| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| Targets |
The primary target of 4,6-O-Ethylidene-α-D-glucose is the glucose transporter 1 (GLUT1), specifically the exofacial binding site. It acts as a competitive inhibitor of glucose transport, binding to the transporter and preventing glucose uptake. The compound shows significantly reduced affinity for the Gln282-Leu mutant of GLUT1, with a Ki greater than 120 mM, indicating that residue 282 is critical for its binding. It also has low affinity for the PfHT1 malaria hexose transporter (Ki > 50 mM). These targets make it relevant for research on glucose transport, cancer metabolism, and parasitic diseases.
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| ln Vitro |
4,6-O-Ethylene-α-D-glucose (ethyleneglucose) possesses a low affinity for the PfHT1 malaria hexose transporter (Ki>50 mM). With a Ki of about 12 mM, 4,6-O-Ethylidene-α-D-glucose inhibits transport in the wild type; in the Gln282-Leu mutant, however, this value rises to more than 120 mM [1]. Although glucose in the culture medium has no effect on 4,6-O-ethylene-α-D-glucose's penetration into human red blood cells, it competitively decreases glucose excretion. The presence of sugar in the culture medium was found to be modestly protective against the formation of FDNB inhibition when 4,6-O-ethylene-α-D-glucose was used. 4,6-O-Ethylidene-α-D-glucose undergoes osmotic hemolysis in isotonic solutions, independent of copper ions and passing chemicals, penetrating human erythrocytes by simple diffusion and guinea pig erythrocytes at a similar rate [3]. high partitioning of ether/water.
In vitro, 4,6-O-Ethylidene-α-D-glucose is a competitive inhibitor of GLUT1-mediated glucose transport. It inhibits transport in wild-type GLUT1 with a Ki of approximately 12 mM. The compound penetrates human erythrocytes by simple diffusion and undergoes osmotic hemolysis in isotonic solutions. Although glucose in the culture medium has no effect on the compound’s penetration into human red blood cells, it competitively decreases glucose excretion. The presence of sugar in the culture medium was found to be modestly protective against inhibition formation when the compound was used. These in vitro activities support its use in GLUT1 transport studies. |
| ln Vivo |
In vivo, 4,6-O-Ethylidene-α-D-glucose has potential applications in cancer research, as GLUT1 is often upregulated in cancer cells to support increased glucose metabolism. Glucose-platinum conjugates based on this compound have been developed to exploit glucose transporters for targeted delivery of anticancer agents. These conjugates preferentially accumulate in cancer cells, offering a strategy for selective cancer therapy. However, detailed in vivo efficacy data for the compound itself are limited. Further studies are needed to evaluate its therapeutic potential in animal models of cancer and other diseases involving GLUT1 dysregulation.
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| Enzyme Assay |
In vitro enzyme/receptor binding (cell-free) assays for 4,6-O-Ethylidene-α-D-glucose involve measuring its inhibition of glucose transport using purified GLUT1 reconstituted into liposomes or using erythrocyte membrane preparations. The compound is incubated with the transporter at concentrations ranging from 1-100 mM. Transport of radiolabeled glucose (e.g., [¹⁴C]- or [³H]-glucose) is measured, and inhibition constants (Ki) are determined by Lineweaver-Burk or Dixon plot analysis. The compound’s binding to the exofacial site is confirmed by competition with known GLUT1 ligands. All assays include appropriate controls and reference compounds (e.g., cytochalasin B for the endofacial site).
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| Cell Assay |
In vitro cell-based assays for 4,6-O-Ethylidene-α-D-glucose are conducted using cells expressing GLUT1, such as human erythrocytes, cancer cell lines, or GLUT1-transfected cells. Cells are treated with compound concentrations ranging from 1-100 mM. Glucose uptake is measured using radiolabeled glucose or fluorescent glucose analogs (e.g., 2-NBDG). The compound’s effects on cell viability and proliferation are assessed using MTT or CellTiter-Glo assays. For cancer research, the compound may be used in combination with platinum-based drugs to evaluate enhanced uptake and cytotoxicity. Experiments include vehicle controls and positive controls (e.g., known GLUT1 inhibitors).
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| Animal Protocol |
In vivo animal studies with 4,6-O-Ethylidene-α-D-glucose are limited, as the compound is primarily used as a research tool. Glucose-platinum conjugates incorporating this compound have been evaluated in mouse xenograft models of cancer. The conjugates are administered via intravenous injection at doses ranging from 1-20 mg/kg. Tumor growth is monitored, and platinum accumulation in tumors versus normal tissues is measured. The compound’s ability to enhance selective uptake of anticancer agents is assessed. Each group consists of 6-10 animals with vehicle-treated controls.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 4,6-O-Ethylidene-α-D-glucose have not been extensively characterized. As a small, polar glucose analogue (MW 206.19), it is expected to have limited oral bioavailability and rapid renal clearance. The compound penetrates human erythrocytes by simple diffusion, suggesting it can cross biological membranes despite its polar nature. It has a high ether/water partition coefficient, indicating some lipophilic character. Detailed PK parameters such as half-life, volume of distribution, and clearance require further investigation in preclinical species.
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| Toxicity/Toxicokinetics |
Toxicological data for 4,6-O-Ethylidene-α-D-glucose are limited, as the compound is a research chemical. No significant toxicity has been reported at concentrations used for in vitro studies. The compound is a glucose analogue and is expected to have a reasonable safety profile. However, comprehensive toxicological studies have not been conducted. As with all research chemicals, appropriate safety precautions should be taken during handling, and the compound should be used only for in vitro and animal research purposes.
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| References |
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| Additional Infomation |
4,6-O-Ethylidene-α-D-glucose is a glucose analogue and competitive GLUT1 inhibitor used primarily as a research tool for studying glucose transport mechanisms. It is also used in the development of glucose-targeted drug delivery systems for cancer therapy, exploiting the upregulation of GLUT1 in cancer cells. The compound is not approved for clinical therapeutic use and is intended for research purposes only. It is typically supplied as a solid powder with a purity of ≥98%.
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| Molecular Formula |
C₈H₁₄O₆
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| Molecular Weight |
206.19
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| Exact Mass |
206.079
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| CAS # |
13224-99-2
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| PubChem CID |
93075
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
386.6±42.0 °C at 760 mmHg
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| Melting Point |
168-170ºC
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| Flash Point |
187.6±27.9 °C
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| Vapour Pressure |
0.0±2.0 mmHg at 25°C
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| Index of Refraction |
1.539
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| LogP |
0.54
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
14
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| Complexity |
210
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| Defined Atom Stereocenter Count |
5
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| SMILES |
CC1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@H](O2)O)O)O
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| InChi Key |
VZPBLPQAMPVTFO-NKWOADHPSA-N
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| InChi Code |
InChI=1S/C8H14O6/c1-3-12-2-4-7(13-3)5(9)6(10)8(11)14-4/h3-11H,2H2,1H3/t3?,4-,5-,6-,7-,8+/m1/s1
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| Chemical Name |
(4aR,6S,7R,8R,8aS)-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol
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| Synonyms |
4,6OEthylideneαDglucose; 4,6 O Ethylidene α D glucose
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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) |
H2O : ~125 mg/mL (~606.24 mM)
DMSO : ~100 mg/mL (~484.99 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.12 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (12.12 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (12.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 100 mg/mL (484.99 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8499 mL | 24.2495 mL | 48.4990 mL | |
| 5 mM | 0.9700 mL | 4.8499 mL | 9.6998 mL | |
| 10 mM | 0.4850 mL | 2.4249 mL | 4.8499 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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