{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 451565458 | Reference = <ref name="Merck">''Merck Index'', 11th Edition, '''4362'''</ref> | ImageFile = Glucuronolactone.png | ImageSize = 180 | ImageClass = skin-invert | ImageAlt = Skeletal formula | ImageFile1 = Glucuronolactone-(aldehyde)-3D-balls.png | ImageClass1 = bg-transparent | ImageSize1 = 170 | ImageAlt1 = Space-filling model | IUPACName = <small>D</small>-Glucurono-6,3-lactone | SystematicName = (2''R'')-2-[(2''S'',3''R'',4''S'')-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/cm<sup>3</sup> (30&nbsp;°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.<ref name="Merck"/> It is sometimes used in energy drinks.<ref name=":0">{{Cite web|title=V Energy|url=https://v.co.nz/products/v|access-date=2021-07-22|website=v.co.nz|language=en|archive-date=2021-07-22|archive-url=https://web.archive.org/web/20210722070230/https://v.co.nz/products/v|url-status=dead}}</ref><ref>{{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}}</ref> Unfounded claims<ref name=":1">{{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}}</ref> that glucuronolactone can be used to reduce "brain fog"<ref>{{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}}</ref> 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.<ref name="Merck"/>

== 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&nbsp;°C.<ref name="Merck"/> The compound can exist in a monocyclic aldehyde form or in a bicyclic hemiacetal (lactol) form. :[[File:Glucuronolactone-hemiacetal.svg|thumb|left|class=skin-invert-image|Lactol form of glucuronolactone]]{{clear left}}

== Uses ==

Glucuronolactone is an ingredient used in some energy drinks,<ref name=":0"/> often in unnaturally high doses. Research into Glucuronolactone is too limited to assert claims about its safety<ref>{{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}}</ref> 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.<ref name=":2" />

According to ''The Merck Index'', glucuronolactone is used as a detoxicant.<ref>''Merck Index'', 14th ed., '''4467'''</ref>

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.<ref>{{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}}</ref>

Glucuronolactone is approved in China and Japan as an over-the-counter "hepatoprotectant",<ref>{{cite web |title=KEGG Drug: Glucuronolactone |url=https://www.genome.jp/entry/D01800 |website=www.genome.jp |access-date=7 January 2024}}</ref><ref>{{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] [...] |access-date=2024-01-07 |archive-date=2024-01-07 |archive-url=https://web.archive.org/web/20240107122225/https://yp.120ask.com/detail/9391.html |url-status=dead }}</ref><ref>{{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 }}</ref> though there is a conspicuous lack of systematic reviews on this use.<ref>{{cite web |title=NCATS Inxight Drugs — Glucurolactone |url=https://drugs.ncats.io/drug/XE4Y3016M9 |website=drugs.ncats.io |language=en}}</ref>

== Safety == The EFSA evaluated the safety of D-glucurono-γ-lactone at the levels used in energy drinks, and determined it to be "not of safety concern."<ref name=":2">{{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 | quote=The Panel concludes that the exposure to taurine and D-glucurono-γ-lactone at the levels presently used in “energy” drinks and mentioned above is not of safety concern.}}</ref> 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.<ref name=":1" /><ref>{{cite web| url= http://www.snopes.com/medical/potables/redbull.asp|title=Bull Marketed| work=Snopes.com |date=21 January 2013 }}</ref>

== See also == * Glucuronic acid * Glucono delta-lactone * International Programme on Chemical Safety

== References == {{reflist}}

Category:Monosaccharides Category:Gamma-lactones Category:Tetrahydrofurans