Saccharic acid

Saccharic acid
Names
	IUPAC name D-glucaric acid
	Other names (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
Identifiers
CAS Number	87-73-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16002 ;
ChemSpider	30577 ;
ECHA InfoCard	100.001.608
PubChem CID	33037;
UNII	QLZ991V4A2 ;
CompTox Dashboard (EPA)	DTXSID60859455 ;
	InChI 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 Key: DSLZVSRJTYRBFB-LLEIAEIESA-N ; 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;
	SMILES O=C(O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O;
Properties
Chemical formula	C6H10O8
Molar mass	210.1388
Melting point	125-126 °C (decomposes)
Solubility in water	912 g/L
Acidity (pKa)	pKa1 = 3.01; pKa2 = 3.94
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H228, H314
Precautionary statements	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). verify (what is ?) Infobox references

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

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]

References

↑ "Human Metabolome Database: Showing metabocard for Glucaric acid (HMDB0000663)". www.hmdb.ca. Retrieved 2025-06-17.
1 2 PubChem. "Glucaric Acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-06-17.
↑ Shendurse, A.M.; Khedkar, C.D. (2016). "Glucose: Properties and Analysis". Encyclopedia of Food and Health. Elsevier. pp. 239–247. doi:10.1016/b978-0-12-384947-2.00353-6. ISBN 978-0-12-384953-3. Retrieved 2025-08-10.
1 2 Shendurse, A. M.; Khedkar, C. D. (2016-01-01), "Glucose: Properties and Analysis", in Caballero, Benjamin; Finglas, Paul M.; Toldrá, Fidel (eds.), 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.
1 2 BeMiller, James N. (2019-01-01), "2 - Carbohydrate Reactions", in BeMiller, James N. (ed.), Carbohydrate Chemistry for Food Scientists (Third Edition), AACC International Press, pp. 25–48, ISBN 978-0-12-812069-9, retrieved 2025-06-17
1 2 3 "D-Glucaric acid". American Chemical Society. 2017-06-27. Archived from the original on 2025-05-19. Retrieved 2025-10-26.
↑ 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. PMID 17933501.
↑ 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. PMID 2208084.
↑ 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.

External links

Media related to Glucaric acid at Wikimedia Commons

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[1] "Human Metabolome Database: Showing metabocard for Glucaric acid (HMDB0000663)". www.hmdb.ca. Retrieved 2025-06-17.

[PubChem-2] 1 2 PubChem. "Glucaric Acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-06-17.

[x826-3] Shendurse, A.M.; Khedkar, C.D. (2016). "Glucose: Properties and Analysis". Encyclopedia of Food and Health. Elsevier. pp. 239–247. doi:10.1016/b978-0-12-384947-2.00353-6. ISBN 978-0-12-384953-3. Retrieved 2025-08-10.

[:1-4] 1 2 Shendurse, A. M.; Khedkar, C. D. (2016-01-01), "Glucose: Properties and Analysis", in Caballero, Benjamin; Finglas, Paul M.; Toldrá, Fidel (eds.), 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.

[:2-6] 1 2 BeMiller, James N. (2019-01-01), "2 - Carbohydrate Reactions", in BeMiller, James N. (ed.), Carbohydrate Chemistry for Food Scientists (Third Edition), AACC International Press, pp. 25–48, ISBN 978-0-12-812069-9, retrieved 2025-06-17

[:0-7] 1 2 3 "D-Glucaric acid". American Chemical Society. 2017-06-27. Archived from the original on 2025-05-19. Retrieved 2025-10-26.

[Kogawa_2017-8] 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. PMID 17933501.

[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. PMID 2208084.

[q288-11] 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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