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| Targets |
Tri-O-acetyl-D-glucal is a synthetic intermediate and building block used in carbohydrate chemistry. As a building block, it does not have specific biological receptors as its primary targets. The compound's primary applications are in the synthesis of bioactive sugar derivatives, including glycomimetics and vaccine candidates. The acetyl groups protect the hydroxyl groups during chemical synthesis and can be selectively deprotected to reveal reactive sites for further functionalization. The compound's glucal structure allows for various transformations, including glycosylation and oxidation reactions.
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| ln Vitro |
For the synthesis of oligosaccharides in both solution and solid phase, 3,4,6-Tri-O-acetyl-D-glucal is a building block. It is also utilized in the production of D-arabino-1,5-anhydro-2-deoxy-hex-1-enitol via preparation.
In vitro, tri-O-acetyl-D-glucal is used as a biochemical reagent and organic compound for life science research. It is a partially protected derivative of D-glucal used in the synthesis of bioactive sugar derivatives, vaccine candidates, and glycomimetic drug molecules. Cellular assays are typically performed on the final glycosylated compounds synthesized from this building block rather than on the building block itself. The compound's acetylated glucal scaffold allows for various chemical transformations, making it valuable for carbohydrate chemistry and drug discovery. |
| ln Vivo |
In vivo data for tri-O-acetyl-D-glucal is limited, as it is primarily a research reagent and synthetic intermediate. The compound is classified for research use only and is not intended for human or veterinary therapeutic applications. However, glycomimetic drugs and vaccine candidates synthesized using this building block may have various biological activities. The compound's primary value lies in its use as a synthetic intermediate for preparing bioactive carbohydrate derivatives. Specific in vivo data for the parent compound is not available in the public literature.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for tri-O-acetyl-D-glucal are not typically performed, as it is primarily a synthetic intermediate. The compound is used as a building block in carbohydrate synthesis to prepare glycosylated compounds. A typical assay involves using the compound in chemical reactions, such as glycosylation or deprotection, to prepare final compounds. The compound is dissolved in organic solvents such as dichloromethane or THF. The resulting products can be evaluated for biological activity. Enzyme inhibition or receptor binding assays can be performed on the final synthesized glycomimetic compounds. IC₅₀ or binding affinity values are calculated from dose-response curves.
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| Cell Assay |
Cellular assays for tri-O-acetyl-D-glucal are not standard, as the compound is primarily a synthetic intermediate. The compound is used in the preparation of bioactive sugar derivatives and vaccine candidates. A typical protocol for evaluating the biological activity of synthesized compounds involves culturing appropriate cell lines in growth medium at 37°C with 5% CO₂. Cells are treated with synthesized compounds at varying concentrations for 24-72 hours. Cell viability, proliferation, or specific signaling readouts are assessed. IC₅₀ or EC₅₀ values are calculated from dose-response curves. The compound itself is not typically tested in cellular assays.
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| Animal Protocol |
In vivo animal studies for tri-O-acetyl-D-glucal are not standard, as it is a synthetic intermediate rather than a therapeutic candidate. The compound is classified for research use only and is not intended for human or veterinary applications. Any animal studies would typically be conducted on the final glycomimetic drugs or vaccine candidates synthesized using this building block. These studies would evaluate efficacy, pharmacokinetics, and safety in appropriate animal models. The compound's primary value lies in its use as a synthetic intermediate for preparing bioactive carbohydrate derivatives.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for tri-O-acetyl-D-glucal is limited, as it is primarily a research reagent. The compound has a molecular weight of 272.25 g/mol and a molecular formula of C₁₂H₁₆O₇. It is a solid at room temperature with a melting point of 53.0-56.0°C. It has a specific rotation [α]20/D of -13.0 to -16.0° (c=2, EtOH). As an acetylated sugar, it may undergo ester hydrolysis in biological systems to release the parent glucal. Specific ADME data is not available. The compound is stored in a dry, cool place.
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| Toxicity/Toxicokinetics |
Tri-O-acetyl-D-glucal is classified for research use only and is not intended for human or veterinary applications. Standard safety precautions include handling with appropriate personal protective equipment (gloves, lab coat, safety goggles) in a well-ventilated area. The compound should be stored in a dry, cool place away from incompatible materials. Acute toxicity data is not readily available in the public literature. As with all research chemicals, appropriate laboratory safety practices should be followed. No specific LD₅₀ values or detailed toxicological profiles are available in the public domain.
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| Additional Infomation |
See also: 3,4,6-tri-O-acetylglucuronide (note moved to).
Tri-O-acetyl-D-glucal (CAS 2873-29-2) is a biochemical reagent with the molecular formula C₁₂H₁₆O₇. It is a partially protected derivative of D-glucal featuring three acetyl groups on the sugar ring. The compound is valuable in developing bioactive sugar derivatives, vaccine candidates, and glycomimetic drug molecules. It is classified as a research-use-only compound not intended for diagnostic or therapeutic purposes. It is available from multiple commercial suppliers in various pack sizes. No clinical trials or approved drug status exist for this compound as it is not a therapeutic agent. |
| Molecular Formula |
C12H16O7
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|---|---|
| Molecular Weight |
272.25
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| Exact Mass |
272.089
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| CAS # |
2873-29-2
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| Related CAS # |
Tri-O-acetyl-D-glucal-13C;478529-35-0;Tri-O-acetyl-D-glucall-13C-1;478529-36-1;Tri-O-acetyl-D-glucal-13C13C-2;478529-37-2
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| PubChem CID |
688303
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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 |
343.1±42.0 °C at 760 mmHg
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| Melting Point |
51-53ºC
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| Flash Point |
149.2±27.9 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.484
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| LogP |
0.36
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
19
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| Complexity |
388
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| Defined Atom Stereocenter Count |
3
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| SMILES |
O1C([H])=C([H])[C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])OC(C([H])([H])[H])=O)OC(C([H])([H])[H])=O)OC(C([H])([H])[H])=O
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| InChi Key |
LLPWGHLVUPBSLP-UTUOFQBUSA-N
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| InChi Code |
InChI=1S/C12H16O7/c1-7(13)17-6-11-12(19-9(3)15)10(4-5-16-11)18-8(2)14/h4-5,10-12H,6H2,1-3H3/t10-,11-,12+/m1/s1
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| Chemical Name |
[(2R,3S,4R)-3,4-diacetyloxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
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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 | 3.6731 mL | 18.3655 mL | 36.7309 mL | |
| 5 mM | 0.7346 mL | 3.6731 mL | 7.3462 mL | |
| 10 mM | 0.3673 mL | 1.8365 mL | 3.6731 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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