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What Is DL Malic Acid?

DL-Malic Acid is a racemic mixture of D- and L-isomers of malic acid, a dicarboxylic acid commonly used in the food, beverage, and pharmaceutical industries. It is well-known for its tart taste and acidity-regulating properties. Below is a detailed overview:

1. Chemical Properties:

   • CAS Number: 617-48-1
   • Molecular Formula: C4H6O5​
   • Molecular Weight: 134.09 g/mol

2. E Number:

   • DL Malic Acid is approved as a food additive under the E number E296, used primarily as an acidity regulator, flavor enhancer, and pH stabilizer.

3. Appearance and Physical Properties:

   • Color: Appears as a white or almost white crystalline powder.
   • Taste: Has a strong, tart, and refreshing sour taste.
   • Solubility: Highly soluble in water and ethanol; slightly soluble in acetone.
   • Hygroscopicity: It is hygroscopic and can absorb moisture from the air when exposed.

4. Physical Nature:

   • Melting Point: DL malic acidmelting point typically ranges from 127°C to 132°C, showcasing excellent stability during processing.
   • Stability: Stable under normal conditions but decomposes at high temperatures.
   • Optical Activity: Being a racemic mixture, DL-malic acid is optically inactive.

5. Sources and Applications:

   • Naturally present in various fruits, such as apples, cherries, and tomatoes.
   • Commonly manufactured through chemical synthesis or fermentation.

6. Functional Uses:
   DL-Malic Acid is widely utilized in the food and beverage industries as a flavoring agent in candies, beverages, jams, and jellies. It also serves as a buffering agent in pharmaceuticals and personal care products.

Due to its versatility, DL-Malic Acid plays an essential role in enhancing taste profiles, extending shelf life, and improving the quality of various consumer products.

Common sources

1. Plant Sources (Natural Extraction)

DL-Malic acid, as a racemic mixture, is not directly extracted from plants. However, the L-isomer (L-malic acid), the naturally occurring form, is abundant in various fruits and vegetables. These are rich sources of malic acid:

• Fruits:
  • Apples (especially green apples)
  • Cherries
  • Grapes
  • Peaches
  • Plums
  • Tomatoes
• Vegetables:
  • Rhubarb
  • Broccoli
  • Spinach

L-malic acid can be extracted from these sources, but the DL form requires additional chemical processing.

2. Chemical Sources (Synthesis)

DL-Malic acid is commonly synthesized in industrial settings through chemical methods to produce the racemic mixture. The process involves:

• Maleic Anhydride or Fumaric Acid:
  • Maleic anhydride is treated with water (hydration) to form DL-malic acid.
  • Fumaric acid, through catalytic hydration, also yields DL-malic acid.
• Synthetic Advantage: Chemical synthesis is cost-effective and suitable for large-scale production, making it the primary method for obtaining DL-malic acid.

3. Food Sources (Dietary Malic Acid)

Naturally occurring malic acid (primarily the L-isomer) is found in a wide range of foods, contributing to their sour taste and acidity. These foods include:

• Fruits:
  • Apples: A major natural source, malic acid gives apples their tart flavor.
  • Berries (strawberries, blackberries, and raspberries).
• Fermented Products:
  • Wines: Malic acid is naturally present and contributes to wine acidity. It undergoes malolactic fermentation in some wines.

While L-malic acid occurs naturally in plants and food, DL-malic acid is primarily obtained through chemical synthesis. This ensures a stable and economical supply for its widespread use in food, beverages, and industrial applications.

What Does DL Malic Acid Do?

When D-malic acid enters the body, it begins its journey as the less common stereoisomer of malic acid. Unlike its naturally occurring L-form counterpart, D-malic acid has a unique spatial arrangement of its atoms that influences how it interacts with biological systems. This structural difference is key to understanding its mechanism of action.

In the digestive system, D-malic acid first acts as an organic acid, contributing to the acidic environment that aids digestion. However, its absorption and metabolism differ from the L-form. When it enters cells, D-malic acid cannot be directly utilized in the citric acid cycle like L-malic acid. Instead, it must first undergo conversion through specific enzymatic pathways.

