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

General Description

2,3-Diketo-L-gulonic acid is a organic compound that is a key intermediate in the biosynthesis of L-ascorbic acid, also known as vitamin C. It is an important chemical component in the pharmaceutical and food industries, where it is used in the production of vitamin C supplements and fortified foods. 2,3-Diketo-L-gulonic acid is synthesized through a series of enzymatic reactions in plants and some animals, and is also produced through microbial fermentation. It is a highly sought-after chemical due to its essential role in the synthesis of vitamin C, which is a crucial nutrient for human health and development.

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

• 33012-61-2 2,3-bis-(2,4-dinitro-phenylhydrazono)-L_g-threo-2,3-dideoxy-hexonic acid 
• 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) 

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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