D-Glucurone
- Iupac Name：(2R)-2-[(2S,3R,4S)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetaldehyde
- CAS No.: 32449-92-6
- Molecular Weight：176.12400
- Modify Date.: 2022-11-25 02:27
- Introduction: D-Glucurone is a glucuronic acid derivative. It is used for treating canine hepatitis.
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1. Names and Identifiers
- 1.1 Name
- D-Glucurone
- 1.2 Synonyms
D-Glucofuranurono-6,3-lactone D-Glucuronic acid lactone D-Glucuronic acid γ-lactone D-Glucuronic acid, gamma-lactone D-Glucuronic acid, γ-lactone D-Glucurono-3,6-lactone D-Glucurono-6,3-lactone D-Glucurono-g-lactone D-Glucuronolactone D-Glucurono-γ-lactone Dicurone Glucoxy Glucurolactone Glucurone Glucuronic acid γ-lactone Glucuronic acid, γ-lactone, D- Glucuronicacid, g-lactone, D- (6CI,8CI) Glucurono-6,3-lactone Glucuronolactone Glucuronosan Glycurone Guronsan NSC 656 Reulatt S.S.
- 1.3 CAS No.
- 32449-92-6
- 1.4 CID
- 92283
- 1.5 EINECS(EC#)
- 251-053-3
- 1.6 Molecular Formula
- C6H8O6 (isomer)
- 1.7 Inchi
- InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h1-5,8-10H/t2-,3+,4-,5+/m0/s1
- 1.8 InChIkey
- UYUXSRADSPPKRZ-SKNVOMKLSA-N
- 1.9 Canonical Smiles
- C(=O)C(C1C(C(C(=O)O1)O)O)O
- 1.10 Isomers Smiles
- C(=O)[C@@H]([C@@H]1[C@@H]([C@@H](C(=O)O1)O)O)O
2. Properties
- 2.1 Density
- 1,76 g/cm3
- 2.1 Melting point
- 172-175°C(lit.)
- 2.1 Boiling point
- 403.5ºC at 760 mmHg
- 2.1 Refractive index
- 18.5 ° (C=5, H2O)
- 2.1 Flash Point
- 174.9ºC
- 2.1 Precise Quality
- 176.03200
- 2.1 PSA
- 104.06000
- 2.1 logP
- -2.80660
- 2.1 Solubility
- water: soluble25mg/mL, clear, colorless
- 2.2 Appearance
- White Crystals or Crystalline Powder
- 2.3 Chemical Properties
- white crystals or crystalline powder
- 2.4 Color/Form
- White
- 2.5 pKa
- 11.96±0.60(Predicted)
- 2.6 Water Solubility
- water: soluble 25mg/mL, clear, colorless
- 2.7 Stability
- Stable under normal temperatures and pressures.
- 2.8 StorageTemp
- Store at RT.
