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| Other Sizes |
| Targets |
Ethyl-alpha-D-thioglucopyranoside targets glycosyltransferases and glycosidases. As a thio-sugar, it is a substrate analog that can be used to study enzyme specificity and mechanism. It acts as a glycosyl donor in transglycosylation reactions. It may also inhibit certain glycosidases due to the sulfur substitution, but specific targets are not well defined.
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| ln Vitro |
In cell-free assays, ethyl-alpha-D-thioglucopyranoside is used as a glycosyl donor in glycosylation reactions. It is incubated with a glycosyltransferase (e.g., alpha-glucosidase or sucrose phosphorylase) and an acceptor sugar in buffer (pH 5-7) at 30-37degC. Product formation is monitored by TLC, HPLC, or MALDI-TOF MS. It has shown antitumor potential in preliminary studies.
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| ln Vivo |
In cell-based assays, ethyl-alpha-D-thioglucopyranoside has been investigated for antitumor activity. Cancer cells (e.g., colon or breast cancer) are treated with the compound (1-100 microM) for 24-72 hours, and cell viability is measured by MTT. No specific IC50 values are reported. It may also affect glucose transport due to structural similarity to glucose.
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| Enzyme Assay |
For non-cell glycosylation assays, ethyl-alpha-D-thioglucopyranoside (10 mM) is incubated with a glycosyltransferase (0.1-1 U) and an acceptor (e.g., p-nitrophenol, 10 mM) in 100 mM phosphate buffer (pH 6.5) at 30degC for 1-24 hours. The reaction is stopped by heating, and the product is analyzed by TLC (silica, eluent: ethyl acetate/methanol/water). Spots are visualized by UV or staining.
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| Cell Assay |
For cell-based cytotoxicity assays, cancer cells are seeded in 96-well plates and treated with ethyl-alpha-D-thioglucopyranoside (0-500 microM) for 48 hours. Cell viability is measured by MTT assay: 10 microL MTT (5 mg/mL) is added per well, incubated for 4 hours at 37degC, formazan solubilized in DMSO, and absorbance read at 570 nm. IC50 values are determined from dose-response curves.
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| Animal Protocol |
No specific in vivo studies for ethyl-alpha-D-thioglucopyranoside are available. For related glycosides, a typical protocol involves oral administration to mice (50-200 mg/kg) to study metabolism and bioavailability. Blood glucose levels and tumor growth may be monitored. However, specific data for this compound is limited.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for ethyl-alpha-D-thioglucopyranoside is not available. Thioglycosides are generally more resistant to enzymatic hydrolysis than O-glycosides, which may improve stability. It may be absorbed from the intestine and distributed in tissues. It is likely excreted in urine. For research use, store as a powder at -20degC, protected from light.
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| Toxicity/Toxicokinetics |
Toxicity data for ethyl-alpha-D-thioglucopyranoside is limited. Thioglycosides are generally low in toxicity. It is a natural product in sake and is considered safe for consumption at low levels in food. For research handling, standard precautions apply. Avoid inhalation and skin contact. Not for human therapeutic use.
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| References | |
| Additional Infomation |
Ethyl-alpha-D-thioglucopyranoside is a research chemical, not an approved drug. It is used in glycosylation chemistry and glycobiology. It serves as a glycosyl donor for the synthesis of complex oligosaccharides and glycoconjugates. It has potential applications in drug development for diabetes and cancer. Purity 97-98% by HPLC. For research use only.
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| Molecular Formula |
C8H16O5S
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|---|---|
| Molecular Weight |
224.27
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| Exact Mass |
224.072
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| CAS # |
13533-58-9
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| PubChem CID |
53720639
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| Appearance |
White to off-white solid powder
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| Density |
1.27 g/cm3
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| Melting Point |
156℃
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| LogP |
0
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
14
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| Complexity |
179
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| Defined Atom Stereocenter Count |
5
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| SMILES |
CCSC1OC(CO)C(O)C(O)C1O
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| InChi Key |
CHAHFVCHPSPXOE-JAJWTYFOSA-N
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| InChi Code |
InChI=1S/C8H16O5S/c1-2-14-8-7(12)6(11)5(10)4(3-9)13-8/h4-12H,2-3H2,1H3/t4-,5-,6+,7-,8-/m1/s1
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| Chemical Name |
(2R,3R,4S,5S,6R)-2-ethylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol
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| Synonyms |
Ethyl α-thioglucopyranoside
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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 | 4.4589 mL | 22.2946 mL | 44.5891 mL | |
| 5 mM | 0.8918 mL | 4.4589 mL | 8.9178 mL | |
| 10 mM | 0.4459 mL | 2.2295 mL | 4.4589 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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