Citric acid

Weak organic acid

"E330" redirects here. For the locomotive, see FS Class E330.

For vitamin C, see ascorbic acid.

Citric acid  |

File:Zitronensäure - Citric acid.svg

File:Citric-acid-3D-balls.png

|

File:Zitronensäure Kristallzucht.jpg

Names
IUPAC name

Citric acid[1]

Preferred IUPAC name

2-Hydroxypropane-1,2,3-tricarboxylic acid[1]

Identifiers

CAS Number

* 77-92-9 File:Yes check.svgY

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:30769 File:Yes check.svgY

ChEMBL |

* ChEMBL1261 File:Yes check.svgY

ChemSpider |

* 305 File:Yes check.svgY

DrugBank |

* DB04272 File:Yes check.svgY

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EC Number |

* 201-069-1

E number | Script error: No such module "Wikidata".

IUPHAR/BPS

* 2478

KEGG |

* D00037 File:Yes check.svgY

PubChem CID

* 311
* 22230 (monohydrate)

RTECS number |

* GE7350000

UNII |

* XF417D3PSL File:Yes check.svgY

InChI

* 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) File:Yes check.svgY

Key: KRKNYBCHXYNGOX-UHFFFAOYSA-N File: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)

Key: KRKNYBCHXYNGOX-UHFFFAOYAM

SMILES

* OC(=O)CC(O)(C(=O)O)CC(=O)O

Properties

Chemical formula

| C6H8O7
Molar mass | 192.123 g/mol (anhydrous), 210.14 g/mol (monohydrate)[2]
Appearance  | white 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]

Solubility in water

| 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

6, CHCl3, CS2, toluene[3]
Solubility in ethanol | 62 g/100 g (25 °C)[3]
Solubility in amyl acetate | 4.41 g/100 g (25 °C)[3]
Solubility in diethyl ether | 1.05 g/100 g (25 °C)[3]
Solubility in 1,4-Dioxane | 35.9 g/100 g (25 °C)[3]
log P | −1.64
Acidity (pKa)  | pKa1 = 3.13[5]
pKa2 = 4.76[5]
pKa3 = 6.39,[6] 6.40[7]

Refractive index (nD)

| 1.493–1.509 (20 °C)[4]
1.46 (150 °C)[3]
Viscosity | 6.5 cP (50% aq. sol.)[4]
Structure

Crystal structure

| Monoclinic
Thermochemistry

Heat capacity (C)

| 226.51 J/(mol·K) (26.85 °C)[8]

Std molar
entropy (S⦵298)

| 252.1 J/(mol·K)[8]

Std enthalpy of
formation (ΔfH⦵298)

| −1543.8 kJ/mol[4]

Heat of combustion, higher value (HHV)

| 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]
Pharmacology

ATC code

| A09AB04 (WHO)
Hazards
Occupational safety and health (OHS/OSH):

Main hazards

| Skin and eye irritant
GHS labelling:

Pictograms

| GHS05: CorrosiveGHS07: Exclamation mark[5]

Signal word

| Warning

Hazard statements

| H290, H319, H315[5]

Precautionary statements

| P305+P351+P338[5]
NFPA 704 (fire diamond)  |

Error: Image is invalid or non-existent.

Flash point | 155 °C (311 °F; 428 K)

Autoignition
temperature

| 345 °C (653 °F; 618 K)
Explosive limits | 8%[5]
Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 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).

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Infobox references

Chemical compound

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

5O3−
7 or C

5O(COO)3−

Citric acid is the citrate anions bonded by hydrogen ions (or protons) making it acidic. This is different than alkali citrate. Instead of protons, alkali citrate has the anions bound to non-proton, positively charged ions like sodium, potassium or magnesium, so that it does not donate protons. In that case, when the citrate anions are metabolized, they consume a proton (equivalent to generating bicarbonate), making it a source of base, or alkali.[11]

## Contents

* 1 Natural occurrence and industrial production
* 2 Chemical characteristics
* 3 Biochemistry
* 3.1 Citric acid cycle
* 3.2 Other biological roles
* 4 Applications
* 4.1 Food and drink
* 4.2 Cleaning and chelating agent
* 4.3 Cosmetics, pharmaceuticals, dietary supplements, and foods
* 4.4 Other uses
* 5 Synthesis of other organic compounds
* 6 Safety
* 7 Compendial status
* 8 See also
* 9 References

## Natural occurrence and industrial production[edit | edit source]

File:Citrus fruits.jpg

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

Citric acid occurs 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[12]).[a] 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 under which the fruit was grown.

