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32449-92-6

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32449-92-6 Usage

Chemical Properties

white crystals or crystalline powder

Uses

Different sources of media describe the Uses of 32449-92-6 differently. You can refer to the following data:
1. D-Glucurone is a glucuronic acid derivative. It is used for treating canine hepatitis.
2. 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.

Definition

The γ-lactone of glucuronic acid. Found in plant gums and animal connective tissues.

General Description

D-(+)-Glucuronic acid γ-lactone (Glucourono-γ-lactone, Glucurone or Glycurone) is a carbohydrate derivative. It converted into L-ascorbic acid in animals and human body. Its molecule contains two five-membered rings. Its crystal structure has been studied.

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 32449-92-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,2,4,4 and 9 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 32449-92:
(7*3)+(6*2)+(5*4)+(4*4)+(3*9)+(2*9)+(1*2)=116
116 % 10 = 6
So 32449-92-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O6/c7-1-3-4(12-5(1)9)2(8)6(10)11-3/h1-5,7-9H/t1-,2-,3-,4-,5-/m1/s1

32449-92-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A15861)  D-Glucurono-6,3-lactone, 99%   

  • 32449-92-6

  • 25g

  • 224.0CNY

  • Detail
  • Alfa Aesar

  • (A15861)  D-Glucurono-6,3-lactone, 99%   

  • 32449-92-6

  • 100g

  • 460.0CNY

  • Detail
  • Alfa Aesar

  • (A15861)  D-Glucurono-6,3-lactone, 99%   

  • 32449-92-6

  • 500g

  • 1956.0CNY

  • Detail
  • Sigma-Aldrich

  • (05566)  D-(+)-Glucuronicacidγ-lactone  analytical standard

  • 32449-92-6

  • 05566-100MG

  • 458.64CNY

  • Detail
  • Aldrich

  • (851450)  D-(+)-Glucuronicacidγ-lactone  ≥99%

  • 32449-92-6

  • 851450-100G-A

  • 574.47CNY

  • Detail
  • Aldrich

  • (851450)  D-(+)-Glucuronicacidγ-lactone  ≥99%

  • 32449-92-6

  • 851450-1KG-A

  • 5,757.57CNY

  • Detail

32449-92-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Glucuronolactone

1.2 Other means of identification

Product number -
Other names glucurone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:32449-92-6 SDS

32449-92-6Synthetic route

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃;A n/a
B n/a
C 5%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
untersucht wurde das Lactonisierungsgleichgewicht in wss. Loesungen vom pH 7 - 8.5;
D-glucaric acid
87-73-0

D-glucaric acid

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With sodium amalgam; sulfuric acid; water
D-myo-inositol
87-89-8

D-myo-inositol

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
beim Behandeln mit einem Enzym-Praeparat aus Ratten-Nieren;
methyl beta-D-glucopyranoside
709-50-2

methyl beta-D-glucopyranoside

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With water; oxygen; sodium hydrogencarbonate in Gegenwart von Platin und Erhitzen des Reaktionsprodukts mit wasserhaltiger Ameisensaeure;
methyl-alpha-D-glucopyranoside
97-30-3

methyl-alpha-D-glucopyranoside

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With water; oxygen; sodium hydrogencarbonate in Gegenwart von Platin und Erhitzen des Reaktionsprodukts mit wasserhaltiger Ameisensaeure;
With dinitrogen tetraoxide anschl. mit wasserhaltiger Ameisensaeure;
With tetrachloromethane; dinitrogen tetraoxide Erwaermen des nach Behandeln mit wss. H2SO4 isolierten Reaktionsprodukts mit Butan-1-ol und konz. H2SO4 und anschl. Erwaermen mit wss. H2SO4;
O1,O2-isopropylidene-α-D-glucofuranuronic acid
2671-19-4

O1,O2-isopropylidene-α-D-glucofuranuronic acid

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With hydrogenchloride; water
With water anschl. Einengen der Reaktionsloesung;
(+)-Menthol glucuronide
114127-73-0

(+)-Menthol glucuronide

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With sulfuric acid; water anschl. Einengen der von H2SO4 befreiten Reaktionsloesung;
D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With formic acid; water
1,2,3,4-tetra-O-acetyl-β-D-glucopyranose
13100-46-4

1,2,3,4-tetra-O-acetyl-β-D-glucopyranose

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With potassium permanganate; acetic acid; acetone anschl. mit Aceton und Ba(OH)2 in Wasser, Behandeln des danach isolierten Barium-Salzes mit wss. H2SO4 und anschl. Einengen der von H2SO4 befreiten wss. Reaktionsloesung;
O1-<(1Ξ)-bornyl>-β-D-glucopyranuronic acid

