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Gluconolactone

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Gluconolactone is a widely used ingredient in cosmetics, personal care, and skincare formulations. Depending on its function, it may serve as a moisturizer, preservative, emulsifier, or active ingredient to enhance the overall effectiveness and performance of a product.

Gluconolactone (Wikipedia)

Glucono-δ-lactone (GDL), also known as gluconolactone, is an organic compound with the formula (HOCH)3(HOCH2CH)CO2. A colorless solid, it is an oxidized derivative of glucose.

D-Gluconic acid δ-lactone
Names
IUPAC name
D-Glucono-1,5-lactone
Systematic IUPAC name
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.833 Edit this at Wikidata
EC Number
  • 202-016-5
E number E575 (acidity regulators, ...)
KEGG
UNII
  • 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 checkY
    Key: PHOQVHQSTUBQQK-SQOUGZDYSA-N checkY
  • 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).
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It is typically produced by the aerobic oxidation of glucose in the presence of the enzyme glucose oxidase. The conversion cogenerates hydrogen peroxide, which is often the key product of the enzyme:

C6H12O6 + O2 → C6H10O6 + H2O2

Gluconolactone spontaneously hydrolyzes to gluconic acid:

C6H10O6 + H2O → C6H12O7
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