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- Oxidation is fed according to the ratio of starch (m): nitric acid (67% ± 0.5%, V): water (V) = 1: 1.5: 8.5.?First put nitric acid into the oxidation kettle, start stirring, and heat to 60℃.?Add starch, (2% of the total amount), raise the temperature to 78°C within 15min for initiation, hold for 5min, then cool down to 50-60°C within 15min, add starch every 20min, divided into two (30% of the total amount) Finally, at a temperature of 47 ℃ ± 1 ℃, add starch every 25min, divided into four times (68% of the total amount).?Control the temperature to increase the average temperature of the reaction by 5°C per hour, keep it for 7-8h, the temperature reaches 68°C, discharge, add water (12% of the total amount) to the liquid, heat it with steam at 70-80°C, remove NO2 within 20min, After standing, add water (88% of the total amount) to obtain carboxy starch liquid.?Starch [HNO3, starch, water] → [47℃±1℃, 7-8h] Hydrolysis of hydroxy starch liquid The carboxyl starch liquid is pumped into the hydrolysis tank, steam is heated to 100 ℃, and yellow smoke and water vapor come out.?Then sealed, the internal pressure increased to 245.25kPa (2.5kgf/cm2), the temperature was 140-142 ℃, hydrolyzed for 2h, to obtain a hydrolysate, that is, a glucuronic acid solution.?Hydroxy starch liquid [245kPa]→[140-142℃, 2h] hydrolyzate (glucuronic acid) lactonized. The above hydrolysate was decolorized by 122 weakly acidic cation exchange resin. The decolorized liquid was pumped into the concentration tank under vacuum The temperature is about 93.33 kPa (700mmHg), below 50-60°C, and concentrated under reduced pressure until 34-36°Be.?Add 1.68 times the amount of starch glacial acetic acid into the concentrated solution, place it in an esterification tank, esterify at room temperature for 16-24h, let cool to 0-5℃ for crystallization, and filter to obtain crude glucuronolactone.?Hydrolysate [112 type resin, ice HAc] → [16-24h] Refining crude glucuronolactone According to crude product (m): distilled water (V): ethanol (V): activated carbon (m) = 1: 0.7: 0.4: 0.01-0.03 ratio of feeding.?Put the crude product and distilled water in a refining tank, heat and stir continuously to make it completely dissolved, add activated carbon to decolorize, then add ethanol, stir evenly, suction filter, the filtrate is cooled to 0-5 ℃, put it for 16h, spin filter, filter cake Wash once with absolute ethanol, spin dry, and dry below 80 ℃, that is, glucuronolactone boutique.?Crude glucuronolactone [distilled water, ethanol, activated carbon] → [0-5℃, 16h] glucuronolactone boutique.
- 3.2 Purification Methods
- Dissolve the lactone or mixture of lactone and acid in H2O and concentrate on a steam bath until crystallisation begins. Cool rapidly to room temperature wih stirring. After 2hours the product is filtered off, washed with cold EtOH and dried to m 174-175o and [] D +19.8o (c 5.2, H2O). The amount of free acid can be obtained by titration of an ice-cold aqueous solution with standard alkali. It can be recrystallised from EtOH, EtOH/H2O or MeOH, and the highest recorded m is 180o. [Stacey J Chem Soc 1529 1939, Mehltretter et al. J Am Chem Soc 73 2424 1951, Beilstein 18 III/IV 3055, 18/5 V 33.] D-Glucurone Preparation Products And Raw materials Raw materials
- 3.3 Usage
- D-Glucurone is a glucuronic acid derivative. It is used for treating canine hepatitis.
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- R36/37/38
- 4.1 Safety Statements
- S24/25
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 WGK Germany
- 2
- 4.1 RTECS
- LZ8930000
- 4.1 Report
-
Reported in EPA TSCA Inventory.
- 4.2 Safety
-
Hazard Codes:?
Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25:Avoid contact with skin and eyes.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS: LZ8930000
HS Code: 29322980
- 4.3 Specification
-
?Glucuronic acid lactone?,?its cas register number is 32449-92-6. It also can be called?D-Glucofuranuronic acid, gamma-lactone ; D-Glucuronic acid lactone ; D-Glucurono-3,6-lactone ; D-Glucurono-6,3-lactone ; D-Glucuronolactone ; Dicurone ;
?Glucoxy ; Glucurolactona ; Glucurolactone ; Glucurolactonum ; Glucurono-6,3-lactone ; Glucuronolactone ; Glucuronolattone ; Glucuronosan ; Gluronsan ; Guronsan ; Reulatt S.S. ; gamma-Glukurolakton . Glucuronic acid lactone (CAS NO.32449-92-6) is a?white crystals or crystalline powder.
