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4-O-(α-D-Glucopyranosyl)-D-gluco-hexonic acid is a disaccharide-derived sugar acid formed through the glycosidic linkage between two glucose units, where one glucose is oxidized to a gluconic acid moiety. Specifically, the α-anomeric carbon (C1) of a D-glucopyranose molecule is linked via an O-glycosidic bond to the hydroxyl group at the C4 position of D-gluco-hexonic acid (gluconic acid). This structure retains the pyranose ring conformation of the reducing glucose unit while introducing a carboxylic acid group at the C1 position of the gluconic acid portion, altering its chemical properties.
The α(1→4) glycosidic bond confers stereospecificity, influencing enzymatic recognition and hydrolysis. This compound may arise from partial oxidation of maltose (α-D-glucopyranosyl-(1→4)-D-glucose) or via biochemical modifications. Its amphiphilic nature-combining hydrophilic hydroxyl/carboxyl groups with a glycosidic backbone-suggests potential applications in chelation, surfactants, or as an intermediate in carbohydrate metabolism. Analytical techniques like NMR and mass spectrometry are essential to confirm its regio- and stereochemistry.
Additional information of chemical compound:
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Chemical Formula |
C12H22O12 |
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Exact Mass |
358.11 |
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Molecular Weight |
358.30 |
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m/z |
358.11 (100.0%), 359.11 (13.0%), 360.12 (2.5%) |
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Elemental Analysis |
C, 40.23; H, 6.19; O, 53.58 |
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Melting point |
155-157℃(decomp) |
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Boiling point |
864.7±65.0℃(Predicted) |
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Density |
1.79±0.1 g/cm3(Predicted) |
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4-O-(α-D-Glucopyranosyl)-D-gluco-hexonic acid , as a substance with unique chemical properties, has demonstrated extensive application potential in multiple fields. The following are its main uses:
Cosmetics and skincare products
Maltic acid is one of the fourth generation fruit acids, derived from plants, which gives it special advantages in cosmetics and skincare products. It can gently remove skin keratin, improve skin roughness and dullness, and make the skin smoother and brighter. Maltose acid also helps promote skin metabolism, increase skin elasticity and radiance.
Food and beverage
Maltose acid has a sweet and sour taste and can be used as a food additive to enhance the taste and flavor of food. It can also be used as an acidity regulator for food, improving the acidity balance of food. Maltic acid has the characteristics of low calorie, low sweetness, non hygroscopicity, and non fermentation, making it suitable for making low sugar or sugar free foods and meeting the needs of a healthy diet.
Pharmaceuticals and health products
Maltic acid has certain pharmacological effects and can be used to make certain drugs or health products. It helps regulate the acid-base balance in the human body and improve metabolic function. Maltose acid can also be used as a drug excipient or stabilizer to improve the stability and efficacy of drugs.
Industrial and other applications
Maltose acid can be used as a surfactant, dispersant, emulsifier, etc. in industry to improve the dispersibility and stability of materials. It can also be used in metal surface treatment, electroplating and other processes to improve the smoothness and adhesion of metal surfaces. Maltulose acid can also be used to synthesize other organic compounds, serving as a chemical raw material in laboratory and industrial production. In the textile printing and dyeing industry, maltose acid can be used as a dye and printing aid to improve dyeing effect and printing clarity.
What are the production processes of this substance
1.Chemical catalytic synthesis method
Chemical catalytic synthesis is a chemical method that uses specific catalysts and reaction conditions to convert maltose or other sugar substances into maltose acid. This method usually requires high temperature and pressure, and may produce multiple by-products, resulting in complex and costly subsequent separation and purification steps. Therefore, the chemical catalytic synthesis method is not the preferred method for producing maltose acid.
2.Microbial transformation method
Microbial transformation method utilizes the metabolic activity of microorganisms to convert maltose into maltose acid. This method has the advantages of environmental protection, high efficiency, and low cost, and has gradually become the mainstream method for producing maltose acid.
