glucuronolactone
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 451565458
| Reference = Merck Index, 11th Edition, 4362
| ImageFile = Glucuronolactone.png
| ImageSize = 180
| ImageClass = skin-invert
| ImageAlt = Skeletal formula
| ImageFile1 = Glucuronolactone-(aldehyde)-3D-balls.png
| ImageSize1 = 170
| ImageAlt1 = Space-filling model
| IUPACName = D-Glucurono-6,3-lactone
| SystematicName = (2R)-2-[(2S,3R,4S)-3,4-Dihydroxy-5-oxo-tetrahydrofuran-2-yl]-2-hydroxy-acetaldehyde
| OtherNames = Glucuronic acid lactone; Glucurone; Glucurolactone (INN); D-glucurono-gamma-lactone; glucurono-γ-lactone
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo =32449-92-6
| CASNo_Comment = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = XE4Y3016M9
| PubChem = 92283
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 83317
| SMILES = O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O
| 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
| InChIKey = UYUXSRADSPPKRZ-SKNVOMKLBS
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = UYUXSRADSPPKRZ-SKNVOMKLSA-N
}}
| Section2 = {{Chembox Properties
| C=6 | H=8 | O=6
| Appearance =
| Density =1.76 g/cm3 (30 °C)
| MeltingPtC = 176 to 178
| MeltingPt_notes =
| BoilingPt =
| Solubility =26.9 g/100 mL
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Glucuronolactone or Glucurolactone (INN) is a naturally occurring substance that is an important structural component of nearly all connective tissues. It is sometimes used in energy drinks.{{Cite web|title=V Energy|url=https://v.co.nz/products/v?|access-date=2021-07-22|website=v.co.nz|language=en}}{{Cite journal|last1=Rahnama|first1=Nader|last2=Gaeini|first2=Abbas Ali|last3=Kazemi|first3=Fahimeh|date=2010|title=The effectiveness of two energy drinks on selected indices of maximal cardiorespiratory fitness and blood lactate levels in male athletes|journal=Journal of Research in Medical Sciences |volume=15|issue=3|pages=127–132|issn=1735-1995|pmc=3082800|pmid=21526071}} Unfounded claims{{Cite web|date=2019-12-05|title=Does Glucuronolactone Boost Energy? Benefits vs. Dangers|url=https://selfhacked.com/blog/glucuronolactone/|access-date=2020-10-23|website=SelfHacked|language=en-US}} that glucuronolactone can be used to reduce "brain fog"{{Cite web|date=2015-12-10|title=Glucuronolactone Benefits & Safety in Red Bull Energy Drinks|url=https://nootriment.com/glucuronolactone/|access-date=2021-07-22|website=Nootriment – Health Supplement Reviews and Research|language=en-US}} 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.
Physical and chemical properties
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.
:File:Glucuronolactone-hemiacetal.svg form of glucuronolactone]]{{clear left}}
History
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.{{Cite journal |date=2009|title=The use of taurine and D-glucurono-gamma-lactone as constituents of the so-called "energy" drinks| journal= EFSA Journal |language= en| volume= 7|issue=2| pages= 935 |doi= 10.2903/j.efsa.2009.935|issn=1831-4732|doi-access=free}} 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.{{cite web| url= http://www.snopes.com/medical/potables/redbull.asp|title=Bull Marketed| work=Snopes.com |date=21 January 2013 }}
Uses
Glucuronolactone is an ingredient used in some energy drinks, often in unnaturally high doses. Research into Glucuronolactone is too limited to assert claims about its safety{{Cite web|title=Glucuronolactone: Uses, Side Effects, Interactions, Dosage, and Warning|url=https://www.webmd.com/vitamins/ai/ingredientmono-1624/glucuronolactone#|access-date=2020-10-23|website=www.webmd.com|language=en}} 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.
According to The Merck Index, glucuronolactone is used as a detoxicant.Merck Index, 14th ed., 4467
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.{{cite journal |vauthors=Baker EM, Bierman EL, Plough IC | title = Effect of D-glucuronic acid and D-glucuronolactone on ascorbic acid levels in blood and urine of man and dog | journal = Am J Clin Nutr | volume = 8 | pages = 369–73 | year = 1960 | issue = 3 | doi = 10.1093/ajcn/8.3.369 | pmid = 13795987}}
Glucuronolactone is approved in China and Japan as an over-the-counter "hepatoprotectant",{{cite web |title=KEGG Drug: Glucuronolactone |url=https://www.genome.jp/entry/D01800 |website=www.genome.jp |access-date=7 January 2024}}{{cite web |last1=Beijing Taiyang Pharamaceuticals |script-title=zh:葡醛内酯片说明书 |url=https://yp.120ask.com/detail/9391.html |website=yp.120ask.cot|trans-title=Package insert for Glucurolactone Tablets|quote=OTC 甲类、医保乙类 [OTC drug class A, national health insurance drug list class B] [...] }}{{cite journal |last1=Yu |first1=Z |last2=Wu |first2=F |last3=Tian |first3=J |last4=Guo |first4=X |last5=An |first5=R |title=Protective effects of compound ammonium glycyrrhizin, L‑arginine, silymarin and glucurolactone against liver damage induced by ochratoxin A in primary chicken hepatocytes. |journal=Molecular Medicine Reports |date=September 2018 |volume=18 |issue=3 |pages=2551–2560 |doi=10.3892/mmr.2018.9285 |pmid=30015927|pmc=6102706 }} though there is a conspicuous lack of systematic reviews on this use.{{cite web |title=NCATS Inxight Drugs — Glucurolactone |url=https://drugs.ncats.io/drug/XE4Y3016M9 |website=drugs.ncats.io |language=en}}