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{{chembox {{chembox
|Verifiedfields = changed
| verifiedrevid = 396142714
|Watchedfields = changed
| Reference = <ref>{{Merck13th|4469}}.</ref><ref>Beil. '''18''', V, 5, 11</ref>
|verifiedrevid = 461121308
| Name = <small>D</small>-Gluconic acid δ-lactone
|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>
| ImageFileL1 = Glucono-delta-lactone-2D-skeletal.png
|Name = <small>D</small>-Gluconic acid δ-lactone
| ImageSizeL1 = 120px
| ImageFileR1 = D-glucono-delta-lactone-3D-balls.png |ImageFileL1 = Glucono-delta-lactone-2D-skeletal.svg
|ImageFileR1 = D-glucono-delta-lactone-3D-balls.png
| ImageSizeR1 = 120px
|IUPACName = <small>D</small>-Glucono-1,5-lactone
| IUPACName = (3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2''H''-pyran-2-one
|SystematicName = (3''R'',4''S'',5''S'',6''R'')-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-one<ref name="PubChem"/>
| OtherNames=<small>D</small>-Glucono-1,5-lactone
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}} |UNII_Ref = {{fdacite|correct|FDA}}
|ChEMBL_Ref = {{ebicite|changed|EBI}}
| UNII = WQ29KQ9POT
|ChEMBL = 1200829
| 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
|UNII = WQ29KQ9POT
| InChIKey = PHOQVHQSTUBQQK-SQOUGZDYBO
|KEGG_Ref = {{keggcite|correct|kegg}}
| 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
|KEGG = D04332
| StdInChIKey = PHOQVHQSTUBQQK-SQOUGZDYSA-N
|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
| CASNo = 90-80-2
|InChIKey = PHOQVHQSTUBQQK-SQOUGZDYBO
| CASNo_Ref = {{cascite|correct|CAS}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| EC-number = 202-016-5
|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
| ChemSpiderID = 6760
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| PubChem = 736
|StdInChIKey = PHOQVHQSTUBQQK-SQOUGZDYSA-N
| SMILES = C(1(((C(=O)O1)O)O)O)O
|CASNo = 90-80-2
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|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(1(((C(=O)O1)O)O)O)O
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| Section2 = {{Chembox Properties
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| Density =
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| BoilingPt =
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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 ].
'''Glucono delta-lactone''' ('''GDL''') ] {{Citation needed|date=March 2010}} is a ]-occurring ] used as a ], an ]ifier, or a ], ], or ] {{Citation needed|date=March 2010}}. It is a ] (cyclic ]) of <small>D</small>-]. Pure GDL is a ] ]less ]line powder.


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:
GDL is commonly found in ], ] ]s, and ] {{Citation needed|date=March 2010}}. GDL is neutral, but hydrolyses in water to ] which is acidic, adding a tangy ] to ]s, though it has roughly a third of the ] of ]. It is metabolized to ]; one ] of GDL yields roughly the same amount of ] energy as one gram of ].
:{{chem2|C6H12O6 + O2 -> C6H10O6 + H2O2}}


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>
Upon addition to water, GDL is partially ] to ], with the balance between the lactone form and the acid form established as a ]. The rate of ] of GDL is increased by heat and high ].<ref>{{Cite journal | last1 = Pocker | first1 = Y. | last2 = Green | first2 = Edmond | title = Hydrolysis of <small>D</small>-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 | postscript = <!--None-->}}</ref>
:{{chem2|C6H10O6 + H2O -> C6H12O7}}


==Applications==
GDL may also be useful in controlling ]s by weakening their ].
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.
Termites use GNBP-2 to detect and degrade ]s on the surface of ]. GDL attaches to a crucial pocket on GNBP-2 adjacent to parts of the protein that aid in breaking down microbial ]s.<ref name="thesci_5573">{{cite web|title=Glucose yields sweet pest control - The Scientist|url=http://www.the-scientist.com/blog/display/55753/}} 100405 the-scientist.com</ref><ref name="pnas_12652">{{cite journal |doi=10.1073/pnas.0904063106 |last1=Bulmer |first1=MS |last2=Bachelet |first2=I |last3=Raman |first3=R |last4=Rosengaus |first4=RB |last5=Sasisekharan |first5=R |title=Targeting an antimicrobial effector function in insect immunity as a pest control strategy. |url=http://www.pnas.org/content/106/31/12652 |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=106 |issue=31 |pages=12652–7 |year=2009 | pmid = 19506247 |pmc=2722268 }}</ref>
<!-- I suspect this effect may apply to humans too -->


