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Saccharic acid

Saccharic acid
Names
IUPAC name
D-glucaric acid
Other names
(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.608 Edit this at Wikidata
UNII
  • InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1 checkY
    Key: DSLZVSRJTYRBFB-LLEIAEIESA-N checkY
  • InChI=1/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1
    Key: DSLZVSRJTYRBFB-LLEIAEIEBD
  • O=C(O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O
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:
GHS02: FlammableGHS05: Corrosive
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).
☒N verify (what is checkY☒N ?)

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]

The salts of saccharic acid are called saccharates or glucarates.

Synthesis

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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

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Detergents

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See also: Phosphates in detergent

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

[edit]
See also: Calcium D-glucarate

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]

See also

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References

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  1. ^ "Human Metabolome Database: Showing metabocard for Glucaric acid (HMDB0000663)". www.hmdb.ca. Retrieved 2025-06-17.
  2. ^ a b PubChem. "Glucaric Acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-06-17.
  3. ^ Shendurse, A.M.; Khedkar, C.D. (2016). "Glucose: Properties and Analysis". Encyclopedia of Food and Health. Elsevier. p. 239–247. doi:10.1016/b978-0-12-384947-2.00353-6. ISBN 978-0-12-384953-3. Retrieved 2025-08-10.
  4. ^ 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
  5. ^ "Medical Definition of SACCHARIC ACID". Webster's Medical Dictionary. Retrieved 2023-03-16.
  6. ^ 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
  7. ^ a b c "D-Glucaric acid". American Chemical Society. Retrieved 2025-06-17.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ Ayyadurai, V. A. Shiva; Deonikar, Prabhakar; Fields, Christine (2023-02-01). "Mechanistic Understanding of D-Glucaric Acid to Support Liver Detoxification Essential to Muscle Health Using a Computational Systems Biology Approach". Nutrients. 15 (3): 733. doi:10.3390/nu15030733. ISSN 2072-6643. PMC 9921405. PMID 36771439.

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