Glucuronolactone
 |
|
-3D-balls.png) |
|
| Names | |
|---|---|
|
IUPAC name
(2R)-2-[(2S,3R,4S)-3,4-Dihydroxy-5-oxo-tetrahydrofuran-2-yl]-2-hydroxy-acetaldehyde
|
|
| Other names
Glucuronic acid lactone; Glucurone; Glucurolactone; D-Glucurono-3,6-lactone; D-glucurono-gamma-lactone
|
|
| Identifiers | |
|
3D model (JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.046.397 |
|
PubChem CID
|
|
|
|
|
|
| Properties | |
| C6H8O6 | |
| Molar mass | 176.12 g·mol−1 |
| Density | 1.76 g/cm3 (30 °C) |
| Melting point | 176 to 178 °C (349 to 352 °F; 449 to 451 K) |
| 26.9 g/100 mL | |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
 (what is   ?) |
|
| Infobox references | |
Glucuronolactone is a naturally occurring substance that is an important structural component of nearly all connective tissues. Glucuronolactone is also found in many plant gums.
Glucuronolactone is a white solid odorless compound, soluble in hot and cold water. Its melting point ranges from 176 to 178 °C. The compound can exist in a monocyclic aldehyde form or in a bicyclic hemiacetal (lactol) form.
Glucuronolactone has received some notoriety due to an urban legend that it was a Vietnam War-era drug manufactured by the American government and since banned due to brain tumor-related deaths. However, the quoted British Medical Journal article does not exist; furthermore, no warnings appear on the Food and Drug Administration website regarding its potential to cause brain tumors or other maladies. Moreover, glucuronolactone is hydrolyzed in the body (like butyrolactone) to glucuronic acid, which may be oxidized to glucaric acid, or isomerized to another hexuronic acid, so there is no reasonable toxicity mechanism.
Glucuronolactone is metabolized to glucaric acid, xylitol, and L-xylulose, and humans may also be able to use glucuronolactone as a precursor for ascorbic acid synthesis. According to The Merck Index, it is also used as a detoxicant. The liver uses glucose to create glucuronolactone, which inhibits the enzyme B-glucuronidase (metabolizes glucuronides), which should cause blood-glucuronide levels to rise. Glucuronides combine with toxic substances, such as morphine and depot medroxyprogesterone acetate, by converting them to water-soluble glucuronide-conjugates which are excreted in the urine. Theoretically, higher blood-glucuronides should help remove toxins from the body, leading to the claim that energy drinks are detoxifying. Free glucuronic acid (or its self-ester glucuronolactone) has less effect on detoxification than glucose, because the body synthesizes UDP-glucuronic acid from glucose. Therefore, sufficient carbohydrate intake provides enough UDP-glucuronic acid for detoxication, and foods rich in glucose are usually abundant in developed nations.
...
Wikipedia