Gluconic acid

Last updated
d-Gluconic acid
Skeletal formula of gluconic acid D-Gluconsaure Keilstrich.svg
Skeletal formula of gluconic acid
Ball-and-stick model of gluconic acid D-gluconic-acid-3D-balls.png
Ball-and-stick model of gluconic acid
Names
IUPAC name
d-Gluconic acid
Systematic IUPAC name
(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid
Other names
  • Dextronic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.639 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-401-4
E number E574 (acidity regulators, ...)
PubChem CID
UNII
  • InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1 Yes check.svgY
    Key: RGHNJXZEOKUKBD-SQOUGZDYSA-N Yes check.svgY
  • InChI=1/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1
    Key: RGHNJXZEOKUKBD-SQOUGZDYBY
  • O=C(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Properties
C6H12O7
Molar mass 196.155 g·mol−1
AppearanceColorless crystals
Melting point 131 °C (268 °F; 404 K)
316 g/L [1]
Acidity (pKa)3.86 [2]
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 ?)

Gluconic acid is an organic compound with molecular formula C6H12O7 and condensed structural formula HOCH2(CHOH)4CO2H. A white solid, it forms the gluconate anion in neutral aqueous solution. The salts of gluconic acid are known as "gluconates". Gluconic acid, gluconate salts, and gluconate esters occur widely in nature because such species arise from the oxidation of glucose. Some drugs are injected in the form of gluconates.

Contents

Chemical structure

The chemical structure of gluconic acid consists of a six-carbon chain, with five hydroxyl groups positioned in the same way as in the open-chained form of glucose, terminating in a carboxylic acid group. It is one of the 16 stereoisomers of 2,3,4,5,6-pentahydroxyhexanoic acid.

Production

Gluconic acid is typically produced by the aerobic oxidation of glucose in the presence of the enzyme glucose oxidase. The conversion produces gluconolactone and hydrogen peroxide. The lactone spontaneously hydrolyzes to gluconic acid in water. [3]

C6H12O6 + O2 → C6H10O6 + H2O2
C6H10O6 + H2O → C6H12O7

Variations of glucose (or other carbohydrate-containing substrate) oxidation using fermentation. [4] [5] or noble metal catalysis. [6] [7]

Gluconic acid was first prepared by Hlasiwetz and Habermann in 1870 [8] and involved the chemical oxidation of glucose. In 1880, Boutroux prepared and isolated gluconic acid using the glucose fermentation. [9]

Historical role in development of deep-tank fermentation

The production of gluconic acid by deep-tank fermentation (aerated, pH controlled, and stirred >1000 L tanks) of the filamentous fungi Aspergillus niger in 1929, for use as a food acidity regulator and cleaning agent, was the first successful use of deep-tank fermentation by Pfizer. [10] This expertise later led to Pfizer's successful use of deep-tank fermentation of Penicillium fungi in February 1944, [10] to rapidly scale up penicillin production, resulting in sufficient penicillin to treat the American and British battle casualties of the June 6th Allied D-Day invasion of World War II. [11]

Occurrence and uses

Gluconic acid occurs naturally in fruit, honey, and wine. As a food additive (E574 [12] ), it is now known as an acidity regulator.

The gluconate anion chelates Ca2+, Fe2+, K+, Al3+, and other metals, including lanthanides and actinides. It is also used in cleaning products, where it dissolves mineral deposits, especially in alkaline solution.

Zinc gluconate injections are used to neuter male dogs. [13]

Gluconate is also used in building and construction as a concrete admixture (retarder) to slow down the cement hydration reactions, and to delay the cement setting time. It allows for a longer time to lay the concrete, or to spread the cement hydration heat over a longer period of time to avoid too high a temperature and the resulting cracking. [14] [15] Retarders are mixed in to concrete when the weather temperature is high or to cast large and thick concrete slabs in successive and sufficiently well-mixed layers.