Citric acid was first isolated in 1784 by the chemist Carl Wilhelm Scheele, who crystallized it from lemon juice.[13][14]

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.[15] 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,[16] 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.[17] 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.[18]

Global production was in excess of 2,000,000 tons in 2018.[19] 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.[15]

## Chemical characteristics[edit | edit source]

File: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.[20] The pKa of the hydroxyl group has been found, by means of 13C NMR spectroscopy, to be 14.4.[21] 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.[22] Tables compiled for biochemical studies[23] 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

5Fe(C

2·2H
2O.[24]

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.[25]

## Biochemistry[edit | edit source]

### Citric acid cycle[edit | edit source]

Main article: Citric acid cycle

Citrate is an intermediate in the citric acid cycle, also known as the TCA (TriCarboxylic Acid) cycle or the Krebs cycle, 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 thousands 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[26][27] 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[edit | edit source]

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.[28]

Citrate is a vital component of bone, helping to regulate the size of apatite crystals.[29]

## Applications[edit | edit source]

### Food and drink[edit | edit source]

File: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.[15] 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.[30] 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[edit | edit source]

File:Fe2CITdianion.svg

Structure of an iron(III) citrate complex.[31][32]

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.[15] 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.[33] In the 1950s, it was replaced by the far more efficient[34] EDTA.

In industry, it is used to dissolve rust from steel, and to passivate stainless steels.[35]

### Cosmetics, pharmaceuticals, dietary supplements, and foods[edit | edit source]

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.[36]

Citric acid is commonly used as a buffer to increase the solubility of brown heroin.[37]

Citric acid is used as one of the active ingredients in the production of facial tissues with antiviral properties.[38]

File:Sol-gel processing.png

### Other uses[edit | edit source]

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 both qualitative and quantitative identification of reducing sugars.[39]

Citric acid can be used as an alternative to nitric acid in passivation of stainless steel.[40]

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.[41]

Citric acid/potassium-sodium citrate can be used as a blood acid regulator. The citric acid is included to improve palatability[42]

Citric acid is an excellent soldering flux,[43] 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.

Alkali citrate can be used as an inhibitor of kidney stones by increasing urine citrate levels, useful for prevention of calcium stones, and increasing urine pH, useful for preventing uric acid and cystine stones.[44]

## Synthesis of other organic compounds[edit | edit source]

Citric acid is a versatile precursor to many other organic compounds. Dehydration routes give itaconic acid and its anhydride.[45] Citraconic acid can be produced via thermal isomerization of itaconic acid anhydride.[46] 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:[47]

(HO2CCH2)2C(OH)CO2H → HO2CCH=C(CO2H)CH2CO2H + H2O

Acetonedicarboxylic acid can also be prepared by decarbonylation of citric acid in fuming sulfuric acid:[48]

## Safety[edit | edit source]

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.[49] Long-term or repeated consumption may cause erosion of tooth enamel.[49][50][51]

## Compendial status[edit | edit source]

* British Pharmacopoeia[52]
* Japanese Pharmacopoeia[53]

## See also[edit | edit source]

File:Commons-logo.svg

Wikimedia Commons has media related to Citric acid.

File:Wikisource-logo.svg

Wikisource has the text of the 1911 Encyclopædia Britannica article "Citric Acid".

* The closely related acids isocitric acid, aconitic acid, and propane-1,2,3-tricarboxylic acid (tricarballylic acid, carballylic acid)
* Acids in wine

## References[edit | edit source]

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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.

* v
* t
* e

Digestives, including enzymes (A09)

Enzymes|

* Diastase
* Pancreatin
* Pancrelipase
* Pepsin

Acid preparations|

* Citric acid
* Hydrochloric acid

* v
* t
* e

Citrus

True species|

* Australian and Papuan wild limes
* Citron
* Clymenia
* Ichang papeda
* Kaffir lime
* Kumquats
* Common mandarin
* Mangshanyegan
* Mountain citron
* Pomelo
* Ryukyu mandarin

