576-42-1

Basic information

• Product Name: Potassium bisaccharate
• Synonyms: monopotassiumd-glucarate;D-SACCHARIC ACID MONOPOTASSIUM SALT;D-SACCHARIC ACID POTASSIUM SALT;D-TETRAHYDROXYADIPIC ACID POTASSIUM SALT;D-GLUCARIC ACID MONOPOTASSIUM SALT;D-GLUCOSACCHARIC ACID MONOPOTASSIUM SALT;D-GLUCOSACCHARIC ACID POTASSIUM SALT;GLUCARIC ACID MONOPOTASSIUM SALT
• CAS NO: 576-42-1
• Molecular Formula: C₆H₈O₈*2K
• Molecular Weight: 248.23
• EINECS: 209-402-2
• Mol File: 576-42-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 188 °C (dec.)(lit.)
• Boiling Point: 766.4 °C at 760 mmHg
• Flash Point: 431.2 °C
• Appearance: white crystalline powder
• Density: 1.939g/cm³
• Vapor Pressure: 4.04E-27mmHg at 25°C
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly, Heated, Sonicated), Water (Slightly, Sonicated)
• Stability: Hygroscopic
• CAS DataBase Reference: Potassium bisaccharate(CAS DataBase Reference)
• NIST Chemistry Reference: Potassium bisaccharate(576-42-1)
• EPA Substance Registry System: Potassium bisaccharate(576-42-1)

Safety Data

• WGK Germany: 3
• RTECS: LZ4291900
• Hazardous Substances Data: 576-42-1(Hazardous Substances Data)

Usage

Chemical Properties

Light, off-white powder, p H of solution 3.5. Slightly soluble in cold water; soluble in hot water, acid, or alkaline solutions. Combustible.

Uses

Different sources of media describe the Uses of 576-42-1 differently. You can refer to the following data:
1. D-Glucarate Monopotassium is an intermediate in the synthesis of D-Glucaro-1,4-lactone Monohydrate (G415600), an anticancer agent.
2. Chelating agent, rubber formulations, metal plating, soaps, and detergents.

General Description

D-Saccharic acid potassium salt is present in plants and animals. It is produced by the chemical oxidation of glucose with nitric acid. D-Saccharic acid lowers cholesterol and has chemotherapeutic property. It also has antimutagenic activity.

InChI:InChI=1/C6H10O8.K/c7-1(3(9)5(11)12)2(8)4(10)6(13)14;/h1-4,7-10H,(H,11,12)(H,13,14);/q;+1/p-1

Synthetic route

D-Glucose (2280-44-6) → D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
With potassium hydroxide; chlorine; potassium bromide; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl In water at 0 - 5℃; pH=11.4 - 11.7; Product distribution; Further Variations:; Reagents;	77%

D-glucose (50-99-7) → C6H5O9(3-)*3K(1+) + C6H5O9(3-)*3K(1+) + D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium D-gluconate; potassium hydroxide In water at 5℃; pH=12.2; Electrochemical reaction; optical yield given as %de;	A n/a B n/a C 70%

D-Glucuronic acid (6556-12-3) → D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
With peracetic acid; potassium hydroxide; ethylenediaminetetraacetic acid; cyfluthrin; potassium hydrogencarbonate; potassium bromide In water

D-glucaric acid (87-73-0) → D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
Stage #1: D-glucaric acid With potassium hydroxide In water Stage #2: With hydrogenchloride In water pH=3.4; Cooling with ice;	83.2 g

alpha-D-glucopyranose (492-62-6) → D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
With oxygen; potassium hydroxide In water at 50℃; under 750.075 Torr; for 4h;
With platinum on activated charcoal; oxygen; potassium hydroxide at 50℃; under 750.075 Torr; for 4h; pH=4;

L-gulose (6027-89-0) → D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
Stage #1: L-gulose With nitric acid; potassium hydroxide; sodium nitrite pH=Ca. 9 - Ca. 10; Stage #2: With nitric acid at 15 - 30℃; for 12h; pH=Ca. 3 - Ca. 4;

D-glucaric acid monopotassium salt (576-42-1) → D-glucaric acid (87-73-0) + D-Glucaro-1,4-lacton (389-36-6) + D-glucaro-6,3-lactone (2782-04-9)

