Glucono-δ-lactone

d-Gluconic acid δ-lactone^[1]^[2]
Names
	IUPAC name d-Glucono-1,5-lactone
	Systematic IUPAC name (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one
Identifiers
CAS Number	90-80-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16217 ;
ChEMBL	ChEMBL1200829 ;
ChemSpider	6760 ;
DrugBank	DB04564 ;
ECHA InfoCard	100.001.833
EC Number	202-016-5;
E number	E575 (acidity regulators, ...)
KEGG	D04332 ;
PubChem CID	736;
UNII	WQ29KQ9POT ;
CompTox Dashboard (EPA)	DTXSID0026549 ;
	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/s1 Key: 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 Key: PHOQVHQSTUBQQK-SQOUGZDYBO;
	SMILES C([C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)O)O)O)O;
Properties
Chemical formula	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). verify (what is ?) Infobox references

Glucono-delta-lactone (GDL), also known as gluconolactone, is a food additive with the E-number E575^[3] used as a sequestrant, an acidifier,^[4] 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.^[5] 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.^[6]

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.^[7]

It is also a complete inhibitor of the enzyme amygdalin beta-glucosidase at concentrations of 1 mM.^[8]

References

^ Budavari, Susan, ed. (2001), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.), Merck, ISBN 0911910131, 4469.
^ Beil. 18, V, 5, 11
^ Current EU approved additives and their E Numbers, Food Standards Agency
^ 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.
^ 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)
^ 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.
^ Van Dijken, J. P.; Van Tuijl, A.; Luttik, M. A.; et al. (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.; et al. (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.

[1] Budavari, Susan, ed. (2001), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.), Merck, ISBN 0911910131, 4469.

[2] Beil. 18, V, 5, 11

[3] Current EU approved additives and their E Numbers, Food Standards Agency

[4] 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.

[guardian-2015-02-21-5] 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)

[6] 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.

[7] Van Dijken, J. P.; Van Tuijl, A.; Luttik, M. A.; et al. (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.

[8] Petruccioli, M.; Brimer, L.; Cicalini, A. R.; et al. (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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See also

References