Citric acid

Not to be confused with Vitamin C.

Citric acid
Citric acid
File:Citric-acid-3D-balls.png
IUPAC name 3-carboxy-3-hydroxypentanedioic acid
Other names 2-hydroxypropane- 1,2,3- tricarboxylic acid 3-hydroxypentanedioic acid-3-carboxylic acid Hydrogen citrate
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number	77-92-9 Y
PubChem	311
ChemSpider	305
SMILES
InChI
InChI key	KRKNYBCHXYNGOX-UHFFFAOYAM
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula	C6H8O7
Molar mass	192.124 g/mol (anhydrous) 210.14 g/mol (monohydrate)
Appearance	crystalline white solid
Density	1.665 g/cm3
Melting point	153 °C
Boiling point	decomposes at 175 °C
Solubility in water	133 g/100 ml (22°C)
Solubility in THF, ethanol, methanol	anhydrous: THF 1.80 M, ethanol 1.6 M, methanol 3.08 M monohydrate: THF 1.52 M, ethanol 1.78 M, methanol 2.27 M
Acidity (pKa)	pKa1=3.15 pKa2=4.77 pKa3=6.4
style="background: #F8EABA; text-align: center;" colspan="2" | Hazards
Main hazards	skin and eye irritant
Flash point	?°C
style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds
Related compounds	sodium citrate, calcium citrate
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Citric acid is a weak organic acid. It is a natural preservative and is also used to add an acidic, or sour, taste to foods and soft drinks. In biochemistry, it is important as an intermediate in the citric acid cycle and therefore occurs in the metabolism of virtually all living things. It can also be used as an environmentally benign cleaning agent.

Citric acid exists in greater than trace amounts in a variety of fruits and vegetables, most notably citrus fruits. Lemons and limes have particularly high concentrations of the acid; it can constitute as much as 8% of the dry weight of these fruits (about 47 g/L in the juices). The concentrations of citric acid in citrus fruits range from 0.005 mol/L for oranges and grapefruits to 0.30 mol/L in lemons and limes. Within species these values vary depending on the cultivar and the circumstances in which the fruit was grown.

Properties

File:Zitronensäure im Mikroskop mit Polfilter besser.jpg

Citric acid crystal under polarized light, enlarged 200x

At room temperature, citric acid is a white crystalline powder. It can exist either in an anhydrous (water-free) form or as a monohydrate. The anhydrous form crystallizes from hot water, where as the monohydrate forms when citric acid is crystallized from cold water. The monohydrate can be converted to the anhydrous form by heating above 78 °C. Citric acid also dissolves in absolute (anhydrous) ethanol (76 parts of citric acid per 100 parts of ethanol) at 15 degrees Celsius.

In chemical structure, citric acid shares the properties of other carboxylic acids. When heated above 175°C, it decomposes through the loss of carbon dioxide and water. Citric acid leaves a white crystalline precipitate.

Citric acid is a slightly stronger acid than typical carboxylic acids because the anion can be stabilised by intramolecular hydrogen-bonding from other protic groups on citric acid.

Measurement

Citric acid has been used as an additive to soft drinks, beer, and seltzer, and occurs naturally in many juices. This causes a problem in measurement because the standard measuring technique for sugar is refractive index. The refractive index of sugar and citric acid is almost identical. For soft drinks and orange juice the best measure of sweetness is the sugar/acid ratio. Recently, the use of infrared sensors has allowed measurement of both Brix (sugar content) and acidity by detecting sugars and citric acid through their characteristic molecular vibrations; this gives an accurate assessment of a drink's sweetness.

History

File:Lemon-edit1.jpg

Lemons, oranges, limes, and other citrus fruits contain high concentrations of citric acid

The discovery of citric acid has been credited to the 8th century Islamic alchemist Jabir Ibn Hayyan (Geber). Medieval scholars in Europe were aware of the acidic nature of lemon and lime juices; such knowledge is recorded in the 13th century encyclopedia Speculum Maius (The Great Mirror), compiled by Vincent of Beauvais. Citric acid was first isolated in 1784 by the Swedish chemist Carl Wilhelm Scheele, who crystallized it from lemon juice. Industrial-scale citric acid production began in 1890 based on the Italian citrus fruit industry.

In 1893, C. Wehmer discovered that Penicillium mold could produce citric acid from sugar. However, microbial production of citric acid did not become industrially important until World War I disrupted Italian citrus exports. In 1917, the American food chemist James Currie discovered that certain strains of the mold Aspergillus niger could be efficient citric acid producers, and Pfizer began industrial-level production using this technique two years later, followed by Citrique Belge in 1929.

In this production technique, which is still the major industrial route to citric acid used today, cultures of Aspergillus niger are fed on a sucrose or glucose-containing medium to produce citric acid. The source of sugar is corn steep liquor, molasses, hydrolyzed corn starch or other inexpensive sugary solutions. After the mould is filtered out of the resulting solution, citric acid is isolated by precipitating it with lime (calcium hydroxide) to yield calcium citrate salt, from which citric acid is regenerated by treatment with sulfuric acid.

Krebs cycle

Main article: Citric acid cycle

Citric acid is one of a series of compounds involved in the physiological oxidation of fats, proteins, and carbohydrates to carbon dioxide and water.

This series of chemical reactions is central to nearly all metabolic reactions, and is the source of two-thirds of the food-derived energy in higher organisms. Hans Adolf Krebs received the 1953 Nobel Prize in Physiology or Medicine for the discovery. The series of reactions is known by various names, including the citric acid cycle, the Krebs cycle, and the tricarboxylic acid cycle (or TCA cycle).

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective Wikipedia articles.

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Citric acid cycle [edit]