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; D-glucurono-gamma-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 ?)
Infobox references

Glucuronolactone is a naturally occurring substance that is an important structural component of nearly all connective tissues.[1] It is frequently used in energy drinks to increase energy levels and improve alertness,[2] and can also be used to reduce "brain fog" cause by various medical conditions.[3] Glucuronolactone is also found in many plant gums.[1]

Physical and chemical properties[edit]

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[edit]

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, this claim is completely false, and the quoted British Medical Journal article does not exist; furthermore, glucuronolactone has been repeatedly shown to be completely safe, and no warnings appear on the Food and Drug Administration website regarding its potential to cause brain tumors or other maladies.[4] 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.

Uses[edit]

Glucuronolactone is a popular ingredient in energy drinks because it has been shown to be effective at increasing energy levels and improving alertness.[2][5] Glucuronolactone supplementation also significantly reduces "brain fog" cause by various medical conditions.[3][6] Although levels of glucuronolactone in energy drinks can far exceed those found in the rest of the diet, glucuronolactone is extremely safe and well tolerated.[7] The European Food Safety Authority (EFSA) has concluded that exposure to glucuronolactone from regular consumption of energy drinks is not a safety concern.[2] The no-observed-adverse-effect level of glucuronolactone is 1000 mg/kg/day.[8]

Additionally, according to The Merck Index, glucuronolactone is used as a detoxicant.[9] 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.[10] Higher blood-glucuronides help remove toxins from the body, leading to the claim that energy drinks are detoxifying.[11] Free glucuronic acid (or its self-ester glucuronolactone) has less effect on detoxification than glucose,[citation needed] because the body synthesizes UDP-glucuronic acid from glucose. Therefore, sufficient carbohydrate intake provides enough UDP-glucuronic acid for detoxication,[citation needed] and foods rich in glucose are usually abundant in developed nations.

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.[12]

See also[edit]

References[edit]

  1. ^ a b c d Merck Index, 11th Edition, 4362
  2. ^ a b c "Glucuronolactone - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2020-10-23.
  3. ^ a b "Glucuronolactone Benefits & Safety in Red Bull Energy Drinks". Nootriment - Health Supplement Reviews and Research. 2015-12-10. Retrieved 2020-10-23.
  4. ^ "Bull Marketed". Snopes.
  5. ^ Quigley, Ryan (2020-01-28). "D-Glucuronolactone: Benefits, Dosage & Side Effects". BulkSupplements.com. Retrieved 2020-10-23.
  6. ^ "Does Glucuronolactone Boost Energy? Benefits vs. Dangers". SelfHacked. 2019-12-05. Retrieved 2020-10-23.
  7. ^ "Glucuronolactone: Uses, Side Effects, Interactions, Dosage, and Warning". www.webmd.com. Retrieved 2020-10-23.
  8. ^ "EFSA – Opinion of the Scientific Committee/Scientific Panel: The use of taurine and D-glucurono-gamma-lactone as constituents of the so-called "energy" drinks". European Food Safety Authority. Retrieved 2012-05-04.
  9. ^ Merck Index, 14th ed., 4467
  10. ^ "Depo-Provera (Medroxyprogesterone) Drug Information: Clinical Pharmacology – Prescribing Information at RxList". RxList. Retrieved 25 August 2015.
  11. ^ http://pilarmartinescudero.es/pdf/dopaje/Microgramredbull.pdf
  12. ^ 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. PMID 13795987.