Monosodium citrate

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Monosodium citrate
Monosodium citrate.png
Monosodium citrate.jpg
Names
IUPAC name
Sodium 2-(carboxymethyl)-2,4-dihydroxy-4-oxobutanoate [1]
Other names
sodium dihydrogen 2-hydroxypropane-1,2,3-tricarboxylate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.038.834 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 242-734-6
E number E331i (antioxidants, ...)
PubChem CID
RTECS number
  • GE9750000
UNII
  • InChI=1S/C6H8O7.Na/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);/q;+1/p-1 X mark.svgN
    Key: HWPKGOGLCKPRLZ-UHFFFAOYSA-M X mark.svgN
  • InChI=1/C6H8O7.3Na/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);;;/q;3*+1/p-3
    Key: HRXKRNGNAMMEHJ-DFZHHIFOAL
  • C(C(=O)O)C(CC(=O)O)(C(=O)[O-])O.[Na+]
Properties
C6H7NaO7
Molar mass 214.105 g·mol−1
Appearancewhite powder
hygroscopic
Odor odorless
Melting point 212 °C (414 °F; 485 K)
Boiling point 309.6 °C (589.3 °F; 582.8 K)
soluble
Solubility negligible in ethanol
Acidity (pKa)3.50–3.80
Structure [2]
Monoclinic
P21/a (No. 4)
4
Hazards
Lethal dose or concentration (LD, LC):
5400 mg/kg (mouse, oral) >2000 mg/kg (rat, dermal)
Safety data sheet (SDS) Carl Roth
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Monosodium citrate, more correctly, sodium dihydrogen citrate (Latin: natrium citricum acidulatum), is an acid salt of citric acid. Disodium citrate and trisodium citrate are also known. It can be prepared by partial neutralisation of citric acid [3] with an aqueous solution of sodium bicarbonate or carbonate. It has a slightly acidic taste. [3]

NaHCO3 + C6H8O7 → NaC6H7O7 + CO2 + H2O
Na2CO3 + 2C6H8O7 → 2NaC6H7O7 + CO2 + H2O

It is highly soluble in water and practically insoluble in ethanol. [3] Monosodium citrate is used as an anticoagulant in donated blood. [4] It is used as an alkalinizing agent to prevent kidney stone disease. [5] The crystals form as nearly perfect cubes. [6]

Related Research Articles

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

Citric acid is an organic compound with the skeletal 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">Sodium oxalate</span> Chemical compound

Sodium oxalate, or disodium oxalate, is a chemical compound with the chemical formula Na2C2O4. It is the sodium salt of oxalic acid. It contains sodium cations Na+ and oxalate anions C2O2−4. It is a white, crystalline, odorless solid, that decomposes above 290 °C.

<span class="mw-page-title-main">Dihydrogen phosphate</span> Inorganic ion

Dihydrogen phosphate is an inorganic ion with the formula [H2PO4]. Phosphates occur widely in natural systems.

<span class="mw-page-title-main">Ammonium ferric citrate</span> Chemical compound

Ammonium ferric citrate has the formula [NH+4]5[Fe(C6H4O7)2]5−. The iron in this compound is trivalent. All three carboxyl groups and the central hydroxyl group of citric acid are deprotonated. A distinguishing feature of this compound is that it is very soluble in water, in contrast to ferric citrate which is not very soluble.

<span class="mw-page-title-main">Disodium citrate</span> Chemical compound

Disodium citrate, also known as disodium hydrogen citrate, (Neo-Alkacitron) and sesquihydrate, is an acid salt of citric acid with the chemical formula Na2C6H6O7. It is used as an antioxidant in food and to improve the effects of other antioxidants. It is also used as an acidity regulator and sequestrant. Typical products include gelatin, jam, sweets, ice cream, carbonated beverages, milk powder, wine, and processed cheeses.

Sodium citrate may refer to any of the sodium salts of citric acid :

<span class="mw-page-title-main">Hydrogenoxalate</span> Ion

Hydrogenoxalate or hydrogen oxalate(IUPAC name: 2-Hydroxy-2-oxoacetate) is an anion with chemical formula HC2O−4 or HO−C(=O)−CO−2, derived from oxalic acid by the loss of a single proton; or, alternatively, from the oxalate anion C2O2−4 by addition of a proton. The name is also used for any salt containing this anion. Especially in older literature, hydrogenoxalates may also be referred to as bioxalates, acid oxalates, or monobasic oxalates. Hydrogenoxalate is amphoteric, in that it can react both as an acid or a base.

