575-64-4

Usage

Uses

Used in Food Industry:
Mannurono-gamma-lactone is used as an acidulant and flavoring agent for its sour taste, commonly utilized in the production of soft drinks, fruit juices, and dairy products.
Used in Pharmaceutical Industry:
Mannurono-gamma-lactone is used as a potential drug delivery system and in tissue engineering applications due to its biocompatibility.
Used in Medical Research:
Mannurono-gamma-lactone is used as an area of interest for further research in the medical field, particularly for its potential anticancer activity.

InChI:InChI=1/C6H8O6/c7-1-3-4(12-5(1)9)2(8)6(10)11-3/h1-5,7-9H

Upstream product

• 6556-12-3 D-Glucuronic acid 
• 489-91-8 D-glucuronic acid 
• 69-65-8 mannitol 
• 6635-17-2 1,2,5-tri-O-acetyl-α-D-glucofuranurono-6,3-lactone 
• 15397-08-7 D-glycero-D-galacto-heptono-1,4-lactone 
• 96236-73-6 sodium 1,2-O-isopropylidene-D-glucuronate 
• 151794-98-8 3,5(R)-O-benzylidene-D-glycero-D-gulo-heptono-1,4-lactone 

Downstream Products

• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 150608-10-9 methyl 1,2,3,4-tetra-O-benzoyl-α-D-glucopyranuronate 
• 150608-11-0 methyl 1,2,3,4-tetra-O-benzoyl-β-D-glucopyranuronate 
• 6635-17-2 1,2,5-tri-O-acetyl-α/β-D-glucofuranurono-6,3-lactone 
• 82228-14-6 methyl D-glucopyranuronate 
• 98021-64-8 D-arabinurono-2,5-lactone 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 864160-21-4 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[2-(benzyl-methyl-amino)-propyl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 7057-09-2 1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose 

Relevant academic research and scientific papers

Design and synthesis by click triazole formation of paclitaxel mimics with simplified core and side-chain structures

A library of paclitaxel (taxol) mimics was obtained by a straightforward strategy involving rational design and an efficient synthesis of a simplified taxane core substitute, together with a click-chemistry combinatorial search for phenylisoserine side-chain surrogates.

Current perspectives on microwave-enhanced reactions of monosaccharides promoted by heterogeneous catalysts

Involvement of heterogeneous catalysts as promoters of carbohydrate conversions, in synergy with microwaves as the heating source, is reported. This paper deals with the application of ion-exchange resins, zeolites, clays and metal oxides as convenient mediators for key transformations of carbohydrates. A special emphasis is placed on the use of (doped) mineral supports, in solventless conditions, as clean promoters in combination with microwave dielectric heating.

Three new flavonoid glycosides, byzantionoside B 6′-O-sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula

Three new flavonoid glycosides, demethoxycentaureidin 7-O- β-D-galacturonopyranoside, pectolinarigenin 7-O- α-L-rhamnopyranosyl- (1?→4″)- β-D-glucopyranoside and 7-O- α-L-rhamnopyranosyl-(1?→4″)- β-D- glucuronopyranoside, a new megastigmane glucoside, byzantionoside B 6′-O-sulfate, and a new (Z)-hex-3-en-1-ol O-β-D-xylopyranosyl- (1″→2′)- β-D-glucopyranoside, were isolated from leaves of Ruellia patula JACQ., together with 12 known compounds, β-sitosterol glucoside, vanilloside, bioside (decaffeoyl verbascoside), acteoside (verbascoside), syringin, benzyl alcohol O- β-D-xylopyranosyl- (1″→2′)- β-D-glucopyranoside, cistanoside E, roseoside, phenethyl alcohol O- β-D-xylopyranosyl-(1″→2′)- β-D-glucopyranoside, (+)-lyoniresinol 3 α-O- β-D- glucopyranoside, isoacteoside and 3,4,5-trimethoxyphenol O- α-L- rhamnopyranosyl-(1″→6′)- β-D-glucopyranoside. Their structures were elucidated by means of spectroscopic analyses.