Gluconic acid aqueous solution finds application as a medium for organic synthesis. [16]

Medicine

In medicine, gluconate is used most commonly as a biologically neutral carrier of Zn2+, Ca2+, Cu2+, Fe2+, and K+ to treat electrolyte imbalance. [17]

Calcium gluconate, in the form of a gel, is used to treat burns from hydrofluoric acid; [18] [19] calcium gluconate injections may be used for more severe cases to avoid necrosis of deep tissues, as well as to treat hypocalcemia in hospitalized patients. Gluconate is also an electrolyte present in certain solutions, such as "plasmalyte a", used for intravenous fluid resuscitation. [20] Quinine gluconate is a salt of gluconic acid and quinine, which is used for intramuscular injection in the treatment of malaria.

Ferrous gluconate injections have been proposed in the past to treat anemia. [21]

See also

Related Research Articles

<span class="mw-page-title-main">Penicillin</span> Group of antibiotics derived from Penicillium fungi

Penicillins are a group of β-lactam antibiotics originally obtained from Penicillium moulds, principally P. chrysogenum and P. rubens. Most penicillins in clinical use are synthesised by P. chrysogenum using deep tank fermentation and then purified. A number of natural penicillins have been discovered, but only two purified compounds are in clinical use: penicillin G and penicillin V. Penicillins were among the first medications to be effective against many bacterial infections caused by staphylococci and streptococci. They are still widely used today for various bacterial infections, though many types of bacteria have developed resistance following extensive use.

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

Calcium carbonate is a chemical compound with the chemical formula CaCO3. It is a common substance found in rocks as the minerals calcite and aragonite, most notably in chalk and limestone, eggshells, gastropod shells, shellfish skeletons and pearls. Materials containing much calcium carbonate or resembling it are described as calcareous. Calcium carbonate is the active ingredient in agricultural lime and is produced when calcium ions in hard water react with carbonate ions to form limescale. It has medical use as a calcium supplement or as an antacid, but excessive consumption can be hazardous and cause hypercalcemia and digestive issues.

<span class="mw-page-title-main">Calcium oxide</span> Chemical compound of calcium

Calcium oxide, commonly known as quicklime or burnt lime, is a widely used chemical compound. It is a white, caustic, alkaline, crystalline solid at room temperature. The broadly used term lime connotes calcium-containing inorganic compounds, in which carbonates, oxides, and hydroxides of calcium, silicon, magnesium, aluminium, and iron predominate. By contrast, quicklime specifically applies to the single compound calcium oxide. Calcium oxide that survives processing without reacting in building products, such as cement, is called free lime.

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.

<span class="mw-page-title-main">Hydrofluoric acid</span> Solution of hydrogen fluoride in water

Hydrofluoric acid is a solution of hydrogen fluoride (HF) in water. Solutions of HF are colorless, acidic and highly corrosive. A common concentration is 49% (48-52%) but there are also stronger solutions and pure HF has a boiling point near room temperature. It is used to make most fluorine-containing compounds; examples include the commonly used pharmaceutical antidepressant medication fluoxetine (Prozac) and the material PTFE (Teflon). Elemental fluorine is produced from it. It is commonly used to etch glass and silicon wafers.

<span class="mw-page-title-main">Glucose oxidase</span> Class of enzymes

The glucose oxidase enzyme also known as notatin is an oxidoreductase that catalyses the oxidation of glucose to hydrogen peroxide and D-glucono-δ-lactone. This enzyme is produced by certain species of fungi and insects and displays antibacterial activity when oxygen and glucose are present.

Glucono-δ-lactone (GDL), also known as gluconolactone, is an organic compound with the formula (HOCH)3(HOCH2CH)CO2. A colorless solid, it is an oxidized derivative of glucose.

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

Sodium erythorbate (C6H7NaO6) is a food additive used predominantly in meats, poultry, and soft drinks. Chemically, it is the sodium salt of erythorbic acid.

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

Calcium lactate is a white crystalline salt with formula C
6
H
10
CaO
6
, consisting of two lactate anions H
3
C
(CHOH)CO
2
for each calcium cation Ca2+
. It forms several hydrates, the most common being the pentahydrate C
6
H
10
CaO
6
·5H
2
O
.

