D-(+)-Melibiose CAS 585-99-9

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D-(+)-Melibiose, also known as beet ketone sugar, has a molecular formula of C12H22O11, CAS 585-99-9, and a relative molecular mass of 342.3 g/mol. Colorless crystalline solid, the common form is crystalline powder or crystal. It has good solubility in water, soluble in hot water, but basically insoluble in organic solvents such as alcohol and ether. It is relatively stable at room temperature, but may degrade under high temperature and strong acid conditions. Changes can be made through a series of chemical reactions. For example, it can combine with catechol to form a red-brown complex. In addition, it can also undergo hydrolysis reaction under the action of acid or enzyme to generate the corresponding monosaccharide. It is a disaccharide compound composed of glucose and galactose linked by 1-6-α-bond. Widely used in food industry, medicine field, microbiology research and so on. In the food industry, it is often used as a sweetener; in the field of medicine, it may have certain biological activities, such as anti-inflammatory, anti-tumor, etc.; in microbiology research, it can be used as a component of the culture medium.

D-(+)-Melibiose is a disaccharide compound composed of glucose and galactose linked by 1-6-α-bond. It has various applications in the food industry, the field of medicine, and microbiological research.

1. Food industry application:

It is often used as a sweetener to impart sweetness to food. Due to its relatively low sweetness and low calorie content, it is widely used in food manufacturing, especially low-sugar or sugar-free products, such as low-sugar beverages, chewing gum, cold drinks, candies, etc. It is also used in baby food, diet food and special diet products. In addition, It can also be used as a flavoring agent, thickener and humectant to improve the texture and mouthfeel of food.

2. Application in the field of medicine:

It has certain potential application value in the field of medicine. Studies have shown that it may have anti-inflammatory, anti-tumor, immunomodulatory and bioactive enhancement effects. It is thought to have therapeutic potential for certain inflammatory diseases such as arthritis, rheumatism, etc. In addition, It is also used to prepare drug carriers or nanoparticles to improve drug solubility and bioavailability, and improve drug stability.

3. Microbiology research applications:

It is a common carbon source and media ingredient in microbiological research. Many microorganisms can use it as the only carbon source for growth and metabolism, so as to isolate, culture and identify microorganisms. It is often used in research on intestinal flora, optimization of fermentation process, and research on microbial metabolic pathways. In addition,It can also be used to detect and distinguish specific enzyme activities of certain microorganisms, such as distinguishing Klebsiella and Salmonella by detecting β - galactosidase activity.

4. Other applications:

It has several other applications. For example, it can be used as a humectant and skin care ingredient in cosmetics, with the effect of maintaining skin moisture and improving skin texture. In addition, it can also be used in the preparation of biochemical reagents, experimental tools in scientific research, etc.

It should be noted that when using It, relevant safety operating procedures should be followed, and the dosage and conditions of use should be strictly controlled to ensure its safety and effectiveness.

It is a disaccharide compound composed of glucose and galactose linked by 1-6-α-bond. It can be obtained through several different crafting methods. The main synthesis method for it will be described in detail below.

1. Chemical synthesis method:

a. Chemical synthesis method 1: derived from glucose and galactose

In the first step, glucose and galactose are condensed by an acid-catalyzed reaction to produce glucose-1-galactose.

In the second step, It is obtained by reducing glucose-1-galactose.

b. Chemical Synthesis Method 2: Formation of Galactose Catalyzed by Hydrofluoric Acid

In the first step, galactose is reacted with hydrofluoric acid catalyst to generate 1,6-galactose hydrofluoride.

In the second step, It is generated by reducing 1,6-galactose hydrofluoride.

2. Enzyme synthesis method:

The enzymatic synthesis method uses biological enzymes to catalyze reactions to synthesize target products. For the enzymatic synthesis of product, a two-step reaction of glucose isomerase and β-galactosidase can be used to complete.

In the first step, glucose isomerase isomerizes glucose to galactose.

