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| Other Sizes |
| Targets |
β-D-Glucose pentaacetate does not have a specific pharmacological target in the traditional sense. It is a peracetylated sugar derivative that serves as an active pharmaceutical intermediate and biochemical reagent. The compound's biological activity is primarily related to its ability to stimulate insulin release in pancreatic islets, with the β-anomer showing immediate insulinotropic effects. The mechanism may involve the compound's interaction with glucose-sensing mechanisms or its metabolism to glucose and acetate following deacetylation. This compound is used as an organooxygen compound in biochemical reactions and may serve as a substrate or probe for studying carbohydrate metabolism and insulin secretion pathways.
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| ln Vitro |
In vitro, β-D-Glucose pentaacetate has been reported to stimulate insulin release in rat pancreatic islets. Notably, only the β-anomer of D-glucose pentaacetate causes an immediate increase in insulin output, whereas the α-anomer first transiently inhibits insulin release followed by a secondary rise in secretory rate. This stereospecific effect highlights the importance of anomeric configuration in biological activity. The compound may be used in biochemical reactions as a peracetylated glucose derivative. Its acetyl groups can be removed by esterases to release glucose and acetate, which may contribute to its biological effects. The compound's in vitro activity is primarily relevant to studies of insulin secretion and carbohydrate metabolism.
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| ln Vivo |
In vivo, β-D-Glucose pentaacetate has been reported to stimulate insulin release based on studies in rat pancreatic islets. The compound's ability to increase insulin output suggests potential applications in diabetes research. However, detailed in vivo pharmacokinetic and efficacy data are not extensively reported. As an acetylated sugar derivative, the compound would be expected to be hydrolyzed by esterases to release glucose and acetate, which are then metabolized through normal pathways. The compound is used as an active pharmaceutical intermediate. Further studies are needed to establish its in vivo bioavailability, tissue distribution, and therapeutic potential. β-D-Glucose pentaacetate is intended for research use only.
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| Enzyme Assay |
In vitro enzyme/receptor binding (non-cellular) assays for β-D-Glucose pentaacetate are not standard pharmacological assays, as the compound is primarily a biochemical reagent and pharmaceutical intermediate. However, enzyme activity assays may be conducted to study its interactions with esterases or other enzymes involved in carbohydrate metabolism. The compound may be used as a substrate for esterase activity assays, where the release of acetate is measured spectrophotometrically using coupled enzyme systems or by detecting free acetate using colorimetric or fluorometric methods. Its use in biochemical reactions has been reported. Additionally, the compound may serve as a standard in analytical chemistry for the identification and quantification of acetylated sugars using chromatographic methods.
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| Cell Assay |
In vitro cellular experiments with β-D-Glucose pentaacetate are performed primarily in pancreatic islet models to assess insulin secretion. Rat pancreatic islets are isolated and cultured in appropriate media, then treated with varying concentrations of the compound (typically 1-20 mM) along with glucose and other secretagogues. Insulin release into the medium is measured by radioimmunoassay or ELISA. The stereospecificity of insulinotropic effects is studied by comparing the β- and α-anomers. Cell viability is assessed using MTT or other assays. The compound's effects on intracellular calcium levels, cAMP, and other signaling pathways may also be investigated. Cells are maintained at 37°C in 5% CO₂ with appropriate media supplements.
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| Animal Protocol |
In vivo animal studies with β-D-Glucose pentaacetate have not been extensively reported in the literature. The compound's reported ability to stimulate insulin release in rat pancreatic islets suggests potential for in vivo studies in diabetes models. Standard in vivo studies would involve administration of the compound to rodents via oral or intravenous routes, followed by measurement of blood glucose and insulin levels. The stereospecific effects observed in vitro would be of particular interest. However, detailed in vivo efficacy, pharmacokinetic, and toxicological data for this compound require further investigation. The compound is used as an active pharmaceutical intermediate and is not intended for therapeutic use.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of β-D-Glucose pentaacetate are not extensively characterized for therapeutic applications. The compound has molecular formula C₁₆H₂₂O₁₁ and molecular weight 390.34 g/mol. It appears as a white to off-white crystalline powder with a melting point of 130-132°C. The compound is soluble in chloroform and methanol but insoluble in water. The optical rotation is [α]20/D +4.2° (c=1 in chloroform). Storage: 2-8°C. The LogP is estimated at 0.634. As a peracetylated sugar, the compound would be expected to be hydrolyzed by esterases to release glucose and acetate. Detailed pharmacokinetic parameters require further investigation.
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| Toxicity/Toxicokinetics |
Toxicological information for β-D-Glucose pentaacetate indicates hazard codes Xn (Harmful) and Xi (Irritant). The compound appears as a white to off-white crystalline powder. Standard safety precautions for handling research chemicals apply, including use of personal protective equipment (gloves, safety goggles, lab coat) and working in a well-ventilated area. The compound should be stored at 2-8°C. As an active pharmaceutical intermediate, it should be handled with appropriate care. The compound is for research use only and is not approved for human therapeutic use. Further toxicological studies are needed to establish comprehensive safety data.
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| Additional Infomation |
β-D-glucosopentaacetate is an oxygen-containing organic compound whose function is related to hexacarboxylic acids. It has been reported that β-D-glucosopentaacetate is present in Wendlandia tinctoria, and relevant data are available. See also: Glucosopentaacetate (note moved here).
β-D-Glucose pentaacetate (CAS 604-69-3) is a peracetylated derivative of D-glucose with molecular formula C₁₆H₂₂O₁₁ and molecular weight 390.34 g/mol. It appears as a white to off-white crystalline powder with a melting point of 130-132°C. The compound is soluble in chloroform and methanol but insoluble in water. It is also known as Penta-O-acetyl-β-D-glucopyranose, 1,2,3,4,6-Penta-O-acetyl-β-D-glucose, and β-D-Glucopyranose pentaacetate. β-D-Glucose pentaacetate is used in biochemical reactions and as an active pharmaceutical intermediate. It has been reported to stimulate insulin release in rat pancreatic islets. Purity is typically ≥98%. Storage: 2-8°C. |
| Molecular Formula |
C₁₆H₂₂O₁₁
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|---|---|
| Molecular Weight |
390.34
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| Exact Mass |
390.116
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| CAS # |
604-69-3
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| PubChem CID |
2724702
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
434.8±45.0 °C at 760 mmHg
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| Melting Point |
129-133ºC
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| Flash Point |
188.1±28.8 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.482
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| LogP |
1.68
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
27
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| Complexity |
599
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| Defined Atom Stereocenter Count |
5
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| SMILES |
CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
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| InChi Key |
LPTITAGPBXDDGR-IBEHDNSVSA-N
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| InChi Code |
InChI=1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15-,16-/m1/s1
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| Chemical Name |
[(2R,3R,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate
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| Synonyms |
βDGlucose pentaacetate; β D Glucose pentaacetate
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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: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). 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) |
DMSO : ~100 mg/mL (~256.19 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.40 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5619 mL | 12.8093 mL | 25.6187 mL | |
| 5 mM | 0.5124 mL | 2.5619 mL | 5.1237 mL | |
| 10 mM | 0.2562 mL | 1.2809 mL | 2.5619 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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