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GLUCARIC ACID

GLUCARIC ACID

Prevents deposits of limescale and dirt on fabric or dishes, providing a green replacement for phosphate-based detergents.


Factfile

Name: D-Glucaric acid
Synonyms: Saccharic acid
CAS Number: 87-73-0
Molecular formula: C6H10O8
MW: 210.14 g mol-1
Patents related to synthesis: 20

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Why is it of interest?

Glucaric acid is a polyhydroxy dicarboxylic acid which is accessed from the oxidation of glucose. Glucaric acid has been known of for a long time and there are a number of applications for it directly, in addition to its use in a number of routes to bio-derived drop in replacements, such as to adipic acid for nylon 6-6 production. However, despite being identified as a significant platform molecule by the US Department of Energy, it has yet to reach its potential due to the moderate selectivity and yield of the current industrial route. If more efficient pathways can be brought to industrialisation, glucaric acid markets in food, pharmaceuticals and as a building block are expected to grow significantly.

Feedstocks

The molecular formula for glucaric acid is very similar to that of glucose, having two more oxygens and two less hydrogens, as well as preserving the chirality of the sugar. As such, any feedstock must be converted to glucose before being utilised to form glucaric acid. All chemocatalytic pathways thus far reported start from a pure glucose stream although there is no reason why more complex starches or cellulose itself could not be employed. Fermentation pathways directly to glucaric acid thus far reported have also only used glucose as the carbon source. Again there is no reason to assume other methodologies to produce free sugars would not function. Routes to gluconic acid however have been shown in good yield from a variety of feedstocks including waste paper. Gluconic acid conversion to glucaric acid can proceed in moderate yield.

Applications

The current largest market for glucaric acid is in water softening, where the chelating ability of glucaric acid has also seen it be applied in water treatment and detergent formulations. Similarly another metal scavenging application is the inclusion of glucaric acid and its salts in de-icing technologies where its presence hinders corrosion of iron/steel materials. Other uses are as a food supplement where it has been shown to have many beneficial properties. Mammalian studies showed a diet high in glucaric acid significantly reduced cholesterol levels in rats, specifically that of LDL and serum cholesterol. More significantly, it has been shown to be active in anti-cancer applications, specifically reducing levels of carcinogenesis.