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

Last updated June 24, 2025

Saccharic acid is a chemical compound with the formula C₆H₁₀O₈. It is an aldaric acid, naturally occurring in fruits and vegetables.^[3]

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]

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.
1 2 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.
1 2 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
1 2 3 "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.

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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.

[:1-3] 1 2 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

[4] "Medical Definition of SACCHARIC ACID". Webster's Medical Dictionary. Retrieved 2023-03-16.

[:2-5] 1 2 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

[:0-6] 1 2 3 "D-Glucaric acid". American Chemical Society. Retrieved 2025-06-17.

[Kogawa_2017-7] 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.

[8] 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.

[9] 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.

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