O1-<(1Ξ)-bornyl>-β-D-glucopyranuronic acid

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With sulfuric acid; water anschl. Einengen der von H2SO4 befreiten Reaktionsloesung;
O3,O5-benzylidene-O1,O2-isopropylidene-α-D-glucofuranuronic acid

O3,O5-benzylidene-O1,O2-isopropylidene-α-D-glucofuranuronic acid

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With hydrogenchloride; ethanol; water anschl. Einengen der Reaktionsloesung;
starch

starch

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With water; nitric acid anschl. Erhitzen mit wss. HCl auf 150grad;
Conditions
ConditionsYield
Stage #1: D-glucuronic acid With resin-bound fluoride In N,N-dimethyl-formamide for 3h;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 40℃; for 20h; Further stages. Title compound not separated from byproducts.;
3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-22-O-α-L-rhamnopyranosyl-squasapogenol

3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-22-O-α-L-rhamnopyranosyl-squasapogenol

A

L-Rhamnose
3615-41-6

L-Rhamnose

B

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With water; trifluoroacetic acid for 2h; Reflux;
3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-macedonic acid

3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-macedonic acid

A

L-Rhamnose
3615-41-6

L-Rhamnose

B

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With water; trifluoroacetic acid for 2h; Reflux;
3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-squasapogenol

3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-squasapogenol

A

L-Rhamnose
3615-41-6

L-Rhamnose

B

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With water; trifluoroacetic acid for 2h; Reflux;
6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione
123506-40-1

6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

6-{N'-[(S)-2-((2R,3R,4S)-3,4-Dihydroxy-5-oxo-tetrahydro-furan-2-yl)-2-hydroxy-eth-(Z)-ylidene]-hydrazino}-1,3-dimethyl-1H-pyrimidine-2,4-dione
69471-96-1

6-{N'-[(S)-2-((2R,3R,4S)-3,4-Dihydroxy-5-oxo-tetrahydro-furan-2-yl)-2-hydroxy-eth-(Z)-ylidene]-hydrazino}-1,3-dimethyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
In methanol for 5h; Heating;94%
D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

D-glucuronamide
22140-11-0

D-glucuronamide

Conditions
ConditionsYield
With ammonia In ethanol at 20℃; for 5h;79.6%
1,3-dimethylbarbituric acid
769-42-6

1,3-dimethylbarbituric acid

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

disodium 5-(β-D-glucopyranosyluronate)-1,3-dimethylbarbiturate
129878-35-9

disodium 5-(β-D-glucopyranosyluronate)-1,3-dimethylbarbiturate

Conditions
ConditionsYield
With sodium carbonate In water at 80℃; for 5h;77%
BARBITURIC ACID
67-52-7

BARBITURIC ACID

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

disodium 5-(β-D-glucopyranosysluronate)barbiturate
129878-34-8

disodium 5-(β-D-glucopyranosysluronate)barbiturate

Conditions
ConditionsYield
With sodium carbonate In water at 80℃; for 5h;73%
D-glucuronic acid sodium salt
24016-65-7

D-glucuronic acid sodium salt

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

disodium 5-(β-D-glucopyranosysluronate)barbiturate
129878-34-8

disodium 5-(β-D-glucopyranosysluronate)barbiturate

Conditions
ConditionsYield
With sodium carbonate In water at 80℃; for 5h;66%
acetic anhydride
108-24-7

acetic anhydride

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

A

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
7355-18-2

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

B

methyl 1,2,3,4-tetraacetyl-α-D-glucopyranuronate
5432-32-6

methyl 1,2,3,4-tetraacetyl-α-D-glucopyranuronate

Conditions
ConditionsYield
With pyridine; sodium hydroxide In methanol for 1.5h;A 39%
B 37%
Stage #1: D-glucurono-6,3-lactone With sodium In methanol at 0℃; for 5h; Inert atmosphere;
Stage #2: acetic anhydride With perchloric acid at 20 - 40℃; Inert atmosphere; Overall yield = 93 %; Overall yield = 96.5 g;
Conditions
ConditionsYield
in Gegenwart eines Kationen-Austauschers;
methanol
67-56-1

methanol

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

methyl α-D-glucofuranosidurono-6,3-lactone
17681-01-5

methyl α-D-glucofuranosidurono-6,3-lactone

Conditions
ConditionsYield
in Gegenwart eines Kationen-Austauschers;
2,6-dimethyl-pyrimidine-4-carboxylic acid hydrazide
89897-33-6

