glucuronolactone

Glucuronolactone
	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-3,6-lactone; D-glucurono-gamma-lactone
Identifiers
CAS number	32449-92-6
PubChem	92283
ChemSpider	83317
Jmol-3D images	Image 1
	SMILES O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O ;
	InChI 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 ; Key: UYUXSRADSPPKRZ-SKNVOMKLSA-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 ;
Properties
Molecular formula	C6H8O6
Molar mass	176.12 g mol−1
Density	1.76 g/cm3 (30 °C)
Melting point	176–178 °C
Solubility in water	26.9 g/100 mL
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	Infobox references

グルクロノラクトン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/02/13 10:56:16」(JST)

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Glucuronolactone is a naturally occurring chemical that is an important structural component of nearly all connective tissues.^[1] 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 urban legends that it was a Vietnam War–era drug manufactured by the American government. The rumor goes on to say that it was banned due to brain tumor–related deaths. The rumor has since been proven false, due to irreality of the cited British Medical Journal article and non-event "banning of its consumption". Furthermore, no warnings appear on the Food and Drug Administration website regarding its potential to cause brain tumors or other maladies.^[2]

Uses[edit]

Glucuronolactone is rapidly absorbed and metabolized into non-toxic metabolites such as xylulose. In addition, humans may be able to use glucuronolactone as a precursor for ascorbic acid synthesis.^[3] According to The Merck Index, it is also used as a detoxicant.^[4]

Glucuronolactone is a popular ingredient in energy drinks with claims that it detoxifies the body. Although levels of glucuronolactone in energy drinks can far exceed those found in the rest of the diet, the European Food Safety Authority (EFSA) has concluded that exposure to glucuronolactone from regular consumption of energy drinks is not a safety concern. The no-observed-adverse-effect level of glucuronolactone is 1000 mg/kg/day.^[5]

References[edit]

^ ^a ^b ^c ^d Merck Index, 11th Edition, 4362
^ "Bull Marketed". Snopes.
^ 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.
^ Merck Index, 14th ed., 4467
^ "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.

UpToDate Contents

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1. 非ホルモン性機能改善 non hormonal performance enhancement

English Journal

Positive effects of Red BullR Energy Drink on driving performance during prolonged driving.

Mets MA, Ketzer S, Blom C, van Gerven MH, van Willigenburg GM, Olivier B, Verster JC.SourceDivision of Pharmacology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB, Utrecht, The Netherlands.
Psychopharmacology.Psychopharmacology (Berl).2011 Apr;214(3):737-45. Epub 2010 Nov 10.
BACKGROUND: The purpose of this study was to examine if Red BullR Energy Drink can counteract sleepiness and driving impairment during prolonged driving.METHODS: Twenty-four healthy volunteers participated in this double-blind placebo-controlled crossover study. After 2?h of highway driving in the
PMID 21063868

Short communication: In vitro assessment of erosive potential of energy drinks.

Cavalcanti AL, Costa Oliveira M, Florentino VG, dos Santos JA, Vieira FF, Cavalcanti CL.SourceDepartment of Pediatric Dentistry, School of Dentistry, State University of Paraiba, Avenida Manoel Moraes, 471/802-Manaira 58038-230 Joao Pessoa, PB, Brazil. dralessandro@ibest.com.br
European archives of paediatric dentistry : official journal of the European Academy of Paediatric Dentistry.Eur Arch Paediatr Dent.2010 Oct;11(5):253-5.
AIM: This in vitro study was to evaluate the endogenous pH, titratable acidity, total soluble solids content (TSSC) and nonreducing sugars of energy drinks.METHODS: Nine energy drinks (Bad Boy Power Drink, Red Bull, Red Bull Sugar Free, Flying Horse, Burn, Night Power, Flash Power, Flying Horse Ligh
PMID 20932401

Japanese Journal

Degradation Kinetics of Glucuronic Acid in Subcritical Water

WANG Rongchun,NEOH Tze Loon,KOBAYASHI Takashi,MIYAKE Yasuhito,HOSODA Asao,TANIGUCHI Hisaji,ADACHI Shuji
Bioscience, biotechnology, and biochemistry 74(3), 601-605, 2010-03-23
… The formation of glucuronolactone (GlcL) during the treatment of GlcA in subcritical water was substantiated by ESI-TOF-MS and 1H NMR. …
NAID 10027552940