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Glucono Delta-Lakton (GDL), also known as gluconolactone, is an organic compound with the formula (HOCH)3(HOCH2CH)CO2.
A colorless solid, Glucono Delta-Lakton (GDL) is an oxidized derivative of glucose.
Glucono Delta-Lakton (GDL) is typically produced by the aerobic oxidation of glucose in the presence of the enzyme glucose oxidase.
CAS: 90-80-2
MF: C6H10O6
MW: 178.14
EINECS: 202-016-5
Synonyms
Gluconolactone - CAS 90-80-2 - Calbiochem;Glucono Delta Lactone, Glucono Delta Lactone powder;Cagliflozin Impurity 8;delta-Gluconolactone in stock GMP Factory;1,2,3,4,5-PENTAHYDROXYCAPROIC ACID DELTA-LACTONE;DELTA-GLUCURONOLACTONE;DELTA-GLUCONOLACTONE;D(+)-DEXTRONIC ACID DELTA-LACTONE
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
Glucono Delta-Lakton (GDL) is a lactone of the D-gluconate.
Glucono Delta-Lakton (GDL) is a natural constituent of many foods.
Glucono Delta-Lakton (GDL) can be found in honey, fruit juices, wine and many-fermented products1-3.
Glucono Delta-Lakton (GDL) is used as a food additive with the E number E575 used as a sequestrant, an acidifier (it lower the pH and also help preserve the food from deterioration by enzymes and organisms), or a curing, pickling, or leavening agent.
Glucono Delta-Lakton (GDL) has been marketed for use in feta cheese.
Glucono Delta-Lakton (GDL) is neutral, but hydrolyses in water to gluconic acid that is acidic, adding a tangy taste to foods, though it has roughly a third of the sourness of citric acid.
Glucono Delta-Lakton (GDL) can be used as nutritional supplement in beverage such as in Instant Drinks, Syrups, RTD Tea and Coffee, Sports and Energy Drinks, Waters.
Glucono Delta-Lakton (GDL), molecular weight 178.14, is an inner ester of gluconic acid.
Commonly named Glucono Delta-Lakton (GDL), 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 Delta-Lakton (GDL) tastes sweet initially and has a slightly acid-aftertaste.
Glucono Delta-Lakton (GDL) is an aldono-1,5-lactone obtained from D-gluconic acid.
Glucono Delta-Lakton (GDL) has a role as an animal metabolite and a mouse metabolite.
Glucono Delta-Lakton (GDL) is a gluconolactone and an aldono-1,5-lactone.
Glucono Delta-Lakton (GDL) is functionally related to a D-gluconic acid.
Glucono Delta-Lakton (GDL) is a non-toxic component of the skin.
Glucono Delta-Lakton (GDL) has anti-oxidant and free radical scavenging effects.
Glucono Delta-Lakton (GDL) has antiaging and skin-firming properties.
Glucono Delta-Lakton (GDL) acts as a?β-glucosidase inhibitor.
Glucono Delta-Lakton (GDL) stimulates cellulase gene expression.
Glucono Delta-Lakton (GDL) is the inner lactone of the gluconic acid formed during the production process by crystallization of gluconic acid at elevated temperatures and removal of excess water.
When Glucono Delta-Lakton (GDL) is added into an aqueous medium, the lactonisation is reversed and the gluconic acid is released.
Glucono Delta-Lakton (GDL) is a natural poly-hydroxy acied (PHA) that can be used as an active ingredient in exfoliation products.
PHAs principally have less side effects and are therefore a gentle alternative to alpha-hydroxy acids (AHA).
Moreover Glucono Delta-Lakton (GDL), like sodium gluconate, has chelating and moisturizing properties.
Glucono Delta-Lakton (GDL) or gluconolactone, an inner ester of gluconic acid, is a naturally occurring ingredient commonly used as a coagulant in tofu making, a leavening acid in bakery, a mild acidulant in cheese and meat products, and a sequestrant in some food applications.
The European food additive number for it is E575.
Glucono Delta-Lakton (GDL) is kosher, halal, vegan and GMO free.
In aqueous solution, Glucono Delta-Lakton (GDL) rapidly dissolves and the lactone ring opens up and slowly hydrolyzes to gluconic acid, thus producing mild acidification.
And there is an equilibrium between D-gluconic acid (55% – 66%) and the delta and gamma lactones.