Select microbial strains that can efficiently convert maltose, such as Pseudomonas aeruginosa.Fermentation and cultivation of bacterial strains are carried out to provide suitable nutrients and growth conditions, allowing the strains to reproduce in large quantities and accumulate the enzymes required for transformation.
Centrifuge the fermented and cultured bacterial strains, collect the bacterial cells, and prepare a resting cell solution.Add maltose to the resting cell solution for transformation reaction. During the reaction process, it is necessary to control suitable conditions such as temperature, pH value, and shaking speed to improve conversion efficiency and product quality.
After the conversion reaction is completed, calcium maltose or sodium maltose is extracted through steps such as centrifugation, evaporation concentration, and ethanol precipitation.Finally, maltose acid product is obtained through sulfuric acid displacement reaction, and further purified through ion exchange, crystallization and other steps to improve its purity and yield.
3.Enzyme catalyzed oxidation method
Enzymatic oxidation method is the use of specific enzymes (such as sugar oxidase and catalase) to catalyze the oxidation reaction of maltose, producing maltose acid. This method has the advantages of mild reaction conditions, easy control, and low environmental pollution.
Choose enzymes that can catalyze the maltose oxidation reaction, such as sugar oxidase and catalase.Add enzymes to maltose solution and control appropriate reaction conditions (such as temperature, pH, and oxygen concentration).
During the reaction process, it is necessary to continuously stir the solution to ensure sufficient contact and reaction between the enzyme and maltose.
Control the reaction rate and product quality by adjusting reaction conditions such as temperature and pH value.
After the reaction is complete, the maltose acid product is extracted and purified through steps such as filtration, concentration, and crystallization.
Which is more environmentally friendly, chemical catalytic synthesis or microbial transformation
Chemical catalytic synthesis method: usually has a high reaction rate and conversion rate, and can efficiently synthesize maltose acid. However, this method may generate multiple by-products, resulting in complex and costly subsequent separation and purification steps.
Microbial transformation method: Utilizing the metabolic activity of microorganisms to convert maltose into maltose acid, its treatment effect is stable and easy to control. This method usually produces only a small amount of by-products or harmless substances, which is beneficial for the extraction and purification of subsequent products.
Chemical catalytic synthesis method: Toxic and harmful catalysts and solvents may be required during the reaction process, which may cause environmental pollution. In addition, the exhaust gas, wastewater, and waste generated during the reaction process also need to be properly treated to avoid further impact on the environment.
Microbial transformation method: mainly relies on the metabolic activity of microorganisms and does not require the introduction of toxic or harmful chemicals. This method usually does not produce harmful by-products or exhaust gas, wastewater, and waste residue during the reaction process, and has a relatively small impact on the environment.
Chemical catalytic synthesis method: usually requires a large amount of energy and raw materials, including catalysts, solvents, and reactants. The consumption of these resources not only increases production costs, but may also put pressure on the environment.
Microbial transformation method: mainly relies on the metabolic activity of microorganisms and does not require additional energy input (except for the nutrients required for microbial growth and suitable environmental conditions). Therefore, this method has relatively low resource consumption.
Chemical catalytic synthesis method: Although it has a high reaction rate and conversion rate, its sustainability may be limited by factors such as high resource consumption and environmental impact. In addition, the by-products and waste generated during the reaction process of this method also need to be properly handled to avoid long-term environmental impact.
Microbial transformation method: It can operate stably for a long time under suitable environmental conditions without producing secondary pollution. This method has a relatively low level of resource consumption and environmental impact, therefore its sustainability is relatively strong.
What is the difference in metabolic pathways between this substance and fructose in the human body
1.The metabolic pathway of maltose acid
Maltose acid first needs to be broken down into maltose in the human body. However, it is worth noting that maltose acid itself does not directly come from food, but may appear as a product of certain chemical reactions or biological processes. In a regular diet, people are more likely to directly consume maltose rather than maltose acid. Maltose is hydrolyzed into two molecules of glucose in the small intestine by maltase (also known as alpha glucosidase).
