Conditions | Yield |
---|---|
In 1,4-dioxane; water for 0.183333h; microwave irradiation; | 92% |
at 50℃; under 20 Torr; | |
at 70 - 80℃; |
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; |
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
D-Glucono-1,5-lactone
Conditions | Yield |
---|---|
at 50℃; under 20 Torr; | |
at 70 - 80℃; |
D-Glucose
nicotinamide adenine dinucleotide
A
NADH
B
D-Glucono-1,5-lactone
Conditions | Yield |
---|---|
at 22℃; ph=7.0, phosphate buffer; glucose dehydrogenase; |
D-Glucose
A
meso-erythritol
B
D-Arabitol
C
D-glucono-1,4-lactone
D
D-Glucono-1,5-lactone
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; |
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; |
D-Glucono-1,5-lactone
Conditions | Yield |
---|---|
With acetic acid |
Conditions | Yield |
---|---|
at 0℃; Rate constant; veschiedenen D-Glucose-Praeparate; unter Einleiten von Kohlendioxid; |
D-sorbitol
A
D-Glucose
B
D-gulono-1,4-lactone
C
D-Glucono-1,5-lactone
Conditions | Yield |
---|---|
With potassium dichromate; perchloric acid In water at 33℃; Kinetics; Further Variations:; pH-values; |
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; |
1-methyl-pyrrolidin-2-one
D-glucose
palladium
D-Glucono-1,5-lactone
Conditions | Yield |
---|---|
In 1,4-dioxane; water |
Conditions | Yield |
---|---|
In methanol |
Conditions | Yield |
---|---|
In N-methyl-acetamide | |
With tetramethylurea | |
In triethylene glycol dimethyl ether | |
In methanol |
Conditions | Yield |
---|---|
In acetic acid methyl ester; water |
Conditions | Yield |
---|---|
In 1,4-dioxane |
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane | |
In methanol; water | |
In diethylene glycol dimethyl ether |
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
A
formaldehyd
B
D-Arabinono-1,5-lactone
C
D-Glucono-1,5-lactone
Conditions | Yield |
---|---|
With N-Bromosuccinimide; sulfuric acid; water; cetyltrimethylammonim bromide at 45℃; Kinetics; Mechanism; Reagent/catalyst; Solvent; Temperature; Concentration; |
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
D-Glucono-1,5-lactone
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
N-bromophthalimide
A
phthalimide
B
D-Glucono-1,5-lactone
Conditions | Yield |
---|---|
With sulfuric acid; mercury(II) diacetate In water at 30℃; Kinetics; |
β-D-glucose 6-phosphate
A
β-D-glucose
B
D-Glucono-1,5-lactone
Conditions | Yield |
---|---|
With Yersinia mollaretii phytase; water; oxygen; glucose oxidase In aq. phosphate buffer Combinatorial reaction / High throughput screening (HTS); Enzymatic reaction; |
Conditions | Yield |
---|---|
With NADPH Electrochemical reaction; |
Conditions | Yield |
---|---|
With oxygen; flavin adenine dinucleotide In aq. phosphate buffer pH=7; Electrochemical reaction; |
Conditions | Yield |
---|---|
With sodium hydroxide at 25℃; for 7.5h; Catalytic behavior; Electrochemical reaction; Alkaline conditions; | |
In water Electrochemical reaction; Inert atmosphere; |
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
D-Glucono-1,5-lactone
Conditions | Yield |
---|---|
In benzene Acylation; Heating; | 100% |
In methanol for 1.5h; Heating; | 96% |
chloro-trimethyl-silane
D-Glucono-1,5-lactone
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
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
D-Glucono-1,5-lactone
(2R,3S)-2-[(acetyloxy)methyl]-6-oxo-3,6-dihydro-2H-pyran-3,5-diyl diacetate
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 |
Conditions | Yield |
---|---|
With 4-methyl-morpholine In tetrahydrofuran at 20 - 30℃; for 8h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; amidation; | 99% |
Conditions | Yield |
---|---|
In methanol for 4h; Reflux; | 99% |
Conditions | Yield |
---|---|
With triethylamine In methanol for 4h; Reflux; | 99% |
Conditions | Yield |
---|---|
With ammonium sulfate In tetrahydrofuran at 70℃; for 15h; Temperature; Time; Solvent; Reagent/catalyst; Inert atmosphere; | 98.5% |
Conditions | Yield |
---|---|
In methanol for 24h; Ambient temperature; | 98% |
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; |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 24h; Condensation; | 97% |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 18h; | 97% |
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% |