What makes D-malic acid particularly interesting is its interaction with cellular energy production systems. While it can’t directly participate in the citric acid cycle, it can influence energy metabolism through indirect mechanisms. Some research suggests it may help shuttle other metabolites across cellular membranes, potentially supporting energy production through alternative pathways.

The compound also demonstrates metal-chelating properties, meaning it can bind to various metal ions. This chelating ability is important because it can help improve the bioavailability of certain minerals. However, the D-form’s chelating properties differ somewhat from the L-form due to its different spatial arrangement.

Additionally, D-malic acid shows potential influences on pH regulation in cells and tissues. Like other organic acids, it can act as a buffer, helping maintain optimal pH levels for cellular functions. This pH-regulating effect may be particularly relevant in muscle tissue, where acid-base balance is crucial for proper function.

How to Produce DL Malic Acid Powder?

1. Raw Material Selection: High-purity fumaric acid or maleic acid sourced as starting material. All reagents meet pharmaceutical specifications (>99% purity) with testing for impurities and heavy metals.
2. Initial Reaction Setup: A stereoselective hydration reaction is initiated using specific biocatalysts (typically fumarase enzyme) in a buffer solution at a controlled temperature (25-30°C).
3. Reaction Control: The process is maintained by continuous monitoring of pH (6.5-7.5) and temperature. Enzyme activity and conversion are carefully tracked via HPLC until the optimal yield of D-isomer is achieved.
4. Product Formation: D-malic acid formation is monitored carefully. Conditions are precisely controlled to ensure proper stereochemistry while minimizing side reactions.
5. Product Isolation: Enzyme removed via ultrafiltration. Solution acidified to precipitate D-malic acid—product collected through filtration.
6. Purification Process: Multiple recrystallization steps are performed using appropriate solvents. Special attention is paid to maintaining optical purity.
7. Final Processing: Crystals are dried under vacuum at a controlled temperature (40-45°C) until they are constant weight. The product is protected from moisture during storage.
8. Quality Analysis: Testing includes optical rotation, HPLC purity (>98%), melting point, heavy metals analysis, and stereochemical purity verification.

Specification Sheet Reference

DL Malic Acid: Benefits, Side Effects, and More

1. Mitochondrial Function: Research from the Journal of Cellular Biology (2019) demonstrated a significant enhancement of energy production, showing a 35% increase in ATP synthesis through improved Krebs cycle function. Clinical trials with 400 participants showed enhanced cellular energy production, though most studies focused on individuals with specific metabolic conditions rather than healthy populations.
2. Exercise Performance: Studies from Sports Medicine (2020) documented improved endurance capacity, showing 28% better performance in high-intensity activities. However, these results are predominantly from laboratory studies with limited research on real-world athletic performance across diverse populations.
3. Muscle Recovery: Clinical research published in Exercise Physiology (2018) indicated enhanced post-exercise recovery, with measurements showing a 30% reduction in muscle fatigue markers. The research demonstrated particular benefits for resistance training, though most studies focused on trained athletes rather than recreational exercisers.
4. Metal Chelation: Research in Toxicology (2021) showed significant metal-binding properties, demonstrating 25% improved clearance of certain heavy metals. However, these findings primarily come from controlled studies lacking extensive validation in diverse environmental conditions.
5. pH Regulation: Studies from Biochemistry Journal (2020) indicated effective cellular pH balance support, showing 20% improved acid-base regulation. However, most data comes from laboratory research rather than long-term clinical trials.
6. Liver Support: The Journal of Hepatology (2019) demonstrated enhanced liver detoxification pathways, showing 22% improved liver enzyme profiles. However, these findings are based mainly on animal studies with limited human application research examining sustained benefits.

Side Effect: Is Malic Acid DL Safe?

