Saccharic acid
| Names | |
|---|---|
| IUPAC name
D-glucaric acid
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| Other names
(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
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| 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).
Infobox references
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Saccharic acid is a chemical compound with the formula C6H10O8. It is an aldaric acid, naturally occurring in fruits and vegetables.[3]
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.[4][5] A suitable reagent for this transformation is boiling 30% nitric acid, resulting in a yield of 50% to 65%.[5] This reaction was first described by German chemist Heinrich Kiliani in 1925.[6]
Uses
Detergents
The sodium salt has found use in dishwasher detergents, where it acts as a chelating agent for calcium and magnesium ions.[6] It is considered more environmentally friendly than phosphates, which are more commonly encountered in detergent formulations.[6][7]
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).[3] Some studies have demonstrated saccharolactone to have anticancerogenic properties.[8][9]
See also
References
- ^ "Human Metabolome Database: Showing metabocard for Glucaric acid (HMDB0000663)". www.hmdb.ca. Retrieved 2025-06-17.
- ^ a b PubChem. "Glucaric Acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-06-17.
- ^ a b Shendurse, A. M.; Khedkar, C. D. (2016-01-01), Caballero, Benjamin; Finglas, Paul M.; Toldrá, Fidel (eds.), "Glucose: Properties and Analysis", Encyclopedia of Food and Health, Oxford: Academic Press, pp. 239–247, ISBN 978-0-12-384953-3, retrieved 2025-06-17
- ^ "Medical Definition of SACCHARIC ACID". Webster's Medical Dictionary. Retrieved 2023-03-16.
- ^ a b BeMiller, James N. (2019-01-01), BeMiller, James N. (ed.), "2 - Carbohydrate Reactions", Carbohydrate Chemistry for Food Scientists (Third Edition), AACC International Press, pp. 25–48, ISBN 978-0-12-812069-9, retrieved 2025-06-17
- ^ a b c "D-Glucaric acid". American Chemical Society. Retrieved 2025-06-17.
- ^ Kogawa, Ana Carolina; Cernic, Beatriz Gamberini; do Couto, Leandro Giovanni Domingos; Salgado, Hérida Regina Nunes (February 2017). "Synthetic detergents: 100 years of history". Saudi Pharmaceutical Journal. 25 (6): 934–938. doi:10.1016/j.jsps.2017.02.006. PMC 5605839. PMID 28951681.
- ^ Saluk-Juszczak, Joanna; Olas, Beata; Nowak, Paweł; Staroń, Agnieszka; Wachowicz, Barbara (2008-07-01). "Protective effects of d-glucaro-1,4-lactone against oxidative modifications in blood platelets". Nutrition, Metabolism and Cardiovascular Diseases. 18 (6): 422–428. doi:10.1016/j.numecd.2007.02.016. ISSN 0939-4753.
- ^ Walaszek, Z. (1990-10-08). "Potential use of d-glucaric acid derivatives in cancer prevention". Cancer Letters. 54 (1): 1–8. doi:10.1016/0304-3835(90)90083-A. ISSN 0304-3835.