90-80-2

Basic information

• Product Name: delta-Gluconolactone
• Synonyms: 1,2,3,4,5-PENTAHYDROXYCAPROIC ACID DELTA-LACTONE;DELTA-GLUCURONOLACTONE;DELTA-GLUCONOLACTONE;D(+)-DEXTRONIC ACID DELTA-LACTONE;D-GLUCONIC ACID LACTONE;D-(+)-GLUCONO-1,5-LACTONE;D-GLUCONO-1,5-LACTONE;D(+)-GLUCONIC ACID DELTA-LACTONE
• CAS NO: 90-80-2
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.14
• EINECS: 202-016-5
• Product Categories: Biochemistry;Glucose;Sugar Acids;Sugars;Dextrins、Sugar & Carbohydrates;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;food additive;stabilizer;Food additives
• Mol File: 90-80-2.mol
• Article Data: 123

Chemical Properties

• Melting Point: 160 °C (dec.)(lit.)
• Boiling Point: 230.35°C (rough estimate)
• Flash Point: 192.294 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 0.6
• Vapor Pressure: 7.6E-10mmHg at 25°C
• Refractive Index: 63.5 ° (C=10, H2O)
• Storage Temp.: Refrigerator
• Solubility: 590g/l Hydrolysis
• PKA: 12.06±0.60(Predicted)
• Water Solubility: 500 g/L (20 ºC)
• Merck: 14,4457
• BRN: 83286
• CAS DataBase Reference: delta-Gluconolactone(CAS DataBase Reference)
• NIST Chemistry Reference: delta-Gluconolactone(90-80-2)
• EPA Substance Registry System: delta-Gluconolactone(90-80-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 21-36/38-46-62-63
• Safety Statements: 24/25-53-36/37-26-25
• WGK Germany: 3
• RTECS: LZ5184000
• F: 21
• TSCA: Yes
• Hazardous Substances Data: 90-80-2(Hazardous Substances Data)

Usage

Description

Delta-Gluconolactone (GDL) is a lactone of the D-gluconate. It is a natural constituent of many foods. It can be found in honey, fruit juices, wine and many-fermented products1-3. It 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. GDL has been marketed for use in feta cheese. 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. It can be used as nutritional supplement in beverage such as in Instant Drinks, Syrups, RTD Tea and Coffee, Sports and Energy Drinks, Waters.

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

Uses

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

Uses

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

Uses

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.

Uses

a product of the oxidation of glucose by glucose oxidase

Uses

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.

Uses

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.

Uses

(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.

Preparation

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

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

Nonflammable

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.

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.]

InChI: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-/m0/s1

Synthetic route

gluconic acid (526-95-4) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
In 1,4-dioxane; water for 0.183333h; microwave irradiation;	92%
at 50℃; under 20 Torr;
at 70 - 80℃;

D-Glucose (2280-44-6) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
[(C4Ph4CO)(CO)2Ru]2 In cyclohexanone at 45℃; for 16h;	86%
With oxygen; catalase; glucose oxidase at 25℃; Rate constant; 0.1M acetate buffer (pH=5.5);
With N-Bromosuccinimide; sulfuric acid; mercury(II) diacetate In water; acetic acid at 26.9℃; Kinetics; Thermodynamic data; Mechanism; further temperatures, also with Ru(III) as a catalyst; ΔG(excit.), ΔS(excit.), ΔH(excit.), Ea;

gluconic acid (526-95-4) → D-glucono-1,4-lactone (1198-69-2) + D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With water
at 78℃; under 12 Torr; beim Trocknen ueber Phosphorpentoxyd;
at 78℃; under 12 Torr; Ueber Phosphorpentoxyd;
In water at 112 - 124℃; for 2h; Sparging with nitrogen;

ethyl D-gluconate (74421-63-9) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
at 50℃; under 20 Torr;
at 70 - 80℃;

D-Glucose (2280-44-6) + nicotinamide adenine dinucleotide (865-05-4) → NADH (58-68-4) + D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
at 22℃; ph=7.0, phosphate buffer; glucose dehydrogenase;

