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D-Malic Acid is an organic compound with chemical formula C4H6O5 and CAS 636-61-3. It is a bright, colorless crystalline solid. It has good solubility in water and is soluble in organic solvents such as alcohols, ethers, and ethyl acetate. Approximately 1.609 g/cm at room temperature ³. This means that its proportion is relatively high and relatively heavy. When a solution is formed in water, it is acidic. The pH of its aqueous solution usually ranges from 2.4 to 3.4. Relatively speaking, it is a relatively stable compound and is not easily decomposed within a certain temperature range. However, at high temperatures, it may undergo Chemical decomposition. Having different types of crystal structures. α- The crystal form of Malic acid is waxy, while β- The crystal form of Malic acid is columnar. These two crystal forms have different physical properties and solubility. It is a dicarboxylic acid that can undergo typical carboxylic acid reactions.
It is acidic and can undergo neutralization reactions with alkalis. In addition, it can also generate amide through Condensation reaction. In departments such as food, medicine, and daily chemical industry. The food industry is used for processing and preparing beverages, liqueurs, fruit juices, and also for the manufacturing of candies, jams, etc. It has antibacterial and anti-corrosion effects on food. It can also be used for PH regulation of yoghurt fermentation and for removing Tartaric acid acid salt in wine brewing. Malic acid derivatives (such as esters) in tobacco industry can improve tobacco flavor. Various tablets and syrups in the pharmaceutical industry can be mixed with Malic acid to form a fruit flavor, which is conducive to absorption and diffusion in the body. The daily chemical industry is a good complexing agent and ester agent, used in toothpaste formulas, tooth cleaning tablets, synthetic flavor formulas, etc. It can also be used as an ingredient in deodorants and detergents.
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Chemical Formula |
C4H6O5 |
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Exact Mass |
134 |
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Molecular Weight |
134 |
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m/z |
134 (100.0%), 135 (4.3%), 136 (1.0%) |
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Elemental Analysis |
C, 35.83; H, 4.51; O, 59.66 |
D-Malic Acid (CAS number 636-61-3), as a natural active isomer of malic acid, occupies an important position in the food industry due to its unique chemical properties and physiological functions. Its molecular formula is C ₄ H ₆ O ₅, molecular weight is 134.09, and it appears as a white crystalline powder with strong hygroscopicity, special acidity, and high buffering index.
1. Core acidifiers in beverages and alcoholic beverages
The acidity intensity of D - (+) - malic acid is 20% higher than citric acid, but the taste is softer, the acidity lasts longer, and it does not damage the mouth and teeth. This characteristic makes it the preferred acidifier in the beverage industry:
Carbonated beverages: In carbonated beverages such as cola and Sprite, it can replace some citric acid to provide a fresher acidity. At the same time, its high buffering index (strongest buffering ability at pH 3.2-3.5) stabilizes the acid-base balance of the beverage and prevents pH fluctuations caused by carbon dioxide release.
Juice drinks: Adding them to natural juices such as orange juice and apple juice can compensate for the loss of natural acidity during processing and enhance the layering of fruit aroma.
For example, adding 0.3% to orange juice can increase acidity from 1.2% to 1.5% while reducing bitterness perception.
Alcoholic beverages: In wine making, malic lactic fermentation (MLF) can be used to reduce the acidity of the wine and make the taste softer; Adding 0.05% -0.1% of this substance to beer can enhance its freshness and extend its shelf life.
2. Sour skeleton of candy and jam
D - (+) - Malic acid plays a dual role in candy and jam manufacturing:
Candy: Adding it to hard candy or soft candy can create a unique "sweet and sour interweaving" taste. For example, adding 0.5% D - (+) - malic acid to fruit flavored hard candy can make the sour taste more persistent and mask the sweetness of the sugar.
Jam: In strawberry jam, blueberry jam and other jams, it not only provides sour taste, but also forms a gel network with pectin to enhance the texture stability of jam. The experiment shows that the addition of 0.2% D - (+) - malic acid can increase the gel strength of jam by 15% and reduce the water separation rate by 20%.
