| Glucuronolactone[1] | |
|---|---|
 |
|
| IUPAC name |
(2R)-2-[(2S,3R,4S)-3,4-Dihydroxy-5-oxo -tetrahydrofuran-2-yl]-2-hydroxy-acetaldehyde
|
| Other names | Glucuronic acid lactone |
| Identifiers | |
| CAS number | 32449-92-6 |
| PubChem | 92283 |
| SMILES |
C(=O)[C@@H]([C@@H]1[C@@H] ([C@@H](C(=O)O1)O)O)O
|
| Properties | |
| Molecular formula | C6H8O6 |
| Molar mass | 176.124 |
| Melting point |
176-178 °C |
| Solubility in water | 26.9 g/100 mL |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Glucuronolactone is a naturally occurring chemical produced by the metabolism of glucose in the human liver. It is an important structural component of nearly all connective tissues.[1] Glucuronolactone is also found in many plant gums.
It has received some notoriety due to urban legends that it was a Vietnam War-era drug manufactured by the American government. The rumor goes on to say that it was banned due to several brain tumor-related deaths. The rumor has since been proven false, as neither the cited British Medical Journal article nor the "banning of its consumption" ever occurred. Furthermore, no warnings appear on the Food and Drug Administration website regarding its potential to cause brain tumors or other maladies.[2]
Glucuronolactone is rapidly absorbed and metabolised into non-toxic metabolites such as xylulose. In addition, humans may be able to use glucuronolactone as a precursor for ascorbic acid synthesis.[3] According to "The Merck Index", it is also used as detoxicant.[4]
Glucuronolactone is a popular ingredient in energy drinks with claims that it detoxifies the body. Although levels of glucuronolactone in energy drinks can far exceed those found in the rest of the diet, the European Food Safety Authority (EFSA) has concluded that exposure to glucuronolactone from regular consumption of energy drinks is not a safety concern (No Observed Adverse Effect Level of glucuronolactone = 1,000mg/kg/day).[5]
See also
References
- ^ a b Merck Index, 11th Edition, 4362
- ^ "Bull Marketed, Snopes". http://www.snopes.com/medical/potables/redbull.asp.
- ^ Baker EM, Bierman EL, Plough IC (1960). "Effect of D-glucuronic acid and D-glucuronolactone on ascorbic acid levels in blood and urine of man and dog". Am J Clin Nutr 8: 369-73.
- ^ Merck Index, 14th ed., 4467
- ^ "EFSA adopts opinion on two ingredients commonly used in some energy drinks". http://www.efsa.europa.eu/EFSA/efsa_locale-1178620753812_1211902328128.htm.
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