Gluconic acid: Difference between revisions

{{distinguish|Glucuronic acid|Glutaconic acid}}

| Verifiedfields = changed

| verifiedrevid = 443836485

| Name = {{sm|d}}-Gluconic acid

| ImageFile = D-Gluconsäure Keilstrich.svg

| ImageSize =

| ImageName = Skeletal formula of gluconic acid

| ImageFile1 = D-gluconic-acid-3D-balls.png

| ImageSize1 =

| ImageName1 = Ball-and-stick model of gluconic acid

| IUPACName = {{sm|d}}-Gluconic acid

| SystematicName = (2''R'',3''S'',4''R'',5''R'')-2,3,4,5,6-Pentahydroxyhexanoic acid

| OtherNames = {{Unbulleted list|Dextronic acid}}

|Section1={{Chembox Identifiers

| 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

| PubChem = 10690

| ChEBI_Ref = {{ebicite|correct|EBI}}

| CASNo_Comment = (''D'')

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2 = 133-42-6

| CASNo2_Comment = (racemate) <!-- also verified at CAS Common Chemistry -->

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = R4R8J0Q44B

| UNII_Comment = (''D'')

| EC_number = 208-401-4

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|Section2={{Chembox Properties

| C=6 | H=12 | O=7

| Appearance = Colorless crystals

| Density =

| Solubility = 316 g/L<ref>{{Cite web|url=https://www.acs.org/content/acs/en/molecule-of-the-week/archive/g/d-gluconic-acid.html|title=D-Gluconic acid|website=American Chemical Society}}</ref>

| MeltingPtC = 131

| pKa = 3.86<ref>Bjerrum, J., et al. ''Stability Constants'', Chemical Society, London, 1958.</ref>

|Section3={{Chembox Structure

| CrystalStruct =

| Dipole =

|Section7={{Chembox Hazards

| ExternalSDS =

| MainHazards =

| FlashPt =

'''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 [[salt (chemistry)|salt]]s of gluconic acid are known as "gluconates". Gluconic acid, gluconate salts, and gluconate [[ester]]s 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 [[glucose#Open-chain form|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.<ref>{{cite journal |doi=10.1007/s00253-008-1407-4 |title=Glucose oxidase: Natural Occurrence, Function, Properties and Industrial Applications |date=2008 |last1=Wong |first1=Chun Ming |last2=Wong |first2=Kwun Hei |last3=Chen |first3=Xiao Dong |journal=Applied Microbiology and Biotechnology |volume=78 |issue=6 |pages=927–938 |pmid=18330562 |s2cid=2246466 }}</ref>

:{{chem2|C6H12O6 + O2 -> C6H10O6 + H2O2}}

:{{chem2|C6H10O6 + H2O -> C6H12O7}}

Variations of glucose (or other carbohydrate-containing substrate) oxidation using [[fermentation]].<ref>{{Cite journal|last1=Singh|first1=Om V.|last2=Kumar|first2=Raj|date=2007|title=Biotechnological production of gluconic acid: future implications|journal=Applied Microbiology and Biotechnology|language=en|volume=75|issue=4|pages=713–722|doi=10.1007/s00253-007-0851-x|pmid=17525864 |s2cid=7700011 |issn=1432-0614}}</ref><ref>{{Cite journal|last1=Pal|first1=Parimal|last2=Kumar|first2=Ramesh|last3=Banerjee|first3=Subhamay|date=2016|title=Manufacture of gluconic acid: A review towards process intensification for green production|url=https://www.sciencedirect.com/science/article/pii/S0255270116300666|journal=Chemical Engineering and Processing: Process Intensification|language=en|volume=104|pages=160–171|doi=10.1016/j.cep.2016.03.009|issn=0255-2701}}</ref> or [[noble metal]] catalysis.<ref>{{Cite journal|last1=Yan|first1=Wenjuan|last2=Zhang|first2=Dongpei|last3=Sun|first3=Yu|last4=Zhou|first4=Ziqi|last5=Du|first5=Yihang|last6=Du|first6=Yiyao|last7=Li|first7=Yushan|last8=Liu|first8=Mengyuan|last9=Zhang|first9=Yuming|last10=Shen|first10=Jian|last11=Jin|first11=Xin|date=2020|title=Structural sensitivity of heterogeneous catalysts for sustainable chemical synthesis of gluconic acid from glucose|journal=Chinese Journal of Catalysis|language=en|volume=41|issue=9|pages=1320–1336|doi=10.1016/S1872-2067(20)63590-2|s2cid=218970877 |issn=1872-2067|doi-access=free}}</ref><ref>{{Cite journal|last1=Zhang|first1=Qiaozhi|last2=Wan|first2=Zhonghao|last3=Yu|first3=Iris K. M.|last4=Tsang|first4=Daniel C. W.|date=2021|title=Sustainable production of high-value gluconic acid and glucaric acid through oxidation of biomass-derived glucose: A critical review|url=https://www.sciencedirect.com/science/article/pii/S0959652621019636|journal=Journal of Cleaner Production|language=en|volume=312|page=127745|doi=10.1016/j.jclepro.2021.127745|hdl=10397/97377 |s2cid=236243315 |issn=0959-6526|hdl-access=free}}</ref>