Glucono Delta-Lakton (GDL) Chemical Properties
Melting point: 160 °C (dec.)(lit.)
Alpha: 65 º (c=1,H2O)
Boiling point: 230.35°C (rough estimate)
Density: 0.6
Bulk density: 750kg/m3
Refractive index: 63.5 ° (C=10, H2O)
Storage temp.: Sealed in dry,Room Temperature
Solubility: 590g/l Hydrolysis
Form: Crystalline Powder
pKA: 12.06±0.60(Predicted)
Color: White to off-white
Odor: wh. cryst. powd., pract. odorless
PH: 3.6 (10g/l, H2O, 20℃)
Biological source: microbial
Water Solubility: 500 g/L (20 ºC)
Merck: 14,4457
BRN: 83286
LogP: -2.38
CAS DataBase Reference: 90-80-2(CAS DataBase Reference)
NIST Chemistry Reference: Glucono Delta-Lakton (GDL)(90-80-2)
EPA Substance Registry System: Glucono Delta-Lakton (GDL) (90-80-2)
Glucono Delta-Lakton (GDL) is the less commonly used than other food acidity regulators, such as citric acid, malic acid and fumaric acid.
Glucono Delta-Lakton (GDL) has two major differentiating properties:
A slow-release acidulant: Glucono Delta-Lakton (GDL) provides a progressive and continuous decrease of pH due to the slow hydrolysis to gluconic acid.
Less tart than other common acidulants: the initial slightly sweet taste making the final flavour of an aqueous solution of GDL Less tart.
Uses
Glucono Delta-Lakton (GDL) 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.
A lactone (cyclic ester) of Glucono Delta-Lakton (GDL) used as a used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent.
Glucono Delta-Lakton (GDL) is used in cosmetics for its anti-acne properties.
Glucono Delta-Lakton (GDL) 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 Glucono Delta-Lakton (GDL) particularly relevant for use in making anti-aging, moisturizing, and possibly sun care products.
Glucono Delta-Lakton (GDL) 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.
Glucono Delta-Lakton (GDL) has low acid release at room temperature and accelerated conversion into gluconic acid at high temperatures.
Glucono Delta-Lakton (GDL) is readily soluble with a solubility of 59 g in 100 ml of water at 20°C.
Glucono Delta-Lakton (GDL) functions as a leavening agent, acidulant, curing and pickling agent, and pH control agent.
Glucono Delta-Lakton (GDL) is comparatively less tart/sour than other food acids.
Glucono Delta-Lakton (GDL) is used in baked goods, fish products, desserts, and dressings.
Glucono Delta-Lakton (GDL) is the lactone derivative of D-gluconic acid.
Glucono Delta-Lakton (GDL) is widely used as a food additive to achieve a curing, pickling or leavening effect.
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.
Glucono Delta-Lakton (GDL) is a food additive with the E-number E575 used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent.
Glucono Delta-Lakton (GDL) is a lactone of D-gluconic acid.
Pure Glucono Delta-Lakton (GDL) is a white odorless crystalline powder.
Glucono Delta-Lakton (GDL) has been marketed for use in feta cheese.
Glucono Delta-Lakton (GDL) is pH-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.
Glucono Delta-Lakton (GDL) 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, Glucono Delta-Lakton (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 Glucono Delta-Lakton (GDL) is increased by heat and high pH.
The yeast Maudiozyma bulderi can be used to ferment gluconolactone to ethanol and carbon dioxide.
The pH value greatly affects culture growth.
Glucono Delta-Lakton (GDL) at 1 or 2% in a mineral media solution causes the pH to drop below 3.
Glucono Delta-Lakton (GDL) is also a complete inhibitor of the enzyme amygdalin beta-glucosidase at concentrations of 1 mM.
Preparation
Glucono Delta-Lakton (GDL) is prepared commercially by the oxidation of glucose with bromine water.
Glucono Delta-Lakton (GDL) is produced by direct crystallization from the aqueous solution of gluconic acid which can be produced by the oxidation of D -glucose with bromine water or with microorganisms or with enzymes derived from these microorganisms.
Corn starch is the major source of glucose.
Biochem/physiol Actions
Glucono Delta-Lakton (GDL) increased the doubling time and activated enzymes involved in the oxidative pentose phosphate pathway of Saccharomyces cerevisiae.
