Malic acid

Last updated
Malic acid
Apfelsaure3.svg
Malic-acid-3D-balls.png
Sample of racemic malic acid.jpg
DL-Malic acid
Names
Preferred IUPAC name
2-Hydroxybutanedioic acid
Other names
  • Hydroxybutanedioic acid
  • 2-Hydroxysuccinic acid
  • (L/D)-Malic acid
  • (±)-Malic acid
  • (S/R)-Hydroxybutanedioic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.027.293 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 230-022-8
E number E296 (preservatives)
KEGG
PubChem CID
UNII
  • InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9) Yes check.svgY
    Key: BJEPYKJPYRNKOW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
    Key: BJEPYKJPYRNKOW-UHFFFAOYAM
  • O=C(O)CC(O)C(=O)O
Properties
C4H6O5
Molar mass 134.09 g/mol
AppearanceColorless
Density 1.609 g⋅cm−3
Melting point 130 °C (266 °F; 403 K)
558 g/L (at 20 °C) [1]
Acidity (pKa)pKa1 = 3.40
pKa2 = 5.20 [2]
pKa3 = 14.5 [3]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Flash point 203 °C [4]
Related compounds
Other anions
Malate
Succinic acid
Tartaric acid
Fumaric acid
Related compounds
Butanol
Butyraldehyde
Crotonaldehyde
Sodium malate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Malic acid is an organic compound with the molecular formula HO2CCH(OH)CH2CO2H. It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally. The salts and esters of malic acid are known as malates. The malate anion is a metabolic intermediate in the citric acid cycle.

Contents

Etymology

The word 'malic' is derived from Latin mālum, meaning 'apple'. The related Latin word mālus, meaning 'apple tree', is used as the name of the genus Malus , which includes all apples and crabapples; [5] and is the origin of other taxonomic classifications such as Maloideae, Malinae, and Maleae.

Biochemistry

L-Malic acid is the naturally occurring form, whereas a mixture of L- and D-malic acid is produced synthetically.

Malate plays an important role in biochemistry. In the C4 carbon fixation process, malate is a source of CO2 in the Calvin cycle. In the citric acid cycle, (S)-malate is an intermediate, formed by the addition of an -OH group on the si face of fumarate. It can also be formed from pyruvate via anaplerotic reactions.

Malate is also synthesized by the carboxylation of phosphoenolpyruvate in the guard cells of plant leaves. Malate, as a double anion, often accompanies potassium cations during the uptake of solutes into the guard cells in order to maintain electrical balance in the cell. The accumulation of these solutes within the guard cell decreases the solute potential, allowing water to enter the cell and promote aperture of the stomata.

In food

Malic acid was first isolated from apple juice by Carl Wilhelm Scheele in 1785. [6] Antoine Lavoisier in 1787 proposed the name acide malique , which is derived from the Latin word for apple, mālum as is its genus name Malus . [7] [8] In German it is named Äpfelsäure (or Apfelsäure) after plural or singular of a sour thing from the apple fruit, but the salt(s) are called Malat(e). Malic acid is the main acid in many fruits, including apricots, blackberries, blueberries, cherries, grapes, mirabelles, peaches, pears, plums, and quince, [9] and is present in lower concentrations in other fruits, such as citrus. It contributes to the sourness of unripe apples. Sour apples contain high proportions of the acid. It is present in grapes and in most wines with concentrations sometimes as high as 5 g/L. [10] It confers a tart taste to wine; the amount decreases with increasing fruit ripeness. The taste of malic acid is very clear and pure in rhubarb, a plant for which it is the primary flavor. It is also the compound responsible for the tart flavor of sumac spice. It is also a component of some artificial vinegar flavors, such as "salt and vinegar" flavored potato chips. [11]

The process of malolactic fermentation converts malic acid to much milder lactic acid. Malic acid occurs naturally in all fruits and many vegetables, and is generated in fruit metabolism. [12]

Malic acid, when added to food products, is denoted by E number E296. It is sometimes used with or in place of the less sour citric acid in sour sweets. These sweets are sometimes labeled with a warning stating that excessive consumption can cause irritation of the mouth. It is approved for use as a food additive in the EU, [13] US [14] and Australia and New Zealand [15] (where it is listed by its INS number 296).

Malic acid contains 10 kJ (2.39 kilocalories) of energy per gram. [16]

Production and main reactions

Racemic malic acid is produced industrially by the double hydration of maleic anhydride. In 2000, American production capacity was 5,000 tons per year. The enantiomers may be separated by chiral resolution of the racemic mixture. S-Malic acid is obtained by fermentation of fumaric acid. [17]

Self-condensation of malic acid in the presence of fuming sulfuric acid gives the pyrone coumalic acid: [18]

2 HO2CCH(OH)CH2CO2H → HO2CC4H3O2 + 2 CO + 4 H2O

Carbon monoxide and water are liberated during this reaction.

