Citric acid

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Citric acid
Zitronensaure - Citric acid.svg
Zitronensaure Kristallzucht.jpg
IUPAC name
Citric acid [1]
Preferred IUPAC name
2-Hydroxypropane-1,2,3-tricarboxylic acid [1]
3D model (JSmol)
ECHA InfoCard 100.000.973 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-069-1
E number E330 (antioxidants, ...)
PubChem CID
RTECS number
  • GE7350000
  • InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12) Yes check.svgY
  • InChI=1/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
  • OC(=O)CC(O)(C(=O)O)CC(=O)O
Molar mass 192.123 g/mol (anhydrous), 210.14 g/mol (monohydrate) [2]
Appearancewhite solid
Odor Odorless
Density 1.665 g/cm3 (anhydrous)
1.542 g/cm3 (18 °C, monohydrate)
Melting point 156 °C (313 °F; 429 K)
Boiling point 310 °C (590 °F; 583 K)decomposes from 175 °C [3]
54% w/w (10 °C)
59.2% w/w (20 °C)
64.3% w/w (30 °C)
68.6% w/w (40 °C)
70.9% w/w (50 °C)
73.5% w/w (60 °C)
76.2% w/w (70 °C)
78.8% w/w (80 °C)
81.4% w/w (90 °C)
84% w/w (100 °C) [4]
Solubility Soluble in acetone, alcohol, ether, ethyl acetate, DMSO
Insoluble in C
, CHCl3, CS2, toluene [3]
Solubility in ethanol 62 g/100g (25 °C) [3]
Solubility in amyl acetate 4.41 g/100g (25 °C) [3]
Solubility in diethyl ether 1.05 g/100g (25 °C) [3]
Solubility in 1,4-Dioxane 35.9 g/100g (25 °C) [3]
log P −1.64
Acidity (pKa)pKa1 = 3.13 [5]
pKa2 = 4.76 [5]
pKa3 = 6.39, [6] 6.40 [7]
1.493–1.509 (20 °C) [4]
1.46 (150 °C) [3]
Viscosity 6.5 cP (50% aq. sol.) [4]
226.51 J/(mol·K) (26.85 °C) [8]
252.1 J/(mol·K) [8]
−1543.8 kJ/mol [4]
1985.3 kJ/mol (474.5 kcal/mol, 2.47 kcal/g), [4] 1960.6 kJ/mol [8]
1972.34 kJ/mol (471.4 kcal/mol, 2.24 kcal/g) (monohydrate) [4]
A09AB04 ( WHO )
Occupational safety and health (OHS/OSH):
Main hazards
Skin and eye irritant
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg [5]
H290, H319, H315 [5]
P305+P351+P338 [5]
NFPA 704 (fire diamond)
Flash point 155 °C (311 °F; 428 K)
345 °C (653 °F; 618 K)
Explosive limits 8% [5]
Lethal dose or concentration (LD, LC):
3000 mg/kg (rats, oral)
Safety data sheet (SDS) HMDB
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. [9] It is a colorless weak organic acid. [9] 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. [9]


More than two million tons of citric acid are manufactured every year. It is used widely as an acidifier, as a flavoring, and a chelating agent. [10]

A citrate is a derivative of citric acid; that is, the salts, esters, and the polyatomic anion found in solution. An example of the former, a salt is trisodium citrate; an ester is triethyl citrate. When part of a salt, the formula of the citrate anion is written as C
or C

Natural occurrence and industrial production

Lemons, oranges, limes, and other citrus fruits possess high concentrations of citric acid Citrus fruits.jpg
Lemons, oranges, limes, and other citrus fruits possess high concentrations of citric acid

Citric acid exists 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 [11] ). [lower-alpha 1] 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; these values vary within species depending upon the cultivar and the circumstances in which the fruit was grown.

