D-Raffinose, D-(+)-棉子糖五水合物

Raffinose: Definition, Properties, Synthesis, Characterization, Biological Properties, Toxicity, Applications, Current Research, Limitations, and Future Directions

Introduction:

Raffinose is a trisaccharide composed of glucose, galactose, and fructose. It is a type of oligosaccharide that belongs to the family of carbohydrates. Raffinose is commonly found in plants, such as legumes, broccoli, and spinach. It can also be found in milk, honey, and other food products. Raffinose has multiple biological properties and potential applications in various fields of research and industry. This paper will discuss the definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experimentation, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions of raffinose.

Definition and background:

Raffinose is a trisaccharide composed of glucose, galactose, and fructose. It is a type of oligosaccharide that is commonly found in plants, such as legumes, broccoli, and spinach. Raffinose was discovered in 1876 by the French chemist Maurice Gaffiot. It is also known by other names, such as melitose, raffinose trihydrate, and alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranosyl-(1<->2)-beta-D-fructofuranoside. Raffinose is used by plants as a transportable source of energy and a storage compound.

Physical and Chemical Properties:

Raffinose is a white, crystalline powder that is soluble in water. Its chemical formula is C18H32O16, and its molecular weight is 504.43 g/mol. Raffinose has a melting point of 84-85 ℃ and is stable at room temperature. Its pH is neutral, and it does not have a specific odor or taste. Raffinose is a non-reducing sugar that does not react with Fehling's solution. Its structure consists of a galactose molecule bonded to a glucose molecule through an α(1→6) linkage, and a fructose molecule bonded to the glucose molecule through a β(2→1) linkage.

Synthesis and Characterization:

Raffinose can be synthesized from sucrose by the enzyme α-galactosidase, which cleaves the α(1→6) linkage between the galactose and glucose molecules. This produces raffinose and free glucose. Raffinose can be characterized by various analytical techniques, such as high-performance liquid chromatography (HPLC), infrared spectroscopy (IR), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS).

Analytical Methods:

Raffinose can be analyzed by various analytical methods, such as HPLC, IR spectroscopy, NMR spectroscopy, and MS. HPLC is commonly used to quantify raffinose in different samples. IR spectroscopy can be used to identify the functional groups present in raffinose. NMR spectroscopy can provide structural information about raffinose. MS can be used to determine the molecular weight of raffinose.

Biological Properties:

Raffinose has multiple biological properties, such as prebiotic activity, immune-stimulatory activity, antioxidant activity, and anti-inflammatory activity. Raffinose acts as a prebiotic by promoting the growth of beneficial bacteria, such as Lactobacillus and Bifidobacterium, in the gut. This can improve gut health and the immune system. Raffinose can also stimulate the production of cytokines, which are proteins that regulate the immune response. Furthermore, raffinose has been found to have antioxidant and anti-inflammatory properties, which can reduce oxidative stress and inflammation in the body.

Toxicity and Safety in Scientific Experiments:

Raffinose is generally considered safe for consumption in food products. However, high doses of raffinose can cause gastrointestinal side effects, such as bloating, gas, and diarrhea. In scientific experiments, raffinose is used in doses that are within safe limits. The toxicity of raffinose has been evaluated in animal studies, and it has been found to be safe when used appropriately.

Applications in Scientific Experiments:

Raffinose has multiple applications in scientific experiments, such as in the production of vaccines, the study of protein folding, and the preservation of cells and tissues. Raffinose is commonly used as a stabilizer in vaccines to protect the active ingredients from degradation during storage and transportation. Raffinose can also be used as a cryoprotectant to preserve cells and tissues during freezing and thawing. In addition, raffinose can be used as a crowding agent to mimic the crowded cellular environment and study protein folding.

Current State of Research:

Raffinose is an area of active research in various fields, such as biotechnology, food science, and medicine. Researchers are investigating the potential applications of raffinose in vaccine development, tissue engineering, and drug delivery. Furthermore, researchers are exploring the mechanisms of raffinose's biological properties and its interactions with cells and proteins.

Limitations:

One of the major limitations of raffinose is its solubility and stability in water. Raffinose has limited solubility in water, which makes it less effective as a cryoprotectant and stabilizer for some applications. In addition, raffinose can undergo hydrolysis, which can reduce its stability and effectiveness.

Future Directions:

There are several future directions for research on raffinose, such as:

1. Developing new methods for synthesizing raffinose with improved solubility and stability.

2. Investigating the mechanisms of raffinose's prebiotic activity and its effects on the gut microbiota.

3. Exploring the potential applications of raffinose in tissue engineering and regenerative medicine.

4. Developing new formulations of raffinose as a stabilizer and cryoprotectant for vaccines and other biologics.

5. Assessing the potential toxicity of raffinose in long-term studies.

6. Exploring the interactions between raffinose and cellular membranes and proteins to better understand its mechanisms of action.

Conclusion:

Raffinose is a trisaccharide with multiple biological properties and potential applications in various fields of research and industry. Its properties, synthesis, characterization, and limitations have been discussed in this paper. The current state of research on raffinose has also been presented, and future directions for research have been proposed. Raffinose has the potential to contribute to the development of new vaccines, regenerative therapies, and biologic products. However, its limitations need to be overcome, and its safety needs to be carefully evaluated in future studies.

COA:

Product name: D(+)-Raffinose pentahydrate

CAS: 512-69-6        M.F.: C₁₈H₃₂O₁₆^.5(H₂O)            M.W._: 594.51  

Title: Raffinose

CAS Registry Number: 512-69-6

CAS Name: b-D-Fructofuranosyl-O-a-D-galactopyranosyl-(1®6)-a-D-glucopyranoside

Additional Names: gossypose; melitose; melitriose

Molecular Formula: C18H32O16

Molecular Weight: 504.44

Percent Composition: C 42.86%, H 6.39%, O 50.75%

Literature References: A trisaccharide built from 1 mol each of D-galactose, D-glucose, and D-fructose which are obtained from it by acid hydrolysis. Invertase splits it into melibiose and saccharose. Occurs in Australian manna (from Eucalyptus spp, Myrtaceae); in cottonseed meal. Prepn: C. S. Hudson, T. S. Harding, J. Am. Chem. Soc. 36, 2110 (1914); E. P. Clark, ibid. 44, 210 (1922); Harding, Sugar 25, 82 (1923); Hungerford, Nees, Ind. Eng. Chem. 26, 462 (1934). Configuration: Haworth et al., J. Chem. Soc. 1923, 3125; Charlton et al.; Haworth et al., ibid. 1927, 1527, 3146. Structure: Hassid, Ballou in W. Pigman, The Carbohydrates (Academic Press, New York, 1957) p 517. Synthesis: Suami et al., Carbohydr. Res. 26, 234 (1973). Review: E. B. Rathbone, Dev. Food Carbohydr. 2, 145-185 (1980).

Derivative Type: Pentahydrate

Properties: Crystals in clusters from dil alc. Indifferent taste. d 1.465. mp 80°. Loses water of crystn upon slow heating to 100°. The anhydrous form dec 118-119°. [a]D20 +105.2° (c = 4). One gram dissolves in 7 ml water (soly table: Hungerford, Nees), in 10 ml methanol. Sol in pyridine, slightly sol in alc. Does not form an osazone and does not reduce Fehling's soln.

Melting point: mp 80°

Optical Rotation: [a]D20 +105.2° (c = 4)

Density: d 1.465

References:

1. Saleki-Gerhardt A, Stowell JG, Byrn SR, Zografi G, J. Pharm. Sci. 1995, 84(3), 318-23