66009-10-7, D-Melibiose,
D-(+)-密二糖,
6-O-α-D-吡喃半乳糖基-D-葡萄糖,
α-D-蜜二糖,
蜜二糖水合物,
CAS: 66009-10-7
C12H22O11 / 342.30
MFCD00198188
Melibiose is a disaccharide consisting of one glucose and one galactose molecule. It is found in certain types of honey, and several plants and microorganisms. It has garnered significant scientific interest due to its unique physical and chemical properties, making it suitable for various applications in research and industry. This paper will explore the definition, background, synthesis, characterization, analytical methods, biological properties, toxicity, safety, applications, current state of research, potential implications, limitations, and future directions of melibiose.
Definition and Background
Melibiose is a disaccharide made of a glucose molecule and a galactose molecule, linked by a β(1→6) glycosidic bond. It was first isolated from honey by French chemist Louis Henry in 1857, and later described by German chemist Emil Fischer in 1895. It is also referred to as galactosyl-glucose, α-D-galactopyranosyl-(1→6)-D-glucose, or 6-O-α-D-galactopyranosyl-D-glucose.
Synthesis and Characterization
Melibiose can be synthesized from lactose using an enzyme called melibiase, which cleaves lactose into glucose and galactose. It can also be synthesized by chemical means, using methyl α-galactoside and α-D-glucopyranosyl bromide. Melibiose can be characterized using various techniques such as nuclear magnetic resonance (NMR) spectroscopy, X-ray crystallography, and mass spectrometry.
Analytical Methods
Several analytical methods are available to detect the presence of melibiose, including thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), and capillary electrophoresis (CE). These methods can identify and quantify melibiose in complex mixtures, making it suitable for use in various research fields.
Biological Properties
Melibiose has been found to have several biological properties, including prebiotic effects, immunomodulatory effects, and antibacterial activity. It has been shown to promote the growth of beneficial gut bacteria such as bifidobacteria and lactobacilli, and enhance the immune response in humans and animals. Melibiose has also been found to exhibit antibacterial activity against various pathogenic bacteria, including Escherichia coli, Salmonella typhimurium, and Staphylococcus aureus.
Toxicity and Safety in Scientific Experiments
Melibiose has been found to be nontoxic and safe for use in scientific experiments. It has been approved by the Food and Drug Administration (FDA) as a Generally Recognized As Safe (GRAS) substance, and is commonly used as a food additive. However, caution should be taken when administering high doses of melibiose, as it may cause gastrointestinal discomfort and diarrhea in some individuals.
Applications in Scientific Experiments
Melibiose has several applications in scientific experiments, including as a carbon source for microorganisms, a substrate for enzyme assays, a cryoprotectant for cells and tissues, and a marker for mammalian cell differentiation. It is also used in the production of other chemicals such as 3-hydroxypropionic acid, an important intermediate in the production of biodegradable plastics.
Current State of Research
The current state of research on melibiose is focused on its potential as a prebiotic, an immunomodulatory agent, and an antibacterial agent. Several studies have demonstrated its ability to promote the growth of beneficial gut bacteria, enhance the immune response, and inhibit the growth of pathogenic bacteria. Further research is warranted to explore its potential in other areas such as cancer therapy and metabolic disorders.
Potential Implications in Various Fields of Research and Industry
Melibiose has potential implications in various fields of research and industry, including the food industry, biotechnology, and medicine. It can be used as a food additive to promote gut health and enhance the nutritional value of food products. In biotechnology, it can be used as a substrate for enzyme assays and in the production of biodegradable plastics. In medicine, it has potential as an antibacterial agent and as a cryoprotectant for cells and tissues.
Limitations and Future Directions
Despite its potential, melibiose has some limitations that need to be addressed. It is less soluble than other disaccharides, making it less suitable for certain applications. Further research is needed to explore its potential in other areas such as cancer therapy and metabolic disorders. Future directions for research on melibiose include exploring its mechanism of action as a prebiotic and immunomodulatory agent, and investigating its potential use in combination with other drugs for the treatment of various diseases.