Citric acid was first isolated in 1784 by the chemist Carl Wilhelm Scheele, who crystallized it from lemon juice. [12] [13]

Industrial-scale citric acid production first began in 1890 based on the Italian citrus fruit industry, where the juice was treated with hydrated lime (calcium hydroxide) to precipitate calcium citrate, which was isolated and converted back to the acid using diluted sulfuric acid. [14] In 1893, C. Wehmer discovered 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, American food chemist James Currie discovered certain strains of the mold Aspergillus niger could be efficient citric acid producers, and the pharmaceutical company 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 A. 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 solution. [15] After the mold is filtered out of the resulting solution, citric acid is isolated by precipitating it with calcium hydroxide to yield calcium citrate salt, from which citric acid is regenerated by treatment with sulfuric acid, as in the direct extraction from citrus fruit juice.

In 1977, a patent was granted to Lever Brothers for the chemical synthesis of citric acid starting either from aconitic or isocitrate/alloisocitrate calcium salts under high pressure conditions; this produced citric acid in near quantitative conversion under what appeared to be a reverse, non-enzymatic Krebs cycle reaction. [16]

Global production was in excess of 2,000,000 tons in 2018. [17] More than 50% of this volume was produced in China. More than 50% was used as an acidity regulator in beverages, some 20% in other food applications, 20% for detergent applications, and 10% for applications other than food, such as cosmetics, pharmaceuticals, and in the chemical industry. [14]

Chemical characteristics

Speciation diagram for a 10-millimolar solution of citric acid Citric acid speciation.svg
Speciation diagram for a 10-millimolar solution of citric acid

Citric acid can be obtained as an anhydrous (water-free) form or as a monohydrate. The anhydrous form crystallizes from hot water, while the monohydrate forms when citric acid is crystallized from cold water. The monohydrate can be converted to the anhydrous form at about 78 °C. Citric acid also dissolves in absolute (anhydrous) ethanol (76 parts of citric acid per 100 parts of ethanol) at 15 °C. It decomposes with loss of carbon dioxide above about 175 °C.

Citric acid is a tribasic acid, with pKa values, extrapolated to zero ionic strength, of 3.128, 4.761, and 6.396 at 25 °C. [18] The pKa of the hydroxyl group has been found, by means of 13C NMR spectroscopy, to be 14.4. [19] The speciation diagram shows that solutions of citric acid are buffer solutions between about pH 2 and pH 8. In biological systems around pH 7, the two species present are the citrate ion and mono-hydrogen citrate ion. The SSC 20X hybridization buffer is an example in common use. [20] Tables compiled for biochemical studies [21] are available.

On the other hand, the pH of a 1 mM solution of citric acid will be about 3.2. The pH of fruit juices from citrus fruits like oranges and lemons depends on the citric acid concentration, with a higher concentration of citric acid resulting in a lower pH.

Acid salts of citric acid can be prepared by careful adjustment of the pH before crystallizing the compound. See, for example, sodium citrate.

The citrate ion forms complexes with metallic cations. The stability constants for the formation of these complexes are quite large because of the chelate effect. Consequently, it forms complexes even with alkali metal cations. However, when a chelate complex is formed using all three carboxylate groups, the chelate rings have 7 and 8 members, which are generally less stable thermodynamically than smaller chelate rings. In consequence, the hydroxyl group can be deprotonated, forming part of a more stable 5-membered ring, as in ammonium ferric citrate, (NH
. [22]

Citric acid can be esterified at one or more of its three carboxylic acid groups to form any of a variety of mono-, di-, tri-, and mixed esters. [23]


Citric acid cycle

Citrate is an intermediate in the TCA cycle (akaTriCarboxylic Acid cycle, or Krebs cycle, Szent-Györgyi), a central metabolic pathway for animals, plants, and bacteria. Citrate synthase catalyzes the condensation of oxaloacetate with acetyl CoA to form citrate. Citrate then acts as the substrate for aconitase and is converted into aconitic acid. The cycle ends with regeneration of oxaloacetate. This series of chemical reactions 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.