Conditions | Yield |
---|---|
With ammonium sulfate In tetrahydrofuran at 70℃; for 15h; Inert atmosphere; | 96.7% |
Conditions | Yield |
---|---|
With ammonium sulfate In tetrahydrofuran at 70℃; for 15h; Inert atmosphere; | 96.6% |
Conditions | Yield |
---|---|
With ammonium sulfate In tetrahydrofuran at 70℃; for 15h; Inert atmosphere; | 96.4% |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 24h; | 96% |
In methanol for 3h; Heating; | 86% |
In water |
Conditions | Yield |
---|---|
In water at 20℃; for 24h; Condensation; | 96% |
In water |
D-Glucono-1,5-lactone
N-(2-acrylamidoethyl)-D-gluconamide
Conditions | Yield |
---|---|
With triethylamine; hydroquinone In methanol at 20℃; for 5h; | 96% |
acetic anhydride
D-Glucono-1,5-lactone
(3-acetoxy-2-oxo-2H-pyran-6-yl) methyl acetate
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
D-Glucono-1,5-lactone
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
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
D-Glucono-1,5-lactone
2,3,4,5,6-pentahydroxyhexanoic acid hexadecylamide
Conditions | Yield |
---|---|
In methanol | 95% |
With methanol | |
With ethanol |
acetic anhydride
D-Glucono-1,5-lactone
2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone
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
2,2-dimethoxy-propane
D-Glucono-1,5-lactone
methyl 3,4:5,6-di-O-isopropylidene-D-gluconate
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
D-Glucono-1,5-lactone
2,3,4,6-tetra-O-(methoxymethyl)-δ-D-gluconolactone
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
Nε-lauroyl-L-lysine ethyl ester
Conditions | Yield |
---|---|
In methanol at 50℃; for 6h; | 95% |
2,2-dimethoxy-propane
D-Glucono-1,5-lactone
methyl 3,4:5,6-di-O-isopropylidene-D-gluconate
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
D-Glucono-1,5-lactone
2,3,4,6-tetrakis-O-(triethylsilyl)-D-glucopyrano-1,5-lactone
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% |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 24h; | 94% |
In methanol at 20℃; for 24h; | 72% |
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; |
Systematic Name: (3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one (non-preferred name)
SMILES: O=C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
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-/m1/s1
InChIKey: PHOQVHQSTUBQQK-SQOUGZDYBO
Empirical Formula: C6H10O6
Molecular Weight: 178.14
EINECS: 202-016-5
Product Categories: Biochemistry; Glucose; Sugar Acids; Sugars; Dextrins、Sugar & Carbohydrates
Melting Point: 160 °C (dec.)(lit.)
alpha: 65 °(c=1,H2O)
refractive index: 63.5 ° (C=10, H2O)
Water Solubility: 500 g/L (20 °C)
Index of Refraction: 1.607
Molar Refractivity: 35.79 cm3
Molar Volume: 103.5 cm3
Surface Tension: 98.4 dyne/cm
Density: 1.72 g/cm3
Flash Point: 192.3 °C
Enthalpy of Vaporization: 81.3 kJ/mol
Boiling Point: 446.4 °C at 760 mmHg
Vapour Pressure: 7.6E-10 mmHg at 25 °C
Classification Code of 1,5-Gluconolactone (CAS NO.90-80-2): Chelating agent; Mutation data
1,5-Gluconolactone (CAS NO.90-80-2) 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.
1. | uns-mic-uns 5 mmol/L | AMICCW Archives of Microbiology. 109 (1976),157. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xn,Xi
Risk Statements:
R21: Harmful in contact with skin
R46: May cause heritable genetic damage
R62: Possible risk of impaired fertility
R63: Possible risk of harm to the unborn child
R36/37: Irritating to eyes and respiratory system
Safety Statements:
S25: Avoid contact with eyes
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S53: Avoid exposure - obtain special instruction before use
S24/25: Avoid contact with skin and eyes
S36/37: Wear suitable protective clothing and gloves
WGK Germany: 3
RTECS: LZ5184000
F: 21
Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
1,5-Gluconolactone (CAS NO.90-80-2), its Synonyms are D-Gluconic acid delta-lactone ; D-Gluconic acid lactone ; D-Gluconic delta-lactone ; D-Glucono-1,5-lactone ; D-delta-Gluconolactone ; Deltagluconolactone ; Gluconic acid lactone (6CI) ; Gluconic delta-lactone ; Glucono delta lactone ; Glucono delta-lactone ; Gluconolactone ; delta-Gluconolactone ; beta-Glucono-1,5-lactone .
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