D-Glucose (2280-44-6) → meso-erythritol (909878-64-4) + D-Arabitol (488-82-4) + D-glucono-1,4-lactone (1198-69-2) + D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; Wilkinson's catalyst at 130℃; for 6h; Product distribution; Mechanism; other unprotected aldose sugars; other rhodium-catalysts; var. temp. and reaction times;

β-D-glucose (492-61-5) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With oxygen In water Thermodynamic data; Kinetics; Mechanism; Ambient temperature; Eact, other object of study: steady state catalytic current density; condition: Redox Polymer Films Glucose oxidase/PEG/POs-EA on a vitreous-carbon-disk electrode; different conditions: air, nitrogen, different temperatures;
With glucose oxidase at 25℃; Rate constant; reductive half-reaction; also in the presence of one-elctron redox cosubstrates (differently substituted ferroceniums and promazine cation); var. pH values;
ferrocenium(III) tetrafluoroborate In water at 25℃; Rate constant; glucose oxidase from Aspergillus Niger; n-octyl-β-D-glucopyrannoside; enzymatic electrocatalysis: working electrode: glassy carbon disk, reference elektrode: SCE;

sodium D gluconate → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With acetic acid

D-glucose (50-99-7) + water + bromine (7726-95-6) + barium bromide + barium carbonate → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
at 0℃; Rate constant; veschiedenen D-Glucose-Praeparate; unter Einleiten von Kohlendioxid;

D-sorbitol (50-70-4) → D-Glucose (2280-44-6) + D-gulono-1,4-lactone (6322-07-2) + D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With potassium dichromate; perchloric acid In water at 33℃; Kinetics; Further Variations:; pH-values;

alpha-D-glucopyranose (492-62-6) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With Tris-HCl buffer; Bacillus subtilis inositol dehydrogenase EC 1.1.1.18; nicotinamide adenine dinucleotide In water at 25℃; pH=9.0; Enzyme kinetics;
With N-Bromosuccinimide; sulfuric acid; mercury(II) diacetate; ruthenium trichloride In water; acetic acid at 34.84℃; Kinetics; Thermodynamic data; Further Variations:; Reagents; Temperatures;
With ammonium vanadate; sulfuric acid; sodium dodecyl-sulfate In water at 40℃; Kinetics; Further Variations:; Reagents;

D-glucose (50-99-7) + palladium (7440-05-3) + butan-1-ol (71-36-3) → D-Glucono-1,5-lactone (90-80-2)

1-methyl-pyrrolidin-2-one (872-50-4) + D-glucose (50-99-7) + palladium (7440-05-3) → D-Glucono-1,5-lactone (90-80-2)

D-glucose (50-99-7) + palladium (7440-05-3) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
In 1,4-dioxane; water

1,2-dimethoxyethane (110-71-4) + D-glucose (50-99-7) + platinum (7440-06-4) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
In methanol

D-glucose (50-99-7) + platinum (7440-06-4) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
In N-methyl-acetamide
With tetramethylurea
In triethylene glycol dimethyl ether
In methanol

palladium-barium carbonate + D-glucose (50-99-7) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
In acetic acid methyl ester; water

platinum-calcium carbonate + D-glucose (50-99-7) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
In 1,4-dioxane

palladium-activated carbon + D-glucose (50-99-7) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
In 1,2-dimethoxyethane
In methanol; water
In diethylene glycol dimethyl ether

D-glucose (50-99-7) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With potassium permanganate; cetyltrimethylammonim bromide In water; benzene at 30℃; Kinetics; Further Variations:; Reagents;
With horseradish peroxidase type VI; glucose oxidase type VII from Aspergillus niger; [Os(II)(bpy)2Cl(PyCOOH)]Cl; oxygen; 3-mercaptopropionic acid at 20℃; for 1h; pH=5; aq. acetate buffer; Enzymatic reaction;
With glucose dehydrogenase from Pseudomonas sp.; nicotinamide adenine dinucleotide at 20℃; for 1h; pH=7.6; aq. buffer; Enzymatic reaction;

Sucrose (57-50-1) → formaldehyd (50-00-0) + D-Arabinono-1,5-lactone (73745-98-9) + D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid; water; cetyltrimethylammonim bromide at 45℃; Kinetics; Mechanism; Reagent/catalyst; Solvent; Temperature; Concentration;

alpha-D-glucopyranose (492-62-6) → gluconic acid (526-95-4) + D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With gold nanoparticles supported on carbon nanotubes; potassium hydroxide In water at 24.99℃; Electrochemical reaction;

