Gluconic acid

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d-Gluconic acid
D-Gluconsaure Keilstrich.svg
D-gluconic-acid-3D-balls.png
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]

Occurrence and uses

Gluconic acid occurs naturally in fruit, honey, and wine. As a food additive (E574 [10] ), 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. [11]

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. [12] [13] 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. [14]

Medicine

In medicine, gluconate is used most commonly as a biologically neutral carrier of Zn2+, Ca2+, Cu2+, Fe2+, and K+ to treat electrolyte imbalance. [15]

Calcium gluconate, in the form of a gel, is used to treat burns from hydrofluoric acid; [16] [17] 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. [18] 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. [19]

See also

Related Research Articles

<span class="mw-page-title-main">Glucose</span> Naturally produced monosaccharide

Glucose is a sugar with the molecular formula C6H12O6. Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world.

<span class="mw-page-title-main">Silicate</span> Any polyatomic anion containing silicon and oxygen

In chemistry, a silicate is any member of a family of polyatomic anions consisting of silicon and oxygen, usually with the general formula [SiO(4-2x)−
4−x
]
n
, where 0 ≤ x < 2. The family includes orthosilicate SiO4−4, metasilicate SiO2−3, and pyrosilicate Si2O6−7. The name is also used for any salt of such anions, such as sodium metasilicate; or any ester containing the corresponding chemical group, such as tetramethyl orthosilicate. The name "silicate" is sometimes extended to any anions containing silicon, even if they do not fit the general formula or contain other atoms besides oxygen; such as hexafluorosilicate [SiF6]2−.Most commonly, silicates are encountered as silicate minerals.

<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">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. 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">Zinc chloride</span> Chemical compound

Zinc chloride is the name of inorganic chemical compounds with the formula ZnCl2·nH2O, with x ranging from 0 to 4.5, forming hydrates. Zinc chloride, anhydrous and its hydrates are colorless or white crystalline solids, and are highly soluble in water. Five hydrates of zinc chloride are known, as well as four forms of anhydrous zinc chloride. This salt is hygroscopic and even deliquescent. Zinc chloride finds wide application in textile processing, metallurgical fluxes, and chemical synthesis. No mineral with this chemical composition is known aside from the very rare mineral simonkolleite, Zn5(OH)8Cl2·H2O.

Glucono-delta-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.

Neodymium(III) chloride or neodymium trichloride is a chemical compound of neodymium and chlorine with the formula NdCl3. This anhydrous compound is a mauve-colored solid that rapidly absorbs water on exposure to air to form a purple-colored hexahydrate, NdCl3·6H2O. Neodymium(III) chloride is produced from minerals monazite and bastnäsite using a complex multistage extraction process. The chloride has several important applications as an intermediate chemical for production of neodymium metal and neodymium-based lasers and optical fibers. Other applications include a catalyst in organic synthesis and in decomposition of waste water contamination, corrosion protection of aluminium and its alloys, and fluorescent labeling of organic molecules (DNA).

<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. When used in processed meat such as hot dogs and beef sticks, it increases the rate at which nitrite reduces to nitric oxide, thus facilitating a faster cure and retaining the pink coloring. As an antioxidant structurally related to vitamin C, it helps improve flavor stability and prevents the formation of carcinogenic nitrosamines. When used as a food additive, its E number is E316. The use of erythorbic acid and sodium erythorbate as a food preservative has increased greatly since the U.S. Food and Drug Administration banned the use of sulfites as preservatives in foods intended to be eaten fresh (such as ingredients for fresh salads) and as food processors have responded to the fact that some people are allergic to sulfites. It can also be found in bologna, and is occasionally used in beverages, baked goods, and potato salad. Sodium erythorbate is produced from sugars derived from different sources, such as beets, sugarcane, and corn. Sodium erythorbate is usually produced via a fermentation process from D-glucose by Pseudomonas fluorescens bacteria. Most syntheses proceed through the 2-keto-D-gluconic acid intermediate. An urban myth claims that sodium erythorbate is made from ground earthworms; however, there is no truth to the myth. It is thought that the origin of the legend comes from the similarity of the chemical name to the words earthworm and bait.

<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">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.

<span class="mw-page-title-main">Alkali–silica reaction</span> Chemical reaction damaging concrete

The alkali–silica reaction (ASR), also commonly known as concrete cancer, is a deleterious internal swelling reaction that occurs over time in concrete between the highly alkaline cement paste and the reactive amorphous silica found in many common aggregates, given sufficient moisture.

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

Oleuropein is a glycosylated seco-iridoid, a type of phenolic bitter compound found in green olive skin, flesh, seeds, and leaves. The term oleuropein is derived from the botanical name of the olive tree, Olea europaea.

<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">Isosaccharinic acid</span> Organic compound complexing radionuclides arising from the degradation of cellulose

Isosaccharinic acid (ISA) is a six-carbon sugar acid which is formed by the action of calcium hydroxide on lactose and other carbohydrates. It is of interest because it may form in intermediate-level nuclear waste stores when cellulose is degraded by the calcium hydroxide in cements such as Portland cement. The calcium salt of the alpha form of ISA is very crystalline and quite insoluble in cold water, but in hot water it is soluble.

<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.

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.

Lutetium compounds are compounds formed by the lanthanide metal lutetium (Lu). In these compounds, lutetium generally exhibits the +3 oxidation state, such as LuCl3, Lu2O3 and Lu2(SO4)3. Aqueous solutions of most lutetium salts are colorless and form white crystalline solids upon drying, with the common exception of the iodide. The soluble salts, such as nitrate, sulfate and acetate form hydrates upon crystallization. The oxide, hydroxide, fluoride, carbonate, phosphate and oxalate are insoluble in water.

References

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  2. Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
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  10. Current EU approved additives and their E Numbers. Food Standards Agency.
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