DEXTRONIC ACID

Dextronic acid is an organic compound occurring widely in nature arising from the glucose oxidation. 
Dextronic acid is naturally found in fruit, honey and wine. 
Dextronic acid can also be used as a food additive to regulate acidity and a cleaning agent in alkaline solution. 

CAS Number: 526-95-4
Molecular Formula: C6H12O7
Molecular Weight: 196.16
EINECS Number: 208-401-4

Synonyms: Gluconic acid, D-gluconic acid, 526-95-4, dextronic acid, maltonic acid, Glycogenic acid, (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid, Glosanto, Pentahydroxycaproic acid, gluconate, Gluconic acid, D-, D-Gluco-hexonic acid, Glyconic acid, Gluconic acid (VAN), 133-42-6, HSDB 487, D-Gluconsaeure, D-Glukonsaeure, BRN 1726055, EINECS 208-401-4, UNII-R4R8J0Q44B, NSC 77381, R4R8J0Q44B, DTXSID8027169, CHEBI:33198, 2,3,4,5,6-Pentahydroxyhexanoic acid, GLUCONAL GA-50, Hexonic acid, DTXCID307169, INS NO.574, DTXSID8042000, INS-574, EC 208-401-4, 4-03-00-01255 (Beilstein Handbook Reference), Dextronate, Glycogenate, Glyconate, Maltonate, NSC-77381, E-574, GCO, GLUCONIC ACID (MART.), GLUCONIC ACID [MART.], AMMONIUM GLUCONATE, D-Gluconic Acid (50% in Water), 124423-64-9, 19222-41-4, NSC77381, sodium-gluconate, ketogluconic acid, D-?Gluconic acid, Pentahydroxycaproate, MFCD00004240, SCHEMBL971, bmse000084, GLUCONIC ACID [MI], Pesticide Code: 000104, GLUCONIC ACID [HSDB], GLUCONIC ACID [VANDF], CHEMBL464345, D-Gluconic acid 50% in water, GLUCONIC ACID [WHO-DD], CHEBI:24266, DTXCID201012074, GluconicAcid(containsGluconolactone), HY-Y0569, 2,3,4,5,6-pentahydroxy-hexanoate, Tox21_202745, s3595, 2,3,4,5,6-Pentahydroxycaproic acid, AKOS015895892, DB13180, 2,3,4,5,6-pentahydroxy-hexanoic acid, GLUCONIC ACID (50% IN WATER), NCGC00260293-01, CAS-526-95-4, E574, CS-0015343, G0036, NS00008847, 2,3,4,5,6-Pentahydroxycaproic acid solution, C00257, D70789, SBI-0635367.0002, EN300-7392806, Q407569, BRD-K93201765-001-01-0, 6E52B5FC-5676-4139-977A-4D643EDDB159, 2,3,4,5,6-PENTAHYDROXYCAPROIC ACID;GLYCOGENIC ACID;GLUCONIC ACID;PENTAHYDROXYCAPROIC ACID;glyconicacid;Hexonic acid;Ultra-Mg [as magnesium salt dihydrate];MALTONIC ACID

Dextronic acids calcium salt, calcium gluconate can be used to treat burns from hydrofluoric acid and avoid necrosis of deep tissues as well as treating the verapamil poisoning and hypocalcemia in hospitalized patient. 
Some salts of gluconate can also be used to treat malaria (quinidine gluconate) and anemia (ferrous gluconate). 
In microbiology, gluconate is a common carbon source that can be supplemented to the medium for cell growth.

Dextronic acid, also known as D-Gluconic acid, is an organic compound that belongs to the family of sugar acids and is derived from the oxidation of glucose. 
It is a mild organic acid that occurs naturally in fruits, honey, and wine, and is commonly produced by the microbial fermentation of glucose using certain bacteria or fungi. 
The chemical structure of dextronic acid consists of a six-carbon chain with five hydroxyl (–OH) groups and one carboxyl (–COOH) group, making it highly soluble in water and contributing to its chelating properties. 

