Glucuronolactone

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Glucuronolactone[1]
Skeletal formula
Space-filling model
Names
IUPAC name
D-Glucurono-6,3-lactone
Systematic 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 (INN); D-glucurono-gamma-lactone; glucurono-γ-lactone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h1-5,8-10H/t2-,3+,4-,5+/m0/s1 N
    Key: UYUXSRADSPPKRZ-SKNVOMKLSA-N N
  • InChI=1/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h1-5,8-10H/t2-,3+,4-,5+/m0/s1
    Key: UYUXSRADSPPKRZ-SKNVOMKLBS
  • O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O
Properties
C6H8O6
Molar mass 176.124 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).

Glucuronolactone or Glucurolactone (INN) is a naturally occurring substance that is an important structural component of nearly all connective tissues.[1] It is sometimes used in energy drinks.[2][3] Unfounded claims[4] that glucuronolactone can be used to reduce "brain fog"[5] are based on research conducted on energy drinks that contain other active ingredients that have been shown to improve cognitive function, such as caffeine. Glucuronolactone is also found in many plant gums.[1]

Physical and chemical properties

[edit | edit source]

Glucuronolactone is a white solid odorless compound, soluble in hot and cold water. Its melting point ranges from 176 to 178 °C.[1] The compound can exist in a monocyclic aldehyde form or in a bicyclic hemiacetal (lactol) form.

File:Glucuronolactone-hemiacetal.svg
Lactol form of glucuronolactone

Glucuronolactone is an ingredient used in some energy drinks,[2] often in unnaturally high doses. Research into Glucuronolactone is too limited to assert claims about its safety[6] The European Food Safety Authority (EFSA) has concluded that it is unlikely that glucurono-γ-lactone would have any interaction with caffeine, taurine, alcohol or the effects of exercise. The Panel also concluded, based on the data available, that additive interactions between taurine and caffeine on diuretic effects are unlikely.[7]

According to The Merck Index, glucuronolactone is used as a detoxicant.[8]

Glucuronolactone is also metabolized to glucaric acid, xylitol, and L-xylulose, and humans may also be able to use glucuronolactone as a precursor for ascorbic acid synthesis.[9]

Glucuronolactone is approved in China and Japan as an over-the-counter "hepatoprotectant",[10][11][12] though there is a conspicuous lack of systematic reviews on this use.[13]

Safety

[edit | edit source]

It is unknown if glucuronolactone is safe for human consumption due to a lack of proper human or animal trials. However, it likely has limited effects on the human body.[7] Furthermore research on isolated supplements of glucuronolactone is limited, no warnings appear on the Food and Drug Administration website regarding its potential to cause brain tumors or other maladies.[4][14]

See also

[edit | edit source]

References

[edit | edit source]
  1. ^ a b c d Merck Index, 11th Edition, 4362
  2. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  4. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  5. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  6. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  7. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  8. ^ Merck Index, 14th ed., 4467
  9. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  10. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  11. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  12. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  13. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  14. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).