D-(+)-Glucono-1,5-lactone

Description

Glucono delta-lactone (C6H10O6), molecular weight 178.14, is an inner ester of gluconic acid. Commonly named gluconolactone, other synonyms include D-gluconic acid delta-lactone, D-glucono- 1, 5-lactone, and D-delta-gluconolactone. Some of its earliest uses as a food ingredient were as a flavoring (e.g., sherbets) and to reduce fat absorption in doughnuts and cones. Glucono deltalactone tastes sweet initially and has a slightly acid-aftertaste.

Chemical properties

Powder

The Uses of D-(+)-Glucono-1,5-lactone

Geogard(R)Ultra is a synergistic blend of gluconolactone and sodium benzoate. This blend provides broad spectrum protection against product spoilage in a variety of personal care formulations. Product Data Sheet

The Uses of D-(+)-Glucono-1,5-lactone

A lactone (cyclic ester) of D-gluconic acid used as a used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent.

The Uses of D-(+)-Glucono-1,5-lactone

D-glucono-1,5-lactone is the lactone derivative of D-gluconic acid. D-glucono-1,5-lactone is widely used as a food additive to achieve a curing, pickling or leavening effect.

The Uses of D-(+)-Glucono-1,5-lactone

a product of the oxidation of glucose by glucose oxidase

The Uses of D-(+)-Glucono-1,5-lactone

Component of many cleaning cmpds because of the sequestering ability of the gluconate radical which remains active in alk solutions; in the dairy industry to prevent milkstone; in breweries to prevent beerstone; as latent acid catalyst for acid colloid resins, particularly in textile printing; as a coagulant for tofu.

The Uses of D-(+)-Glucono-1,5-lactone

gluconolactone is used in cosmetics for its anti-acne properties. It can also help improve skin hydration given its water-binding ability. In addition, formulators may select gluconolactone for its action as a product stabilizer (chelating agent). Some studies indicate potential free-radical scavenging capacities as well. These properties would make it particularly relevant for use in making anti-aging, moisturizing, and possibly sun care products.

The Uses of D-(+)-Glucono-1,5-lactone

(GDL) An acidulant. It hydrolyzes to form gluconic acid in water solution and thereby creates the desired pH. The rate of acid formation is affected by temperature, concentration, and the pH of the solution. It has low acid release at room temperature and accelerated conversion into gluconic acid at high temperatures. It is readily soluble with a solubility of 59 g in 100 ml of water at 20°C. It functions as a leavening agent, acidulant, curing and pickling agent, and pH control agent. It is comparatively less tart/sour than other food acids. It is used in baked goods, fish products, desserts, and dressings.

Background

Gluconolactone is a naturally-occurring food additive used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent. It is a cyclic ester of D-gluconic acid. Pure gluconolactone is a white odorless crystalline powder.

Preparation

Glucono delta-lactone is prepared commercially by the oxidation of glucose with bromine water.

Definition

ChEBI: D-glucono-1,5-lactone is an aldono-1,5-lactone obtained from D-gluconic acid. It has a role as an animal metabolite and a mouse metabolite. It is a gluconolactone and an aldono-1,5-lactone. It is functionally related to a D-gluconic acid.

General Description

Gluconolactone is a non-toxic component of the skin. It has anti-oxidant and free radical scavenging effects. Gluconolactone has antiaging and skin-firming properties. It acts as a?β-glucosidase inhibitor. Gluconolactone stimulates cellulase gene expression.

Flammability and Explosibility

Non flammable

Biochem/physiol Actions

Glucono-d-lactone increased the doubling time and activated enzymes involved in the oxidative pentose phosphate pathway of Saccharomyces cerevisiae.

Safety Profile

Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Metabolism

Not Available

Purification Methods

Crystallise Dglucono-lactone from ethylene glycol monomethyl ether and dry for 1hour at 110o. It can be freed from other sugars via a column of Celite and charcoal (750g of each, 90 x 7.5cm) which is washed with 0.01N formic acid until the pH of the wash is equal to that of the entering acid. The lactone is applied in H2O and eluted with 0.01N formic acid (7L), then eluted with 7.5% EtOH/0.01N formic acid (8L), then 15% EtOH/0.01N formic acid (8L) which removes pentose and isomaltose (the optical rotation of the eluates are used for sugar detection) and finally elution with aqueous formic acid provides glucolactone which is obtained by evaporating or freeze drying. Its solubility in H2O is 60% and 1% in EtOH. A solution in H2O is slightly acidic, and the lactone dissolves in an equivalent of aqueous NaOH to form sodium D-gluconate [527-07-1] M 218.1, m 2002 0 6o(dec), [ ] D 25 +12o (c 10, H2O), pK2 5 3.6. [cf p 553, Smith & Whelan Biochemical Preparations 10 127 1963, Beilstein 3 IV 1255.]