Common NameD-glucarate
DescriptionGlucaric acid, also known as glucarate or D-saccharic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucaric acid is a sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups. D-glucaric acid is found in fruits, vegetables, and mammals. The highest concentrations of glucaric acid are found in grapefruits, apples, oranges, and cruciferous vegetables (PMID: 18772850 ). Glucaric acid is produced through the oxidation of glucose. Cytochrome P450 is thought to be responsible for the production of D-glucaric acid in vivo (PMID: 3779687 ). In mammals, D-glucaric acid and D-glucaro-l,4-lactone are also known end-products of the D-glucuronic acid pathway (PMID: 18772850 ). Glucaric is available as a dietary supplement in the form of calcium D-glucarate and has been studied for therapeutic purposes including cholesterol reduction and cancer chemotherapy (PMID: 9101079 ). D-Glucaric acid has a potential use as a building block for a number of polymers, including new nylons and hyperbranched polyesters. D-glucaric acid produced from D-glucose has been successfully utilized to produce a hydroxylated nylon.
Structure
Molecular FormulaC6H10O8
Average Mass210.13880
Monoisotopic Mass210.03757
IUPAC Name(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
Traditional NameSaccharic acid
CAS Registry Number87-73-0
SMILESO=C([O-])[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)[O-]
InChI IdentifierInChI=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
InChI KeyDSLZVSRJTYRBFB-LLEIAEIESA-N
CHEBI IDCHEBI:30612
HMDB IDHMDB0000663
StateSolid
Water Solubility6.31e+01 g/l
logP-1.77
logS-0.52
pKa (Strongest Acidic)2.83
pKa (Strongest Basic)-3.73
Hydrogen Acceptor Count8
Hydrogen Donor Count6
Polar Surface Area155.52 Ų
Rotatable Bond Count5
Physiological Charge-2
Formal Charge0
Refractivity38.14 m³·mol⁻¹
Polarizability16.80

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