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Merck
CN

851450

D-(+)-Glucuronic acid γ-lactone

≥99%

Synonym(s):

D-(+)-Glucurono-6,3-lactone, D-Glucurone, D-Glucurono-6,3-lactone, Glucuronolactone

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About This Item

Empirical Formula (Hill Notation):
C6H8O6
CAS Number:
32449-92-6
Molecular Weight:
176.12
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
24888207
EC Number:
251-053-3
Beilstein/REAXYS Number:
83595
MDL number:
MFCD00135622

Key Documents

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InChI key

UYUXSRADSPPKRZ-SKNVOMKLSA-N

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

SMILES string

O=C([C@@H]([C@@H](O1)[C@H](O)[C@H](O)C1=O)O)[H]

assay

≥99%

form

powder

optical activity

[α]24/D +18.8°, c = 8 in H2O

mp

172-175 °C (lit.)

solubility

water: soluble 25 mg/mL, clear, colorless

Quality Level

200

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General description

D-(+)-Glucuronic acid γ-lactone (Glucourono-γ-lactone, Glucurone or Glycurone) is a carbohydrate derivative. It converted into L-ascorbic acid in animals and human body. Its molecule contains two five-membered rings. Its crystal structure has been studied.

Application

D-(+)-Glucuronic acid γ-lactone may be used in the following studies:
  • As starting ragent in the synthesis of 2,3,4,-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester, required for the preparation of 1-O-acyl glucuronide of the anti-inflammatory drug ML-3000.
  • Synthesis of optically active glucopyranoses.
  • Synthesis of long-chain alkyl glucofuranosides.

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB6656
SDBB4637
SDBB2389
STBH1181
STBK9804

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C Alford et al.
Amino acids, 21(2), 139-150 (2001-10-23)
The effects of Red Bull Energy Drink, which includes taurine, glucuronolactone, and caffeine amongst the ingredients, were examined over 3 studies in a total of 36 volunteers. Assessments included psychomotor performance (reaction time, concentration, memory), subjective alertness and physical endurance.
Rec. Trav. Chim., 113, 79-79 (1994)
J M Hsu et al.
The Journal of nutrition, 111(1), 141-145 (1981-01-01)
The effect of feeding 0.25% ethionine for 3-10 weeks to male and female rats on urinary and tissue ascorbate contents were studied. The concentrations of ascorbic acid in the urine, blood, liver and adrenals were significantly reduced in the rats
J A Horne et al.
Amino acids, 20(1), 83-89 (2001-04-20)
500 ml of a glucose based "energy" drink versus a control without the active ingredients (caffeine, taurine, glucuronolactone) were given double blind to 11 sleepy participants driving an interactive real-car driving simulator. Lane drifting and a secondary task (reaction time)
P Florio et al.
Carbohydrate research, 328(4), 445-448 (2000-11-28)
A concise route to novel mimetics of Kdn2en, based on delta4-uronic acids, from D-glucurono-6,3-lactone is presented. Uronic acid-based mimetics in which an aliphatic ether (O-glycoside), a thioether (S-glycoside), or acetamide takes the place of the natural C-6 glycerol sidechain of
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