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L-Gulonic acid γ-lactone, also known as L-Gulono-1,4-lactone, CAS 1128-23-0, molecular formula C6H10O6, molecular weight 178.140, is a colorless crystal or white to off white crystalline powder. Low solubility in water, but soluble in organic solvents such as DMSO and methanol. Its solubility is influenced by various factors such as temperature, solvent type, and substance purity. Mass spectrometry analysis can determine molecular weight and infer its structure through fragment ion peaks. In the mass spectrum, molecular ion peaks and fragment ion peaks generated by molecular fragmentation can be observed. It is a chemical substance of significant importance in biochemical and metabolic research. But it is worth mentioning that this compound has important metabolic functions in organisms. It is a key intermediate in the biosynthesis pathway of vitamin C (ascorbic acid). In most mammals, vitamin C is converted into vitamin C through a series of enzymatic reactions, while humans and some primates must obtain vitamin C from their diet due to a lack of this synthetic pathway.
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Chemical Formula |
C6H10O6 |
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Exact Mass |
178 |
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Molecular Weight |
178 |
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m/z |
178 (100.0%), 179 (6.5%), 180 (1.2%) |
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Elemental Analysis |
C, 40.45; H, 5.66; O, 53.89 |
L-Gulonic acid γ-lactone, as a compound that occupies an important position in biochemical and metabolic research, has a wide and diverse range of applications.
(1) Iron fortifier: can be used as an iron fortifier in nutritional supplements. In the food industry, adding it to products such as milk powder and dairy products can increase the iron content and bioavailability of the products, which helps prevent and treat nutritional deficiencies such as iron deficiency anemia.
(2) Dietary supplements: With increasing attention to healthy eating and nutritional supplements, they have also been developed as active ingredients in dietary supplements. By supplementing, the production and storage of vitamin C in the body can be indirectly increased, thereby enhancing the body's antioxidant capacity and immunity.
Industrial applications
(1) Water treatment agent: can be used as a water treatment agent in industry. Through its specific chemical properties, it can react with harmful substances in water to achieve the goal of purifying water quality. This application is of great significance for protecting water resources and ecological environment.
(2) Printing plate corrosion agent: In the printing industry, it can be used as a corrosion agent for printing plate making. It can help plate making materials form the required patterns and structures under specific conditions, improving the quality and accuracy of printed materials.
(3) Oxidants and mordants in the dye industry: They can be used as oxidants and mordants in the dye industry. By reacting chemically with dye molecules, the color and properties of the dye can be changed to meet the demand for dye products in different fields.
(1) Drug metabolism research: It has important value in drug metabolism research. By studying the metabolic pathways and mechanisms in the body, we can understand the transformation process and effects of drugs in the organism, providing scientific basis for drug development and optimization.
(2) Research on the impact on the immune system: In recent years, an increasing number of studies have shown significant effects on the immune system. By regulating metabolic levels, the activity and function of immune cells can be affected, thereby regulating the body's immune response and disease resistance. This discovery provides important ideas for the development of new immunomodulatory drugs.
(3) Anti inflammatory and antioxidant effects: It also has anti-inflammatory and antioxidant effects. It can alleviate tissue damage and promote tissue repair by clearing free radicals in the body and inhibiting inflammatory reactions. This characteristic makes it potentially valuable in the fields of anti-inflammatory drugs and antioxidant health products.
Analytical reagents
L-gulonic acid - γ - lactone plays an important role in analytical chemistry. As an analytical reagent, it can be used for qualitative and quantitative analysis of various substances. For example, it can be used to determine the content of metal elements such as arsenic, lithium, tin, selenium, vanadium, as well as the concentration of inorganic compounds such as thiocyanate and ferrocyanide. In addition, in biochemical analysis, L-gulonic acid - γ - lactone can also be used to determine the content of biomolecules such as total cholesterol in serum, providing important basis for clinical diagnosis and disease monitoring.
