Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Glucono delta-lactone: Difference between pages

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 461121308

|Reference = <ref>{{Merck13th|4469}}.</ref><ref name="PubChem">{{Cite web|last=PubChem|title=D-Gluconic acid, delta-lactone|url=https://pubchem.ncbi.nlm.nih.gov/compound/736|access-date=2022-05-03|website=pubchem.ncbi.nlm.nih.gov|language=en|archive-date=2022-02-25|archive-url=https://web.archive.org/web/20220225070041/https://pubchem.ncbi.nlm.nih.gov/compound/736|url-status=live}}</ref><ref>Beil. '''18''', V, 5, 11</ref>

|Name = <small>D</small>-Gluconic acid δ-lactone

|ImageFileL1 = Glucono-delta-lactone-2D-skeletal.svg

|ImageFileR1 = D-glucono-delta-lactone-3D-balls.png

|IUPACName = <small>D</small>-Glucono-1,5-lactone

|SystematicName = (3''R'',4''S'',5''S'',6''R'')-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-one<ref name="PubChem"/>

|Section1={{Chembox Identifiers

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

|ChEMBL_Ref = {{ebicite|changed|EBI}}

|ChEMBL = 1200829

|UNII = WQ29KQ9POT

|KEGG_Ref = {{keggcite|correct|kegg}}

|KEGG = D04332

|InChI = 1/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1

|InChIKey = PHOQVHQSTUBQQK-SQOUGZDYBO

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = PHOQVHQSTUBQQK-SQOUGZDYSA-N

|CASNo = 90-80-2

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

|EC_number = 202-016-5

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

|ChemSpiderID = 6760

|PubChem = 736

|DrugBank_Ref = {{drugbankcite|correct|drugbank}}

|DrugBank = DB04564

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

|ChEBI = 16217

|SMILES = C([C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)O)O)O)O

|Section2={{Chembox Properties

|C=6 |H=10 |O=6

|MeltingPtC = 150-153

}}

'''Glucono-delta-lactone''' ('''GDL'''), also known as gluconolactone, is an organic compound with the formula {{chem2|(HOCH)3(HOCH2CH)CO2}}. A colorless solid, it is an oxidized derivative of glucose.

It is typically produced by the aerobic oxidation of glucose in the presence of the enzyme [[glucose oxidase]]. The conversion cogenerates [[hydrogen peroxide]], which is often the key product of the enzyme:

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

Gluconolactone spontaneously hydrolyzes to [[gluconic acid]]:<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|C6H10O6 + H2O -> C6H12O7}}

==Applications==

Gluconolactone is a [[food additive]] with the [[E number|E-number]] E575<ref>{{cite web|url=https://www.food.gov.uk/business-guidance/approved-additives-and-e-numbers#:~:text=E575,lactone|title=Current EU approved additives and their E Numbers|archive-url=https://web.archive.org/web/20220422201759/https://www.food.gov.uk/business-guidance/approved-additives-and-e-numbers|archive-date=22 April 2022|publisher=[[Food Standards Agency]]}}</ref> used as a [[sequestrant]], an [[acidifier]],<ref>{{Cite journal |last1= Martin |first1= F. |last2= Cayot |first2= N. |last3= Marin |first3= A. |last4= Journaux |first4= L. |last5= Cayot |first5= P. |last6= Gervais |first6= P. |last7= Cachon |first7= R. |display-authors= 3 |doi= 10.3168/jds.2009-2491 |title= Effect of oxidoreduction potential and of gas bubbling on rheological properties and microstructure of acid skim milk gels acidified with glucono-δ-lactone |journal= Journal of Dairy Science |volume= 92 |issue= 12 |pages= 5898–5906 |year= 2009 |pmid= 19923593 |url= https://hal.archives-ouvertes.fr/hal-01191294/file/publi_2559_%7B40AD2DFA-2D5E-4727-A4C1-201FC5A3210E%7D.pdf |doi-access= free |access-date= 2019-08-16 |archive-date= 2020-03-11 |archive-url= https://web.archive.org/web/20200311074809/https://hal.archives-ouvertes.fr/hal-01191294/file/publi_2559_%7B40AD2DFA-2D5E-4727-A4C1-201FC5A3210E%7D.pdf |url-status= live }}</ref> or a [[Curing (food preservation)|curing]], [[pickling]], or [[leavening agent]]. It is a [[lactone]] of <small>D</small>-[[gluconic acid]]. Pure GDL is a white odorless [[crystal]]line powder.

