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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

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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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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
H A Tajmir-Riahi
Biophysical chemistry, 27(3), 243-249 (1987-09-01)
The interaction of D-glucuronic and D-gluconic acids with cis- and trans-PtCl2(NH3)2 (cisplatin and transplatin) has been investigated in aqueous solution and solid complexes of the type cis-[PtL(NH3)2]L.H2O and trans-[PtL2(NH3)2]L.H2O, where L = D-glucuronate or D-gluconate anions, are isolated and characterized
Synthesis and biological identification of the acyl glucuronide of the antiinflammatory drug ML-3000.
Kirschning A, et al.
Bioorganic & Medicinal Chemistry Letters, 7(7), 903-906 (1997)
Matthew I Worthley et al.
The American journal of medicine, 123(2), 184-187 (2010-01-28)
Energy drink consumption has been anecdotally linked with sudden cardiac death and, more recently, myocardial infarction. As myocardial infarction is strongly associated with both platelet and endothelial dysfunction, we tested the hypothesis that energy drink consumption alters platelet and endothelial
Chemical & Pharmaceutical Bulletin, 41, 1197-1197 (1993)
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