2,6-dimethyl-pyrimidine-4-carboxylic acid hydrazide

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

2,6-dimethyl-pyrimidine-4-carboxylic acid-[(S)-2-((2R)-3c,4c-dihydroxy-5-oxo-tetrahydro-[2r]furyl)-2-hydroxy-ethylLiDenehydrazide]
106275-46-1

2,6-dimethyl-pyrimidine-4-carboxylic acid-[(S)-2-((2R)-3c,4c-dihydroxy-5-oxo-tetrahydro-[2r]furyl)-2-hydroxy-ethylLiDenehydrazide]

Conditions
ConditionsYield
With ethanol
ethanol
64-17-5

ethanol

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

α-D-glucopyranuronic acid ethyl ester
13162-11-3

α-D-glucopyranuronic acid ethyl ester

Conditions
ConditionsYield
With sodium ethanolate
With basic anion-exchanger
ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Aldehydo-D-glucurono-6,3-lactone ethylene dithioacetal
72251-95-7

Aldehydo-D-glucurono-6,3-lactone ethylene dithioacetal

Conditions
ConditionsYield
With hydrogenchloride
chloral
75-87-6

chloral

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

O1,O2-((S)-2,2,2-trichloro-ethylidene)-α-D-glucofuranuronic acid-3-lactone

O1,O2-((S)-2,2,2-trichloro-ethylidene)-α-D-glucofuranuronic acid-3-lactone

Conditions
ConditionsYield
With sulfuric acid
4-nitro-aniline
100-01-6

4-nitro-aniline

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

1-(4-nitro-anilino)-1-deoxy-ξ-D-glucofuranuronic acid-3-lactone
108752-94-9

1-(4-nitro-anilino)-1-deoxy-ξ-D-glucofuranuronic acid-3-lactone

Conditions
ConditionsYield
With hydrogenchloride; methanol
With methanol; water; acetone
ethanethiol
75-08-1

ethanethiol

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

6,6-bis-ethylsulfanyl-6-deoxy-L-gulonic acid

6,6-bis-ethylsulfanyl-6-deoxy-L-gulonic acid

Conditions
ConditionsYield
With hydrogenchloride
D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With barium dihydroxide; water
With alkaline solution; water
D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

1-amino-1-deoxy-ξ-D-glucopyranuronic acid amide
3356-20-5

1-amino-1-deoxy-ξ-D-glucopyranuronic acid amide

Conditions
ConditionsYield
With ethanol; ammonia
D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

O1-methyl-ξ-D-arabinofuranuronic acid methyl ester
99094-37-8

O1-methyl-ξ-D-arabinofuranuronic acid methyl ester

Conditions
ConditionsYield
With lead(IV) acetate; acetic acid Erwaermen des Reaktionsprodukts mit Chlorwasserstoff enthaltendem Methanol;
D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
With sulfuric acid; acetone

32449-92-6Relevant articles and documents

-

Hardegger,Spitz

, p. 2165,2168 (1949)

-

-

Sowden

, p. 4377 (1952)

-

Field survey of glycyrrhiza plants in Central Asia (5). Chemical characterization of G. Bucharica Collected in Tajikistan

Hayashi, Hiroaki,Yokoshima, Keiko,Chiba, Ren,Fujii, Isao,Fattokhov, Inoyat,Saidov, Madibron

, p. 534 - 539 (2019/07/22)

One triterpene and five triterpene glycosides, including four new compounds, have been identified in the underground parts of Glycyrrhiza bucharica, which was shown to be closely related to Glycyrrhizin-producing Glycyrrhiza species, G. uralensis, G. glabra and G. inflata, based on their chloroplast rbcL sequences. Two known compounds were identified squasapogenol and macedonoside C. The structures of four new compounds, bucharosides A, B, C, and D, were determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-22-O-α-L-rhamnopyranosyl squasapogenol, 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-macedonic acid, 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-squasapogenol, and 22-O-α-L-rhamnopyranosyl squasapogenol, respectively. Contents of these triterpene glycosides were less than 0.5% of dry weight, and no main saponin, like glycyrrhizin or macedonoside C found in other Glycyrrhiza species, was found in the underground parts of G. bucharica.

Derivatives of basic polyene macrolides and their preparation

-

, (2008/06/13)

The present invention relates to basic polyene macrolide derivatives, characterized in that they comprise a basic polyene macrolide which is N-substituted by a 1-amino-1-deoxyketose group which in turn is substituted or unsubstituted, to a process for their preparation and to their use for obtaining drugs.

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