L-Gulonic acid γ-lactone (GUL) is a chemical substance that plays a critical role in the biological system, particularly in the biosynthesis pathway of vitamin C. Its mechanism of action is complex and intricate, involving multiple biochemical reactions and enzymatic processes. When synthesizing GUL from glucose, we need to recognize that this is a complex biochemical process that typically occurs in organisms capable of naturally synthesizing vitamin C (ascorbic acid). However, under laboratory conditions, we can attempt to simulate the key steps of this process, but may require the use of specific enzymes, chemical catalysts, or genetic engineering techniques.
Detailed steps and equations
Reaction description:
Under the catalysis of glucose oxidase (GOx), glucose is oxidized to gluconic acid, while consuming oxygen and generating hydrogen peroxide as a byproduct.
Reaction equation:
Glucose+O2GOx → Gluconic acid+H2O2
Experimental conditions:
-Enzymatic reactions are usually carried out under mild conditions, such as room temperature to 37 ° C, with a pH value close to the enzyme's optimal pH.
-Sufficient oxygen needs to be provided to ensure the reaction proceeds.
-Hydrogen peroxide may need to be removed or neutralized as it may be harmful to enzymes in subsequent steps.
Reaction description:
In living organisms, this step involves multiple enzymatic reactions, including gluconate kinase (although please note that this is not a standard enzyme name as gluconate is typically not directly converted to phosphate through kinase; here we assume the existence of a similar enzyme or reaction pathway) and other possible isomerization, oxidation, or phosphorylation steps. In the laboratory, this may require complex chemical synthesis or genetic engineering methods to simulate.
Simplified reaction pathway (non direct equation, as it involves multiple steps):
Gluconic acid → (a series of enzymatic reactions) → L-gulose-6-phosphate
Experimental Challenge:
-This step is a bottleneck in the synthesis process, as it requires simulating complex metabolic pathways within the organism.
-Customized synthesis pathways or the use of specific biocatalysts may be required.
Reaction description:
In living organisms, L-gulose-6-phosphate is converted to L-gulose-1,4-lactone through a series of enzymatic reactions, including lactonases. In the laboratory, this also requires specific enzymes or chemical methods.
Simplified reaction pathway (non direct equation):
L-gulose-6-phosphate+lactonase → L-gulose-1,4-lactone+phosphate
Experimental conditions:
-We need to find or design enzymes that can catalyze this reaction.
-The reaction conditions may include appropriate pH, temperature, and substrate concentration.
Due to variations in laboratory conditions, available raw materials, and catalysts, the following is a hypothetical synthesis example:
1. Starting from gluconic acid:
Firstly, glucose is oxidized to gluconic acid by glucose oxidase (as described earlier).
2. Phosphorylation:
Then, a hypothetical 'gluconate kinase' (which may not actually exist, but we can assume the existence of a similar enzyme or chemical method) is used to phosphorylate gluconate to L-gulose-6-phosphate.
3. Lactylation:
Next, a lactonase (or chemical catalyst) is used to convert L-gulose-6-phosphate into GUL. This step may require specific reaction conditions and catalyst design.
4. Purification:
Finally, pure GUL is obtained through appropriate purification steps.
The synthesis of GUL is a complex biochemical process that typically requires simulating or utilizing metabolic pathways within the organism. In the laboratory, this may require a combination of various techniques such as organic chemistry, enzyme engineering, and biochemistry.
L-Gulonic acid γ-lactone (GUL) has significant biochemical and physiological effects in organisms, which are closely related to its key role in the biosynthesis pathway of vitamin C.
Key roles in the biosynthesis pathway of vitamin C
GUL is a direct precursor in the biosynthesis pathway of vitamin C. Through the catalytic action of L-gulonic acid - γ - lactone oxidoreductase (GULO), GUL is oxidized to remove one water molecule and generate vitamin C (ascorbic acid). This step is the final and most crucial step in the synthesis of vitamin C. Therefore, the supply and conversion efficiency of GUL directly affect the content and bioavailability of vitamin C in organisms.
