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Gluconic acid

 
Sci-Tech Dictionary: gluconic acid
(glü′kän·ik ′as·əd)

(organic chemistry) C6H12O7 A crystalline acid obtained from glucose by oxidation; used in cleaning metals.


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Food and Nutrition: gluconic acid
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The acid formed by oxidation of the hydroxyl group on carbon-1 of glucose to a carboxylic acid group. Also termed dextronic acid, maltonic acid, and glycogenic acid.

Medical Dictionary: glu·con·ic acid
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(glū-kŏn'ĭk)
n.

An acid formed from the oxidation of glucose and other sugars.

Wikipedia: Gluconic acid
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D-Gluconic acid
Skeletal formula of gluconic acid
Ball-and-stick model of gluconic acid
IUPAC name
Other names Dextronic acid
Identifiers
CAS number 526-95-4 Yes check.svgY,
133-42-6 (racemate)
EC-number 208-401-4
InChI
ChemSpider ID 10240
Properties
Molecular formula C6H12O7
Molar mass 196.16 g/mol
Appearance Colorless crystals
Melting point

131 °C, 404 K, 268 °F

Solubility in water Good
Acidity (pKa) 3.86
 Yes check.svgY (what is this?)  (verify)
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 2,3,4,5,6-pentahydroxyhexanoic 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

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[1]), 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.

Calcium gluconate, in the form of a gel, is used to treat burns from hydrofluoric acid;[2][3] calcium gluconate injections may be used for more severe cases to avoid necrosis of deep tissues.[4] 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.[5] Iron gluconate injections have been proposed in the past to treat anemia.[6]

References

  1. ^ Current EU approved additives and their E Numbers. Food Standards Agency
  2. ^ el Saadi MS, Hall AH, Hall PK, Riggs BS, Augenstein WL, Rumack BH (1989). "Hydrofluoric acid dermal exposure". Vet Hum Toxicol 31 (3): 243–7. PMID 2741315. 
  3. ^ 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): 889–94. doi:10.1097/01.BCR.0000245767.54278.09 (inactive 2008-10-14). PMID 17091088. 
  4. ^ 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
  5. ^ 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
  6. ^ 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.

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Sci-Tech Dictionary. McGraw-Hill Dictionary of Scientific and Technical Terms. Copyright © 2003, 1994, 1989, 1984, 1978, 1976, 1974 by McGraw-Hill Companies, Inc. All rights reserved.  Read more
Food and Nutrition. A Dictionary of Food and Nutrition. Copyright © 1995, 2003, 2005 by A. E. Bender and D. A. Bender. All rights reserved.  Read more
Medical Dictionary. The American Heritage® Stedman's Medical Dictionary Copyright © 2002, 2001, 1995 by Houghton Mifflin Company Read more
Wikipedia. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article "Gluconic acid" Read more