2,3,4,5,6-Pentahydroxyhexanoic acid

HCID 604
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Basic information

CAS
526-95-4
Standard SMILES
O=C(O)C(O)C(O)C(O)C(O)CO
InChIKey
RGHNJXZEOKUKBD-UHFFFAOYSA-N
Molecular formula
C6H12O7
Average molar mass
196.16 g/mol

Overview

Isohexonic acid is a carbonyl compound.

Names & identifiers

Preferred name
2,3,4,5,6-Pentahydroxyhexanoic acid
IUPAC
2,3,4,5,6-pentahydroxyhexanoic acid
English name
Gluconic acid
Molecular formula
C6H12O7
Molecular weight
196.16

Names & synonyms

2,3,4,5,6-Pentahydroxyhexanoic acidRefChem:935246GlyTouCan:G56169UCG56169UCGulonic6622-52-2D-Galactonic Acid-d6Glyconic acidC6H12O7Isohexonic acidMFCD00004240NSC 77381
Show more names
gluconic(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acidHexonic acidD-Gluconic acid solutionGLUCONIC ACId-gluconicaciglosanto
2,3,4,5,6-Pentahydroxycaproic acidGluconic acid, technical5328-41-6SCHEMBL433662CHEMBL3039603CHEBI:192972RGHNJXZEOKUKBD-UHFFFAOYSA-NHMS5086L04

Database identifiers

CAS
526-95-4
PubChem CID
604
ChEMBL
CHEMBL3039603
ChEBI
CHEBI:192972
Nikkaji
J3.681.442J

Properties

Computed structural properties

XLogP
-3.4
Topological polar surface area
138 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
7
Rotatable bonds
5
Heavy atoms
13

Physicochemical properties

Melting point
15 °C · 15 °C
Boiling point
102 °C · 102 °C
alpha
20 · D20 -6.7° (c = 1)
Density
1.23 · 1.23
refractive index
1.4161 · 1.4161
storage temp.
30 °C · Store below +30°C.

Safety & regulation

Safety & protection

Minimum Risk LevelChronic Inhalation: 0.0003 mg/m3 (L134)

Toxicology

Health Effects · 1 item

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 RoutesOral (L228) ; inhalation (L228)
Toxicity Summary · 1 item

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 · 1 item

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 ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
-
tsca
TSCA listed
rtecs
LZ5057100
ridadr
3265
hs_code
29181600

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Manganese is absorbed mainly via ingestion, but can also be inhaled. It binds to alpha-2-macroglobulin, albumin, or transferrin in the plasma and is distributed to the brain and all other mammalian tissues, though it tends to accumulate more in the liver, pancreas, and kidney. Manganese is capable of existing in a number of oxidation states and is believed to undergo changes in oxidation state within the body. Manganese oxidation state can influence tissue toxicokinetic behavior, and possibly toxicity. Manganese is excreted primarily in the faeces. (L228)

Applications · 6 items

DescriptionGluconic 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.

DescriptionGluconic 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.

OccurrenceGluconic 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.

UsesA chemical used in glycolytic pathway studies.

UsesGluconic 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.

UsesGluconic acid occurs naturally in fruit, honey, and wine. As a food additive it is an acidity regulator. It is also used in cleaning products.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes

DefinitionA soluble crystalline organic acid made by the oxidation of glucose (using specific molds). It is used in paint strippers.

Definitiongluconic acid: An opticallyactive hydroxycarboxylic acid,CH2(OH)(CHOH)4COOH. It is the carboxylicacid corresponding to the aldosesugar glucose, and can be madeby the action of certain moulds.

Related reactions

4 records
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Compound notes

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