| Size | Price | Stock | Qty |
|---|---|---|---|
| 100g |
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| Other Sizes |
| Targets |
alpha‑D‑Mannose pentaacetate does not have a specific biological target; it is a chemical precursor. The acetyl groups serve as protecting groups for the hydroxyls of mannose, enabling selective deprotection and further functionalization of the carbohydrate core. After deacetylation, free mannose is used by cells as an energy source and as a building block for glycosylation. The compound is an inert biomaterial that participates in life science research as a synthetic intermediate.
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|---|---|
| ln Vitro |
In vitro, alpha‑D‑Mannose pentaacetate is used in glycosylation reactions to form mannosyl‑containing glycans. It serves as a glycosyl donor upon activation at the anomeric position. It is also used to synthesize novel synthetic inhibitors of selectin‑mediated cell adhesion. It is a standard substrate for enzyme assays, such as for mannosidases, which cleave mannose residues. The peracetylated form is also cell-permeable and is used as a pro‑drug for intracellular delivery of free mannose upon esterase hydrolysis.
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| ln Vivo |
alpha‑D‑Mannose pentaacetate is not a drug and is not intended for in vivo animal studies. It is a biochemical reagent. For studies on mannose metabolism in animals, unmodified D‑mannose or its free monosaccharide is used. The peracetylated form can be administered to animals to deliver mannose intracellularly. After administration, esterases hydrolyze the acetyl groups, releasing free mannose. This approach is sometimes used in metabolic studies to improve cellular uptake.
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| Enzyme Assay |
The deacetylation of alpha‑D‑Mannose pentaacetate by porcine liver esterase is measured in a cell‑free system using a pH indicator assay. The compound (0.1 mM) is incubated with porcine liver esterase (1-5 U/mL) in 50 mM HEPES buffer (pH 7.4) containing 50 mM NaCl at 25degC for 30 min. The release of acetic acid causes a drop in pH, which is detected using a pH meter or by a colorimetric pH indicator (phenol red, λ 560 nm). The rate of deacetylation is calculated from the absorbance change. The formation of free mannose is confirmed by HPLC with pulsed amperometric detection.
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| Cell Assay |
alpha‑D‑Mannose pentaacetate (1-10 uM) is added to the culture medium of human cells, such as HeLa or HEK293, to study the effect of mannose supplementation on protein glycosylation. After 24-72 h of incubation, the cells are harvested and lysed. The acetylated form is cell-permeable, and once inside the cell, it is deacetylated to free mannose. The mannose is then incorporated into the glycosylation pathway. The cell viability is assessed by MTT assay; high concentrations (>500 uM) may cause cytotoxicity due to the release of acetic acid.
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| Animal Protocol |
alpha‑D‑Mannose pentaacetate is not directly used in animal experiments. To study mannose as a dietary supplement, unlabeled D‑mannose is administered orally (5-10 mg per g body weight) to mice. However, the peracetylated derivative can be used in an experimental mouse model to test its effect on a bacterial infection. Mice can be injected intraperitoneally with alpha‑D‑Mannose pentaacetate (0.5-5 mg). Acetylation prolongs the systemic circulation half‑life of mannose, making it a potential vehicle to increase bioavailability.
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| ADME/Pharmacokinetics |
alpha‑D‑Mannose pentaacetate is a solid compound. It is soluble in organic solvents such as DMSO and ethanol but poorly soluble in water. When administered intravenously, the acetyl groups are rapidly cleaved by serum esterases, resulting in the release of free mannose. The plasma half‑life of the pentaacetate form is therefore very short (minutes). The free mannose is then excreted renally, but a portion is taken up by cells via glucose transporters (GLUTs). For storage, it should be kept at −20 degC to prevent hydrolysis. The compound is stable for at least 2 years.
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| Toxicity/Toxicokinetics |
The safety profile of alpha‑D‑Mannose pentaacetate has not been fully evaluated. As a common biochemical reagent, it may be a skin and eye irritant. It may be harmful if swallowed or inhaled. Standard laboratory safety precautions should be taken: use in a well‑ventilated area, wear gloves, safety goggles, and a lab coat. No carcinogenicity data are available. The acute oral LD₅0 is not determined, but it is expected to be low, similar to that of mannose (>5000 mg/kg).
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| References | |
| Additional Infomation |
alpha‑D‑Mannose pentaacetate is not a drug; it is a research‑only biochemical reagent. It is used as a building block for the chemical synthesis of oligosaccharides and glycoproteins. The peracetylated form is also used as a cell‑permeable mannose donor for studying intracellular glycosylation. It is an important tool for studying the role of mannosylation in cellular processes and for the development of mannosylated drug delivery systems. It is also used as a reference standard in carbohydrate chemistry.
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| Molecular Formula |
C16H22O11
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|---|---|
| Molecular Weight |
390.34
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| Exact Mass |
390.116
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| CAS # |
4163-65-9
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| PubChem CID |
11741089
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| Appearance |
Solid powder
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| Density |
1.3g/cm3
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| Boiling Point |
434.8ºC at 760mmHg
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| Melting Point |
64-75ºC
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| Flash Point |
188.1ºC
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| Index of Refraction |
1.482
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| LogP |
0.6
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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 |
O1[C@@]([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)OC(C([H])([H])[H])=O)OC(C([H])([H])[H])=O
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| InChi Key |
LPTITAGPBXDDGR-OWYFMNJBSA-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,5S,6R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate
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| Synonyms |
1,2,3,4,6-Penta-O-acetyl-α-D-mannopyranose
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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 | 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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