Common NameD-glucono-1,5-lactone
DescriptionGluconolactone, also known as glucono-delta-lactone or GDL (gluconate), belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids (PHAs) containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone is a lactone of D-gluconic acid. Gluconolactone can be produced by enzymatic oxidation of D-glucose via the enzyme glucose oxidase. It is a fundamental metabolite found in all organisms ranging from bacteria to plants to animals. Gluconolactone has metal chelating, moisturizing and antioxidant activities. Its ability in free radicals scavenging accounts for its antioxidant properties. Gluconolactone, is also used as a food additive with the E-number E575. In foods it is used as a sequestrant, an acidifier or a curing, pickling, or leavening agent. Gluconolactone is also used as a coagulant in tofu processing. Gluconolactone is widely used as a skin exfoliant in cosmetic products, where it is noted for its mild exfoliating and hydrating properties. Pure gluconolactone is a white odorless crystalline powder. It is pH-neutral, but hydrolyses in water to gluconic acid which is acidic, adding a tangy taste to foods. Gluconic acid has roughly a third of the sourness of citric acid. One gram of gluconolactone yields roughly the same amount of metabolic energy as one gram of sugar.
Structure
Molecular FormulaC6H10O6
Average Mass178.14000
Monoisotopic Mass178.04774
IUPAC Name(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
Traditional NameGluconolactone
CAS Registry Number90-80-2
SMILESO=C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI IdentifierInChI=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
InChI KeyPHOQVHQSTUBQQK-SQOUGZDYSA-N
CHEBI IDCHEBI:16217
HMDB IDHMDB0000150
Pathways
NameSMPDB/PathBank
pentose phosphate pathway
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
StateNot Available
Water Solubility5.86e+02 g/l
logP-2.16
logS0.52
pKa (Strongest Acidic)11.62
pKa (Strongest Basic)-2.99
Hydrogen Acceptor Count5
Hydrogen Donor Count4
Polar Surface Area107.22 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity34.78 m³·mol⁻¹
Polarizability15.42

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