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Wikipedia

Gluconic acid

February 16, 2024

Not to be confused with Glucuronic acid or Glutaconic acid.

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.

d-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
  • 526-95-4 (D) Y
  • 133-42-6 (racemate) Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:33198 Y
ChEMBL
  • ChEMBL464345 Y
ChemSpider
  • 10240 Y
ECHA InfoCard 100.007.639
EC Number
  • 208-401-4
E number E574 (acidity regulators, ...)
  • 10690
UNII
  • R4R8J0Q44B (D) Y
  • DTXSID8027169
  • 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 Y
    Key: RGHNJXZEOKUKBD-SQOUGZDYSA-N Y
  • 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 YN ?)

Chemical structure edit

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 edit

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.[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 edit

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 edit

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 edit

References edit

  1. ^ "D-Gluconic acid". American Chemical Society.
  2. ^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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. doi:10.1016/j.cep.2016.03.009. ISSN 0255-2701.
  6. ^ 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.
  7. ^ 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. doi:10.1016/j.jclepro.2021.127745. hdl:10397/97377. ISSN 0959-6526. S2CID 236243315.
  8. ^ 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 German). 3 (1): 486–495. doi:10.1002/cber.187000301162. 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. ^ 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
  12. ^ 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. doi:10.1016/0040-6031(92)80081-7. ISSN 0040-6031.
  13. ^ 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.
  14. ^ 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. doi:10.1016/j.scp.2021.100443. ISSN 2352-5541. S2CID 235547468.
  15. ^ 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.
  16. ^ 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.
  17. ^ 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.
  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 edit

  • Gluconic acid on NIST.gov
  • ChemSub Online: D-Gluconic acid.

February 16, 2024
gluconic, acid, confused, with, glucuronic, acid, glutaconic, acid, organic, compound, with, molecular, formula, c6h12o7, condensed, structural, formula, hoch2, choh, 4co2h, white, solid, forms, gluconate, anion, neutral, aqueous, solution, salts, gluconic, ac. Not to be confused with Glucuronic acid or Glutaconic acid 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 d Gluconic acid NamesIUPAC name d Gluconic acidSystematic IUPAC name 2R 3S 4R 5R 2 3 4 5 6 Pentahydroxyhexanoic acidOther names Dextronic acidIdentifiersCAS Number 526 95 4 D Y133 42 6 racemate Y3D model JSmol Interactive imageChEBI CHEBI 33198 YChEMBL ChEMBL464345 YChemSpider 10240 YECHA InfoCard 100 007 639EC Number 208 401 4E number E574 acidity regulators PubChem CID 10690UNII R4R8J0Q44B D YCompTox Dashboard EPA DTXSID8027169InChI 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 YKey RGHNJXZEOKUKBD SQOUGZDYSA N YInChI 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 s1Key RGHNJXZEOKUKBD SQOUGZDYBYSMILES O C O C H O C H O C H O C H O COPropertiesChemical formula C 6H 12O 7Molar mass 196 155 g mol 1Appearance Colorless crystalsMelting point 131 C 268 F 404 K Solubility in water 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 Y N Infobox references Contents 1 Chemical structure 2 Production 3 Occurrence and uses 3 1 Medicine 4 See also 5 References 6 External linksChemical structure editThe 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 editGluconic 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 3 C6H12O6 O2 C6H10O6 H2O2 C6H10O6 H2O C6H12O7Variations 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 editGluconic 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 edit 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 editUronic acid Glucuronic acid Isosaccharinic acid ISA References edit D Gluconic acid American Chemical Society Bjerrum J et al Stability Constants Chemical Society London 1958 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 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 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 doi 10 1016 j cep 2016 03 009 ISSN 0255 2701 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 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 doi 10 1016 j jclepro 2021 127745 hdl 10397 97377 ISSN 0959 6526 S2CID 236243315 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 German 3 1 486 495 doi 10 1002 cber 187000301162 ISSN 1099 0682 Boutroux L 1880 Sur une fermentation nouvelle du glucose On a new fermentation product of glucose Comptes Rendus de l Academie des Sciences in French 91 236 238 Current EU approved additives and their E Numbers Food Standards Agency 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 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 doi 10 1016 0040 6031 92 80081 7 ISSN 0040 6031 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 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 doi 10 1016 j scp 2021 100443 ISSN 2352 5541 S2CID 235547468 Mycielska ME Mohr MTJ Schmidt K Drexler K Rummele 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 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 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 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 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 editGluconic acid on NIST gov ChemSub Online D Gluconic acid Retrieved from https en wikipedia org w index php title Gluconic acid amp oldid 1207032419, wikipedia, wiki, book, books, library,

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