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6322-07-2,D-Gulonic acid-1,4-lactone, CAS:6322-07-2

6322-07-2,D-Gulonic acid-1,4-lactone,
C6H10O6 / 178.14

D-Gulonic acid-1,4-lactone


D-Gulonic acid-1,4-lactone is a naturally occurring compound that is formed from L-gulonic acid and a 1,4-lactone ring. It has been shown to have inhibitory properties against the matrix metalloproteinases MMP-2 and MMP-9. It also has an effect on dehydroascorbic acid, which plays an important role in the regulation of bioavailability of vitamin C. D-Gulonic acid-1,4-lactone has been found to stimulate collagen synthesis in human skin cells, which may be due to its ability to increase the activity of enzymes such as pyruvate kinase and lactate dehydrogenase. The structural analysis of this compound reveals a pyrazole ring with two hydroxyl groups (OH).

D-Gulono-1,4-lactone is a compound that is known for its importance in various biological processes, mainly as a biosynthetic precursor for L-ascorbic acid (vitamin C). The aim of this paper is to provide a comprehensive overview of D-gulono-1,4-lactone, including its definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, and limitations and future directions.

Definition and Background

D-gulono-1,4-lactone (GULO) is a carbohydrate lactone compound that is synthesized in the liver of most mammals, including humans, and synthesized by plants, fungi, and some bacteria. GULO acts as a precursor for the biosynthesis of L-ascorbic acid (vitamin C), which is essential for maintaining health in humans and certain other animals. GULO is known as a nonessential nutrient for humans because the majority of animals can synthesize vitamin C from glucose, however, humans have lost the ability to synthesize vitamin C from glucose due to mutation in the gene encoding GULO.

Physical and Chemical Properties

GULO is a white or yellowish solid organic compound with a molecular formula of C6H10O6 and a molecular weight of 178.14 g/mol. It is a lactone, a cyclic ester, of hexose sugar d-glucose and has a five-membered ring structure. GULO is readily soluble in water and has a melting point of 148.5 to 149.5°C and a boiling point of 443.1°C.

Synthesis and Characterization

GULO can be synthesized by various methods, including the oxidation of d-glucose using various oxidizing agents, such as sodium hypochlorite or potassium permanganate, as well as the condensation of formaldehyde and l-gulonic acid. The synthesized GULO can be characterized using various analytical techniques, such as nuclear magnetic resonance (NMR) spectroscopy, x-ray crystallography, and mass spectrometry.

Analytical Methods

The most common analytical methods for GULO analysis include high-performance liquid chromatography (HPLC), liquid chromatography–mass spectrometry (LC-MS), gas chromatography (GC), and NMR spectrometry. GC can be used to determine the purity and molecular weight of GULO, while LC-MS can be used to determine its concentration in biological samples.

Biological Properties

GULO is known to play a crucial role in the biosynthesis of vitamin C, which is essential for maintaining health in humans and other animals. Vitamin C is involved in the synthesis of collagen, carnitine, and neurotransmitters, and acts as an antioxidant that protects cells from damage caused by free radicals. In addition, GULO has also been associated with the regulation of lipid metabolism, energy metabolism, and glucose homeostasis.

Toxicity and Safety in Scientific Experiments

In scientific experiments, GULO has been shown to have low toxicity, with no significant adverse effects reported in studies involving animals and humans. However, the long-term effects of GULO supplementation on human health and safety remain unknown, and further research is needed to determine its safety.

Applications in Scientific Experiments

GULO has applications in various scientific experiments, including the investigation of vitamin C biosynthesis and metabolism, the regulation of lipid and energy metabolism, and the prevention and treatment of scurvy in vitamin C deficient animals. GULO has also been used in the development of animal models for studying vitamin C metabolism and related diseases.

Current State of Research

Research on GULO is ongoing, with studies focusing on the synthesis of GULO, its biological properties, and its potential applications in various fields, including nutrition, medicine, and agriculture. Some recent studies have investigated the use of GULO as a supplement to improve vitamin C status in humans and animals, and its potential role in the treatment and prevention of chronic diseases, such as cancer and cardiovascular disease.

Potential Implications in Various Fields of Research and Industry

There are various potential implications of GULO in various fields of research and industry, including nutrition, medicine, and agriculture. GULO has the potential to be used as a supplement to improve vitamin C status in humans and animals, and its role in the prevention and treatment of diseases is being investigated. In agriculture, GULO can be used to improve the vitamin C content of crops, and as a natural preservative to extend the shelf-life of fruits and vegetables.

Limitations and Future Directions

One of the major limitations of GULO research is the lack of clarity regarding its safety for long-term use in humans. Further studies are needed to determine the long-term effects of GULO supplementation on human health and safety. In addition, more research needs to be conducted on the potential applications of GULO in various fields, and new analytical methods need to be developed for the accurate and precise measurement of GULO in biological samples.

Some of the future directions for GULO research include investigating alternative methods for the synthesis of GULO, identifying other potential biological functions of GULO in humans and other animals, and developing more effective methods for GULO analysis in biological samples. Additionally, further research is needed to establish the optimal dosage and duration of GULO supplementation for improving vitamin C status in humans and animals. Finally, the potential applications of GULO in the prevention and treatment of chronic diseases, such as cancer and cardiovascular disease, warrant further investigation.

CAS Number6322-07-2
Product NameD-Gulono-1,4-lactone
IUPAC Name(3R,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
Molecular FormulaC6H10O6
Molecular Weight178.14 g/mol
Synonymsgulonolactone, gulonolactone, (D)-isomer, gulonolactone, (L)-isomer
Canonical SMILESC(C(C1C(C(C(=O)O1)O)O)O)O
Isomeric SMILESC([C@H]([C@H]1[C@H]([C@H](C(=O)O1)O)O)O)O
CAS No: 6322-07-2 Synonyms: D-Gulonolactone MDL No: MFCD00005391 Chemical Formula: C6H10O6 Molecular Weight: 178.14

References: 1. Fleet GW, Ramsden NG, Nash RJ, Fellows LE, Jacob GS, Molyneux RJ, di Bello IC, Winchester B, Carbohydr. Res. 1990, 

205, p2692. Hajek J, Pozsgay V, Carbohydr. Res. 1999, 321, p116


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