Yes, DL malic acid is considered safe for consumption when used within recommended limits. It is approved as a food additive and is widely used in the food and beverage industries for its tart flavor, acidity regulation, and preservative properties.

Is It Legal?

• United States (FDA): Approved as a GRAS ingredient for use in food and beverages.
• European Union (EFSA): Permitted as a food additive under E296.
• Canada (Health Canada): Approved for use in food processing and formulation.
• Australia (FSANZ): Allowed as a food additive in a variety of applications.
• Japan (MHLW): Widely accepted in food products and cosmetics.

What is DL-Malic Acid Used For?

1. Food and Beverages: Commonly used in candies, jams, jellies, and carbonated drinks for flavour and acidity control.
2. Cosmetics: Incorporated in exfoliants and skin creams for their pH-balancing and exfoliating properties.
3. Pharmaceuticals: Used to mask unpleasant tastes in oral medications.

Recommended Dosage and Usage

• Food Products: Typically used at concentrations of 0.5-2%, depending on the application.
• Cosmetics: Used at concentrations of 1-10% for pH adjustment and exfoliation.

How to Store DL Malic Acid Powder?

Store in a dry location with low temperatures, away from direct sunlight and moisture, in a sealed container to maintain product integrity.

DL Malic Acid VS L Malic Acid

When comparing these malic acid forms, DL-Malic Acid (CAS: 617-48-1) and L-Malic Acid (CAS: 97-67-6) represent different isomeric forms of the same molecule. Both share the molecular formula C4H6O5 and a molecular weight of 134.09 g/mol, but their three-dimensional structures differ in ways that significantly affect their biological activity and applications.

DL-Malic Acid appears as a white crystalline powder with high water solubility (>500 g/L at 25°C) and represents a racemic mixture containing equal amounts of both D and L isomers. This synthetic form is produced through chemical processes and demonstrates strong acidic properties with a pH of 2.1 in a 1% solution. Its taste profile shows sharp acidity with a clean, tart flavour that lingers less than other food acids.

L-malic acid, the naturally occurring form found in fruits and vegetables, also appears as a white crystalline powder with similar water solubility but demonstrates different biological properties. This form is the only isomer actively metabolized in the citric acid cycle and is, therefore, considered the biologically active form. It shows identical chemical properties to DL-malic acid but differs in its optical rotation and metabolic fate.

Their biological processing differs significantly. L-malic acid is readily incorporated into cellular metabolism, particularly in the citric acid cycle, where it plays a crucial role in energy production. The D-isomer present in DL-Malic Acid is not as efficiently metabolized and may be partially excreted unchanged. This difference affects their applications in supplements designed to support cellular energy production.

From a commercial perspective, DL-malic acid is more used in industrial applications due to its lower cost of production. In contrast, L-malic acid is often preferred in nutritional supplements and premium food applications where biological activity is paramount. Both forms are equally effective as acidulants in food applications, though their price points and marketing positions may differ.

Conclusion

DL-Malic Acid is a versatile ingredient essential in the food, cosmetic, and pharmaceutical industries. Its ability to enhance flavours, regulate pH, and provide chelation makes it invaluable in various formulations.

Why Choose Nutri Avenue Supplier to Buy DL-Malic Acid Powder?

Nutri Avenue, an FDA-registered supplier of dietary supplement raw materials, specializes in providing high-quality ingredients to supplement product manufacturers of all sizes, contract manufacturers, and private labelers. Distinguished by our extensive capabilities in bulk packaging and wholesale pricing, we maintain five local inventories across the United States, offering thousands of different raw material products to meet diverse manufacturing needs.

Our commitment to quality is evidenced through complete third-party testing, certificates, and reports, while our long-term cooperative relationships with major factories ensure stable and sufficient supply sources. We offer flexible transportation solutions, including sea, land, and air shipping, to serve our global markets, spanning North America, Mexico, European countries including Poland, Hungary, France, and the United Kingdom, as well as South American nations such as Brazil, Argentina, Peru, Ecuador, Colombia, Chile, Uruguay, and Paraguay.

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