Some bacteria (notably E. coli ) can produce and consume citrate internally as part of their TCA cycle, but are unable to use it as food because they lack the enzymes required to import it into the cell. After tens of thousand of evolutions in a minimal glucose medium that also contained citrate during Richard Lenski's Long-Term Evolution Experiment, a variant E. coli evolved with the ability to grow aerobically on citrate. Zachary Blount, a student of Lenski's, and colleagues studied these "Cit+" E. coli [24] [25] as a model for how novel traits evolve. They found evidence that, in this case, the innovation was caused by a rare duplication mutation due to the accumulation of several prior "potentiating" mutations, the identity and effects of which are still under study. The evolution of the Cit+ trait has been considered a notable example of the role of historical contingency in evolution.

Other biological roles

Citrate can be transported out of the mitochondria and into the cytoplasm, then broken down into acetyl-CoA for fatty acid synthesis, and into oxaloacetate. Citrate is a positive modulator of this conversion, and allosterically regulates the enzyme acetyl-CoA carboxylase, which is the regulating enzyme in the conversion of acetyl-CoA into malonyl-CoA (the commitment step in fatty acid synthesis). In short, citrate is transported into the cytoplasm, converted into acetyl-CoA, which is then converted into malonyl-CoA by acetyl-CoA carboxylase, which is allosterically modulated by citrate.

High concentrations of cytosolic citrate can inhibit phosphofructokinase, the catalyst of a rate-limiting step of glycolysis. This effect is advantageous: high concentrations of citrate indicate that there is a large supply of biosynthetic precursor molecules, so there is no need for phosphofructokinase to continue to send molecules of its substrate, fructose 6-phosphate, into glycolysis. Citrate acts by augmenting the inhibitory effect of high concentrations of ATP, another sign that there is no need to carry out glycolysis. [26]

Citrate is a vital component of bone, helping to regulate the size of apatite crystals. [27]


Food and drink

Powdered citric acid being used to prepare lemon pepper seasoning Lemon pepper preparation.jpg
Powdered citric acid being used to prepare lemon pepper seasoning

Because it is one of the stronger edible acids, the dominant use of citric acid is as a flavoring and preservative in food and beverages, especially soft drinks and candies. [14] Within the European Union it is denoted by E number E330. Citrate salts of various metals are used to deliver those minerals in a biologically available form in many dietary supplements. Citric acid has 247 kcal per 100 g. [28] In the United States the purity requirements for citric acid as a food additive are defined by the Food Chemicals Codex, which is published by the United States Pharmacopoeia (USP).

Citric acid can be added to ice cream as an emulsifying agent to keep fats from separating, to caramel to prevent sucrose crystallization, or in recipes in place of fresh lemon juice. Citric acid is used with sodium bicarbonate in a wide range of effervescent formulae, both for ingestion (e.g., powders and tablets) and for personal care (e.g., bath salts, bath bombs, and cleaning of grease). Citric acid sold in a dry powdered form is commonly sold in markets and groceries as "sour salt", due to its physical resemblance to table salt. It has use in culinary applications, as an alternative to vinegar or lemon juice, where a pure acid is needed. Citric acid can be used in food coloring to balance the pH level of a normally basic dye.[ citation needed ]

Cleaning and chelating agent

Structure of an iron(III) citrate complex. Fe2CITdianion.svg
Structure of an iron(III) citrate complex.

Citric acid is an excellent chelating agent, binding metals by making them soluble. It is used to remove and discourage the buildup of limescale from boilers and evaporators. [14] It can be used to treat water, which makes it useful in improving the effectiveness of soaps and laundry detergents. By chelating the metals in hard water, it lets these cleaners produce foam and work better without need for water softening. Citric acid is the active ingredient in some bathroom and kitchen cleaning solutions. A solution with a six percent concentration of citric acid will remove hard water stains from glass without scrubbing. Citric acid can be used in shampoo to wash out wax and coloring from the hair. Illustrative of its chelating abilities, citric acid was the first successful eluant used for total ion-exchange separation of the lanthanides, during the Manhattan Project in the 1940s. [31] In the 1950s, it was replaced by the far more efficient [32] EDTA.

