2,3,4,5,6-Pentahydroxyhexanoic acid
gluconic · (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid · Hexonic acid · Glyconic acid · D-Gluconic acid solution · 2,3,4,5,6-Pentahydroxyhexanoic acid · GLUCONIC ACI · d-gluconicaci
Identifiers & Physical Properties
| CAS No. | 526-95-4 |
|---|---|
| Molecular formula | C6H12O7 |
| Average molar mass | 196.16 g/mol |
| SMILES | O=C(O)C(O)C(O)C(O)C(O)CO |
| InChIKey | RGHNJXZEOKUKBD-UHFFFAOYSA-N |
| PubChem CID | 604 |
| ChEMBL | CHEMBL3039603 |
| ChEBI | CHEBI:192972 |
Chemical & Physical Properties
| XLogP | -3.4 |
|---|---|
| Topological polar surface area | 138 |
| Hydrogen bond donors | 6 |
| Hydrogen bond acceptors | 7 |
| Rotatable bonds | 5 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 170 |
| Melting point | 15 °C |
| Boiling point | 102 °C |
| alpha | D20 -6.7° (c = 1) |
| Density | 1.23 |
| Refractive index | 1.4161 |
| Storage conditions | Store below +30°C. |
| Solubility | DMSO (Slightly), Methanol (Slightly), WaterSoluble in water. |
| Physical state | Crystalline Powder or Crystals |
| pKa (acidity coefficient) | pK (25°) 3.60 |
| Color | White to light yellow |
| Specific gravity | 1.234 |
| pH | 2.2 (20°C, 500g/L in H2O) |
| Odor | commercial 50 aq. soln. lt. amber, faint odor of vinegar |
| optical activity | [α]/D +9.0 to 15.5° |
| Merck | 14,4456 |
| BRN | 1726055 |
| Cosmetics Ingredients Functions | CHELATINGPERFUMING |
| Cosmetic Ingredient Review (CIR) | Gluconic acid (526-95-4) |
| 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 |
| InChIKey | RGHNJXZEOKUKBD-SQOUGZDYSA-N |
| SMILES | OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O |
| LogP (partition coefficient) | -2.116 (est) |
| CAS DataBase Reference | 526-95-4(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | D-GLUCONIC ACID |
| EWG's Food Scores | 1 |
| FDA UNII | R4R8J0Q44B |
| NIST Chemistry Reference | Gluconic acid(526-95-4) |
| EPA Substance Registry System | D-Gluconic acid (526-95-4) |
| UNSPSC Code | 12352201 |
| NACRES | NA.22 |
| GHS pictogram | GHS05 |
| Signal word | Danger |
| GHS hazard statements | H318-H314 |
| GHS precautionary statements | P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501-P260h-P301+P330+P331-P303+P361+P353-P305+P351+P338-P501a |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xi,C |
| Risk statements (R) | 36/37/38-34 |
| Safety statements (S) | 37/39-26-45-36/37/39 |
| UN transport number | 3265 |
| Water hazard class (WGK) | - |
| RTECS number | LZ5057100 |
| TSCA inventory status | TSCA listed |
| Hazard class | 8 |
| Packing group | III |
| Customs code | 29181600 |
| Storage class | 10 - Combustible liquids |
| Hazardous substances data | 526-95-4(Hazardous Substances Data) |
| REACH registrations | Active |
Safety & Regulations
| Minimum Risk Level | Chronic Inhalation: 0.0003 mg/m3 (L134) |
|---|---|
| Health effects | Manganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as “manganism”. (L228) |
| Exposure routes | Oral (L228)inhalation (L228) |
| Toxicity summary | Manganese is a cellular toxicant that can impair transport systems, enzyme activities, and receptor functions. It primarily targets the central nervous system, particularily the globus pallidus of the basal ganglia. It is believed that the manganese ion, Mn(II), enhances the autoxidation or turnover of various intracellular catecholamines, leading to increased production of free radicals, reactive oxygen species, and other cytotoxic metabolites, along with a depletion of cellular antioxidant defense mechanisms, leading to oxidative damage and selective destruction of dopaminergic neurons. In addition to dopamine, manganese is thought to perturbations other neurotransmitters, such as GABA and glutamate. In order to produce oxidative damage, manganese must first overwhelm the antioxidant enzyme manganese superoxide dismutase. The neurotoxicity of Mn(II) has also been linked to its ability to substitute for Ca(II) under physiological conditions. It can enter mitochondria via the calcium uniporter and inhibit mitochondrial oxidative phosphorylation. It may also inhibit the efflux of Ca(II), which can result in a loss of mitochondrial membrane integrity. Mn(II) has been shown to inhibit mitochondrial aconitase activity to a significant level, altering amino acid metabolism and cellular iron homeostasis. (L228) |
| Signs and Symptoms | Manganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as “manganism”. (L228) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | - |
| TSCA inventory status |
Applications & Uses
Description
Gluconic acid (also known as gluconate) is an organic compound occurring widely in nature arising from the glucose oxidation. It is naturally found in fruit, honey and wine. It can also be used as a food additive to regulate acidity and a cleaning agent in alkaline solution. Its 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.
Description
Gluconic 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". 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.
Occurrence
Gluconic acid occurs naturally in fruit, honey, kombucha tea, and wine. As a food additive ( E574 ), it is an acidity regulator. It 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 gluconic 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.
Uses
A chemical used in glycolytic pathway studies.
Uses
Gluconic Acid is an acidulant that is a mild organic acid which is the hydrolyzed form of glucono-delta-lactone. it is prepared by the fermentation of dextrose, whereby the physiological d-form is produced. it is soluble in water with a solubility of 100 g/100 ml at 20°c. it 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.