| Revision as of 15:30, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 455561019 of page Glucono_delta-lactone for the Chem/Drugbox validation project (updated: 'ChEMBL'). |
Latest revision as of 18:41, 15 September 2024 edit SilverLocust (talk | contribs)Administrators24,823 edits cleanup from move |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Watchedfields = changed |
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| verifiedrevid = 396144453 |
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|verifiedrevid = 461121308 |
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| Reference = <ref>{{Merck13th|4469}}.</ref><ref>Beil. '''18''', V, 5, 11</ref> |
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|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> |
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| Name = <small>D</small>-Gluconic acid δ-lactone |
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|Name = <small>D</small>-Gluconic acid δ-lactone |
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| ImageFileL1 = Glucono-delta-lactone-2D-skeletal.png |
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|ImageFileL1 = Glucono-delta-lactone-2D-skeletal.svg |
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| ImageSizeL1 = 120px |
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| ImageFileR1 = D-glucono-delta-lactone-3D-balls.png |
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|ImageFileR1 = D-glucono-delta-lactone-3D-balls.png |
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|IUPACName = <small>D</small>-Glucono-1,5-lactone |
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| ImageSizeR1 = 120px |
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| IUPACName = (3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2''H''-pyran-2-one |
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|SystematicName = (3''R'',4''S'',5''S'',6''R'')-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-one<ref name="PubChem"/> |
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|Section1={{Chembox Identifiers |
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| OtherNames=<small>D</small>-Glucono-1,5-lactone |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| Section1 = {{Chembox Identifiers |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|ChEMBL_Ref = {{ebicite|changed|EBI}} |
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|ChEMBL = 1200829 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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|UNII = WQ29KQ9POT |
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| ChEMBL = <!-- blanked - oldvalue: 1200829 --> |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| UNII = WQ29KQ9POT |
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|KEGG = D04332 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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|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 |
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| KEGG = D04332 |
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|InChIKey = PHOQVHQSTUBQQK-SQOUGZDYBO |
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| 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 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = PHOQVHQSTUBQQK-SQOUGZDYBO |
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|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 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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|StdInChIKey = PHOQVHQSTUBQQK-SQOUGZDYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|CASNo = 90-80-2 |
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| StdInChIKey = PHOQVHQSTUBQQK-SQOUGZDYSA-N |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 90-80-2 |
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|EC_number = 202-016-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| EC-number = 202-016-5 |
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|ChemSpiderID = 6760 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|PubChem = 736 |
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| ChemSpiderID = 6760 |
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|DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| PubChem = 736 |
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|DrugBank = DB04564 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| DrugBank = DB04564 |
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|ChEBI = 16217 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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|SMILES = C(1(((C(=O)O1)O)O)O)O |
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| ChEBI = 16217 |
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| SMILES = C(1(((C(=O)O1)O)O)O)O |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6|H=10|O=6 |
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|C=6 |H=10 |O=6 |
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|MeltingPtC = 150-153 |
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}} |
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| Section3 = {{Chembox Hazards |
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'''Glucono-δ-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 ]. |
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It is typically produced by the aerobic oxidation of glucose in the presence of the enzyme ]. The conversion cogenerates ], which is often the key product of the enzyme: |
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:{{chem2|C6H12O6 + O2 -> C6H10O6 + H2O2}} |
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Gluconolactone spontaneously hydrolyzes to ]:<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> |
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:{{chem2|C6H10O6 + H2O -> C6H12O7}} |
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==Applications== |
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Gluconolactone is a ] with the ] 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=]}}</ref> used as a ], an ],<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 ], ], or ]. It is a ] of <small>D</small>-]. Pure GDL is a white odorless ]line powder. |
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GDL has been marketed for use in ].<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 ] of ]. It is metabolized to ]; one gram of GDL yields roughly the same amount of ] energy as one gram of ]. |
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Upon addition to water, GDL is partially ] to gluconic acid, with the balance between the lactone form and the acid form established as a ]. The rate of hydrolysis of GDL is increased by heat and high ].<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> |
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The yeast ''Maudiozyma 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> |
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It is also a complete inhibitor of the enzyme ] 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> |
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== See also == |
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*] |
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== References == |
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{{reflist}} |
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