In the second step, β-galactosidase catalyzes the reaction to connect galactose to the already generated galactose to form product.

3. Microbial fermentation method:

The microbial fermentation method uses specific strains to metabolize and synthesize target products under suitable conditions. For the microbial fermentation synthesis of D-(+)-Melibiose, microorganisms with galactase activity can be selected for cultivation.

In the first step, strains are selected and pre-cultured, and an appropriate amount of glucose and galactose are added to the medium as carbon sources.

The second step is to control the appropriate fermentation conditions, such as temperature, pH value, oxygen supply, etc., to promote the metabolism of the strain to produce.

The third step is to obtain the target product through extraction and purification.

It should be noted that when choosing a synthesis method, comprehensive consideration should be made according to actual needs and conditions, and appropriate optimization and improvement should be carried out. In addition, when using chemical methods for synthesis, attention should be paid to proper experimental operating conditions and safety measures to ensure the smooth progress of the experiment.

1. Chemical modification:

- The chemical structure of It can be changed by chemical modification, such as introducing different chemical groups on its specific functional groups.

- This modification can expand the use of product, such as the preparation of new bioactive molecules and drugs.

2. Restorability:

- It is reducing because it contains two reducing ends, glucose and galactose.

- It can be reduced to glucose and galactose in the presence of reducing agents such as sodium hydroxide.

3. Acidity and alkalinity:

- It can be partially dissociated in water to produce ionic forms of glucose and galactose.

- Under acidic conditions, the degree of dissociation is low; under alkaline conditions, the degree of dissociation is high.

4. Optical properties:

- It is optically active and has optically active properties.

- It can deflect plane-polarized light, and the direction of rotation is right-handed (D-type).

- This optical activity is due to the stereoconfiguration of product.

5. Oxidation:

This substance can undergo oxidation reaction under the action of oxidants.

- In the presence of strong oxidizing agents such as hydrogen peroxide, it can be oxidized to the corresponding acid or aldehyde.

6. Glycation reaction:

- It reacts with amine compounds (such as amino acids and peptides) to generate glycosylated products.

- This reaction has important applications in food, medicine and biological research.

7. Enzymatic degradation:

- It can be degraded by specific enzymes (eg galactase, glucose isomerase).

- Catalyzed by galactase, it is hydrolyzed into glucose and galactose.

- Glucose isomerase can isomerize product to galactose.

D-(+)-Melibiose is a white crystalline solid whose crystal structure can be studied and described by X-ray diffraction technique. In the analysis of the crystal structure, we can understand how the molecules of product are arranged and how they interact. It belongs to the disaccharide compound, which is composed of two monosaccharide molecules (one glucose and one galactose) linked by 1-6-α-bond. In the crystal structure, it molecules are linked to each other by hydrogen bonds and other interaction forces.

The crystal structure of it usually adopts the space group P2₁2₁2₁ and has the following characteristics:

1. Cell parameters:
- a = 13.2 Å
- b = 17.9 Å
- c = 13.7 Å
2. Molecules in crystals:
The molecule exhibits a twisted chair conformation.
- The rings of glucose and galactose are in 4C₁ and 1C₄ conformations, respectively.
- Two monosaccharides linked by a 1-6-α-bond to form a product disaccharide.
3. Hydrogen bond:
- Multiple hydrogen bond interactions are formed between it molecules.
- The main hydrogen bonding is through the hydrogen bonding between the 1-OH group of glucose and the 2-OH group of galactose.
- The action of hydrogen bonds helps to stabilize the crystal structure and affects the physical and chemical properties of the crystal.
4. Molecular packing:
The molecule is arranged in layers within the crystal.
- The layers are held together by hydrogen bonds and van der Waals interactions.
- Layer-to-layer interactions lead to the stability of the entire crystal.

It should be noted that the above is a general description of the crystal structure of product. The specific crystal structure analysis depends on the experimental data and the results of simulation calculations. Meanwhile, it under different sources and preparation conditions may have slight structural differences.

