Gluconic acid

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Names
IUPAC name
Page Template:Smallcaps/styles.css has no content.d-Gluconic acid
Systematic IUPAC name
(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid
Other names
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  • Dextronic acid
Identifiers
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3D model (JSmol)
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  • 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
Density 1.23 g/cm3[1]
Melting point 131 °C (268 °F; 404 K)
316 g/L[2]
Acidity (pKa) 3.86[3]
Hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Gluconic acid is an organic compound with molecular formula C6H12O7 and condensed structural formula HOCH2(CHOH)4CO2H. A white solid, it forms the gluconate anion in neutral aqueous solution. 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.

Chemical structure

The chemical structure of gluconic acid consists of a six-carbon chain, with five hydroxyl groups positioned in the same way as in the open-chained form of glucose, terminating in a carboxylic acid group. It is one of the 16 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 glucose oxidase. The conversion produces gluconolactone and hydrogen peroxide. The lactone spontaneously hydrolyzes to gluconic acid in water.[4]

Page Module:Chem2/styles.css has no content.C6H12O6 + O2 → C6H10O6 + H2O2
Page Module:Chem2/styles.css has no content.C6H10O6 + H2O → C6H12O7

Variations of glucose (or other carbohydrate-containing substrate) oxidation using fermentation.[5][6] or noble metal catalysis.[7][8]

Gluconic acid was first prepared by Hlasiwetz and Habermann in 1870[9] and involved the chemical oxidation of glucose. In 1880, Boutroux prepared and isolated gluconic acid using the glucose fermentation.[10]

Historical role in development of deep-tank fermentation

The production of gluconic acid by deep-tank fermentation (aerated, pH controlled, and stirred >1000 L tanks) of the filamentous fungi Aspergillus niger in 1929, for use as a food acidity regulator and cleaning agent, was the first successful use of deep-tank fermentation by Pfizer.[11] This expertise later led to Pfizer's successful use of deep-tank fermentation of Penicillium fungi in February 1944,[11] to rapidly scale up penicillin production, resulting in sufficient penicillin to treat the American and British battle casualties of the June 6th Allied D-Day invasion of World War II.[12]

Occurrence and uses

Gluconic acid occurs naturally in fruit, honey, and wine. As a food additive (E574[13]), it is now known as an acidity regulator.

The gluconate anion chelates Ca2+, Fe2+, Page Module:Chem2/styles.css has no content.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.[14]

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.[15][16] 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.[17]

Medicine

In medicine, gluconate is used most commonly as a biologically neutral carrier of Page Module:Chem2/styles.css has no content.Zn2+, Page Module:Chem2/styles.css has no content.Ca2+, Page Module:Chem2/styles.css has no content.Cu2+, Page Module:Chem2/styles.css has no content.Fe2+, and Page Module:Chem2/styles.css has no content.K+ to treat electrolyte imbalance.[18]

Calcium gluconate, in the form of a gel, is used to treat burns from hydrofluoric acid;[19][20] 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.[21] 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.[22]

