Glucoronic acid

Glucuronic acid

Names
IUPAC name (2S,3S,4S,5R,6R)-3,4,5,6-​Tetrahydroxyoxane-2-carboxylic acid
Other names β-D-Glucopyranuronic acid
Identifiers
CAS Number	6556-12-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28860 N
ChemSpider	392615 Y
DrugBank	DB03156 Y
ECHA InfoCard	100.026.807
KEGG	C00191 Y
MeSH	Glucuronic+acid
PubChem CID	441478
UNII	8A5D83Q4RW Y
InChI InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1 Y Key: AEMOLEFTQBMNLQ-WAXACMCWSA-N Y InChI=1/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1 Key: AEMOLEFTQBMNLQ-WAXACMCWBB
SMILES O=C(O)[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O
Properties
Chemical formula	C6H10O7
Molar mass	194.14 g·mol−1
Melting point	159 to 161 °C (318 to 322 °F; 432 to 434 K)
Related compounds
Related uronic acids	Alluronic acid, Altruronic acid, Arabinuronic acid, Fructuronic acid, Galacturonic acid, Guluronic acid, Iduronic acid, Lyxuronic acid, Mannuronic acid, Psicuronic acid, Riburonic acid, Ribuluronic acid, Sorburonic acid, Tagaturonic acid, Taluronic acid, Xyluluronic acid, Xyluronic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Glucuronic acid (from Ancient Greek γλυκύς "sweet" + οὖρον "urine") is a uronic acid that was first isolated from urine (hence the name). It is found in many gums such as gum arabic (c. 18%) and xanthan, and is important for the metabolism of microorganisms, plants and animals.

Glucuronic acid is a sugar acid derived from glucose, with its sixth carbon atom oxidized to a carboxylic acid. In living beings, this primary oxidation occurs with UDP-α-D-glucose (UDPG), not with the free sugar.

Glucuronic acid, like its precursor glucose, can exist as a linear (carboxo-)aldohexose (<1%), or as a cyclic hemiacetal (furanose or pyranose). Aldohexoses such as D-glucose are capable of forming two furanose forms (α and β) and two pyranose forms (α and β). By the Fischer convention, glucuronic acid has two stereoisomers (enantiomers), D- and L-glucuronic acid, depending on its configuration at C-5. Most physiological sugars are of the D-configuration. Due to ring closure, cyclic sugars have another asymmetric carbon atom (C-1), resulting in two more stereoisomers, named anomers. Depending on the configuration at C-1, there are two anomers of glucuronic acid, α- and β-form. In β-D-glucuronic acid the C-1 hydroxy group is on the same side of the pyranose ring as the carboxyl group. In the free sugar acid, the β-form is prevalent (~64%), whereas in the organism, the α-form UDP-α-D-glucuronic acid (UDPGA) predominates.

Carbohydrate stereoisomers, which differ in configuration at only one (other) asymmetric C-atom, are named epimers. For example, D-mannuronic (C-2), D-alluronic (C-3), D-galacturonic (C-4), and L-iduronic acid (C-5) are epimers of glucuronic acid.