Gluconic acid

D-Gluconic acid

IUPAC name[hide]
D-Gluconic

acid

Other names[hide]
Dextronic acid

CAS number
PubChem
ChemSpider
EC-number
ChEBI
ChEMBL
Jmol-3D images

Identifiers
526-95-4 ,
133-42-6 (racemate)
10690
10240
208-401-4
CHEBI:33198
CHEMBL464345
Image 1
SMILES

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InChI
[show]
Molecular formula
Molar mass
Appearance
Melting point
Solubility in water
Acidity (pKa)

Properties
C6H12O7
196.16 g/mol
Colorless crystals
131 C, 404 K, 268 F

Good
3.86[1]
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Except where noted otherwise, data are given for materials in
their standard state (at 25 C, 100 kPa)
Infobox references

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 2,3,4,5,6pentahydroxyhexanoic 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.

Contents

1 Chemical structure

2 Occurrence and uses

3 References

4 External links

Chemical structure
The chemical structure of gluconic 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.

Occurrence and uses

Gluconic acid occurs naturally in fruit, honey, kombucha tea, and wine. As a food additive
(E574[2]), 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.[3]
Calcium gluconate, in the form of a gel, is used to treat burns from hydrofluoric acid;[4][5]
calcium gluconate injections may be used for more severe cases to avoid necrosis of deep
tissues.[6] 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.[7] Iron gluconate injections have been proposed in the past to treat anemia.
[8]

References
1.

^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.

2.

^ Current EU approved additives and their E Numbers. Food Standards

Agency

3.

^ "All Chemistry". Time magazine. May 13, 1929. Retrieved 2010-07-12. "Dr.
Horace T. Herrick (U. S. Department of Agriculture) told of experiments aiming to
produce tartaric acid from mold. They did not succeed in their aim, but a way was
found of procuring gluconic acid. This acid formerly cost $100 per lb., can now be
made for less than 35. It can be used in dyestuff manufacture at the new price; also,
to make calcium gluconate, valuable medicinally in the treatment of hemorrhages."

4.

^ el Saadi MS, Hall AH, Hall PK, Riggs BS, Augenstein WL, Rumack BH
(1989). "Hydrofluoric acid dermal exposure". Vet Hum Toxicol 31 (3): 2437.
PMID 2741315.

5.

^ Roblin I, Urban M, Flicoteau D, Martin C, Pradeau D (2006). "Topical

treatment of experimental hydrofluoric acid skin burns by 2.5% calcium gluconate". J
Burn Care Res 27 (6): 88994. DOI:10.1097/01.BCR.0000245767.54278.09.
PMID 17091088.

6.

^ 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

7.

^ Julie K. Levy, P. Cynda Crawford, Leslie D. Appel, Emma L. Clifford

(2008), Comparison of intratesticular injection of zinc gluconate versus surgical
castration to sterilize male dogs. American Journal of Veterinary Research Vol. 69,
No. 1, Pages 140-143. doi:10.2460/ajvr.69.1.140

8.

^ 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 Thereapy, volume 59 issue 2, page 182.

http://en.wikipedia.org/wiki/Gluconic_acid