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (4304-12-5) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: β-glucosidase / pH 6.2 / Enzymatic reaction 2: Thermoplasma acidophilum glucose dehydrogenase; NADP / Enzymatic reaction View Scheme

D-Glucose (2280-44-6) + N-bromophthalimide (2439-85-2) → phthalimide (136918-14-4) + D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With sulfuric acid; mercury(II) diacetate In water at 30℃; Kinetics;

β-D-glucose 6-phosphate (299-31-0, 15209-11-7, 15209-12-8, 33163-99-4, 40436-57-5, 40436-58-6, 40436-60-0, 40436-61-1) → β-D-glucose (492-61-5) + D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With Yersinia mollaretii phytase; water; oxygen; glucose oxidase In aq. phosphate buffer Combinatorial reaction / High throughput screening (HTS); Enzymatic reaction;

D-gulose (4205-23-6) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With NADPH Electrochemical reaction;

D-glucose (50-99-7) → dihydrogen peroxide (7722-84-1) + D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With oxygen; flavin adenine dinucleotide In aq. phosphate buffer pH=7; Electrochemical reaction;

D-Glucose (2280-44-6) → gluconic acid (526-95-4) + D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With sodium hydroxide at 25℃; for 7.5h; Catalytic behavior; Electrochemical reaction; Alkaline conditions;
In water Electrochemical reaction; Inert atmosphere;

4-nitrophenyl-β-D-glucoside (2492-87-7) → D-Glucono-1,5-lactone (90-80-2)

Conditions	Yield
With C14H19Cl2CuN5O8; dihydrogen peroxide In aq. buffer at 30℃; for 24h; pH=10.5; Kinetics; Reagent/catalyst; pH-value;

1-[4-(diphenylphosphino)phenyl]methanamine (201011-40-7) + D-Glucono-1,5-lactone (90-80-2) → N-[(4-diphenylphosphinophenyl)methyl] D-gluconamide

Conditions	Yield
In benzene Acylation; Heating;	100%
In methanol for 1.5h; Heating;	96%

chloro-trimethyl-silane (75-77-4) + D-Glucono-1,5-lactone (90-80-2) → (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9)

Conditions	Yield
With 4-methyl-morpholine; dmap In tetrahydrofuran at 13 - 22℃; for 2.33333h;	100%
With 4-methyl-morpholine; dmap In tetrahydrofuran at 13 - 22℃; for 2.33333h; Industry scale;	100%
With 4-methyl-morpholine In tetrahydrofuran; cyclohexane at -5 - 25℃; for 17h; Solvent; Inert atmosphere;	100%

acetic anhydride (108-24-7) + D-Glucono-1,5-lactone (90-80-2) → (2R,3S)-2-[(acetyloxy)methyl]-6-oxo-3,6-dihydro-2H-pyran-3,5-diyl diacetate (22860-23-7)

Conditions	Yield
With perchloric acid In water at 20℃; for 1h;	100%
Stage #1: acetic anhydride; D-Glucono-1,5-lactone at 23℃; for 1h; Stage #2: With trimethylamine at 0 - 23℃; Reagent/catalyst; Temperature;	79%
Stage #1: acetic anhydride; D-Glucono-1,5-lactone With perchloric acid Stage #2: With triethylamine In dichloromethane

chloro-trimethyl-silane (75-77-4) + D-Glucono-1,5-lactone (90-80-2) → (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions	Yield
With 4-methyl-morpholine In tetrahydrofuran at 20 - 30℃; for 8h; Inert atmosphere;	100%

1,5-diamino-3-azapentane (111-40-0) + D-Glucono-1,5-lactone (90-80-2) → (2S,3R,4S,5R)-2,3,4,5,6-Pentahydroxy-hexanoic acid {2-[2-((2S,3R,4S,5R)-2,3,4,5,6-pentahydroxy-hexanoylamino)-ethylamino]-ethyl}-amide

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; amidation;	99%

triethylamine (121-44-8) + D-Glucono-1,5-lactone (90-80-2) + 12-Aminododecanoic acid (693-57-2) → 12-(D-gluconoylamino)dodecanoic acid triethylamine salt

