3445-22-5

Basic information

• Product Name: 2,3-Diketo-L-gulonic acid
• Synonyms: 2,3-Diketo-L-gulonic acid;2,3-Dioxo-2,3-dideoxy-L-gulonic acid;2,3-L-Diketogulonate;2,3-L-Diketogulonic acid;L-threo-2,3-Hexodiurosonic acid;2,3-Diketo-L-gluonic acid
• CAS NO: 3445-22-5
• Molecular Formula: C₆H₈O₇
• Molecular Weight: 192.12
• Mol File: 3445-22-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 580.3°C at 760 mmHg
• Flash Point: 318.8°C
• Appearance: /
• Density: 1.751g/cm³
• Vapor Pressure: 6.99E-16mmHg at 25°C
• Refractive Index: 1.569
• PKA: 1.22±0.54(Predicted)
• CAS DataBase Reference: 2,3-Diketo-L-gulonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Diketo-L-gulonic acid(3445-22-5)
• EPA Substance Registry System: 2,3-Diketo-L-gulonic acid(3445-22-5)

Safety Data

• Hazardous Substances Data: 3445-22-5(Hazardous Substances Data)

Usage

Description

2,3-Diketo-L-gulonic acid is an organic compound that serves as a key intermediate in the biosynthesis of L-ascorbic acid, commonly known as vitamin C. It is a significant chemical component in the pharmaceutical and food industries, playing a crucial role in the production of vitamin C supplements and fortified foods. Synthesized through enzymatic reactions in plants and some animals, as well as through microbial fermentation, 2,3-Diketo-L-gulonic acid is highly sought after due to its essential role in vitamin C synthesis, which is vital for human health and development.

Uses

Used in Pharmaceutical Industry:
2,3-Diketo-L-gulonic acid is used as a precursor for the production of vitamin C supplements, which are essential for maintaining good health and supporting the immune system. It is also used in the development of pharmaceutical formulations that require vitamin C as an active ingredient.
Used in Food Industry:
2,3-Diketo-L-gulonic acid is used as a fortifying agent in various food products to enhance their vitamin C content. This helps to improve the nutritional value of these foods and contributes to a balanced diet.
Used in Microbial Fermentation:
2,3-Diketo-L-gulonic acid is used as a substrate in microbial fermentation processes to produce vitamin C. This method is an efficient and sustainable way to obtain large quantities of the compound for commercial use.
Used in Enzymatic Synthesis:
2,3-Diketo-L-gulonic acid is used as a starting material in enzymatic synthesis processes, where it is converted into vitamin C through a series of enzymatic reactions. This method allows for the production of high-quality vitamin C with minimal environmental impact.

InChI:InChI=1/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)/t2-,3+/m0/s1

Upstream product

• 50-81-7 ascorbic acid 
• 490-83-5 L-dehydroascorbic acid 

Downstream Products

• 50-81-7 ascorbic acid 
• 144-62-7 oxalic acid 
• 7732-18-5 water 
• 490-83-5 L-dehydroascorbic acid 
• 18485-91-1 dehydro-L-ascorbic acid bis((2,4-dinitrophenyl)hydrazone) 
• 33012-61-2 2,3-bis-(2,4-dinitro-phenylhydrazono)-L_g-threo-2,3-dideoxy-hexonic acid 

Relevant articles and documents

Variation in ascorbic acid oxidation routes in H2O2 and cupric ion solution as determined by GC/MS

Recent reports have suggested that ascorbic acid protects low-density lipoprotein from peroxide-induced oxidation, but does not protect and may actually function as a prooxidant in the presence of cupric ions. However, dehydroascorbic acid, (the first oxidation product of ascorbic acid) has been shown to protect low-density lipoprotein from cupric ion oxidation but not peroxide-induced oxidation. We have examined the degradation of ascorbic acid, uniformly labeled [13C6]ascorbic acid, and [6,6-2H2]ascorbic acid in hydrogen peroxide and cupric ion solutions using gas chromatography/mass spectrometry to determine products and routes of oxidation using different oxidant sources. We have found that hydrogen peroxide leads to the formation of a six-carbon product with a mass increment of 32 (a double oxygen addition) relative to ascorbic acid, consistent with the oxidation sequence of ascorbic acid (mass 176) going to dehydroascorbic acid (mass 174) to 2,3-diketogulonic acid (mass 192) to 2,3-diketo-4,5,5,6-tetrahydroxyhexanoic acid (mass 208). Cupric ion solutions, on the other hand, do not appear to induce significant amounts of 2,3-diketo-4,5,5,6-tetrahydroxyhexanoic acid but rather lead to the formation of a threo-hexa-2,4-dienoic acid lactone (mass 174) as the major six-carbon species. These data suggest that different oxidation stresses lead to solutions containing different ascorbic acid oxidation products. These ascorbic acid-derived species could, in turn, interact differently with other substances in the aqueous environment, including free metal ions and low-density lipoprotein. This may help explain previous reports showing divergent protective effects of ascorbic acid and dehydroascorbic acid on low-density lipoprotein when different oxidation methods are used.

Iron-mediated cleavage of C-C bonds in vicinal tricarbonyl compounds in water

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