Common NameGalactarate
DescriptionGalactaric acid, also known as mucic acid or galactarate, 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. Technically, galactaric acid is an aldaric acid obtained by oxidation of galactose. Galactaric acid exists as a white crystalline powder, which melts at 210 - 230 oC. It is insoluble in alcohol, and nearly insoluble in cold water (1 g/300 mL) but more soluble in hot water (1 g/60 mL).. Galactaric acid exists in all living organisms, ranging from bacteria to plants to humans. In plants, galactaric acid is commonly produced or utilized as an osmorgulator (PMID: 31505987 ). Galactaric acid has been detected, but not quantified in, several different foods, such as fruits, vegetables and bovine milk. A recent large-scale dietary study found that galactaric acid can serve as a biomarker for long-term dairy intake and for the consumption of carotenoid-rich vegetables (PMID: 33566801 ). In food production, galactaric acid can be used to replace tartaric acid in self-rising flour or fizzies.
Structure
Molecular FormulaC6H10O8
Average Mass210.13880
Monoisotopic Mass210.03757
IUPAC Name(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
Traditional NameGlucaric acid
CAS Registry Number526-99-8
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-
InChI KeyDSLZVSRJTYRBFB-DUHBMQHGSA-N
CHEBI IDCHEBI:16537
HMDB IDHMDB0000639
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
Polarizability17.14

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