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 ].
== References ==

{{reflist}}
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>

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>

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>


== See also == == See also ==
*]
* ]

* ]
== References ==
* ]
{{reflist}}


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Latest revision as of 18:41, 15 September 2024

D-Gluconic acid δ-lactone
Names
IUPAC name D-Glucono-1,5-lactone
Systematic IUPAC name (3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.833 Edit this at Wikidata
EC Number
  • 202-016-5
E number E575 (acidity regulators, ...)
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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/s1Key: PHOQVHQSTUBQQK-SQOUGZDYSA-N
  • 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/s1Key: PHOQVHQSTUBQQK-SQOUGZDYBO
SMILES
  • C(1(((C(=O)O1)O)O)O)O
Properties
Chemical formula C6H10O6
Molar mass 178.140 g·mol
Melting point 150–153 °C (302–307 °F; 423–426 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Glucono-δ-lactone (GDL), also known as gluconolactone, is an organic compound with the formula (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:

C6H12O6 + O2 → C6H10O6 + H2O2

Gluconolactone spontaneously hydrolyzes to gluconic acid:

C6H10O6 + H2O → C6H12O7

Applications

Gluconolactone is a food additive with the E-number E575 used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent. It is a lactone of D-gluconic acid. Pure GDL is a white odorless crystalline powder.

GDL has been marketed for use in feta cheese. 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 sourness of citric acid. It is metabolized to 6-phospho-D-gluconate; one gram of GDL yields roughly the same amount of metabolic energy as one gram of sugar.

Upon addition to water, GDL is partially 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.

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.

It is also a complete inhibitor of the enzyme amygdalin beta-glucosidase at concentrations of 1 mM.

See also

References

  1. Budavari, Susan, ed. (2001). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.). Merck. ISBN 0911910131., 4469.
  2. ^ PubChem. "D-Gluconic acid, delta-lactone". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2022-02-25. Retrieved 2022-05-03.
  3. Beil. 18, V, 5, 11
  4. 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. "Current EU approved additives and their E Numbers". Food Standards Agency. Archived from the original on 22 April 2022.
  6. Martin, F.; Cayot, N.; Marin, A.; et al. (2009). "Effect of oxidoreduction potential and of gas bubbling on rheological properties and microstructure of acid skim milk gels acidified with glucono-δ-lactone" (PDF). Journal of Dairy Science. 92 (12): 5898–5906. doi:10.3168/jds.2009-2491. PMID 19923593. Archived (PDF) from the original on 2020-03-11. Retrieved 2019-08-16.
  7. Blythman, Joanna (21 February 2015). "Inside the food industry: the surprising truth about what you eat". The Guardian. Archived from the original on 13 August 2016. Retrieved 28 October 2016.{{cite web}}: CS1 maint: bot: original URL status unknown (link)
  8. Pocker, Y.; Green, Edmond (1973). "Hydrolysis of D-Glucono-δ-lactone. I. General Acid–Base Catalysis, Solvent Deuterium Isotope Effects, and Transition State Characterization". J. Am. Chem. Soc. 95 (1): 113–19. doi:10.1021/ja00782a019. PMID 4682891.
  9. Van Dijken, J. P.; Van Tuijl, A.; Luttik, M. A.; Middelhoven, W. J.; Pronk, J. T. (2002). "Novel pathway for alcoholic fermentation of delta-gluconolactone in the yeast Saccharomyces bulderi". Journal of Bacteriology. 184 (3): 672–678. doi:10.1128/JB.184.3.672-678.2002. PMC 139522. PMID 11790736.
  10. Petruccioli, M.; Brimer, L.; Cicalini, A. R.; Federici, F. (1999). "Production and Properties of the Linamarase and Amygdalase Activities of Penicillium aurantiogriseum P35". Bioscience, Biotechnology, and Biochemistry. 63 (5): 805–812. doi:10.1271/bbb.63.805. PMID 10380623.
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