5627-26-9

Basic information

• Product Name: (2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid
• Synonyms: (2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid;6-Oxo-D-gulonic acid;L-Glucaric acid;L-Glucosaccharic acid
• CAS NO: 5627-26-9
• Molecular Formula: C₆H₁₀O₈
• Molecular Weight: 210.1388
• Mol File: 5627-26-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid(5627-26-9)
• EPA Substance Registry System: (2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid(5627-26-9)

Safety Data

• Hazardous Substances Data: 5627-26-9(Hazardous Substances Data)

Usage

Description

(2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid is a polyhydroxy acid with the chemical formula C6H10O8. It is a tetrahydroxy derivative of adipic acid, a six-carbon dicarboxylic acid. (2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid features four hydroxyl (OH) groups attached to its carbon backbone, which contributes to its unique structure and reactivity. It is commonly utilized in the synthesis of pharmaceuticals and bioactive compounds due to these distinctive properties.

Uses

Used in Pharmaceutical Synthesis:
(2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid serves as a key intermediate in the creation of various pharmaceuticals. Its unique structure allows it to be a versatile building block for the development of new drugs, enhancing the range of treatments available for different medical conditions.
Used in Green Chemistry:
(2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid is also valuable in the field of green chemistry. Its properties make it suitable for use in sustainable chemical processes, contributing to the development of environmentally friendly practices in the chemical industry.
Used in Biodegradable Polymers Production:
(2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid plays a crucial role as an intermediate in the production of biodegradable polymers. Its involvement in the synthesis of such polymers supports the creation of eco-friendly materials that can reduce plastic pollution and environmental harm.
Used in High-Value Compounds Synthesis:
(2S,3R,4R,5R)-2,3,4,5-Tetrahydroxyadipic acid is instrumental in the synthesis of other high-value compounds, making it an important precursor in various chemical reactions. Its presence in these processes helps in generating specialty chemicals that have a broad range of applications across different industries.

Upstream product

• 157663-13-3 L-gluconic acid 
• 526-97-6 D-gluconic acid 
• 7697-37-2 nitric acid 
• 5328-37-0 L-arabinose 
• 526-95-4 gluconic acid 
• 50-99-7 D-glucose 
• 1986-15-8 α-L-guluronic acid 
• 921-60-8 L-glucose 
• 133-42-6 gluconic acid 
• 551-72-4 inositol 
• 87-89-8 D-myo-inositol 
• 133-42-6 dl-mannonic acid 
• 3588-17-8 (2E,4E)-2,4-hexadienedioic acid 
• 98221-46-6 Tetra-O-acetyl-dialdehydo-DL-ido-hexodialdose 

Downstream Products

• 7404-38-8 idaric acid bis-(N'-phenyl-hydrazide) 
• 80876-58-0 L-idaric acid 
• 33012-63-4 galactaric acid 
• 70332-45-5 L-glucuronic acid 
• 576-37-4 DL-altruronic acid 
• 113973-57-2 tetra-O-acetyl-allo-mucic acid 
• 5469-75-0 (2R,3S,4R,5S)-2,3,4,5-tetraacetoxyhexanedioic acid 

Relevant articles and documents

PROCESSES FOR PREPARING ALDARIC, ALDONIC, AND URONIC ACIDS

Various processes for preparing aldaric acids, aldonic acids, uronic acids, and/or lactone(s) thereof are described. For example, processes for preparing a C2-C7 aldaric acid and/or lactone(s) thereof by the catalytic oxidation of a C2-C7 aldonic acid and/or lactone(s) thereof and/or a C2-C7 aldose are described.

Catalytic oxidation of cellobiose over TiO2 supported gold-based bimetallic nanoparticles

A series of Au-M (M = Cu, Co, Ru and Pd) bimetallic catalysts were supported on TiO2via a deposition-precipitation (DP) method, using urea as a precipitating agent. The resulting catalysts were employed in the catalytic oxidation of cellobiose to gluconic acid and the properties of these catalysts were carefully examined using various characterization techniques. Cu-Au/TiO2 and Ru-Au/TiO2 catalysts demonstrated excellent catalytic activities in the oxidation of cellobiose to gluconic acid, though with contrasting reaction mechanisms. Complete conversion of cellobiose (100%) with a gluconic acid selectivity of 88.5% at 145 °C within 3 h was observed for reactions performed over Cu-Au/TiO2; whereas, a conversion of 98.3% with a gluconic acid selectivity of 86. 9% at 145°C within 9 h was observed for reactions performed over Ru-Au/TiO2. A reaction pathway was proposed based on the distribution of reaction products and kinetic data. It is suggested that cellobiose is converted to cellobionic acid (4-O-beta-d-glucopyranosyl-d-gluconic acid) and then gluconic acid is formed through the cleavage of the β-1,4 glycosidic bond in cellobionic acid over Cu-Au/TiO2 catalysts. On the other hand, for reactions over the Ru-Au/TiO2 catalyst, glucose was observed as the reaction intermediate and gluconic acid was formed as a result of glucose oxidation. For reactions over Co-Au/TiO2 and Pd-Au/TiO2 catalysts, fructose was observed as the reaction intermediate, along with small amounts of glucose. Co and Pd remarkably promoted the successive retro-aldol condensation reactions of fructose to glycolic acid, instead of the selective oxidation to gluconic acid. This journal is