Glucono delta-lactone

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

90-80-2^Y

3D model (Jmol)

Interactive image

ChEBI

CHEBI:16217^Y

ChemSpider

6760^Y

DrugBank

DB04564^Y

202-016-5

E575 (acidity regulators, ...)

KEGG

D04332^Y

PubChem CID

UNII

WQ29KQ9POT^Y

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^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

SMILES

C([C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)O)O)O)O

Properties

Chemical formula

C₆H₁₀O₆

Molar mass

178.14 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).

(what is ^YN ?)

Infobox references

Glucono delta-lactone (GDL), also known as 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 is commonly found in honey, fruit juices, personal lubricants, wine, and has been marketed for use in feta cheese. 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 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 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.

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