Promote the generation and utilization of vitamin C
Increasing the synthesis of vitamin C:
GUL, as a direct precursor of vitamin C, its sufficient supply can promote the synthesis of vitamin C, thereby maintaining the homeostasis of vitamin C in the body. This is particularly important for organisms that cannot autonomously synthesize vitamin C, such as humans and some primates, as they must obtain sufficient GUL or vitamin C from their food to meet their physiological needs.
Improving the bioavailability of vitamin C:
The process of converting GUL into vitamin C is an efficient biochemical reaction that can rapidly occur within the organism. This means that GUL can not only promote the synthesis of vitamin C, but also improve its bioavailability, allowing vitamin C to function faster.
Other physiological effects
Promoting collagen synthesis:
Vitamin C is an important cofactor in collagen synthesis. GUL promotes the synthesis of vitamin C, which helps to synthesize and stabilize collagen, thereby maintaining the health of tissues such as skin, bones, and teeth.
Participate in iron metabolism:
Vitamin C can promote the absorption and utilization of iron, which is of great significance for the prevention and treatment of iron deficiency anemia. GUL, as a precursor of vitamin C, also indirectly participates in this process.
Enzymatic reaction process
Under the action of GUL oxidoreductase (also known as L-gulonolactone oxidase, GULO), GUL is oxidized to remove one water molecule and generate vitamin C (ascorbic acid). This step is the final and most crucial step in the synthesis of vitamin C. The presence or absence of GULO enzyme directly determines whether an organism can autonomously synthesize vitamin C. For example, humans and some primates are unable to synthesize vitamin C autonomously due to the absence of the gene encoding GULO enzyme in their genomes, and must obtain it from food.
Functions within living organisms
Promoting the synthesis of vitamin C:
GUL, as a direct precursor of vitamin C, its presence and conversion efficiency directly affect the content of vitamin C in organisms. Adequate supply of GUL is crucial for maintaining the homeostasis of vitamin C in organisms capable of autonomously synthesizing vitamin C.
Antioxidant effect:
Although GUL itself does not directly exert antioxidant effects, its transformed product vitamin C is a potent antioxidant. Vitamin C can eliminate free radicals in the body, protect cells from oxidative damage, and maintain the health of organisms.
Participate in other biochemical reactions:
In addition to being a precursor of vitamin C, GUL may also participate in other biochemical reactions that have not been fully elucidated. For example, studies have shown that GUL may also play a role in drug metabolism and immune system regulation.
Adverse reactions
L-Gulonic acid gamma lactone is a naturally occurring organic compound commonly used as a precursor or intermediate in the synthesis of vitamin C (ascorbic acid), and is also used in the fields of food, medicine, and cosmetics. Its adverse reactions are relatively rare, but potential risks still need to be noted, especially when exposed to high doses or special populations. The following are possible adverse reactions and precautions:
Adverse health reactions
Skin and mucosal irritation
Direct contact may cause mild skin irritation, manifested as redness, itching, or dryness, especially at high concentrations or long-term exposure. Eye contact may irritate the conjunctiva, causing tears, pain, or temporary blurred vision, and immediate rinsing with water is necessary. Inhaling powder or vapor may irritate the respiratory tract, causing coughing, sneezing, or throat discomfort (rare as it is typically used in solid or solution form).
Gastrointestinal reactions
Oral ingestion of high doses may cause mild nausea, bloating, or diarrhea, especially on an empty stomach. This is related to the acidic substances that may be released during the synthesis of vitamin C, but the symptoms are usually mild and short-lived.
allergic reaction
A very small number of people may be allergic to L-gulonic acid gamma lactone or its metabolites, manifested as rash, urticaria, asthma, or anaphylactic shock (rare). People with allergies should use it with caution.
Metabolic effects
As a precursor of vitamin C, excessive intake may indirectly lead to hypervitamin C (such as long-term high-dose supplementation), causing an increased risk of diarrhea, nausea, headache, or kidney stones (due to increased excretion of vitamin C metabolite oxalate).
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