4Omethylglucuronic

4-O-methylglucuronic acid, also referred to as 4-O-methyl-D-glucuronic acid, is a derivative of D-glucuronic acid in which the hydroxyl group at the 4-position is converted to a methoxy ether. It is an O-methyl ether of a uronic sugar and is primarily of interest in carbohydrate chemistry as a protected or modified glucuronic unit.

Chemically, it retains the carboxyl group characteristic of glucuronic acid and forms furanose or pyranose rings in solution. The introduction of a methoxy group at C4 reduces the number of hydrogen-bond donors at that position and can influence anomeric equilibria, solubility, and reactivity in subsequent glycosylation steps. The compound is typically polar and water-soluble.

Natural occurrence is limited; 4-O-methylglucuronic acid is not widely reported as a common metabolite in plants or animals. It is more often encountered as a synthetic intermediate or building block in carbohydrate synthesis, produced by selective O-methylation of protected D-glucuronic acid derivatives, followed by deprotection. Common strategies include the use of methylating agents on a 4-protected glucuronic acid precursor.

Applications include serving as a protected sugar unit in the construction of oligosaccharides and glycoconjugate mimics, as well as in studies of glycosidic bond formation and enzymatic glucuronidation models. Its use is specialized and typically limited to research or medicinal chemistry contexts.

Safety and handling follow general carbohydrate chemistry guidelines. The compound should be handled with appropriate protective equipment, and standard precautions for chemical synthesis should be observed. Detailed hazard data are not widely published.