Gluconic acid was first prepared by Hlasiwetz and Habermann in 1870<ref>{{Cite journal|last1=Hlasiwetz|first1=H.|last2=Habermann|first2=J.|date=1870|title=Zur Kenntniss einiger Zuckerarten. (Glucose, Rohrzucker, Levulose, Sorbin, Phloroglucin.)|trans-title= [Contribution] to our knowledge of some types of sugars: glucose, sucrose, fructose, sorbin, phloroglucinol |url=https://babel.hathitrust.org/cgi/pt?id=uiug.30112025693463&seq=494 |journal=Berichte der Deutschen Chemischen Gesellschaft |language=de|volume=3|issue=1|pages=486–495|doi=10.1002/cber.187000301162|issn=1099-0682}}</ref> and involved the chemical oxidation of glucose. In 1880, Boutroux prepared and isolated gluconic acid using the glucose fermentation.<ref>{{Cite journal|last=Boutroux |first=L. |date=1880 |title=Sur une fermentation nouvelle du glucose |trans-title=On a new fermentation [product] of glucose |journal=Comptes Rendus de l'Académie des Sciences |volume=91 |pages=236–238 |language=fr |url=https://babel.hathitrust.org/cgi/pt?id=nyp.33433009682679&seq=244 }}</ref>

Gluconic acid occurs naturally in [[fruit]], [[honey]], and [[wine]]. As a [[food additive]] (E574<ref>[http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist ''Current EU approved additives and their E Numbers'']. Food Standards Agency.</ref>), it is now known as an [[acidity regulator]].

The gluconate anion [[chelating agent|chelates]] [[calcium|Ca²⁺]], [[iron|Fe²⁺]], [[Potassium|{{chem2|K+}}]], [[aluminium|Al³⁺]], and other metals, including [[lanthanide]]s and [[actinide]]s. It is also used in [[cleaning agent|cleaning products]], where it dissolves mineral deposits, especially in alkaline solution.

[[Zinc gluconate]] injections are used to [[neutering|neuter]] male dogs.<ref>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}}</ref>

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.<ref name="RamachandranLowery1992">{{cite journal|last1=Ramachandran|first1=V.S.|last2=Lowery|first2=M.S.|title=Conduction calorimetric investigation of the effect of retarders on the hydration of Portland cement|journal=Thermochimica Acta|volume=195|year=1992|pages=373–387|issn=0040-6031|doi=10.1016/0040-6031(92)80081-7}}</ref><ref name="MaLi2015">{{cite journal|last1=Ma|first1=Suhua|last2=Li|first2=Weifeng|last3=Zhang|first3=Shenbiao|last4=Ge|first4=Dashun|last5=Yu|first5=Jin|last6=Shen|first6=Xiaodong|title=Influence of sodium gluconate on the performance and hydration of Portland cement|journal=Construction and Building Materials|volume=91|year=2015|pages=138–144|issn=0950-0618|doi=10.1016/j.conbuildmat.2015.05.068}}</ref> 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]].<ref>{{Cite journal|last1=Lim|first1=Han Yin|last2=Dolzhenko|first2=Anton V.|date=2021|title=Gluconic acid aqueous solution: A bio-based catalytic medium for organic synthesis|url=https://www.sciencedirect.com/science/article/pii/S235255412100070X|journal=Sustainable Chemistry and Pharmacy|language=en|volume=21|page=100443|doi=10.1016/j.scp.2021.100443|s2cid=235547468 |issn=2352-5541}}</ref>

===Medicine===

In medicine, gluconate is used most commonly as a biologically neutral carrier of {{chem2|Zn(2+)}}, {{chem2|Ca(2+)}}, {{chem2|Cu(2+)}}, {{chem2|Fe(2+)}}, and {{chem2|K+}} to treat [[electrolyte imbalance]].<ref>{{cite journal |last1=Mycielska |first1=ME |last2=Mohr |first2=MTJ |last3=Schmidt |first3=K |last4=Drexler |first4=K |last5=Rümmele |first5=P |last6=Haferkamp |first6=S |last7=Schlitt |first7=HJ |last8=Gaumann |first8=A |last9=Adamski |first9=J |last10=Geissler |first10=EK |title=Potential Use of Gluconate in Cancer Therapy. |journal=Frontiers in Oncology |date=2019 |volume=9 |page=522 |doi=10.3389/fonc.2019.00522 |pmid=31275855|pmc=6593216 |doi-access=free }}</ref>

[[Calcium gluconate]], in the form of a gel, is used to treat burns from [[hydrofluoric acid]];<ref name="pmid2741315">{{cite journal |author=el Saadi M. S. |author2=Hall A. H. |author3=Hall P. K. |author4=Riggs B. S. |author5=Augenstein W. L. |author6=Rumack B. H. |title=Hydrofluoric acid dermal exposure |journal=Vet Hum Toxicol |volume=31 |issue=3 |pages=243–7 |year=1989 |pmid=2741315}}</ref><ref name="pmid17091088">{{cite journal |author=Roblin I. |author2=Urban M. |author3=Flicoteau D. |author4=Martin C. |author5=Pradeau D. |title=Topical treatment of experimental hydrofluoric acid skin burns by 2.5% calcium gluconate |journal=J Burn Care Res |volume=27 |issue=6 |pages=889–94 |year=2006 |pmid=17091088 |doi=10.1097/01.BCR.0000245767.54278.09|s2cid=3691306 }}</ref> 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 "[[Plasma-lyte|plasmalyte a]]", used for intravenous fluid resuscitation.<ref>

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}}</ref> [[Quinine]] gluconate is a salt of gluconic acid and quinine, which is used for [[intramuscular injection]] in the treatment of [[malaria]].

[[Iron(II) gluconate|Ferrous gluconate]] injections have been proposed in the past to treat [[anemia]].<ref>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.</ref>

== See also ==

* [[Uronic acid]]

* [[Glucuronic acid]]

* [[Isosaccharinic acid]] (ISA)

== References ==

== External links ==

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[[Category:Gluconates| ]]

[[Category:Acids in wine]]

[[Category:Alpha hydroxy acids]]

[[Category:Concrete admixtures]]

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[[Category:Food additives]]

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[[Category:Vicinal diols]]

[[Category:Substances discovered in the 19th century]]