Courses
Courses for Kids
Free study material
Offline Centres
More
Store Icon
Store

Malic Acid: Properties, Uses & Biochemistry

Reviewed by:
ffImage
hightlight icon
highlight icon
highlight icon
share icon
copy icon
SearchIcon

How Does Malic Acid Function in Cellular Metabolism?

Malic acid has the molecular formula C4H6O5 and is an organic compound. It is a dicarboxylic acid produced by all living organisms and is used as a food additive. Pure malic acid contributes to the sour taste of fruits. Malic acid comes in two stereoisomeric variants (L- and D-enantiomers), but only the L-isomer is present in nature. Malates refer to the salts and esters of malic acid. The malate anion is a citric acid cycle intermediate.

The word 'malic' comes from the Latin word 'malum,' which means 'apple.' It's also the scientific name for the Malus family, which contains both apples and crabapples.


Malic Acid Malate Biochemistry

Super Malic Acid (Malic Acid Purpose)

Malate is a critical part of biochemistry. Malate is a source of CO2 in the Calvin cycle during the C4 carbon fixation process. (S)-malate is an intermediate in the citric acid cycle, formed by adding a -OH group to the si face of fumarate. Anaplerotic reactions can also generate it from pyruvate. 

Malate is also produced in plant leaves by carboxylation of phosphoenolpyruvate in the guard cells. Malate, as a double anion, often accompanies potassium cations during solute uptake into guard cells to keep the cell's electrical balance. The accumulation of these solutes in the guard cell reduces the solute potential, allowing water to reach the cell and promoting stomata aperture.


Synthesis of Malate and Malic Acid

Maleic anhydride is double hydrated to produce racemic malic acid in the industrial environment. In the year 2000, the United States' annual production potential was 5000 tonnes. The (S)- enantiomer can be obtained precisely by fermentation of fumaric acid, and both enantiomers can be isolated by chiral resolution of the racemic mixture. 

The pyrone coumaric acid is formed when malic acid self-condenses with fuming sulfuric acid.


Natural Malic Acid

Malic acid is the predominant acid found in apricots, blackberries, blueberries, cherries, grapes, peaches, pears, plums, and quince, as well as other fruits with lower concentrations, such as citrus. It leads to unripe apple's sourness.


Malic Acid Purpose

  1. Energy Enhancer

The human body develops malic acid, which is an essential component of the Krebs . Eating malic acid helps in the synthesis of carbohydrates, proteins, and fatty acids to cycle generate adenosine triphosphate, or simply ATP, which is part of this cycle. All living organisms on the planet rely on this complex organic chemical for cellular energy.

  1. Fibromyalgia and Chronic Fatigue Syndrome Are Treated With This Supplement. 

Magnesium and malic acid are used together as an alternative treatment for fibromyalgia, but further research is required. Magnesium malate supplementation has been linked to a reduction in fibromyalgia symptoms in some studies. 

Magnesium malate is also used to treat chronic fatigue syndrome in some cases. 

Extreme fatigue is the most common symptom of chronic fatigue syndrome or CFS. Another disorder of exhaustion as a key symptom is fibromyalgia.

  1. Encourages Better Fitness Efficiency 

Malic acid is used as a supplement to increase athletic efficiency and avoid muscle exhaustion during exercise. It's often mixed with creatine, which is a common supplement for people trying to gain lean muscle mass.

  1. Helps With Common Skin Issues (like Wrinkles and Breakouts) 

It is not unusual for this acid to be used in skincare products. It's widely used for several skin issues, including fine lines and wrinkles, hyperpigmentation, acne, large pores, milia, warts, calluses, and more, due to its antioxidant and exfoliation benefits. 

It can be derived naturally, but it can also be synthesized or produced. It's commonly used in combination with glycolic and lactic acids. 

Since it facilitates the shedding of the outer layer of skin cells, malic acid is such an efficient skin refiner. Since cell turnover slows as we age, the shedding it encourages may have anti-aging benefits.

  1. Oral Health Is Strengthened (Malic Acid Safe for Mouth)

According to some studies, this acid can help with the symptoms of xerostomia (dry mouth) by stimulating saliva production in the mouth. Saliva development is also critical in preventing oral bacteria overgrowth.

  1. Increases the Absorption of Iron 

Everyone requires iron in their diet. It's particularly crucial for pregnant women and people who suffer from anemia to get enough of this nutrient. 

According to one study, vegetables high in vitamin C and malic acid (such as tomatoes and potatoes) are excellent choices for growing iron absorption.


Did You Know?

  • Malic acid intake in food is widely regarded as healthy and does not result in any harmful malic acid side effects. 