Conditions	Yield
In methanol for 4h; Reflux;	99%

D-Glucono-1,5-lactone (90-80-2) + 12-Aminododecanoic acid (693-57-2) → C18H35NO8

Conditions	Yield
With triethylamine In methanol for 4h; Reflux;	99%

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + D-Glucono-1,5-lactone (90-80-2) → C18H42O6Si4

Conditions	Yield
With ammonium sulfate In tetrahydrofuran at 70℃; for 15h; Temperature; Time; Solvent; Reagent/catalyst; Inert atmosphere;	98.5%

1,8-diaminooctan (373-44-4) + D-Glucono-1,5-lactone (90-80-2) → N-<8-(D-gluconamido)octyl>-D-gluconamide

Conditions	Yield
In methanol for 24h; Ambient temperature;	98%

N-Boc-1,3-diaminopropane (75178-96-0) + D-Glucono-1,5-lactone (90-80-2) → C14H28N2O8

Conditions	Yield
In methanol at 70℃; for 24h;	98%
In methanol for 4h; Reflux;	98%
In methanol for 4h; Reflux;	90%
In methanol for 4h; Reflux;

isopropylamine (75-31-0) + D-Glucono-1,5-lactone (90-80-2) → N-isopropyl-D-gluconamide

Conditions	Yield
With pyridine at 20℃; for 24h; Condensation;	97%

Propargylamine (2450-71-7) + D-Glucono-1,5-lactone (90-80-2) → tetra-O-acetyl-β-D-ribofuranose

Conditions	Yield
With pyridine at 20℃; for 18h;	97%

chloro-trimethyl-silane (75-77-4) + D-Glucono-1,5-lactone (90-80-2) → C18H42O6Si4

Conditions	Yield
With dmap; N-methylcyclohexylamine In tetrahydrofuran at 0 - 20℃; for 0.5h; Temperature; Reagent/catalyst; Inert atmosphere;	96.6%
With ammonium sulfate In tetrahydrofuran at 70℃; for 15h; Inert atmosphere;	96.7%

bis(triethylsilyl)amine (2117-18-2) + D-Glucono-1,5-lactone (90-80-2) → C30H66O6Si4

Conditions	Yield
With ammonium sulfate In tetrahydrofuran at 70℃; for 15h; Inert atmosphere;	96.7%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + D-Glucono-1,5-lactone (90-80-2) → C18H42O6Si4

Conditions	Yield
With ammonium sulfate In tetrahydrofuran at 70℃; for 15h; Inert atmosphere;	96.6%

1,1,3,3-tetramethyldisilazane (15933-59-2) + D-Glucono-1,5-lactone (90-80-2) → C14H34O6Si4

Conditions	Yield
With ammonium sulfate In tetrahydrofuran at 70℃; for 15h; Inert atmosphere;	96.4%

benzylamine (100-46-9) + D-Glucono-1,5-lactone (90-80-2) → N-benzyl-D-gluconamide (100569-46-8, 5438-33-5)

Conditions	Yield
With pyridine at 20℃; for 24h;	96%
In methanol for 3h; Heating;	86%
In water

methylamine (74-89-5) + D-Glucono-1,5-lactone (90-80-2) → N-methyl-D-gluconamide (24758-59-6)

Conditions	Yield
In water at 20℃; for 24h; Condensation;	96%
In water

N-(2-aminoethyl)prop-2-enamide hydrochloride + D-Glucono-1,5-lactone (90-80-2) → N-(2-acrylamidoethyl)-D-gluconamide (959773-24-1)

Conditions	Yield
With triethylamine; hydroquinone In methanol at 20℃; for 5h;	96%

acetic anhydride (108-24-7) + D-Glucono-1,5-lactone (90-80-2) → (3-acetoxy-2-oxo-2H-pyran-6-yl) methyl acetate (66530-16-3)

Conditions	Yield
With pyridine at 80℃; for 1h;	96%
With zinc(II) chloride at 190℃; for 0.333333h; Reagent/catalyst; Temperature; Time; Microwave irradiation;	73%

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + D-Glucono-1,5-lactone (90-80-2) → (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9)