In industry, it is used to dissolve rust from steel and passivate stainless steels. [33]

Cosmetics, pharmaceuticals, dietary supplements, and foods

Citric acid is used as an acidulant in creams, gels, and liquids. Used in foods and dietary supplements, it may be classified as a processing aid if it was added for a technical or functional effect (e.g. acidulent, chelator, viscosifier, etc.). If it is still present in insignificant amounts, and the technical or functional effect is no longer present, it may be exempt from labeling <21 CFR §101.100(c)>.

Citric acid is an alpha hydroxy acid and is an active ingredient in chemical skin peels. [34]

Citric acid is commonly used as a buffer to increase the solubility of brown heroin. [35]

Citric acid is used as one of the active ingredients in the production of facial tissues with antiviral properties. [36]

Other uses

The buffering properties of citrates are used to control pH in household cleaners and pharmaceuticals.

Citric acid is used as an odorless alternative to white vinegar for fabric dyeing with acid dyes.

Sodium citrate is a component of Benedict's reagent, used for identification both qualitatively and quantitatively of reducing sugars. [37]

Citric acid can be used as an alternative to nitric acid in passivation of stainless steel. [38]

Citric acid can be used as a lower-odor stop bath as part of the process for developing photographic film. Photographic developers are alkaline, so a mild acid is used to neutralize and stop their action quickly, but commonly used acetic acid leaves a strong vinegar odor in the darkroom. [39]

Citric acid/potassium-sodium citrate can be used as a blood acid regulator. [40]

Citric acid is an excellent soldering flux, [41] either dry or as a concentrated solution in water. It should be removed after soldering, especially with fine wires, as it is mildly corrosive. It dissolves and rinses quickly in hot water.

Synthesis of other organic compounds

Citric acid is a versatile precursor to many other organic compounds. Dehydration routes give itaconic acid and its anhydride. [42] Citraconic acid can be produced via thermal isomerization of itaconic acid anhydride. [43] The required itaconic acid anhydride is obtained by dry distillation of citric acid. Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid: [44]


Acetonedicarboxylic acid can also be prepared by decarbonylation of citric acid in fuming sulfuric acid: [45]


Although a weak acid, exposure to pure citric acid can cause adverse effects. Inhalation may cause cough, shortness of breath, or sore throat. Over-ingestion may cause abdominal pain and sore throat. Exposure of concentrated solutions to skin and eyes can cause redness and pain. [46] Long-term or repeated consumption may cause erosion of tooth enamel. [46] [47] [48]

Compendial status

See also

Related Research Articles

Acid Chemical compound giving a proton or accepting an electron pair

An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen ion, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid.

Citric acid cycle Metabolic pathway

The citric acid cycle (CAC)—also known as the Krebs cycle or the TCA cycle —is a series of chemical reactions to release stored energy through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins. The Krebs cycle is used by organisms that respire to generate energy, either by anaerobic respiration or aerobic respiration. In addition, the cycle provides precursors of certain amino acids, as well as the reducing agent NADH, that are used in numerous other reactions. Its central importance to many biochemical pathways suggests that it was one of the earliest components of metabolism and may have originated abiogenically. Even though it is branded as a 'cycle', it is not necessary for metabolites to follow only one specific route; at least three alternative segments of the citric acid cycle have been recognized.

pH Measure of the acidity or basicity of an aqueous solution

In chemistry, pH, historically denoting "potential of hydrogen" (or "power of hydrogen") is a scale used to specify the acidity or basicity of an aqueous solution. Acidic solutions (solutions with higher concentrations of H+ ions) are measured to have lower pH values than basic or alkaline solutions.

A buffer solution is an aqueous solution consisting of a mixture of a weak acid and its conjugate base, or vice versa. Its pH changes very little when a small amount of strong acid or base is added to it. Buffer solutions are used as a means of keeping pH at a nearly constant value in a wide variety of chemical applications. In nature, there are many systems that use buffering for pH regulation. For example, the bicarbonate buffering system is used to regulate the pH of blood, and bicarbonate also acts as a buffer in the ocean.

Tartaric acid 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 bananas, tamarinds, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. It 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 is an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.