- 4.4 Toxicity
- Oral-rat LD50: 10700 mg/kg; Oral-Mouse LD50: >20000 mg/kg
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
32449-92-6Total: 9 Synthesis Route
9. Other Information
- 9.0 Storage Conditions
- Oxidation is fed according to the ratio of starch (m): nitric acid (67% ± 0.5%, V): water (V) = 1: 1.5: 8.5.?First put nitric acid into the oxidation kettle, start stirring, and heat to 60℃.?Add starch, (2% of the total amount), raise the temperature to 78°C within 15min for initiation, hold for 5min, then cool down to 50-60°C within 15min, add starch every 20min, divided into two (30% of the total amount) Finally, at a temperature of 47 ℃ ± 1 ℃, add starch every 25min, divided into four times (68% of the total amount).?Control the temperature to increase the average temperature of the reaction by 5°C per hour, keep it for 7-8h, the temperature reaches 68°C, discharge, add water (12% of the total amount) to the liquid, heat it with steam at 70-80°C, remove NO2 within 20min, After standing, add water (88% of the total amount) to obtain carboxy starch liquid.?Starch [HNO3, starch, water] → [47℃±1℃, 7-8h] Hydrolysis of hydroxy starch liquid The carboxyl starch liquid is pumped into the hydrolysis tank, steam is heated to 100 ℃, and yellow smoke and water vapor come out.?Then sealed, the internal pressure increased to 245.25kPa (2.5kgf/cm2), the temperature was 140-142 ℃, hydrolyzed for 2h, to obtain a hydrolysate, that is, a glucuronic acid solution.?Hydroxy starch liquid [245kPa]→[140-142℃, 2h] hydrolyzate (glucuronic acid) lactonized. The above hydrolysate was decolorized by 122 weakly acidic cation exchange resin. The decolorized liquid was pumped into the concentration tank under vacuum The temperature is about 93.33 kPa (700mmHg), below 50-60°C, and concentrated under reduced pressure until 34-36°Be.?Add 1.68 times the amount of starch glacial acetic acid into the concentrated solution, place it in an esterification tank, esterify at room temperature for 16-24h, let cool to 0-5℃ for crystallization, and filter to obtain crude glucuronolactone.?Hydrolysate [112 type resin, ice HAc] → [16-24h] Refining crude glucuronolactone According to crude product (m): distilled water (V): ethanol (V): activated carbon (m) = 1: 0.7: 0.4: 0.01-0.03 ratio of feeding.?Put the crude product and distilled water in a refining tank, heat and stir continuously to make it completely dissolved, add activated carbon to decolorize, then add ethanol, stir evenly, suction filter, the filtrate is cooled to 0-5 ℃, put it for 16h, spin filter, filter cake Wash once with absolute ethanol, spin dry, and dry below 80 ℃, that is, glucuronolactone boutique.?Crude glucuronolactone [distilled water, ethanol, activated carbon] → [0-5℃, 16h] glucuronolactone boutique.
- 9.1 Storage features
- Warehouse ventilated, low temperature and dry
- 9.2 Mesh Entry Terms
- glucuronic acid, gamma-lactone
- 9.3 Manufacturing Info
- D-Glucuronic acid, .gamma.-lactone: ACTIVE
- 9.4 Use Classification
- Cosmetics -> Skin conditioning
- 9.5 Usage
- D-Glucurono-6,3-lactone is a glucuronic acid derivative studied for its effectiveness against canine hepatitis. It is utilized in the studies such as starting regent in the synthesis of 2,3,4,-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester, required for the preparation of 1-O-acyl glucuronide of the anti-inflammatory drug ML-3000, synthesis of optically active glucopyranoses, synthesis of long-chain alkyl glucofuranosides.
10. Computational chemical data
- Molecular Weight: 176.12400g/mol
- Molecular Formula: C6H8O6
- Compound Is Canonicalized: True
- XLogP3-AA: -1.8
- Exact Mass: 176.03208797
- Monoisotopic Mass: 176.03208797
- Complexity: 202
- Rotatable Bond Count: 2
- Hydrogen Bond Donor Count: 3
- Hydrogen Bond Acceptor Count: 6
- Topological Polar Surface Area: 104
- Heavy Atom Count: 12
- Defined Atom Stereocenter Count: 4
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBgOAAAAAAAAAAAAAAAAAAAASAAAAAAAAAAAAAAAAAAAAAAGgAACAAACBSggAIACAAABgAIAAiQiAIAAAAAAAAAAAFAAAABEBYAAAACQAAFIAADAAHKbARAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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