Due to its ability to form stable complexes with metal ions, dextronic acid is often used in industrial, pharmaceutical, and food applications as a pH regulator, a metal sequestrant, and a biodegradable alternative to synthetic chelating agents.
Dextronic acid is an organic compound with molecular formula C6H12O7 and condensed structural formula HOCH2(CHOH)4COOH. 
It is one of the 16 stereoisomers of 2,3,4,5,6-penta hydroxy hexanoic acid.

In aqueous solution at neutral pH, gluconic acid forms the gluconate ion. 
The salts of gluconic acid are known as "gluconates".
Dextronic 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.
Dextronic acid is an acid sugar composed of white crystals with a milk-acidic taste. 
In aqueous solutions, it is in equilibrium with gamma- and delta-gluconolactones. 

Dextronic acid is prepared by enzymatic oxidation of glucose and strains of the microorganisms used to supply the enzyme action are nonpathogenic and nontoxicogenic to man or other animals. 
Dextronic acid is used as a component of bottle rinsing formulations, at levels not to exceed good manufacturing practice.
Dextronic 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". 
Dextronic 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.
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. 
Dextronic acid is one of the 16 stereoisomers of 2,3,4,5,6-pentahydroxyhexanoic acid.

Dextronic 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.

C6H12O6 + O2 → C6H10O6 + H2O2
C6H10O6 + H2O → C6H12O7
Variations of glucose (or other carbohydrate-containing substrate) oxidation using fermentation or noble metal catalysis.

Dextronic acid was first prepared by Hlasiwetz and Habermann in 1870 and involved the chemical oxidation of glucose. 
In 1880, Boutroux prepared and isolated gluconic acid using the glucose fermentation.
Dextronic acid, also known as D-Gluconic acid, is a naturally occurring organic acid that is derived from the oxidation of D-glucose, where the aldehyde (-CHO) group at the first carbon is converted into a carboxyl (-COOH) group. 

This transformation makes it a mild, non-corrosive acid that is commonly found in nature, especially in fruits, honey, and wine, as well as in various metabolic pathways within living organisms. 
Dextronic acid is produced both biologically through enzymatic oxidation by glucose oxidase and industrially via microbial fermentation using Aspergillus niger and other fungi or bacteria.

This acid is highly soluble in water due to its multiple hydroxyl (-OH) groups, which also contribute to its strong chelating properties, allowing it to bind metal ions such as calcium, magnesium, iron, and aluminum. 
Because of this, dextronic acid is widely used as a chelating agent in cleaning solutions, metal surface treatments, and rust removal products, where it helps prevent metal ion precipitation and enhances cleaning efficiency.

Melting point: 15 °C
Boiling point: 102 °C
alpha: D20 -6.7° (c = 1)
Density: 1.23
refractive index: 1.4161
storage temp.: Store below +30°C.
solubility: DMSO (Slightly), Methanol (Slightly), Water
form: Crystalline Powder or Crystals
pka: pK (25°) 3.60
color: White to light yellow
Specific Gravity: 1.234
Odor: commercial 50 aq. soln. lt. amber, faint odor of vinegar
PH: 2.2 (20°C, 500g/L in H2O)
optical activity: [α]/D +9.0 to 15.5°
Water Solubility: Soluble in water.
Merck: 14,4456
BRN: 1726055
LogP: -2.116 (est)

Dextronic acid, also known as D-Gluconic acid, is a naturally occurring organic acid that results from the oxidation of D-glucose, where the aldehyde functional group at the first carbon is converted into a carboxyl group. 
Dextronic acid is a mild, non-toxic acid that is widely found in nature, particularly in fruits, honey, and wine, and can also be produced through microbial fermentation using fungi such as Aspergillus niger or certain bacteria. 
The chemical structure of dextronic acid consists of a six-carbon backbone with multiple hydroxyl (-OH) groups, making it highly hydrophilic and water-soluble.

One of its key properties is its ability to chelate metal ions, particularly calcium, iron, and aluminum, forming stable complexes that prevent metal precipitation. 
Because of this, it is frequently used as a chelating agent in cleaning products, metal surface treatments, and industrial applications. 
Dextronic acid also plays a role as a pH regulator in food and pharmaceutical formulations, where it helps maintain acidity and improve the stability of certain products.