Malic acid was important in the discovery of the Walden inversion and the Walden cycle, in which (−)-malic acid first is converted into (+)-chlorosuccinic acid by action of phosphorus pentachloride. Wet silver oxide then converts the chlorine compound to (+)-malic acid, which then reacts with PCl5 to the (−)-chlorosuccinic acid. The cycle is completed when silver oxide takes this compound back to (−)-malic acid.

L-malic acid is used to resolve α-phenylethylamine, a versatile resolving agent in its own right. [19]

Plant defense

Soil supplementation with molasses increases microbial synthesis of malic acid. This is thought to occur naturally as part of soil microbe suppression of disease, so soil amendment with molasses can be used as a crop treatment in horticulture. [20]

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

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WP534.png go to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to WikiPathwaysgo to articlego to Entrezgo to article
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Glycolysis and Gluconeogenesis edit
  1. The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

See also

Related Research Articles

<span class="mw-page-title-main">Food additive</span> Substances added to food

Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salting), smoke (smoking), sugar (crystallization), etc. This allows for longer-lasting foods such as bacon, sweets or wines. With the advent of ultra-processed foods in the second half of the twentieth century, many additives have been introduced, of both natural and artificial origin. Food additives also include substances that may be introduced to food indirectly in the manufacturing process, through packaging, or during storage or transport.

<span class="mw-page-title-main">Vinegar</span> Liquid consisting mainly of acetic acid and water

Vinegar is an aqueous solution of acetic acid and trace compounds that may include flavorings. Vinegar typically contains from 5% to 18% acetic acid by volume. Usually, the acetic acid is produced by a double fermentation, converting simple sugars to ethanol using yeast and ethanol to acetic acid using acetic acid bacteria. Many types of vinegar are made, depending on source materials. The product is now mainly used in the culinary arts as a flavorful, acidic cooking ingredient or in pickling. Various types are used as condiments or garnishes, including balsamic vinegar and malt vinegar.

<span class="mw-page-title-main">Citric acid</span> Weak organic acid

Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in the metabolism of all aerobic organisms.

<span class="mw-page-title-main">Tartaric acid</span> Organic acid found in many fruits

Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. Potassium bitartrate is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation. The acid itself is added to foods as an antioxidant E334 and to impart its distinctive sour taste. Naturally occurring tartaric acid is a useful raw material in organic chemical synthesis. Tartaric acid, an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics and is a dihydroxyl derivative of succinic acid.

Pyruvic acid (IUPAC name: 2-oxopropanoic acid, also called acetoic acid) (CH3COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate base, CH3COCOO, is an intermediate in several metabolic pathways throughout the cell.

<span class="mw-page-title-main">Lactic acid</span> Group of stereoisomers

Lactic acid is an organic acid. It has the molecular formula CH3CH(OH)COOH. It is white in the solid state and it is miscible with water. When in the dissolved state, it forms a colorless solution. Production includes both artificial synthesis as well as natural sources. Lactic acid is an alpha-hydroxy acid (AHA) due to the presence of a hydroxyl group adjacent to the carboxyl group. It is used as a synthetic intermediate in many organic synthesis industries and in various biochemical industries. The conjugate base of lactic acid is called lactate. The name of the derived acyl group is lactoyl.

<i>Umeboshi</i> Sour, pickled Japanese fruit

Umeboshi are pickled (brined) ume fruits common in Japan. The word umeboshi is often translated into English as 'salted Japanese plums', 'Japanese plums' or 'preserved plums'. Ume is a species of fruit-bearing tree in the genus Prunus, which is often called a "plum", but is actually more closely related to the apricot. Pickled ume which are not dried are called umezuke (梅漬け).

<span class="mw-page-title-main">Fumaric acid</span> Organic compound

Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H. A white solid, fumaric acid occurs widely in nature. It has a fruit-like taste and has been used as a food additive. Its E number is E297. The salts and esters are known as fumarates. Fumarate can also refer to the C
4
H
2
O2−
4
ion (in solution). Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

<span class="mw-page-title-main">Food browning</span> Food process

Browning is the process of food turning brown due to the chemical reactions that take place within. The process of browning is one of the chemical reactions that take place in food chemistry and represents an interesting research topic regarding health, nutrition, and food technology. Though there are many different ways food chemically changes over time, browning in particular falls into two main categories: enzymatic versus non-enzymatic browning processes.

<span class="mw-page-title-main">Malolactic fermentation</span> Process in winemaking

Malolactic conversion is a process in winemaking in which tart-tasting malic acid, naturally present in grape must, is converted to softer-tasting lactic acid. Malolactic fermentation is most often performed as a secondary fermentation shortly after the end of the primary fermentation, but can sometimes run concurrently with it. The process is standard for most red wine production and common for some white grape varieties such as Chardonnay, where it can impart a "buttery" flavor from diacetyl, a byproduct of the reaction.

<span class="mw-page-title-main">Oxaloacetic acid</span> Organic compound

Oxaloacetic acid (also known as oxalacetic acid or OAA) is a crystalline organic compound with the chemical formula HO2CC(O)CH2CO2H. Oxaloacetic acid, in the form of its conjugate base oxaloacetate, is a metabolic intermediate in many processes that occur in animals. It takes part in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, fatty acid synthesis and the citric acid cycle.