Conditions	Yield
With H(1+) resin Rexyn 100(H) In water for 3h; lactonization;	A n/a B n/a C 69.1%

ethanol (64-17-5) + D-glucaric acid monopotassium salt (576-42-1) → diethyl glucarate (45214-05-9) + (S)-((2S,3R,4R)-3,4-Dihydroxy-5-oxo-tetrahydro-furan-2-yl)-hydroxy-acetic acid ethyl ester + D-glucarate-6,3-lactone ethyl ester (261900-70-3)

Conditions	Yield
With REXYN 101(H) at 55℃; for 4h;	A n/a B n/a C 58.9%

methanol (67-56-1) + D-glucaric acid monopotassium salt (576-42-1) → glucaric acid dimethyl ester (3868-17-5) + methyl D-glucarate 1,4-lactone (22140-16-5) + Methyl D-glucarate 6,3-lactone (155976-55-9)

Conditions	Yield
With hydrogenchloride for 4h; Heating;	A n/a B 58.89% C n/a
With hydrogenchloride for 4h; Heating;

[Cu4(μ-OH)(μ-α-D-glucose-1-phosphate(2-))2(2,2'-bipyridyl)4(H2O)2](NO3)3*10H2O + D-glucaric acid monopotassium salt (576-42-1) → [Cu4(μ-α-D-glucose-1-phosphate(2-))2(μ-D-glucaratoH)2(2,2'-bipyridyl)4](NO3)2*2H2O

Conditions	Yield
In water; N,N-dimethyl-formamide K glucarate (2 equiv.) in H2O added to soln. of Cu complex in DMF; stirred for 5 min; solvent removed under reduced pressure; crystd. from MeOH at room temp. for several d; crystals collected; washed with Et2O; dried under vac.; elem. anal.;	49%

[Cu4(μ-OH)(μ-α-D-glucose-1-phosphate(2-))2(2,2'-bipyridyl)4(H2O)2](NO3)3*10H2O + D-glucaric acid monopotassium salt (576-42-1) → ([Cu4(μ-α-D-glucose-1-phosphate(2-))2(μ-D-glucarateH)2(2,2'-bipyridyl)4](NO3)2*8H2O)(n)

Conditions	Yield
In N,N-dimethyl-formamide K glucarate (1 equiv.) added to soln. of Cu complex in DMF; stirred for 5 min; solvent removed under reduced pressure; crystd. from MeOH at room temp. for several d; crystals collected; washed with Et2O; dried under vac.; elem. anal.;	34%

D-glucaric acid monopotassium salt (576-42-1) + butan-1-ol (71-36-3) → glucaric acid di-n-butyl ester

Conditions	Yield
With Amberlyst-15 at 75℃; for 1.5h; Time;	25%

methanol (67-56-1) + D-glucaric acid monopotassium salt (576-42-1) → glucaric acid dimethyl ester (3868-17-5)

Conditions	Yield
With ion-exchange resin + form>

diethyl sulfate (64-67-5) + ethyl iodide (75-03-6) + D-glucaric acid monopotassium salt (576-42-1) → Tetraaethylzuckersaeure-diaethylester (109721-79-1)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 1209714/, (iii) /BRN= 505934/, Ag2O; Multistep reaction;

D-glucaric acid monopotassium salt (576-42-1) + dimethyl sulfate (77-78-1) → tetramethyl-d-saccharic acid (14307-81-4)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 635994/; Multistep reaction;

D-glucaric acid monopotassium salt (576-42-1) + dimethyl sulfate (77-78-1) + methyl iodide (74-88-4) → O2,O3,O4,O5-tetramethyl-D-glucaric acid dimethyl ester (102264-45-9)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 635994/, (iii) /BRN= 969135/, Ag2O; Multistep reaction;

D-glucaric acid monopotassium salt (576-42-1) + methyl iodide (74-88-4) → O2,O3,O4,O5-tetramethyl-D-glucaric acid dimethyl ester (102264-45-9)

Conditions	Yield
(i) aq. NH3, AgNO3, (ii) /BRN= 969135/, DMF, (iii) /BRN= 969135/, Ag2O; Multistep reaction;

formaldehyd (50-00-0) + D-glucaric acid monopotassium salt (576-42-1) → 2,4:3,5-di-O-methylene-D-glucaric acid dimethyl ester (4539-77-9, 7595-91-7, 114006-01-8, 114421-41-9)

