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Glucuronolactone

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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 100.046.397 Edit this at Wikidata
UNII
  • 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).
☒N verify (what is checkY☒N ?)

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

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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.

Lactol form of glucuronolactone

History

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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.[6] 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][7]

Uses

[edit]

Glucuronolactone is an ingredient used in some energy drinks[2] Although levels of glucuronolactone in energy drinks can far exceed those found in the rest of the diet. Research into Glucuronolactone is too limited to assert claims about its safety[8] 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.[6]

According to The Merck Index, glucuronolactone is used as a detoxicant.[9]

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.[10]

Glucuronolactone is approved in China and Japan as an over-the-counter "hepatoprotectant",[11][12][13] though there is a conspicuous lack of systematic reviews on this use.[14]

See also

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References

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  1. ^ a b c d Merck Index, 11th Edition, 4362
  2. ^ a b "V Energy". v.co.nz. Retrieved 2021-07-22.
  3. ^ Rahnama, Nader; Gaeini, Abbas Ali; Kazemi, Fahimeh (2010). "The effectiveness of two energy drinks on selected indices of maximal cardiorespiratory fitness and blood lactate levels in male athletes". Journal of Research in Medical Sciences. 15 (3): 127–132. ISSN 1735-1995. PMC 3082800. PMID 21526071.
  4. ^ a b "Does Glucuronolactone Boost Energy? Benefits vs. Dangers". SelfHacked. 2019-12-05. Retrieved 2020-10-23.
  5. ^ "Glucuronolactone Benefits & Safety in Red Bull Energy Drinks". Nootriment - Health Supplement Reviews and Research. 2015-12-10. Retrieved 2021-07-22.
  6. ^ a b "The use of taurine and D-glucurono-gamma-lactone as constituents of the so-called "energy" drinks". EFSA Journal. 7 (2): 935. 2009. doi:10.2903/j.efsa.2009.935. ISSN 1831-4732.
  7. ^ "Bull Marketed". Snopes.com. 21 January 2013.
  8. ^ "Glucuronolactone: Uses, Side Effects, Interactions, Dosage, and Warning". www.webmd.com. Retrieved 2020-10-23.
  9. ^ Merck Index, 14th ed., 4467
  10. ^ 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 (3): 369–73. doi:10.1093/ajcn/8.3.369. PMID 13795987.
  11. ^ "KEGG DRUG: Glucuronolactone". www.genome.jp. Retrieved 7 January 2024.
  12. ^ Beijing Taiyang Pharamaceuticals. 葡醛内酯片说明书 [Package insert for Glucurolactone Tablets]. yp.120ask.cot. OTC 甲类、医保乙类 [OTC drug class A, national health insurance drug list class B] [...]
  13. ^ Yu, Z; Wu, F; Tian, J; Guo, X; An, R (September 2018). "Protective effects of compound ammonium glycyrrhizin, L‑arginine, silymarin and glucurolactone against liver damage induced by ochratoxin A in primary chicken hepatocytes". Molecular Medicine Reports. 18 (3): 2551–2560. doi:10.3892/mmr.2018.9285. PMC 6102706. PMID 30015927.
  14. ^ "NCATS Inxight Drugs — GLUCUROLACTONE". drugs.ncats.io.
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