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Glucono-δ-lactone

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D-Gluconic acid δ-lactone
Names
IUPAC name (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one
Other names D-Glucono-1,5-lactone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.833 Edit this at Wikidata
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
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 delta-lactone (GDL) is a naturally-occurring food additive with the E number E575 used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent. It is a lactone (cyclic ester) of D-gluconic acid. Pure GDL is a white odorless crystalline powder.

GDL is commonly found in honey, fruit juices, personal lubricants, and wine . GDL is 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 glucose; 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.

References

  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. 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.

See also

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