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Glucono delta-lactone

Glucono-delta-lactone (GDL), also known as gluconolactone, is a food additive with the E-number E575[4] used as a sequestrant, an acidifier,[5] or a curing, pickling, or leavening agent. It is a lactone of D-gluconic acid. Pure GDL is a white odorless crystalline powder.

D-Gluconic acid δ-lactone[1][2][3]
Names
IUPAC name
D-Glucono-1,5-lactone
Systematic IUPAC name
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-one[2]
Identifiers
  • 90-80-2 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16217 Y
ChEMBL
  • ChEMBL1200829 N
ChemSpider
  • 6760 Y
DrugBank
  • DB04564 Y
ECHA InfoCard 100.001.833
EC Number
  • 202-016-5
E number E575 (acidity regulators, ...)
KEGG
  • D04332 Y
  • 736
UNII
  • WQ29KQ9POT Y
  • DTXSID0026549
  • 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/s1 Y
    Key: PHOQVHQSTUBQQK-SQOUGZDYSA-N Y
  • 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
    Key: PHOQVHQSTUBQQK-SQOUGZDYBO
  • C([C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)O)O)O)O
Properties
C6H10O6
Molar mass 178.140 g·mol−1
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 [77 °F], 100 kPa).
N verify (what is YN ?)

GDL has been marketed for use in feta cheese.[6] 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.[7]

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.[8]

It is also a complete inhibitor of the enzyme amygdalin beta-glucosidase at concentrations of 1 mM.[9]

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. ^ a b PubChem. "D-Gluconic acid, delta-lactone". pubchem.ncbi.nlm.nih.gov. from the original on 2022-02-25. Retrieved 2022-05-03.
  3. ^ Beil. 18, V, 5, 11
  4. ^ . Food Standards Agency. Archived from the original on 22 April 2022.
  5. ^ 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. (PDF) from the original on 2020-03-11. Retrieved 2019-08-16.
  6. ^ Blythman, Joanna (21 February 2015). . The Guardian. Archived from the original on 13 August 2016. Retrieved 28 October 2016.{{cite web}}: CS1 maint: bot: original URL status unknown (link)
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.

glucono, delta, lactone, glucono, delta, lactone, also, known, gluconolactone, food, additive, with, number, e575, used, sequestrant, acidifier, curing, pickling, leavening, agent, lactone, gluconic, acid, pure, white, odorless, crystalline, powder, gluconic, . Glucono delta lactone GDL also known as gluconolactone is a food additive with the E number E575 4 used as a sequestrant an acidifier 5 or a curing pickling or leavening agent It is a lactone of D gluconic acid Pure GDL is a white odorless crystalline powder D Gluconic acid d lactone 1 2 3 NamesIUPAC name D Glucono 1 5 lactoneSystematic IUPAC name 3R 4S 5S 6R 3 4 5 Trihydroxy 6 hydroxymethyl oxan 2 one 2 IdentifiersCAS Number 90 80 2 Y3D model JSmol Interactive imageChEBI CHEBI 16217 YChEMBL ChEMBL1200829 NChemSpider 6760 YDrugBank DB04564 YECHA InfoCard 100 001 833EC Number 202 016 5E number E575 acidity regulators KEGG D04332 YPubChem CID 736UNII WQ29KQ9POT YCompTox Dashboard EPA DTXSID0026549InChI 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 s1 YKey PHOQVHQSTUBQQK SQOUGZDYSA N YInChI 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 SQOUGZDYBOSMILES C C H 1 C H C H C H C O O1 O O O OPropertiesChemical formula C 6H 10O 6Molar mass 178 140 g mol 1Melting 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 77 F 100 kPa N verify what is Y N Infobox references GDL has been marketed for use in feta cheese 6 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 7 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 8 It is also a complete inhibitor of the enzyme amygdalin beta glucosidase at concentrations of 1 mM 9 See also EditGlucuronolactoneReferences Edit Budavari Susan ed 2001 The Merck Index An Encyclopedia of Chemicals Drugs and Biologicals 13th ed Merck ISBN 0911910131 4469 a b PubChem D Gluconic acid delta lactone pubchem ncbi nlm nih gov Archived from the original on 2022 02 25 Retrieved 2022 05 03 Beil 18 V 5 11 Current EU approved additives and their E Numbers Food Standards Agency Archived from the original on 22 April 2022 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 d 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 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 a href Template Cite web html title Template Cite web cite web a CS1 maint bot original URL status unknown link Pocker Y Green Edmond 1973 Hydrolysis of D Glucono d 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 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 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 Retrieved from https en wikipedia org w index php title Glucono delta lactone amp oldid 1170205976, wikipedia, wiki, book, books, library,

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