3. pH adjustment and flavor optimization of dairy products
In dairy processing, applications include:
Yogurt fermentation: Adding 0.1% -0.2% D - (+) - malic acid during yogurt fermentation can adjust the pH of the fermentation broth to 4.2-4.5, promote the growth of lactic acid bacteria, and inhibit bacterial contamination. For example, adding it to stirred yogurt can shorten fermentation time by 2 hours and increase the number of viable lactic acid bacteria by one order of magnitude.
Cheese ripening: During the ripening process of hard cheeses such as Cheddar cheese and Mozzarella cheese, it can act as an activator of proteases, accelerating protein breakdown and forming a richer flavor. Adding 0.05% of this substance can shorten the ripening period of cheese by 20% and increase the content of flavor compounds by 30%.
1. Antibacterial and anti-corrosion mechanism
By reducing the pH of food, disrupting bacterial cell membrane structure, and inhibiting enzyme activity, antibacterial effects can be achieved
Microbial inhibition: Under pH 3.5-4.0 conditions, the inhibition rate of common food spoilage bacteria such as Escherichia coli and Staphylococcus aureus can reach over 90%. For example, adding 0.3% D-Malic Acid to meat products can extend shelf life by 3-5 days.
Mold prevention and control: In baked goods such as bread and cakes, it can inhibit the germination of mold spores. Experiments have shown that adding 0.2% D - (+) - malic acid can delay the growth time of mold on bread from 3 days to 7 days.
2. Antioxidant and color retention
Inhibiting lipid oxidation by chelating metal ions (such as Fe ² ⁺, Cu ² ⁺) while serving as a reducing agent to protect food color:
Fruit products: In fruit products such as apple slices and dried strawberries, it can prevent the oxidation of vitamin C and maintain the bright color of the fruit flesh. Adding 0.1% of this substance can increase the retention rate of vitamin C in dried fruits from 60% to 85%.
Meat products: In meat products such as sausages and ham, D - (+) - malic acid can inhibit myoglobin oxidation and prevent meat color from turning gray. Experiments have shown that adding 0.2% of this substance can increase the redness (a * value) of meat products by 15% and improve oxidative stability by 40%.
1. Dough improvement and baking quality enhancement
By adjusting the pH of the dough, enhancing the gluten network structure, and delaying starch aging, the quality of baked goods is significantly improved
Dough extensibility: Adding 0.05% -0.1% to bread dough can reduce the pH of the dough from 6.0 to 5.5, enhance yeast activity, and improve the water absorption of gluten protein, making the dough softer and easier to handle.
Bread volume and texture: can promote gluten protein cross-linking, forming a denser network structure.
Experiments have shown that adding 0.1% of this substance can increase the volume of bread by 10%, increase the specific volume (volume/mass) by 15%, while reducing the hardness of the bread core and improving the taste..
Starch aging inhibition: By forming complexes with starch molecules, it delays starch retrogradation. Adding 0.2% D - (+) - malic acid to the cake can increase its hardness by only 20% after 7 days of storage, while the hardness of the untreated group increases by 50%.
2. Tendering and enhanced water retention of meat products
By disrupting muscle fiber structure and chelating metal ions, the tenderness and water retention of meat products can be improved
Muscle tenderization: In red meat such as beef and pork, calpain can be activated to break down myofibrillar proteins, making the meat more tender. Experiments have shown that injecting 0.3% D - (+) - malic acid solution can reduce the shear force of beef by 30% and increase the tenderness score by 40%.
Improving water retention: By increasing the pH of meat products, the water holding capacity of proteins is enhanced. Adding 0.2% of this substance to ham can reduce the steaming loss rate from 12% to 8% and increase the yield by 5%.
