.
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| ln Vivo |
In vivo studies have demonstrated that 1,3-oxazolidine-2-thione increases thyroid size and severely depresses hepatic trimethylamine oxidase activity in brown-egg laying hens. The compound is administered in the diet of laying hens, and thyroid size is measured post-mortem. Hepatic trimethylamine oxidase activity is assessed in liver homogenates using enzymatic assays. These in vivo effects confirm the compound's goitrogenic activity and its ability to modulate hepatic enzyme function. The compound's effects on thyroid function are consistent with those of other goitrogens, such as thiourea and thiouracil derivatives.
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| Enzyme Assay |
Non-cell-based assays for 1,3-oxazolidine-2-thione include enzyme inhibition studies using purified thyroid peroxidase or hepatic trimethylamine oxidase. Thyroid peroxidase activity is measured by monitoring the iodination of tyrosine or the oxidation of guaiacol in the presence of hydrogen peroxide. Various concentrations of the compound are tested to determine the IC₅₀ value. Trimethylamine oxidase activity is measured in liver homogenates or microsomal preparations using trimethylamine as substrate and monitoring the production of trimethylamine N-oxide. Standard analytical methods including HPLC, NMR, and mass spectrometry are used for compound characterization.
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| Cell Assay |
Cell-based assays for 1,3-oxazolidine-2-thione are limited. For studying thyroid hormone synthesis, thyroid follicular cells (e.g., FRTL-5 cells) can be treated with the compound and iodine uptake, thyroglobulin iodination, and thyroid hormone production can be measured. For studying effects on trimethylamine metabolism, hepatocytes or hepatic cell lines can be treated with the compound and trimethylamine oxidase activity assessed. Cytotoxicity is assessed using standard cell viability assays such as MTT or LDH release. The compound's effects on gene expression can be studied using qPCR or microarray analysis.
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| Animal Protocol |
In vivo studies of 1,3-oxazolidine-2-thione have been conducted in brown-egg laying hens. The compound is administered in the diet at various concentrations. Thyroid size is measured by weighing the thyroid gland post-mortem, and histopathological examination is performed to assess thyroid morphology. Hepatic trimethylamine oxidase activity is measured in liver homogenates using enzymatic assays. Blood samples may be collected for measurement of thyroid hormone levels (T₃, T₄, TSH) and trimethylamine N-oxide levels. These studies confirm the compound's goitrogenic activity and its effects on hepatic enzyme function.
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| ADME/Pharmacokinetics |
1,3-Oxazolidine-2-thione has a molecular weight of 103.14 g/mol and a molecular formula of C₃H₅NOS. The IUPAC name is oxazolidine-2-thione, and the SMILES notation is S=C1OCCN1. The compound is soluble in organic solvents and can be formulated for in vivo administration in the diet or by gavage. Standard laboratory storage conditions apply. It is intended for research and analytical applications only.
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| Toxicity/Toxicokinetics |
1,3-Oxazolidine-2-thione is a goitrogen that increases thyroid size and depresses hepatic trimethylamine oxidase activity. The compound interferes with thyroid hormone synthesis by inhibiting iodine uptake and thyroid peroxidase activity. As a goitrogen, it may cause hypothyroidism and related metabolic disturbances at high doses. The compound should be handled with appropriate safety precautions, including the use of personal protective equipment. It is intended for research use only and is not for human consumption. No carcinogenic or genotoxic effects have been specifically reported for this compound.
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| References |
[1]. Goh, Y. K., et al. Influence of glucosinolates and free oxazolidinethione in a laying diet containing a constant amount of sinapine on the thyroid size and hepatic trimethylamine oxidase activity of brown-egg layers. Canadian Journal of Animal Science. 19
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| Additional Infomation |
2-Thiotetrahydro-1,3-oxazole is an oxazole compound. 1,3-Oxazolidine-2-thione has been reported in capparis (Capparis masaikai), and relevant data are available.
1,3-Oxazolidine-2-thione is a heterocyclic compound containing both sulfur and nitrogen atoms. It belongs to the class of oxazolidinethiones, which are characterized by a five-membered ring containing oxygen, nitrogen, and sulfur. The compound is of interest in medicinal chemistry and toxicology for its goitrogenic properties and its ability to interfere with thyroid hormone synthesis. Derivatives of 1,3-oxazolidine-2-thione have shown promising biological activities including goitrogenic, antimicrobial, and enzyme inhibitory effects. The compound also serves as a precursor or intermediate in the synthesis of more complex sulfur- and nitrogen-containing compounds for pharmaceutical and agrochemical research. It is for research use only. |
| Molecular Formula |
C3H5NOS
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|---|---|
| Molecular Weight |
103.14
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| Exact Mass |
103.009
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| CAS # |
5840-81-3
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| PubChem CID |
2733223
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| Appearance |
White to off-white solid powder
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| Density |
1.31 g/cm3
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| Boiling Point |
120.7ºC at 760 mmHg
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| Melting Point |
97-99ºC
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| Flash Point |
26.8ºC
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| LogP |
0.219
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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 |
0
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| Heavy Atom Count |
6
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| Complexity |
73.2
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| Defined Atom Stereocenter Count |
0
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| SMILES |
S=C1OCCN1
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| InChi Key |
UMURLIQHQSKULR-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C3H5NOS/c6-3-4-1-2-5-3/h1-2H2,(H,4,6)
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| Chemical Name |
1,3-oxazolidine-2-thione
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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: 250 mg/mL (2423.89 mM)
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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 | 9.6956 mL | 48.4778 mL | 96.9556 mL | |
| 5 mM | 1.9391 mL | 9.6956 mL | 19.3911 mL | |
| 10 mM | 0.9696 mL | 4.8478 mL | 9.6956 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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