14362-29-9

Basic information

• Product Name: α-D-glucurono-γ-lactone
• Synonyms: α-D-glucurono-γ-lactone
• CAS NO: 14362-29-9
• Molecular Weight: 176.126
• Mol File: 14362-29-9.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: α-D-glucurono-γ-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: α-D-glucurono-γ-lactone(14362-29-9)
• EPA Substance Registry System: α-D-glucurono-γ-lactone(14362-29-9)

Safety Data

• Hazardous Substances Data: 14362-29-9(Hazardous Substances Data)

Usage

General Description

α-D-glucurono-γ-lactone, also known as gluconolactone, is a chemical compound that is structurally similar to glucose and is derived from glucose through a process of oxidation. It is commonly used in the food industry as a food additive and preservative, as well as in the cosmetic industry as an ingredient in skincare products. It is also used in medical and pharmaceutical applications, particularly as a precursor in the synthesis of vitamin C. Gluconolactone is a mild acid and is often used as a pH adjuster in cosmetic formulations. It also has antioxidant properties and is believed to offer gentle exfoliating and hydrating effects when applied to the skin. Due to its ability to chelate metal ions, it is also commonly used in metal ion detection and complexation studies.

Upstream product

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

Downstream Products

• 82228-14-6 methyl D-glucopyranuronate 
• 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 
• 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 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 43139-78-2 5-(N-benzyloxycarbonyl)amino-5-deoxy-1,2-O-isopropylidene-β-L-iduronolactone 
• 302593-22-2 2R,3R,4R-dihydroxyproline 
• 43139-79-3 5-(N-benzyloxycarbonyl)amino-5-deoxy-D-glucuronolactone 
• 43139-79-3 5-(N-benzyloxycarbonyl)amino-5-deoxy-L-iduronolactone 
• 54612-59-8 5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranurono-6,3-lacton 
• 150607-94-6 methyl 1,2,3,4-tetra-O-isobutyryl-β-D-glucopyranuronate 
• 1256381-91-5 C₂₁H₃₀Cl₂N₂O₆ 

Relevant articles and documents

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.

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.