Saccharic acid
Chemical substance
From Wikipedia, the free encyclopedia
Saccharic acid or glucaric acid[3] is a chemical compound with the formula C6H10O8. It is an aldaric acid, naturally occurring in fruits and vegetables.[4]
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| Names | |
|---|---|
| IUPAC name
D-glucaric acid | |
| Other names
(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.608 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H10O8 | |
| Molar mass | 210.1388 |
| Melting point | 125-126 °C (decomposes) |
| 912 g/L[1] | |
| Acidity (pKa) | pKa1 = 3.01[2] pKa2 = 3.94[2] |
| Hazards | |
| GHS labelling: | |
  | |
| Danger | |
| H228, H314 | |
| P210, P240, P241, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The salts of saccharic acid are called saccharates or glucarates.
Synthesis
Saccharic acid can be prepared by oxidizing both the aldehydic and primary alcohol groups in an aldose, such as glucose, forming the dicarboxylic acid.[5][6] A suitable reagent for this transformation is boiling 30% nitric acid, resulting in a yield of 50% to 65%.[6] This reaction was first described by German chemist Heinrich Kiliani in 1925.[7]
Uses
Detergents
The sodium salt has found use in dishwasher detergents, where it acts as a chelating agent for calcium and magnesium ions.[7] It is considered more environmentally friendly than phosphates, which are more commonly encountered in detergent formulations.[7][8]
Dietary supplement
Saccharic acid salts have found use in dietary supplements, where they act as precursors to the β-glucuronidase inhibitor saccharolactone (d-glucaro-1,4-lactone).[4] Some preclinical studies have demonstrated saccharolactone to have anticancerogenic and detoxification properties, although more clinical research is needed to confirm health impacts in humans.[9][10][11]