Acetyl-CoA Chemical compound

Acetyl-CoA is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle to be oxidized for energy production. Coenzyme A consists of a β-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3'-phosphorylated ADP. The acetyl group of acetyl-CoA is linked to the sulfhydryl substituent of the β-mercaptoethylamine group. This thioester linkage is a "high energy" bond, which is particularly reactive. Hydrolysis of the thioester bond is exergonic (−31.5 kJ/mol).

Malic acid Dicarboxylic acid responsible for apple acidity

Malic acid is an organic compound with the molecular formula C4H6O5. 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, though only the L-isomer exists naturally. The salts and esters of malic acid are known as malates. The malate anion is an intermediate in the citric acid cycle.

Lime (fruit) Citrus fruit

A lime is a citrus fruit, which is typically round, green in color, 3–6 centimetres (1.2–2.4 in) in diameter, and contains acidic juice vesicles.

Malonic acid Carboxylic acid with chemical formula CH2(COOH)2

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.

Trisodium citrate Chemical compound

Trisodium citrate has the chemical formula of Na3C6H5O7. It is sometimes referred to simply as "sodium citrate", though sodium citrate can refer to any of the three sodium salts of citric acid. It possesses a saline, mildly tart flavor, and is a mild alkali.

Food browning 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.

Oxaloacetic acid 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.

Acetic anhydride Chemical compound

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

Itaconic acid Chemical compound

Itaconic acid, or methylidenesuccinic acid, is an organic compound. This dicarboxylic acid is a white solid that is soluble in water, ethanol, and acetone. Historically, itaconic acid was obtained by the distillation of citric acid, but currently it is produced by fermentation. The name itaconic acid was devised as an anagram of aconitic acid, another derivative of citric acid.

Citrate synthase

The enzyme citrate synthase E.C. ] exists in nearly all living cells and stands as a pace-making enzyme in the first step of the citric acid cycle. Citrate synthase is localized within eukaryotic cells in the mitochondrial matrix, but is encoded by nuclear DNA rather than mitochondrial. It is synthesized using cytoplasmic ribosomes, then transported into the mitochondrial matrix.

Acetic acid Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

Lemon Yellow citrus fruit

The lemon is a species of small evergreen trees in the flowering plant family Rutaceae, native to Asia, primarily Northeast India (Assam), Northern Myanmar or China.

Iron(II) citrate Chemical compound

Ferrous citrate, or iron(II) citrate, describes coordination complexes containing citrate anions with Fe2+ formed in aqueous solution. Although a number of complexes are possible (or even likely), only one complex has been crystallized. That complex is the coordination polymer with the formula [Fe(H2O)6]2+{[Fe(C6H5O7)(H2O)]}2.2H2O, where C6H5O73- is HOC(CH2CO2)2(CO2, i.e., the triple conjugate base of citric acid wherein the three carboxylic acid groups are ionized. Ferrous citrates are all paramagnetic, reflecting the weak crystal field of the carboxylate ligands.

Citraconic acid Chemical compound

Citraconic acid is an organic compound with the formula CH3C2H(CO2H)2. It is a white solid. It is the cis-isomer of mesaconic acid. It is one of the pyrocitric acids formed upon the heating of citric acid. Citraconic acid can be produced, albeit inefficiently, by oxidation of xylene and methylbutanols. The acid displays the unusual property of spontaneously forming the anhydride, which, unlike maleic anhydride, is a liquid at room temperature.

Itaconic anhydride Chemical compound

Itaconic anhydride is the cyclic anhydride of itaconic acid and is obtained by the pyrolysis of citric acid. It is a colourless, crystalline solid, which dissolves in many polar organic solvents and hydrolyzes forming itaconic acid. Itaconic anhydride and its derivative itaconic acid have been promoted as biobased "platform chemicals" and bio- building blocks. ) These expectations, however, have not been fulfilled.


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  1. This still does not make the lemon particularly strongly acidic. This is because, as a weak acid, most of the acid molecules are not dissociated so not contributing to acidity inside the lemon or its juice.