Dextronic acid is biodegradable and environmentally friendly, making it a preferable alternative to synthetic chelating agents such as EDTA in many applications.
In the food industry, it is commonly used as a pH regulator, acidity controller, and sequestrant in processed foods and beverages, where it helps stabilize formulations and extend shelf life. 
Dextronic acid is also used in pharmaceutical and medical applications, particularly in intravenous (IV) solutions, mineral supplements, and oral medications, where it improves the bioavailability of essential minerals. 

Dextronic acid is found in cosmetic formulations, acting as a humectant and pH adjuster in skincare and personal care products.
One of the key advantages of dextronic acid is that it is biodegradable and environmentally friendly, making it a safer alternative to synthetic chelating agents such as EDTA (Ethylenediaminetetraacetic acid), which can persist in the environment and contribute to water pollution. 
Due to its non-toxic and biocompatible nature, it is widely used in eco-friendly cleaning products, wastewater treatment, and agriculture, where it enhances nutrient absorption in plants.

The chemical structure of Dextronic acid consists of a six-carbon chain with five hydroxyl groups terminating in a carboxylic acid group. 
In aqueous solution, gluconic acid exists in equilibrium with the cyclic ester glucono delta-lactone.
Dextronic acid occurs naturally in fruit, honey, kombucha tea, and wine. As a food additive ( E574 ), it is an acidity regulator. 

Dextronic acid is also used in cleaning products where it dissolves mineral deposits especially in alkaline solution. 
The gluconate anion chelates Ca2+,Fe2+, Al3+, and other metals. 
In 1929 Horace Terhune Herrick developed a process for producing the salt by fermentation.

Calcium gluconate, in the form of a gel, is used to treat burns from hydrofluoric acid; calcium gluconate injections may be used for more severe cases to avoid necrosis of deep tissues. 
Quinine gluconate is a salt between Dextronic acid and quinine, which is used for intramuscular injection in the treatment of malaria. 
Zinc gluconate injections are used to neuter male dogs. 

Iron gluconate injections have been proposed in the past to treat anemia.
A soluble crystalline organic acid made by the oxidation of glucose (using specific molds). 
Dextronic acid is used in paint strippers.

Dextronic acid is commercially produced by submerged fed-batch cultivations of Aspergillus niger using glucose as substrate. 
A. niger produces citric acid and gluconic acid growing on glucose. 
Dextronic acid concentration and yields of the product depend on the fermentation conditions. 

For optimal gluconic acid production, high glucose concentrations (110–250 g.L-1), low concentrations of nitrogen and phosphorus in the medium, a limitation of metal ion concentrations, a pH value in the range of 4.5–6.5, and high aeration rates for the oxygen supply are needed.
Much research has been carried out to find new ways for cheaper production. 
Different microorganisms have been studied (e.g. G. oxydans, Z. mobilis, A. methanolicous, and P. fluorescence. 

Moreover, new microbial strains have been developed by mutagenesis or genetic engineering. 
Additionally, the fermentation process and recovery have been optimized. 
New inexpensive substrates (e.g. cornstarch, grape or banana must, figs, and cheese whey) have been tested.

One example of a new and efficient production process of gluconic acid is the cultivation of Aureobasidium pullulans growing on glucose. 
Using a continuous process with biomass retention by crossover filtration, a product concentration of 375 g.L-1, a yield of 0.83 g of gluconic acid per gram of glucose, and a productivity of 17 g.L-1.h-1 could be achieved at a residence time of 22 h. 

In this process, 100 % of the glucose is converted. This process might be interesting for industrial applications. 
In continuous gluconic acid production with immobilized mycelia of A. niger, product concentrations of 120–140 g.L-1 have been achieved.

Uses Of Dextronic acid:
Dextronic acid is an acidulant that is a mild organic acid which is the hydrolyzed form of glucono-delta-lactone. 
Dextronic acid is prepared by the fermentation of dextrose, whereby the physiological d-form is produced. 
Dextronic acid is soluble in water with a solubility of 100 g/100 ml at 20°c. 

