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(2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride

(2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal HCl is an endogenously produced metabolite.
(2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride
(2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride Chemical Structure CAS No.: 5505-63-5
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
10g
Other Sizes
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Product Description
(2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal HCl is an endogenously produced metabolite.
(2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride, also known as D-Mannosamine hydrochloride, is a six-carbon amino sugar and an amino derivative of D-mannose. It has the molecular formula C6H14ClNO5 and a molecular weight of 215.63. This compound serves as a precursor for glycosaminoglycan synthesis and is used in the development of mannosylated liposomes for bioadhesive oral drug delivery.
Biological Activity I Assay Protocols (From Reference)
Targets
D-Mannosamine hydrochloride targets mannose receptors on cell surfaces. By blocking mannose receptors, it can modulate cellular interactions and immune responses. It is also involved in glycosaminoglycan biosynthesis pathways, serving as a key intermediate in the formation of extracellular matrix components.
ln Vitro
In vitro, D-mannosamine hydrochloride is used to study the role of mannose receptors in cellular processes. It can block the binding of mannose-containing ligands to these receptors, thereby inhibiting mannose receptor-mediated endocytosis and signaling. The compound is also used in studies of glycosaminoglycan synthesis and the development of bioadhesive drug delivery systems.
ln Vivo
In vivo, D-mannosamine hydrochloride is used in the development of mannosylated liposomes for bioadhesive oral drug delivery via M cells of Peyer's patches. The compound's ability to target mannose receptors on these cells facilitates the uptake of drug-loaded liposomes, enhancing oral bioavailability. It is also used in metabolic studies of amino sugar metabolism.
Enzyme Assay
In vitro enzyme assays for D-mannosamine hydrochloride typically measure the activity of enzymes involved in amino sugar metabolism, such as glucosamine-6-phosphate synthase or mannosamine kinases. The compound is used as a substrate or inhibitor to study enzyme kinetics and the effects of various modulators on amino sugar biosynthesis pathways.
Cell Assay
In vitro cell experiments with D-mannosamine hydrochloride involve treating cell lines with the compound to study mannose receptor function or to evaluate drug delivery systems. Cells such as macrophages or intestinal epithelial cells are cultured with the compound to assess receptor binding, uptake, and downstream signaling. The compound may also be used in the preparation of mannosylated liposomes for targeted drug delivery studies.
Animal Protocol
In vivo animal experiments with D-mannosamine hydrochloride involve oral administration of mannosylated liposomes formulated with the compound to study their bioadhesive properties and drug delivery efficiency. Animal models such as rats or mice are used to assess the pharmacokinetics, biodistribution, and therapeutic efficacy of the mannosylated formulations. Tissue samples are collected and analyzed to evaluate the targeting of M cells in Peyer's patches.
ADME/Pharmacokinetics
Pharmacokinetic data for D-mannosamine hydrochloride are limited. As an amino sugar, it is expected to be absorbed from the gastrointestinal tract and metabolized through amino sugar pathways. The compound's ability to target mannose receptors may enhance its accumulation in tissues expressing these receptors. The hydrochloride salt form improves aqueous solubility for laboratory use.
Toxicity/Toxicokinetics
Toxicological data for D-mannosamine hydrochloride are limited. As a naturally occurring amino sugar derivative, it is expected to have low toxicity at physiological concentrations. The compound is intended for research use only and not for human consumption. Comprehensive toxicological studies have not been performed.
Additional Infomation
D-(+)-galactosamine is a hexose.
See also: D-galactosamine (note moved to); glucosamine hydrochloride (note moved to).
D-Mannosamine hydrochloride is a research compound with applications in glycobiology, drug delivery, and glycosaminoglycan research. It is used as a precursor in the synthesis of glycosaminoglycans and as a tool to study mannose receptor function. No clinical trials or approved therapeutic indications exist for this compound. Its mechanism of action involves the blockade of mannose receptors and participation in amino sugar metabolism.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H14CLNO5
Molecular Weight
215.63
Exact Mass
215.056
CAS #
5505-63-5
PubChem CID
5351447
Appearance
White to off-white solid powder
Boiling Point
532.5ºC at 760 mmHg
Melting Point
168ºC (dec.)
Flash Point
275.8ºC
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
5
Heavy Atom Count
13
Complexity
142
Defined Atom Stereocenter Count
0
SMILES
C([C@H]([C@H]([C@@H]([C@@H](C=O)N)O)O)O)O.Cl
InChi Key
CBOJBBMQJBVCMW-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H13NO5.ClH/c7-3(1-8)5(11)6(12)4(10)2-9;/h1,3-6,9-12H,2,7H2;1H
Chemical Name
2-amino-3,4,5,6-tetrahydroxyhexanal;hydrochloride
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: 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)
Solubility Data
Solubility (In Vitro)
DMSO: 25 mg/mL (115.94 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.59 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 (11.59 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (11.59 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 4.6376 mL 23.1879 mL 46.3757 mL
5 mM 0.9275 mL 4.6376 mL 9.2751 mL
10 mM 0.4638 mL 2.3188 mL 4.6376 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.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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