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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All Photos(3)
About This Item
Empirical Formula (Hill Notation):
C6H8O6
CAS Number:
Molecular Weight:
176.12
Beilstein:
83595
EC Number:
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
SMILES string
O=C([C@@H]([C@@H](O1)[C@H](O)[C@H](O)C1=O)O)[H]
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
InChI key
UYUXSRADSPPKRZ-SKNVOMKLSA-N
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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 Code
11 - Combustible Solids
WGK
WGK 2
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Rongchun Wang et al.
Bioscience, biotechnology, and biochemistry, 74(3), 601-605 (2010-03-09)
The degradation kinetics of glucuronic acid (GlcA) under subcritical conditions from 160 to 200 degrees C was studied in a continuous tubular reactor. The formation of glucuronolactone (GlcL) during the treatment of GlcA in subcritical water was substantiated by ESI-TOF-MS
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
Chemical & Pharmaceutical Bulletin, 41, 1197-1197 (1993)
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)
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
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