Dextronic acid has a mild taste and at 1% has a ph of 2.8. 
It functions as an antioxidant and enhances the function of other antioxidants. 
In beverages, syrups, and wine, it can eliminate calcium turbidities. 

It is used as a leavening component in cake mixes, and as an acid component in dry-mix desserts and dry beverage mixes.
Dextronic acid occurs naturally in fruit, honey, and wine. 
As a food additive it is an acidity regulator. 

Dextronic acid is also used in cleaning products.
Dextronic acid occurs naturally in fruit, honey, and wine. 
As a food additive (E574), it is now known as an acidity regulator.

The gluconate anion chelates Ca2+, Fe2+, K+, Al3+, and other metals, including lanthanides and actinides. 
Dextronic acid is also used in cleaning products, where it dissolves mineral deposits, especially in alkaline solution.
Zinc gluconate injections are used to neuter male dogs.

Dextronic acid 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.
Dextronic acid 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.
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.

Dextronic acid aqueous solution finds application as a medium for organic synthesis.
In medicine, Dextronic acid is used most commonly as a biologically neutral carrier of Zn2+, Ca2+, Cu2+, Fe2+, and K+ to treat electrolyte imbalance.
Calcium gluconate, in the form of a gel, is used to treat burns from hydrofluoric acid; 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. 

Dextronic acid is also an electrolyte present in certain solutions, such as "plasmalyte a", used for intravenous fluid resuscitation.
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.

Dextronic acid, also known as D-gluconic acid, has a wide range of uses across various industries due to its biodegradable, non-toxic, and mildly acidic properties. 
In the food and beverage industry, it is commonly employed as an acidity regulator, helping to maintain the pH balance in products such as processed fruits, dairy, and soft drinks. 
Dextronic acid also serves as a sequestrant, binding to metal ions like calcium and iron, preventing unwanted interactions and ensuring the stability and consistency of food products.

In the pharmaceutical sector, dextronic acid is used as a chelating agent in intravenous solutions to improve the bioavailability of essential minerals, such as calcium and iron, making these nutrients more accessible for absorption by the body. 
Dextronic acid is also utilized in certain oral medications and dietary supplements to enhance mineral absorption, particularly in individuals with nutrient deficiencies or those on specialized diets.
Dextronic acid is a valuable component in the cosmetic and personal care industry, where it functions as a pH adjuster in formulations like shampoos, body lotions, and facial creams, helping to stabilize the product’s pH for optimal skin compatibility. 

Its humectant properties also make it effective in attracting moisture, promoting skin hydration, and maintaining the product’s texture and consistency.
In cleaning products, dextronic acid is used for its ability to act as a metal chelator, removing stains caused by metal ions and calcium deposits, particularly in household cleaners and limescale removers. 
Dextronic acid can also be found in industrial applications for cleaning metal surfaces, where it helps to dissolve corrosion and rust without causing damage to the underlying material.

Additionally, dextronic acid is used in environmentally friendly products, such as eco-friendly detergents, as it is biodegradable and safe for the environment. 
Dextronic acid is also used in agriculture, where it enhances the availability of nutrients to plants by chelating trace minerals in the soil, making them more accessible to plant roots. 
The acid is utilized in wastewater treatment as well, where it helps to reduce water hardness and improve the efficiency of water purification systems.

Safety Profile Of Dextronic acid:
Dextronic acid is generally considered to be non-toxic and biodegradable. 
However, like many chemicals, it may pose certain hazards under specific conditions or in large quantities.
While Dextronic acid is typically mild, it can cause irritation to the skin and eyes if in direct contact, especially in concentrated forms. 

Prolonged exposure can lead to redness, dryness, or discomfort. 
Protective measures like wearing gloves and goggles are recommended when handling concentrated solutions.
Inhalation of dust or aerosolized particles of dextronic acid can potentially irritate the respiratory system. 

This may cause symptoms like coughing, wheezing, or shortness of breath. 
However, such risks are minimal in typical consumer-use concentrations.

When in very concentrated forms, Dextronic acid can have corrosive effects on metals and may lead to the degradation of surfaces if improperly handled. 
Proper storage and handling are essential to avoid reactions with certain materials.