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851450

Sigma-Aldrich

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
Beilstein:
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 Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
Chemical & Pharmaceutical Bulletin, 41, 1197-1197 (1993)
W C Koller et al.
Neurology, 42(9), 1807-1808 (1992-09-01)
The metabolism of oral glucurolactone to serum D-glucarate by the hepatic cytochrome P450 enzyme system was no different in 20 untreated Parkinson's disease (PD) patients as compared with 20 age- and sex-matched controls. There was no evidence for a deficit
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
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