<span class="mw-page-title-main">Methanetetracarboxylate</span> Ion

In chemistry, methanetetracarboxylate is a tetravalent anion with formula C5O4−8 or C(−CO−2)4. It has four carboxylate groups attached to a central carbon atom; so it has the same carbon backbone as neopentane. It is an oxocarbon anion, that is, consists only of carbon and oxygen.

<span class="mw-page-title-main">Iron(II) citrate</span> Chemical compound

Ferrous citrate, also known as iron(II) citrate or iron(2+) 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.

<span class="mw-page-title-main">Sodium tetrachloroaurate</span> Chemical compound

Sodium tetrachloroaurate is an inorganic compound with the chemical formula NaAuCl4. It is composed of the ions Na+ and AuCl4. It exists in the anhydrous and dihydrate states. At room temperature, it exists as a golden-orange solid. The anhydrous and dihydrate forms are available commercially.

<span class="mw-page-title-main">Germanium(IV) iodide</span> Chemical compound

Germanium(IV) iodide is an inorganic compound with the chemical formula GeI4.

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

Dithymoquinone is a bioactive isolate of Nigella sativa. Chemically, it is a dimer of thymoquinone.

<span class="mw-page-title-main">18-Deoxyaldosterone</span> Chemical compound

18-Deoxyaldosterone is a steroidal antimineralocorticoid with mixed agonist–antagonist but predominantly antagonistic activity at the mineralocorticoid receptor.

4-Chlorobenzaldehyde is an organic compound with the chemical formula C7H5ClO. It can be produced by the oxidation of 4-chlorobenzyl alcohol. It can be further oxidized to 4-chlorobenzoic acid. It will react with malononitrile to form 4-chlorobenzylidenylmalononitrile. 4-Chlorobenzaldehyde reacts with benzylamine to produce N-(4-chlorobenzylidenyl)benzylamine。

Trisodium borate is a chemical compound of sodium, boron, and oxygen, with formula Na3BO3, or (Na+)3[BO3]3−. It is a sodium salt of the orthoboric acid B(OH)3.

Alkali citrate is an inhibitor of kidney stones. It is used to increase urine citrate levels - this prevents calcium oxalate stones by binding to calcium and inhibiting its binding to oxalate. It is also used to increase urine pH - this prevents uric acid stones and cystine stones.

Bromocyclopropane is a organobromine compound with the chemical formula C3H5Br. It is a member of haloalkane family.

Monosodium acetylide is an organosodium compound with the formula NaC≡CH. It is a sodium salt of acetylene, consisting of sodium cations Na+ and hydrogen acetylide anions C≡CH. It is a derived from acetylene by deprotonation using a sodium base, typically sodium amide.

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

Azomethane is an organic compound with the chemical formula CH3-N=N-CH3. It exhibits cis-trans isomerism. It can be produced by the reaction of 1,2-dimethylhydrazine dihydrochloride with copper(II) chloride in sodium acetate solution. The reaction produces the azomethane complex of copper(I) chloride, which can produce free azomethane by thermal decomposition. It is the source of methyl radical in laboratory.

References

  1. https://pubchem.ncbi.nlm.nih.gov/compound/23662352#section=IUPAC-Name&fullscreen=true [ bare URL ]
  2. Glusker, Jenny P.; van der Helm, D.; Love, Warner E.; Dornberg, Marilyn L.; Patterson, A. L. (June 1960). "The State of Ionization of Crystalline Sodium Dihydrogen Citrate1". Journal of the American Chemical Society. 82 (11): 2964–2965. doi:10.1021/ja01496a071. ISSN   0002-7863 . Retrieved 22 July 2022.
  3. 1 2 3 "Monosodium Citrate - Jungbunzlauer". www.jungbunzlauer.com. Retrieved 17 July 2022.
  4. Clinical Hematology: Theory and Procedures, Mary Louise Turgeon
  5. PubChem. "Monosodium citrate". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-08-02.
  6. Hitchcock, David I. (March 1946). "Sodium Hydrogen Citrates". Journal of the American Chemical Society. 68 (3): 524–525. doi:10.1021/ja01207a507. ISSN   0002-7863. PMID   21015754 . Retrieved 22 July 2022.