Conditions	Yield
With N-methylimidazolium hexafluorophosphate at 0 - 5℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere;	95.9%
With iodine In dichloromethane at 15 - 30℃; for 4h; Reagent/catalyst; Solvent; Temperature;	85%
With iodine In dichloromethane Reflux;	25 g

hexadecylamine (143-27-1) + D-Glucono-1,5-lactone (90-80-2) → 2,3,4,5,6-pentahydroxyhexanoic acid hexadecylamide (18375-65-0)

Conditions	Yield
In methanol	95%
With methanol
With ethanol

acetic anhydride (108-24-7) + D-Glucono-1,5-lactone (90-80-2) → 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone (61259-48-1, 73322-42-6)

Conditions	Yield
With zinc(II) chloride for 0.666667h; Ambient temperature;	95%
With methanesulfonic acid In neat (no solvent) at 30 - 35℃; for 1h; Green chemistry;	95%
With trifluoroacetic acid at 20℃; for 3h;	94%

methanol (67-56-1) + 2,2-dimethoxy-propane (77-76-9) + D-Glucono-1,5-lactone (90-80-2) → methyl 3,4:5,6-di-O-isopropylidene-D-gluconate (114743-85-0)

Conditions	Yield
With toluene-4-sulfonic acid Ambient temperature;	95%
With toluene-4-sulfonic acid	94%
With toluene-4-sulfonic acid In acetone at 20℃; for 12h;	86%

chloromethyl methyl ether (107-30-2) + D-Glucono-1,5-lactone (90-80-2) → 2,3,4,6-tetra-O-(methoxymethyl)-δ-D-gluconolactone (189825-51-2)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In dichloromethane for 48h; Ambient temperature;	95%
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In dichloromethane for 48h;	83%
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h;	83%
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 48h; In the dark;	83%
Stage #1: chloromethyl methyl ether; D-Glucono-1,5-lactone With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; Stage #2: With tetra-(n-butyl)ammonium iodide In dichloromethane at 0 - 20℃; for 48h; darkness;	83%

D-Glucono-1,5-lactone (90-80-2) + Nε-lauroyl-L-lysine ethyl ester (292140-08-0) → Nα-gluconamide-Nε-lauroyl-L-lysine ethyl ester

Conditions	Yield
In methanol at 50℃; for 6h;	95%

2,2-dimethoxy-propane (77-76-9) + D-Glucono-1,5-lactone (90-80-2) → methyl 3,4:5,6-di-O-isopropylidene-D-gluconate (114743-85-0)

Conditions	Yield
With toluene-4-sulfonic acid In methanol; acetone at 20℃; for 48h; Inert atmosphere;	94%
With toluene-4-sulfonic acid In methanol; acetone at 20℃; for 9h;	92%
With toluene-4-sulfonic acid In methanol; acetone for 48h; Ambient temperature;	84%

triethylsilyl chloride (994-30-9) + D-Glucono-1,5-lactone (90-80-2) → 2,3,4,6-tetrakis-O-(triethylsilyl)-D-glucopyrano-1,5-lactone (105539-33-1)

Conditions	Yield
With pyridine; N-ethyl-N,N-diisopropylamine In dichloromethane for 24h; Ambient temperature;	94%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	90%

N-butylamine (109-73-9) + D-Glucono-1,5-lactone (90-80-2) → n-butyl-D-gluconamide (18375-57-0)

Conditions	Yield
With pyridine at 20℃; for 24h;	94%
In methanol at 20℃; for 24h;	72%

propylamine (107-10-8) + D-Glucono-1,5-lactone (90-80-2) → N-propyl-D-gluconamide (24758-61-0)

Conditions	Yield
With pyridine at 20℃; for 24h; Condensation;	93%
In pyridine at 55℃; for 1.5h; Product distribution; prototype reaction, oth. aldonolactones, oth. amines;

Upstream product

• 50-99-7 D(+)-Glucose 
• 526-95-4 Gluconic acid 
• 17194-00-2 Barium hydroxide 
• 299-28-5 Calcium gluconate 
• 9001-05-2 CATALASE 
• 9002-29-3 AMBERLITE(R) IRC-50 
• 9001-37-0 Glucose oxidase 

Downstream Products

• 299-27-4 Potassium gluconate 
• 6485-39-8 Manganese gluconate 

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