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Malic acid

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Malic acid is a specific type of organic compound known as a dicarboxylic acid. It is found in all living organisms and plays many vital roles in biology and chemistry. You might recognize its effects through the sharp, sour taste it provides in many fruits. Because of its unique properties, it is also used widely as a food additive. In the food industry, it is identified by the E number E296.

In the world of biochemistry, malic acid is a key player in how cells function. It exists in two different forms called stereoisomers, which are known as L- and D-enantiomers. While both can be made in a lab, only the L-isomer occurs naturally in living things. This form, called L-malic acid, is a metabolic intermediate in the citric acid cycle. This cycle is a series of chemical reactions that cells use to produce energy.

Malic acid also helps plants manage their gas exchange and water levels. In the C4 carbon fixation process, malate acts as a source of carbon dioxide (CO2) for the Calvin cycle. Within plant leaves, malate is synthesized through the carboxylation of phosphoenolpyruvate in the guard cells. To maintain electrical balance, the malate anion often travels with potassium cations into these cells. This accumulation of solutes decreases the solute potential, which allows water to enter the cells. This process helps open the stomata, which are the tiny pores on a leaf.

Our understanding of this acid began with important scientific discoveries in the late 18th century. In 1785, Carl Wilhelm Scheele first isolated the acid from apple juice. He originally intended to call it "apple acid." However, in 1787, Antoine Lavoisier proposed the name "acide malique." This name is derived from the Latin word for apple, which is "mālum." This is the same root used for the biological genus name, Malus.

Malic acid is found in many different types of food and has specific concentrations in various products. It is the primary acid in fruits such as apricots, blackberries, blueberries, cherries, grapes, peaches, pears, plums, and quince. In grapes, concentrations can reach as high as 5 g/L. This acid gives wine a tart taste, though the amount decreases as the fruit ripens. In some cases, a process called malolactic fermentation is used to convert the sharp malic acid into a milder lactic acid.

Industrial production of malic acid is a significant global activity. Racemic malic acid, which is a mixture of both the L- and D-forms, is produced by the double hydration of maleic anhydride. To get the specific L-form, scientists can use the fermentation of fumaric acid. In the year 2000, the production capacity in the United States was 5,000 tons per year. This acid provides 10 kJ, or 2.39 kilocalories, of energy per gram.

Beyond food and plants, malic acid is a valuable tool in chemical research. It was essential in the discovery of the Walden inversion and the Walden cycle. In this cycle, L-malic acid is converted into (+)-chlorosuccinic acid using phosphorus pentachloride. This chemical process helps scientists understand how molecules change their structure. Malic acid is also used as a resolving agent to help separate other chemical substances like α-phenylethylamine.

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