Degradation kinetics of glucuronic acid in subcritical water

The degradation kinetics of glucuronic acid (GlcA) under subcritical conditions from 160 to 200 °C was studied in a continuous tubular reactor. The formation of glucuronolactone (GlcL) during the treatment of GlcA in subcritical water was substantiated by ESITOF-MS and 1H NMR. The degradation of GlcA consisted of the reversible conversion of GlcA to GlcL and the irreversible degradation of the two compounds. The changes in the concentrations of GlcA and GlcL with residence time could be described by first-order kinetics. Higher temperatures accelerated the degradation of GlcA, and thus resulted in rises in the pH value. The degradation reaction of GlcL under the same conditions was also investigated. The activation energy of the reverse hydrolysis of GlcA to GlcL and that of the hydrolysis of GlcL to GlcA were determined to be 88.5 and 63.2 kJ/mol respectively. The enthalpy change in the reversible conversion between GlcA and GlcL was 25.4 kJ/mol.

Large scale synthesis of the acetonides of l-glucuronolactone and of l-glucose: easy access to l-sugar chirons

1,2-O-Isopropylidene-α-l-glucurono-3,6-lactone may be synthesized on a 100-200 g scale from cheaply available d-glucoheptonolactone in an overall yield of 94% in four steps via l-glucuronolactone. Subsequent elaboration to l-glucose, diacetone-l-glucose (1,2:5,6-di-O-isopropylidene-α-l-glucofuranose), and monoacetone-l-glucose (1,2-O-isopropylidene-α-l-glucofuranose) allows easy access to a range of l-sugar chirons.

Process for selectively oxidizing primary hydroxyl groups of organic compounds, and resin containing adsorbed catalyst for use therein

A method for selectively oxidizing the primary hydroxyl group of an organic compound which comprises reacting a resin having an amine oxide adsorbed thereon and an electrolytically oxidized product of a halogen-containing compound with the organic compound having the primary hydroxyl group.

Kinetics and mechanism of the reduction of chromium(VI) and chromium(V) by D-glucitol and D-mannitol

The oxidation of D-glucitol and D-mannitol by CrVI yields the aldonic acid (and/or the aldonolactone) and CrIII as final products when an excess of alditol over CrVI is used. The redox reaction occurs through a CrVI → CrV → CrIII path, the CrVI → CrV reduction being the slow redox step. The complete rate laws for the redox reactions are expressed by: a) - d[CrVI]/dt = {kM2H [H-]2 +kMH [H+]}[mannitol][CrVI], where kM2H = (6.7 ± 0.3) · 10-2 M-3 S-1 and kMH = (9±2) · 10-3 M-2 S-1: b) - d [CrVI] /dt = {kG2H[H+]2 + kGH [H+]}[GLUCITOL][CrVI]. where kG2H = (8.5 ± 0.2) · 10-2 M-3 S-1 and kGH = (1.8 ± 0.1) · 10-2 M-2S-1 at 330. The slow redox steps are preceded by the formation of a CrVI oxy ester with λMAX 371 nm. at pH 4.5. In acid medium, intermediate CrV reacts with the substrate faster than CrVI does. The EPR spectra show that five- and six-coordinate oxo-CrV intermediates are formed, with the alditol or the aldonic acid acting as bidentate ligands. Pentacoordinate oxo-CrV species are present at any [H+], whereas hexacoordinate ones are observed only at pH V species are not observed, CrV complexes are stable enough to remain in solution for several days to months.

Radical-based asymmetric synthesis: an iterative approach to 1, 3, 5, ... (2n + 1) polyols.

[formula: see text] A conceptually novel approach to 1, 3, 5, ... (2n + 1) polyols based on iterative stereo-controlled homologation of chiral hydroxyalkyl radicals is reported. Starting from alpha-keto ester precursors, the general sequence of (1) ketone