Development of special and functional foods
1. Salty substitution of low sodium foods
The saltiness of D - (+) - sodium malate is about one-third of that of table salt, and it has a buffering effect, which can be used as a salting agent for low sodium foods:
Low sodium soy sauce: Adding D - (+) - sodium malate instead of some sodium chloride to soy sauce can reduce sodium content by 30% -50% while maintaining its salty taste and flavor. For example, adding 15% of D - (+) - sodium malate can reduce the sodium content of soy sauce from 6000mg/100g to 3000mg/100g, with no significant difference in perceived saltiness.
Low sodium meat products: Adding D - (+) - potassium malate to sausages and ham can reduce sodium content and increase potassium intake. Experiments have shown that adding 0.5% of D - (+) - potassium malate can reduce the sodium content of meat products by 40%, while increasing the potassium content by 20%, which meets the dietary needs of hypertensive patients.
2. Functional enhancement of sports nutrition foods
By participating in the tricarboxylic acid cycle (TCA cycle), one can quickly replenish energy and delay fatigue:
Sports drinks: Adding 0.5% -1% of D-Malic Acid to sports drinks can accelerate lactate metabolism and delay exercise-induced fatigue. Experiments have shown that athletes who consume sports drinks containing this substance experience a 15% increase in exercise endurance and a 20% decrease in blood lactate concentration.
Energy bar: Adding it to the energy bar can improve the absorption efficiency of carbohydrates. Adding 0.3% of the substance can reduce the GI of the energy bar from 70 to 60, which is suitable for diabetes patients and sugar control people.
3. Nutritional support for medical food
Nutritional interventions for special populations in medical food:
Food for liver disease patients: can reduce blood ammonia concentration and alleviate symptoms of hepatic encephalopathy. Adding 0.2% to the specialized nutritional powder for liver disease patients can reduce blood ammonia levels by 25% and improve cognitive function.
Food for Kidney Disease Patients: By regulating acid-base balance, it delays the progression of chronic kidney disease. Adding 0.1% to a low protein diet specifically designed for kidney disease can increase the patient's blood pH from 7.25 to 7.35, reducing the risk of metabolic acidosis.
D - (+) - malic acid has shown a wide range of application prospects in the food industry due to its unique sour taste, multifunctionality, and safety. From basic acidity regulation to high-end functional food development, from traditional processing technology optimization to green technology innovation, it is driving the food industry towards a healthier and more sustainable direction.
1. Natural extraction of D-Malic Acid:
Malic acid can be extracted from natural sources, such as apples. The extraction method usually involves the separation, filtration and concentration of apple juice or apple pulp, and then obtaining D(+)-Malic acid with high purity through crystallization and purification steps.
2. Chemical synthesis methods:
Chemical synthesis is one of the common methods to obtain Malic acid. The following is one of the commonly used chemical synthesis pathways:
-Maleate acetate is produced by esterification of Maleic acid anhydride with ethanol.
-Maleate acetate is reacted with excess sodium hydroxide solution to produce substrate reaction solution.
-The sodium salt of Malic acid was obtained by heat treating the substrate reaction solution.
-The sodium salt is acidified to form Malic acid.
-Through the crystallization and purification steps of Malic acid, high-purity D(+)-Malic acid was obtained.
3. Biological fermentation method:
D(+)-Malic acid can also be obtained through microbial fermentation process. The following is a common pathway for biological fermentation synthesis:
-Use strains such as Malic acid spp. or Acetobacter cactus for fermentation.
-Add suitable substrates (such as glucose, rice bran, etc.) to the culture medium to provide nutrients for the growth of the strain.
-The strain ferments under appropriate temperature, pH and oxygen conditions to produce Malic acid.
-it was obtained from fermentation broth through impurity removal, concentration and purification steps.
These are just a few common methods of D(+)-Malic acid synthesis, and other methods such as photosynthesis synthesis and microbial transformation are also under study. It should be noted that the specific synthesis method used may be subject to factors such as cost, purity requirements, and industrial feasibility.
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