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851450

Sigma-Aldrich

D-(+)-Glucuronic acid γ-lactone

≥99%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C6H8O6
Número de CAS:
32449-92-6
Peso molecular:
176.12
Beilstein/REAXYS Number:
83595
EC Number:
251-053-3
MDL number:
MFCD00135622
UNSPSC Code:
12352115
PubChem Substance ID:
24888207
NACRES:
NA.22

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

11 - Combustible Solids

wgk_germany

WGK 2

ppe

Eyeshields, Gloves, type N95 (US)

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Rec. Trav. Chim., 113, 79-79 (1994)
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.
Benjamin J Ayers et al.
The Journal of organic chemistry, 77(18), 7777-7792 (2012-08-30)
The enantiomers of glucuronolactone are excellent chirons for the synthesis of the 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidine ring by nitrogen substitution at C2 and C5, with either retention or inversion of configuration; the stereochemistry at C3 may
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
L A Reyner et al.
Physiology & behavior, 75(3), 331-335 (2002-03-19)
Driver sleepiness is a major cause of serious road crashes. Coffee is often used as an effective countermeasure to driver sleepiness. However, the caffeine levels in coffee are variable, whereas certain proprietary "functional energy drinks" (FEDs) contain known levels of
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