1. Promoting the proliferation of beneficial bacteria: As a major component of the gut microbiota, it is crucial for maintaining a normal gut microbiota. It can increase the abundance of beneficial bacteria such as bifidobacteria, thereby improving intestinal health.
2. Improving fecal quality: It can improve the quality of feces, including pH value, short chain fatty acids (SCFAs), frequency, and consistency, helping to reduce the risk of gastroenteritis and infection.
3. Reduce inflammatory markers: It can lower the levels of inflammatory markers in the intestine, which may have a potential improvement effect on intestinal inflammatory conditions such as inflammatory bowel disease.
4. Regulating glucose and lipid metabolism: It may act as an inhibitor of certain enzymes involved in the metabolism of glucose and fatty acids, as well as the production of inflammatory mediators. It can also act as an agonist for certain receptors, involved in regulating glucose and lipid metabolism.
5. Inhibition of harmful microbial growth: In vitro studies have shown that it can inhibit the growth of certain bacteria, fungi, and viruses, reduce the levels of certain toxins such as polychlorinated biphenyls (PCBs), and help maintain intestinal microbiota balance.
6. Reduce the level of lipid and glucose in the blood: it has been proved to reduce the level of lipid and glucose in the blood, which has potential benefits for the management of metabolic diseases such as diabetes and obesity.
7. Improving intestinal barrier function: It may enhance intestinal barrier function, reduce intestinal permeability, thereby reducing metabolic endotoxemia and improving glucose homeostasis.

D - (+) - Melibiose is an important disaccharide composed of galactose and glucose linked by an alpha-1,6-glycosidic bond. As one of the widely present oligosaccharides in nature, melibiose has significant value in fields such as plant physiology, microbial metabolism, and food science. The research history of melibiose can be traced back to the mid-19th century. In 1856, German chemist Ludwig Armbructer first isolated a new disaccharide while studying the composition of honey. At that time, Armbructer noticed that although the content of this substance in honey was not high, it had unique physical and chemical properties. As it was originally discovered from honey, he named it "melibiose", which comes from the Greek words "meli" (meaning honey) and "biose" (meaning disaccharide). However, due to limitations in analytical techniques at the time, Armbructer was unable to fully determine its chemical structure. In the following decades, the existence of melibiose was questioned by the scientific community until more advanced separation and purification technologies emerged, confirming this discovery. In 1889, French chemist É mile Bourquelot rediscovered this disaccharide while studying sugar beet molasses. Bourquelot preliminarily determined through systematic chemical degradation experiments that melibiose is a reducing disaccharide composed of two types of hexoses. He observed that melibiose can be hydrolyzed by acid to produce monosaccharides with reducing properties, which laid the foundation for subsequent structural studies. At the end of the 19th century and the beginning of the 20th century, with the advancement of organic chemical analysis methods, especially the application of optical rotation measurement and elemental analysis techniques, scientists gradually determined the molecular formula of melibiose as C ₁₂ H ₂ O ₁₁, and determined its specific rotation to be+129 ° (aqueous solution). The determination of these basic physical and chemical properties provides important parameters for further research on melibiose. At the beginning of the 20th century, with the rapid development of sugar chemistry, the structural research of melibiose entered a new stage. In 1909, British chemist Walter Haworth began a systematic study of the structural characteristics of melibiose. Through methylation analysis and partial acid hydrolysis experiments, the Haworth research team determined that melibiose is a disaccharide composed of D-galactose and D-glucose. The key breakthrough occurred in the 1920s, when German chemists Purdie and Irvine developed a new methylation technique. Using this method, scientists have found that complete methylation of melibiose leads to hydrolysis, producing 2,3,4,6-tetra-O-methyl-D-galactose and 2,3,4-tri-O-methyl-D-glucose. This result indicates that the C6 position of the glucose moiety is involved in the formation of glycosidic bonds, while the C1 position of galactose is the other end of the glycosidic bond.

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