Major hybrids|

* Grapefruit
* Lemon
* Lime
* Orange

True and hybrid
cultivars|

* Alemow
* Amanatsu
* Bergamot orange
* Bizzaria
* Bitter orange
* Blood lime
* Blood orange
* Byeonggyul
* Biasong
* Cam sành
* Cara cara navel
* Citrange
* Citrumelo
* Clementine
* Daidai
* Dekopon
* Encore
* Fairchild tangerine
* Florentine citron
* Forbidden fruit
* Haruka
* Hassaku orange
* Hebesu
* Heen naran
* Hyuganatsu
* Imperial lemon
* Indian wild orange
* Iyokan
* Jabara
* Jaffa orange
* Jamaican tangelo
* Kabbad
* Kabosu
* Kakadu lime
* Kalpi
* Kanpei
* Kawachi Bankan
* Key lime
* Khasi papeda
* Kinkoji unshiu
* Kinnow
* Kishu mikan
* Kiyomi
* Kobayashi mikan
* Koji
* Komikan
* Kuchinotsu No. 37
* Laraha
* Lemonade fruit
* Limón de Pica
* Lumia
* Mandelo
* Mandora
* Melanesian papeda
* Melogold
* Meyer lemon
* Micrantha
* Midknight Valencia Orange
* Murcott
* Myrtle-leaved orange tree
* New Zealand grapefruit
* Ōgonkan
* Orangelo/Chironja
* Oroblanco
* Palestinian sweet lime
* Persian lime
* Pixie mandarin
* Pompia
* Ponderosa lemon
* Ponkan
* Rangpur
* Reikou
* Rhobs el Arsa
* Rough lemon
* Samuyao
* Sanbokan
* Satsuma mandarin
* Setoka
* Shangjuan
* Shonan Gold
* Smith Red Valencia
* Sudachi
* Suruga yuko
* Sweet lemon
* Sweet limetta
* Tangelo
* Tangerine
* Tangor
* Valencia orange
* Variegated pink lemon
* Volkamer lemon
* Winged lime
* Xã Đoài orange
* Yuukou mandarin
* Yuzu

Citrons|

* Balady citron
* Corsican citron
* Diamante citron
* Fingered citron/Buddha's hand
* Greek citron
* Moroccan citron
* Yemenite citron

Mandarin oranges|

* Cleopatra mandarin
* Shīkwāsā
* Nanfengmiju
* Tachibana
* Willowleaf orange

Papedas|

* Celebes papeda
* Citrus halimii/Mountain "citron"
* Ichang papeda

Pomelos|

* Banpeiyu
* Dangyuja

Kumquat hybrids
(× Citrofortunella)|

* Calamansi
* Citrangequat
* Limequat
* Mandarinquat
* Procimequat
* Sunquat
* Yuzuquat

Sahul citrus
(former Microcitrus, Eromocitrus,
Clymenia and Oxanthera genera)|

* Australian outback lime
* Australian round lime
* Brown River finger lime
* Desert lime
* Maiden's wild lime
* Mount White lime (Microcitrus)
* New Guinea wild lime
* Russell River lime
* Clymenia
* Orange-flowered oxanthera
* Large-leaf oxanthera
* Wavy-leaf oxanthera
* Oxanthera brevipes

Related genera
(perhaps properly Citrus)|

* Poncirus/Trifoliate orange

Drinks|

* Calamansi juice
* Chūhai
* Curaçao
* Dried lime tea (noomi basra)
* Grapefruit juice
* Lemonade
* Limeade
* Orange juice
* Yuja-hwachae
* Yuja tea

Products|

* Calcium citrate
* Citric acid
* Lemonene
* Limonene
* Neroli
* Orange flower water
* Orange oil
* Orangeat
* Succade
* Zest

Diseases|

* Black spot
* Canker
* CTV/Tristeza
* Exocortis
* Greening
* Mal secco
* Phytophthora
* citricola

Citrus botanists|

* Clara H. Hasse
* Robert Willard Hodgson
* Lena B. Smithers Hughes
* David Mabberley
* Clément Rodier
* Robert Soost
* Walter Tennyson Swingle
* Chōzaburō Tanaka
* Ikuro Takahashi
* Johann Christoph Volkamer
* Herbert John Webber

Related topics|

* The Citrus Industry
* Citrus production
* Citrus rootstock
* Citrus taxonomy
* Cold-hardy citrus
* Hesperidium
* Japanese citrus
* List of citrus fruits
* Mother Orange Tree
* Orangery
* University of California Citrus Experiment Station
* University of California, Riverside Citrus Variety Collection

* Category Category
* Category Production
* Commons page Commons

*[CID]: Compound ID
*[aq. sol.]: aqueous solution
*[H290]: H290: May be corrosive to metals
*[H319]: H319: Causes serious eye irritation
*[H315]: H315: Causes skin irritation
*[P305+P351+P338]: P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
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