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

Zinc gluconate is the zinc salt of gluconic acid. It is an ionic compound consisting of two anions of gluconate for each zinc(II) cation. Zinc gluconate is a popular form for the delivery of zinc as a dietary supplement providing 14.35% elemental zinc by weight.

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

Tantalum pentoxide, also known as tantalum(V) oxide, is the inorganic compound with the formula Ta
2
O
5
. It is a white solid that is insoluble in all solvents but is attacked by strong bases and hydrofluoric acid. Ta
2
O
5
is an inert material with a high refractive index and low absorption, which makes it useful for coatings. It is also extensively used in the production of capacitors, due to its high dielectric constant.

<span class="mw-page-title-main">Calcium lactate gluconate</span> Chemical compound

Calcium lactate gluconate, also known as GLOCAL, is a soluble salt of calcium, lactic acid and gluconic acid used in effervescent calcium tablets. Its chemical formula is Ca5(C3H5O3)6·(C6H11O7)4·2H2O. It was first developed by Sandoz, Switzerland. Calcium lactate gluconate is used in the functional and fortified food industry due to its good solubility and neutral taste. In addition, it is used in various spherification techniques in molecular gastronomy. It can also be used to help neutralize HF (hydrofluoric acid) poisoning.

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

Calcium gluconate is the calcium salt of gluconic acid and is used as a mineral supplement and medication. As a medication it is used by injection into a vein to treat low blood calcium, high blood potassium, and magnesium toxicity. Supplementation is generally only required when there is not enough calcium in the diet. Supplementation may be done to treat or prevent osteoporosis or rickets. It can also be taken by mouth but is not recommended for injection into a muscle.

<span class="mw-page-title-main">Cement clinker</span> Main component of Portland cement

Cement clinker is a solid material produced in the manufacture of portland cement as an intermediary product. Clinker occurs as lumps or nodules, usually 3 millimetres (0.12 in) to 25 millimetres (0.98 in) in diameter. It is produced by sintering limestone and aluminosilicate materials such as clay during the cement kiln stage.

Biotransformation is the biochemical modification of one chemical compound or a mixture of chemical compounds. Biotransformations can be conducted with whole cells, their lysates, or purified enzymes. Increasingly, biotransformations are effected with purified enzymes. Major industries and life-saving technologies depend on biotransformations.

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

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

Sodium gluconate is a compound with formula NaC6H11O7. It is the sodium salt of gluconic acid. Its E number is E576. This white, water-soluble powder has a wide range of applications across industries. Originally derived from gluconic acid in the 19th century, Sodium Gluconate is known for its chelating properties and is utilized as a chelating agent in various processes. It finds applications in textile, metal surface treatment, cement, and more. Moreover, its non-toxic nature and biodegradability contribute to its use in environmentally conscious practices.

<span class="mw-page-title-main">Hydrofluoric acid burn</span> Medical condition

A hydrofluoric acid burn is a chemical burn from hydrofluoric acid. Where it contacts the skin it results in significant pain, swelling, redness, and skin breakdown. If the fumes are breathed in swelling of the upper airway and bleeding may occur. Complications can include electrolyte, heart, lung, kidney, and neurological problems.

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

Diphoterine is a decontamination solution used in first aid for the emergency treatment of chemical spills to the eyes and body.

A sulfite sulfate is a chemical compound that contains both sulfite and sulfate anions [SO3]2− [SO4]2−. These compounds were discovered in the 1980s as calcium and rare earth element salts. Minerals in this class were later discovered. Minerals may have sulfite as an essential component, or have it substituted for another anion as in alloriite. The related ions [O3SOSO2]2− and [(O2SO)2SO2]2− may be produced in a reaction between sulfur dioxide and sulfate and exist in the solid form as tetramethyl ammonium salts. They have a significant partial pressure of sulfur dioxide.

References

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