See also

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."D-Gluconic acid". International Labour Organization.
  2. ^ Page Module:Citation/CS1/styles.css has no content."D-Gluconic acid". American Chemical Society.
  3. ^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Wong, Chun Ming; Wong, Kwun Hei; Chen, Xiao Dong (2008). "Glucose oxidase: Natural Occurrence, Function, Properties and Industrial Applications". Applied Microbiology and Biotechnology. 78 (6): 927–938. doi:10.1007/s00253-008-1407-4. PMID 18330562. S2CID 2246466.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Singh, Om V.; Kumar, Raj (2007). "Biotechnological production of gluconic acid: future implications". Applied Microbiology and Biotechnology. 75 (4): 713–722. doi:10.1007/s00253-007-0851-x. ISSN 1432-0614. PMID 17525864. S2CID 7700011.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Pal, Parimal; Kumar, Ramesh; Banerjee, Subhamay (2016). "Manufacture of gluconic acid: A review towards process intensification for green production". Chemical Engineering and Processing: Process Intensification. 104: 160–171. Bibcode:2016CEPPI.104..160P. doi:10.1016/j.cep.2016.03.009. ISSN 0255-2701.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Yan, Wenjuan; Zhang, Dongpei; Sun, Yu; Zhou, Ziqi; Du, Yihang; Du, Yiyao; Li, Yushan; Liu, Mengyuan; Zhang, Yuming; Shen, Jian; Jin, Xin (2020). "Structural sensitivity of heterogeneous catalysts for sustainable chemical synthesis of gluconic acid from glucose". Chinese Journal of Catalysis. 41 (9): 1320–1336. doi:10.1016/S1872-2067(20)63590-2. ISSN 1872-2067. S2CID 218970877.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Zhang, Qiaozhi; Wan, Zhonghao; Yu, Iris K. M.; Tsang, Daniel C. W. (2021). "Sustainable production of high-value gluconic acid and glucaric acid through oxidation of biomass-derived glucose: A critical review". Journal of Cleaner Production. 312 127745. Bibcode:2021JCPro.31227745Z. doi:10.1016/j.jclepro.2021.127745. hdl:10397/97377. ISSN 0959-6526. S2CID 236243315.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Hlasiwetz, H.; Habermann, J. (1870). "Zur Kenntniss einiger Zuckerarten. (Glucose, Rohrzucker, Levulose, Sorbin, Phloroglucin.)" [[Contribution] to our knowledge of some types of sugars: glucose, sucrose, fructose, sorbin, phloroglucinol]. Berichte der Deutschen Chemischen Gesellschaft (in Deutsch). 3 (1): 486–495. doi:10.1002/cber.187000301162. ISSN 1099-0682.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Boutroux, L. (1880). "Sur une fermentation nouvelle du glucose" [On a new fermentation [product] of glucose]. Comptes Rendus de l'Académie des Sciences (in français). 91: 236–238.
  11. ^ a b Page Module:Citation/CS1/styles.css has no content."Penicillin Production through Deep-tank Fermentation". American Chemical Society. 2008-06-12. Retrieved 2025-01-19.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Richards, Alfred N. (1948). ADVANCES IN MILITARY MEDICINE - Volume 1 (PDF) (1st ed.). Boston: Little, Brown and Company. p. 1ii. Retrieved 19 January 2025.
  13. ^ Current EU approved additives and their E Numbers. Food Standards Agency.
  14. ^ 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. Script error: No such module "CS1 identifiers".
  15. ^ Page Module:Citation/CS1/styles.css has no content.Ramachandran, V.S.; Lowery, M.S. (1992). "Conduction calorimetric investigation of the effect of retarders on the hydration of Portland cement". Thermochimica Acta. 195: 373–387. Bibcode:1992TcAc..195..373R. doi:10.1016/0040-6031(92)80081-7. ISSN 0040-6031.
  16. ^ Page Module:Citation/CS1/styles.css has no content.Ma, Suhua; Li, Weifeng; Zhang, Shenbiao; Ge, Dashun; Yu, Jin; Shen, Xiaodong (2015). "Influence of sodium gluconate on the performance and hydration of Portland cement". Construction and Building Materials. 91: 138–144. doi:10.1016/j.conbuildmat.2015.05.068. ISSN 0950-0618.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Lim, Han Yin; Dolzhenko, Anton V. (2021). "Gluconic acid aqueous solution: A bio-based catalytic medium for organic synthesis". Sustainable Chemistry and Pharmacy. 21 100443. Bibcode:2021SusCP..2100443L. doi:10.1016/j.scp.2021.100443. ISSN 2352-5541. S2CID 235547468.
  18. ^ Page Module:Citation/CS1/styles.css has no content.Mycielska, ME; Mohr, MTJ; Schmidt, K; Drexler, K; Rümmele, P; Haferkamp, S; Schlitt, HJ; Gaumann, A; Adamski, J; Geissler, EK (2019). "Potential Use of Gluconate in Cancer Therapy". Frontiers in Oncology. 9 522. doi:10.3389/fonc.2019.00522. PMC 6593216. PMID 31275855.
  19. ^ Page Module:Citation/CS1/styles.css has no content.el Saadi M. S.; Hall A. H.; Hall P. K.; Riggs B. S.; Augenstein W. L.; Rumack B. H. (1989). "Hydrofluoric acid dermal exposure". Vet Hum Toxicol. 31 (3): 243–7. PMID 2741315.
  20. ^ Page Module:Citation/CS1/styles.css has no content.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. PMID 17091088. S2CID 3691306.
  21. ^ 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 Script error: No such module "CS1 identifiers".
  22. ^ 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.

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