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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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100 G
€74.00
1 KG
€647.00

€74.00


Estimated to ship on12 April 2025


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100 G
€74.00
1 KG
€647.00

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

€74.00


Estimated to ship on12 April 2025


Request a Bulk Order

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.[1]

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.[2]
  • Synthesis of optically active glucopyranoses.[3]
  • Synthesis of long-chain alkyl glucofuranosides.[4]

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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
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
The crystal structure of beta-D-glucurono-gamma-lactone.
S H Kim et al.
Acta crystallographica, 22(5), 733-743 (1967-05-10)

Questions

  1. Does the entry for "Concentration" described as "C=x% H2O after 1 hour" equate to Loss on Drying? If not, what does this specification indicate?

    1 answer
    1. The term "Concentration" denoted as "C=x% H2O after 1 hour" refers to the duration allowed for the material to dissolve in water to reach the specified concentration. This period was implemented because there were reproducibility issues observed when the solution's concentration was measured immediately after mixing.

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