Gluconic acid

Source: Wikipedia, the free encyclopedia.
Not to be confused with Glucuronic acid or Glutaconic acid.
d-Gluconic acid
Skeletal formula of gluconic acid
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 Edit this at Wikidata
EC Number
  • 208-401-4
E number E574 (acidity regulators, ...)
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 checkY
    Key: RGHNJXZEOKUKBD-SQOUGZDYSA-N checkY
  • 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
Appearance Colorless 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).
☒N verify (what is checkY☒N ?)

Gluconic acid is an

oxidation of glucose
. Some drugs are injected in the form of gluconates.

Chemical structure

The

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

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

References

  1. ^ "D-Gluconic acid". American Chemical Society.
  2. ^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
  3. S2CID 2246466
    .
  4. S2CID 7700011
    .
  5. ISSN 0255-2701
    .
  6. S2CID 218970877
    .
  7. S2CID 236243315
    .
  8. ISSN 1099-0682
    .
  9. ^ Boutroux, L. (1880). "Sur une fermentation nouvelle du glucose" [On a new fermentation [product] of glucose]. Comptes Rendus de l'Académie des Sciences (in French). 91: 236–238.
  10. ^ Current EU approved additives and their E Numbers. Food Standards Agency.
  11. doi:10.2460/ajvr.69.1.140
  12. ISSN 0040-6031
    .
  13. ISSN 0950-0618
    .
  14. S2CID 235547468
    .
  15. PMID 31275855
    .
  16. PMID 2741315
    .
  17. S2CID 3691306
    .
  18. ^ D. Thomas, U. Jaeger, I. Sagoschen, C. Lamberti and K. Wilhelm (2009), Intra-Arterial Calcium Gluconate Treatment After Hydrofluoric Acid Burn of the Hand. CardioVascular and Interventional Radiology, Volume 32, Number 1, pages 155–158
    doi:10.1007/s00270-008-9361-1
  19. ^ Paul Reznikoff and Walther F. Goebel (1937), The preparation of ferrous gluconate and its use in the treatment of hypochromic anelia in rats. Journal of Pharmacology and Experimental Therapy, volume 59 issue 2, page 182.

External links

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