  • Consuming it as an additive, supplement, or in some synthetic form, on the other hand, can cause side effects. Excessive intake of malic acid candy (typically sour candies), for example, has been related to mouth, throat, and stomach irritation. 

  • In general, something with added malic acid will irritate your mouth if you eat too much of it. 

  • Stomach upset, diarrhea, nausea, headaches, or allergic reactions are also potential side effects of taking a malic acid supplement.

  • Malic acid acidity- Excessive intake of malic acid can cause acidity.

  • When applied to the skin, it can irritate the skin or eyes. If you encounter any unexpected side effects when using a product containing this acid, avoid using it. 

  • It is not recommended for pregnant or nursing women to take it as a supplement or medication. It is also not recommended for someone prone to low blood pressure because it may lower blood pressure.

FAQs on Malic Acid: Properties, Uses & Biochemistry

1. What exactly is malic acid, and what is its chemical formula?

Malic acid is a naturally occurring dicarboxylic acid that is found in many fruits and plants. It is the substance responsible for the sour or tart taste of fruits like apples. Its chemical formula is C₄H₆O₅, and its IUPAC name is 2-hydroxybutanedioic acid. It plays a crucial role in the metabolic processes of living organisms.

2. What are the key physical and chemical properties of malic acid?

Malic acid exhibits several distinct properties that are important for its applications.

  • Appearance: It is a white, crystalline solid.
  • Taste: It has a clean, smooth, and persistent sour taste.
  • Solubility: It is highly soluble in water and ethanol.
  • Chirality: Malic acid is a chiral molecule, meaning it exists in two mirror-image forms (stereoisomers): L-malic acid (the natural form) and D-malic acid.
  • Acidity: As a dicarboxylic acid, it has two carboxyl groups (-COOH) that can donate protons, making it acidic.

3. What are the primary uses of malic acid in the food and cosmetic industries?

Malic acid is widely used across various industries due to its properties. In the food industry, it is used as a flavour enhancer and acidulant in beverages, candies, and jams to provide a tart taste. In the cosmetic industry, it is used as a pH adjuster and as an alpha-hydroxy acid (AHA) in skin care products for its exfoliating properties.

4. Which foods are considered the best natural sources of malic acid?

Malic acid is most famously associated with apples, from which its name is derived (from the Latin 'malum' for apple). Other significant natural sources include:

  • Grapes
  • Cherries
  • Plums
  • Apricots
  • Peaches
  • Pears
  • Tomatoes
Its presence contributes significantly to the characteristic flavour of these fruits.

5. How is malic acid different from citric acid and maleic acid?

While all are organic acids, they have distinct structures and functions.

  • Malic Acid vs. Citric Acid: Both are used as food additives. Malic acid is a dicarboxylic acid (two carboxyl groups), while citric acid is a tricarboxylic acid (three carboxyl groups), giving it a sharper taste. Both are intermediates in the Krebs cycle.
  • Malic Acid vs. Maleic Acid: This is a common point of confusion. Malic acid (2-hydroxybutanedioic acid) has a hydroxyl (-OH) group. Maleic acid (cis-butenedioic acid) does not; instead, it has a carbon-carbon double bond and is a geometric isomer of fumaric acid. They are structurally very different compounds.

6. What is the biological importance of malic acid in cellular respiration?

Malic acid, in its deprotonated form malate, is a crucial intermediate in the Krebs cycle (also known as the citric acid cycle). This cycle is a central metabolic pathway that generates energy in the form of ATP. In the cycle, fumarate is hydrated to form L-malate, which is then oxidised by the enzyme malate dehydrogenase to regenerate oxaloacetate, producing NADH in the process.

7. Why is malic acid considered a chiral molecule, and what is the significance of its stereochemistry?

Malic acid is chiral because it has a stereocenter—a carbon atom bonded to four different groups (H, OH, COOH, and CH₂COOH). This results in two non-superimposable mirror-image forms called enantiomers: L-malic acid and D-malic acid. The significance is immense in biology, as enzymes are highly specific. The naturally occurring form found in fruits and involved in the Krebs cycle is exclusively L-malic acid. The D-form is not biologically active in the same way.

8. How does malic acid contribute to the flavour profile of wine through malolactic fermentation?

Malolactic fermentation (MLF) is a critical process in winemaking, especially for red wines. During MLF, bacteria convert the harsher-tasting malic acid into the softer, creamier-tasting lactic acid. This deacidification process reduces the wine's sharp tartness, enhances its flavour complexity, and contributes to a rounder, smoother mouthfeel, making the final product more palatable.