Conditions	Yield
With sulfuric acid	4.77 g

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(2-Amino-ethylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 91.7 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(4-Amino-butylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 94.9 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(6-Amino-hexylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 90.9 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(2'-aminoethyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 91.7 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(8-Amino-octylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 93.8 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(4'-aminobutyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 94.9 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(10-Amino-decylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 90.3 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(6'-aminohexyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 90.9 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(12-Amino-dodecylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 91.5 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(8'-aminooctyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 93.8 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(10'-aminodecyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 90.3 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(12'-aminododecyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 91.5 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → N,N'-dimethyl-D-glucaramide (156016-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / 4 h / Heating 2: 90.9 percent / methanol; H2O / 2 h / Ambient temperature View Scheme

D-glucaric acid monopotassium salt (576-42-1) → Dimethyl 2,3,4,5-tetrakis-O--D-glucarate

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / 4 h / Heating 2: 1.) acetyl chloride, 2.) 1,1,1,3,3,3-hexamethyldisilazane, pyridine / 1.) MeOH, reflux, 12 h, 2.) r.t., 2 d View Scheme

D-glucaric acid monopotassium salt (576-42-1) → Methyl 2,4,5-tris-O--D-glucarate 6,3-lactone

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / 4 h / Heating 2: 1.) acetyl chloride, 2.) 1,1,1,3,3,3-hexamethyldisilazane, pyridine / 1.) MeOH, reflux, 12 h, 2.) r.t., 2 d View Scheme

D-glucaric acid monopotassium salt (576-42-1) → Methyl 2,3,5-tris-O--D-glucarate 1,4-lactone

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / 4 h / Heating 2: 1.) acetyl chloride, 2.) 1,1,1,3,3,3-hexamethyldisilazane, pyridine / 1.) MeOH, reflux, 12 h, 2.) r.t., 2 d View Scheme
Multi-step reaction with 2 steps 1: HCl / 4 h / Heating 2: 1,1,1,3,3,3-hexamethyldisilazane, pyridine / methanol / Ambient temperature View Scheme

Upstream product

• 50-99-7 D-glucose 
• 87-73-0 D-glucaric acid 
• 6556-12-3 D-Glucuronic acid 
• 5934-56-5 glucose 
• 5978-95-0 D-idose 
• 6027-89-0 L-gulose 
• 492-62-6 alpha-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 576-42-1 D-saccharic acid potassium salt 

Downstream Products

• 122990-47-0 catena{D-saccharatetriaquamagnesium} 
• 6614-50-2 D-glucaramide 
• 627-93-0 hexanedioic acid dimethyl ester 
• 3238-40-2 furan-2,5-dicarboxylic acid 
• 105-99-7 adipic acid dibutyl ester 
• 87-73-0 D-glucaric acid 
• 826-91-5 D-glucaric acid 1,4:6,3-dilactone 
• 389-36-6 D-Glucaro-1,4-lacton 
• 2782-04-9 D-glucaro-6,3-lactone 
• 4539-77-9 2,4:3,5-di-O-methylene-D-glucaric acid dimethyl ester 

Relevant articles and documents

Modifications in the nitric acid oxidation of d-glucose

The nitric acid oxidation of d-glucose was reinvestigated in an effort to better understand and improve the oxidation and subsequent work up steps. The oxidation was carried out using a computer controlled reactor employing a closed reaction flask under an atmosphere of oxygen which allowed for a catalytic oxidation process with oxygen as the terminal oxidant. Removal of nitric acid from product included the use of both diffusion dialysis and nanofiltration methodologies. Product analysis protocols were developed using ion chromatography.

METHOD FOR PRODUCING ADIPAMIDE AS INTERMEDIATE FOR PRODUCTION OF RAW MATERIAL FOR BIO-BASED NYLON

Disclosed is a method for producing adipamide, which may include the steps of: (a) reacting glucose, nitric acid (HNO3), sodium nitrite (NaNO2) and potassium hydroxide (KOH) to produce a glucaric acidpotassium salt, (b) producing glucamide by reacting the glutaric acid potassium salt, with an acidic solution and removing a potassium ion from the glucaric acid potassium salt, (c) preparing an reaction admixture by adding the glucamide and a catalyst to hydrogen halide and acetic acid, and (d) treating the reaction admixture with hydrogen gas in a reactor thereby producing the adipamide.

METHOD OF PREPARING ADIPIC ACID

Disclosed is a method of preparing adipic acid from d-glucaro-1,4:6,3-dilactone, particularly using a rhenium catalyst and a noble metal catalyst. Further the method may include using an environmentally friendly solvent such as water. Thus, the obtained adipic acid may have high purity as a final product and economic efficiency of the preparation process may be improved.