Absorption and Utilization of Glucose
Glucose is the main energy source for small intestinal epithelial cells and the main component of blood glucose. After being absorbed by the epithelial cells of the small intestine, glucose quickly enters the bloodstream, causing an increase in blood sugar levels. Blood sugar is transported through the bloodstream to various tissues throughout the body for use or storage by cells.
In the liver and muscles, glucose can be converted into glycogen and stored for future energy needs. When the body needs energy, liver glycogen and muscle glycogen can be broken down into glucose and released into the bloodstream, releasing energy inside cells through processes such as glycolysis, citric acid cycle, and oxidative phosphorylation.
2. The metabolic pathway of fructose
Absorption and transport: Fructose is a monosaccharide that can be directly absorbed by small intestinal epithelial cells. With the help of the transporter protein glut5, fructose enters small intestinal cells and is converted into 1-phosphate fructose or other intermediate metabolites within the cells.
Liver metabolism: Most fructose (about 85.5%) enters intestinal cells and portal vein with the help of transporter protein glut2, and is transported to the liver for metabolism.In the liver, fructose is first phosphorylated into fructose-1-phosphate, then broken down into glucose, and further synthesized into substances such as glucose and triglycerides.
Part of the glucose will be released into the bloodstream for use by other tissues in the body; Triglycerides may accumulate in the liver, leading to the occurrence of fatty liver.
Metabolism of other tissues: In addition to the liver, fructose can also be metabolized in other tissues such as the small intestine and kidneys, but the metabolic rate is relatively low.
3.Differences in metabolic pathways
Digestion and absorption
Maltose acid needs to be broken down into maltose first, and then hydrolyzed into glucose for metabolism; Fructose can be directly absorbed by small intestinal epithelial cells.
Metabolic sites
Glucose can be utilized or stored in various tissues throughout the body; The metabolism of fructose mainly occurs in the liver.
Metabolites
The metabolic products of glucose include glycogen, lactate, fatty acids, etc; The metabolites of fructose include glucose, lactate, triglycerides, etc., among which the accumulation of triglycerides in the liver may lead to fatty liver.
Frequently Asked Questions
Q: Why is this compound almost non-fermentable by common yeast strains, even though it is a glucose-derived disaccharide derivative?
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A: Its reducing end is oxidized to a carboxylate (gluconic acid structure), eliminating the free aldehyde group required for yeast glycolysis. In addition, the 4‑O‑α‑glucosidic linkage and the negatively charged carboxylate block recognition by most yeast glycosidases, making it resistant to typical sugar metabolic pathways.
Q: Does 4-O-(α-D-Glucopyranosyl)-D-gluco-hexonic acid have significant chelating ability, and with which metal ions is it most specific?
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A: Yes. The carboxylate group plus multiple adjacent hydroxyl groups enable it to act as a weak polyhydroxy carboxylate chelator. It shows preferential binding to Fe³⁺, Cu²⁺, and Ca²⁺ but not to Mg²⁺, due to the spatial arrangement of its equatorial hydroxyls and the anionic carboxylate.
Q: Why does this acid generally not undergo Maillard browning reactions under food-processing heating conditions?
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A: Maillard reactions require a free reducing sugar aldehyde/ketone group and an amine. This compound is a sugar acid with no free reducing end and no amino group. Even under low-pH heating, it only slowly dehydrates to form lactones without generating colored melanoidins.
Q: Can this compound spontaneously form intramolecular lactones, and which position is favored?
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A: Yes, but only weakly and selectively. Under acidic dehydration, it preferentially forms a 1,4‑lactone involving the C1 carboxylate and the C4 hydroxyl of the gluconic acid moiety. Lactonization with the attached glucopyranosyl unit is sterically unfavorable and rarely observed.
Q: Why is this substance rarely detected by typical anthrone or phenol‑sulfuric acid total sugar assays?
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A: The oxidized gluconic acid terminus changes the dehydration pathway under strong acid. It forms fewer furfural derivatives and absorbs less strongly at the usual 620 nm detection wavelength, leading to underestimation or incomplete color development compared to equivalent neutral oligosaccharides.
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