D-глюкуроноваякислота

Описание

Glucuronic acid (from Ancient Greek γλυκ?? "sweet" + ο?ρον "urine") is a carboxylic acid. Its structure is similar to that of glucose. However, glucuronic acid's sixth carbon is oxidized to a carboxylic acid. Its formula is C₆H₁₀O₇. The salts and esters of glucuronic acid are known as glucuronates; the anion C₆H₉O₇^-is the glucuronate ion.

Химические свойства

White Solid

Использование

1. D-Glucuronic acid is widely distributed in the plant and animal kingdoms. D-Glucuronic acid usually occurs in "paired" form as a glycosidic combination with phenols, alcohols. Such glucuronides form in the liver to detoxify poisonous hydroxyl-containing substances. The glucuronides present in normal urine are those of phenol, cresol, and indoxyl. After the ingestion of poisons such as morphine, chloral hydrate, camphor, or turpentine, glucuronides formed with the poison or its hydroxylated derivatives appear in the urine.
2. Chiral D-Glucuronic acid is a basic building block of hyaluronic acid and chondroitin sulfate. It is a precursor to vitamin C, the chief detoxifying agent in plants and animals.
3. D-Glucuronic Acid is a sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.

Определение

ChEBI: A D-glucopyranuronic acid in which the anomeric centre has alpha-configuration.

Биологические функции

Proteoglycans Glucuronic acid is common in carbohydrate chains of proteoglycans. It is part of mucous animal secretions (such as saliva), cell glycocalyx and intercellular matrix (for instance hyaluronan))
Glucuronidation of toxic substances
In the animal body, glucuronic acid is often linked to the xenobiotic metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve glycosidic bonds, and this linkage process is known as glucuronidation. Glucuronidation occurs mainly in the liver, although the enzyme responsible for its catalysis, UDP-glucuronyltransferase, has been found in all major body organs, e.g., intestine, kidneys, brain, adrenal gland, spleen, and thymus.
Use
Determination of urinary steroids and of steroid conjugates in blood. Contained in some commercially available brands of Kombucha as an antioxidant & organic acid In all plants and mammals - other than guinea pigs and primatesglucuronic acid is a precursor of ascorbic acid , also known as vitamin c.
ConformationUnlike its C5 epimer iduronic acid, which may occur in a number of conformations, glucuronic acid occurs in predominantly the ⁴C₁ conformation.
Glucuronidases
Glucuronidases are those enzymes that hydrolyze the glycosidic bond between glucuronic acid and some other compound.

Общее описание

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Методы очистки

Crystallise the acid from EtOH or EtOAc, wash it with MeOH and dry it in vacuo to give the “ ” form. Heating converts it to the lactone (see below). The sodium salt monohydrate [207300-70-7] M 234.1 has m ~136-138o(dec) [] D 20 +21o (c 2, H2O after 2hours). [Sutter & Reichstein Helv Chim Acta 21 1210 1938, Beilstein 3 H 886, 3 IV 1997.]