GDL has been marketed for use in [[feta cheese]].<ref>{{cite web|url=https://www.theguardian.com/lifeandstyle/2015/feb/21/a-feast-of-engineering-whats-really-in-your-food |title=Inside the food industry: the surprising truth about what you eat |last=Blythman |first=Joanna |date=21 February 2015 |work=The Guardian |language=en |access-date=28 October 2016 |url-status=bot: unknown |archive-url=https://web.archive.org/web/20160813231549/https://www.theguardian.com/lifeandstyle/2015/feb/21/a-feast-of-engineering-whats-really-in-your-food |archive-date=13 August 2016}}</ref> GDL is pH-neutral, but hydrolyses in water to gluconic acid which is acidic, adding a tangy taste to foods, though it has roughly a third of the [[Taste#Sourness|sourness]] of [[citric acid]]. It is metabolized to [[6-phospho-D-gluconate]]; one gram of GDL yields roughly the same amount of [[metabolism|metabolic]] energy as one gram of [[sugar]].

Upon addition to water, GDL is partially [[hydrolysis|hydrolysed]] to gluconic acid, with the balance between the lactone form and the acid form established as a [[chemical equilibrium]]. The rate of hydrolysis of GDL is increased by heat and high [[pH]].<ref>{{Cite journal |last1= Pocker |first1= Y. |last2= Green |first2= Edmond |title= Hydrolysis of D-Glucono-δ-lactone. I. General Acid–Base Catalysis, Solvent Deuterium Isotope Effects, and Transition State Characterization |journal= J. Am. Chem. Soc. |volume= 95 |issue= 1 |pages= 113–19 |year= 1973 |pmid= 4682891 |doi= 10.1021/ja00782a019}}</ref>

The yeast ''[[Saccharomyces]] bulderi'' can be used to ferment gluconolactone to ethanol and carbon dioxide. The pH value greatly affects culture growth. Gluconolactone at 1 or 2% in a mineral media solution causes the pH to drop below 3.<ref>{{Cite journal |last1= Van Dijken |first1= J. P. |last2= Van Tuijl |first2= A. |last3= Luttik |first3= M. A. |last4= Middelhoven |first4= W. J. |last5= Pronk |first5= J. T.|title= Novel pathway for alcoholic fermentation of delta-gluconolactone in the yeast Saccharomyces bulderi |journal= Journal of Bacteriology |volume= 184 |issue= 3 |pages= 672–678 |year= 2002 |pmid= 11790736 |pmc= 139522 |doi= 10.1128/JB.184.3.672-678.2002}}</ref>

It is also a complete inhibitor of the enzyme [[amygdalin beta-glucosidase]] at concentrations of 1 mM.<ref>{{Cite journal |last1= Petruccioli |first1= M. |last2= Brimer |first2= L. |last3= Cicalini |first3= A. R. |last4= Federici |first4= F.|title= Production and Properties of the Linamarase and Amygdalase Activities of Penicillium aurantiogriseum P35 |journal= Bioscience, Biotechnology, and Biochemistry |volume= 63|issue= 5 |pages= 805–812 |year= 1999 |pmid= 10380623 |doi= 10.1271/bbb.63.805|doi-access= free }}</ref>

== See also ==

*[[Glucuronolactone]]

== References ==

{{reflist}}

[[Category:Food acidity regulators]]

[[Category:Curing agents]]

[[Category:Delta-lactones]]

[[Category:Pickling agents]]

[[Category:Leavening agents]]

[[Category:Sequestrants]]

[[Category:Garde manger]]

[[Category:Tetrahydropyrans]]

[[Category:E-number additives]]