<span class="mw-page-title-main">Soured milk</span> Milk-based food product

Soured milk denotes a range of food products produced by the acidification of milk. Acidification, which gives the milk a tart taste, is achieved either through bacterial fermentation or through the addition of an acid, such as lemon juice or vinegar. The acid causes milk to coagulate and thicken, inhibiting the growth of harmful bacteria and improving the product's shelf life. It is not good for making cheese.

<span class="mw-page-title-main">Pickling</span> Procedure of preserving food in brine or vinegar

Pickling is the process of preserving or extending the shelf life of food by either anaerobic fermentation in brine or immersion in vinegar. The pickling procedure typically affects the food's texture and flavor. The resulting food is called a pickle, or, if named, the name is prefaced with the word "pickled". Foods that are pickled include vegetables, fruits, mushrooms, meats, fish, dairy and eggs.

<span class="mw-page-title-main">Sinapinic acid</span> Chemical compound

Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.), is a small naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family. It is a commonly used matrix in MALDI mass spectrometry. It is a useful matrix for a wide variety of peptides and proteins. It serves well as a matrix for MALDI due to its ability to absorb laser radiation and to also donate protons (H+) to the analyte of interest.

<span class="mw-page-title-main">Fermentation in food processing</span> Converting carbohydrates to alcohol or acids using anaerobic microorganisms

In food processing, fermentation is the conversion of carbohydrates to alcohol or organic acids using microorganisms—yeasts or bacteria—under anaerobic (oxygen-free) conditions. Fermentation usually implies that the action of microorganisms is desired. The science of fermentation is known as zymology or zymurgy.

<span class="mw-page-title-main">Acidulant</span> Chemical compounds that give a sour flavor to foods

Acidulants are chemical compounds that give a tart, sour, or acidic flavor to foods or enhance the perceived sweetness of foods. Acidulants can also function as leavening agents and emulsifiers in some kinds of processed foods. Though acidulants can lower pH they differ from acidity regulators, which are food additives specifically intended to modify the stability of food or enzymes within it. Typical acidulants are acetic acid and citric acid. Many beverages, such as colas, contain phosphoric acid. Sour candies often are formulated with malic acid. Other acidulants used in food production include: fumaric acid, tartaric acid, lactic acid and gluconic acid.

<span class="mw-page-title-main">Acids in wine</span>

The acids in wine are an important component in both winemaking and the finished product of wine. They are present in both grapes and wine, having direct influences on the color, balance and taste of the wine as well as the growth and vitality of yeast during fermentation and protecting the wine from bacteria. The measure of the amount of acidity in wine is known as the “titratable acidity” or “total acidity”, which refers to the test that yields the total of all acids present, while strength of acidity is measured according to pH, with most wines having a pH between 2.9 and 3.9. Generally, the lower the pH, the higher the acidity in the wine. There is no direct connection between total acidity and pH. In wine tasting, the term “acidity” refers to the fresh, tart and sour attributes of the wine which are evaluated in relation to how well the acidity balances out the sweetness and bitter components of the wine such as tannins. Three primary acids are found in wine grapes: tartaric, malic, and citric acids. During the course of winemaking and in the finished wines, acetic, butyric, lactic, and succinic acids can play significant roles. Most of the acids involved with wine are fixed acids with the notable exception of acetic acid, mostly found in vinegar, which is volatile and can contribute to the wine fault known as volatile acidity. Sometimes, additional acids, such as ascorbic, sorbic and sulfurous acids, are used in winemaking.

Chinese pickles or Chinese preserved vegetables consist of vegetables or fruits that have been fermented by pickling with salt and brine, or marinated in mixtures based on soy sauce or savory bean pastes. The former is usually done using high-fiber vegetables and fruits, such as Chinese cabbage, carrot, apple and pineapple, while the latter marinated group is made using a wide variety of vegetables, ranging from mustards and cucumbers to winter melon and radishes. As of now, there are more than 130 kinds of pickles.

<span class="mw-page-title-main">Pickled fruit</span> Fruit that has been preserved by anaerobic fermentation in brine or immersion in vinegar

Pickled fruit refers to fruit that has been pickled. Pickling is the process of food preservation by either anaerobic fermentation in brine or immersion in vinegar. Many types of fruit are pickled. Some examples include peaches, apples, crabapples, pears, plums, grapes, currants, tomatoes and olives. Vinegar may also be prepared from fruit, such as apple cider vinegar.

The topic of sulfite food and beverage additives covers the application of sulfites in food chemistry. "Sulfite" is jargon that encompasses a variety of materials that are commonly used as preservatives or food additive in the production of diverse foods and beverages. Although sulfite salts are relatively nontoxic, their use has led to controversy, resulting in extensive regulations. Sulfites are a source of sulfur dioxide (SO2), a bactericide.

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