Conclusion
Melibiose is a disaccharide consisting of a glucose molecule and a galactose molecule, with unique physical and chemical properties that make it suitable for various applications in research and industry. It has several biological properties, and has been found to be safe and nontoxic for use in scientific experiments. Further research is needed to explore its potential in various fields, and to address its limitations.
Title: Melibiose
CAS Registry Number: 66009-10-7
CAS Name: 6-O-a-D-Galactopyranosyl-D-glucose
Additional Names: 6-(a-D-galactosido)-D-glucose
Molecular Formula: C12H22O11
Molecular Weight: 342.30
Percent Composition: C 42.11%, H 6.48%, O 51.41%
Literature References: Prepd from raffinose by fermentation with top yeast which removes the fructose: Hudson, Harding, J. Am. Chem. Soc. 37, 2734 (1915); Fletcher, Diehl, ibid. 74, 5774 (1952). Structure: Haworth, Leitch, J. Chem. Soc. 113, 188 (1918); Charlton et al., ibid. 1926, 99; Charlton et al., ibid. 1927, 1527; Haworth et al., ibid. 3146; Levene, Jorpes, J. Biol. Chem. 86, 403 (1930). Synthesis: Helferich, Bredereck, Ann. 465, 166 (1928).
Derivative Type: Dihydrate
Properties: Monoclinic crystals from water or dil alcohol. mp 84-85°. Shows mutarotation. [a]D20 +111.7° ® +129.5° (c = 4). One gram dissolves in 0.4 ml water, 8.5 ml methanol, 220 ml abs alcohol. Dilute acids hydrolyze melibiose to D-glucose and D-galactose. Also split by emulsin and by bottom yeast. Reduces Fehling's soln. 3.5 g melibiose dihydrate are about as sweet as 1.0 g sucrose.
Melting point: mp 84-85°
Optical Rotation: [a]D20 +111.7° ® +129.5° (c = 4)
CAS Number | 66009-10-7 |
Product Name | Melibiose |
IUPAC Name | (2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol |
Molecular Formula | C12H22O11 |
Molecular Weight | 342.30 g/mol |
InChI | InChI=1S/C12H22O11/c13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h1,4-12,14-21H,2-3H2/t4-,5+,6+,7+,8+,9-,10-,11+,12-/m0/s1 |
InChI Key | DLRVVLDZNNYCBX-ZZFZYMBESA-N |
Solubility | 1000.0 mg/mL |
Synonyms | a-D-Melibiose hydrate |
Canonical SMILES | C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)O)O)O)O)O)O)O)O |
Isomeric SMILES | C([C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O)O)O)O)O)O)O)O |
CAS No: 585-99-9,66009-10-7 Synonyms: 6-O-(a-D-Galactopyranosyl)-D-glucopyranose monohydrate MDL No: MFCD00198188 Chemical Formula: C12H22O11 Molecular Weight: 342.30 | In Stock. 国产现货高纯,白色结晶粉末. |
COA:
Product name :D-Melibiose; 6-O-α-D-Galactopyranosyl-D-glucose
CAS: 66009-10-7 M.F. : C12H22O11 M.W. : 342.30
Items | Standards | Results |
Appearance | White crystalline powder | Positive |
Solubility | Readily soluble in water and should be colorless | Positive |
NMR and MS | Should comply | Complies |
Identification | IR and TLC | Positive |
Water | Max. 6.8% | 4.1% |
Assay | Min. 98% | 99.1% |
D-Melibiose anhydrous is a disaccharide that is used as an excipient in the pharmaceutical industry. It has been shown to be an active enzyme, which may be due to its ability to sequester galactose. D-Melibiose anhydrous has a redox potential of -0.2 V, indicating that it has a high number of oxidizable groups. The molecular weight of this sugar is 324.14 g/mol, and it has a polarizability of 0.16 D, which classifies it as a polyol with hydrogen bonding properties. This sugar is not soluble in water but can be dissolved in ethanol or propylene glycol. D-Melibiose anhydrous also has carbohydrate properties and may be considered a sugar alcohol because it contains six carbon atoms and one oxygen atom.
Reference:
1. Wäckers FL, J. Chem. Ecol. 1999, Vol25, No12, 2863-2877
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