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Merck
CN

05566

D-(+)-Glucuronic acid γ-lactone

analytical standard

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:
85151701
NACRES:
NA.24
PubChem Substance ID:
329748094
EC Number:
251-053-3
Beilstein/REAXYS Number:
83595
MDL number:
MFCD00135622

Key Documents

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Product Name

D-(+)-Glucuronic acid γ-lactone, analytical standard

SMILES string

O=C([C@@H]([C@@H](O1)[C@H](O)[C@H](O)C1=O)O)[H]

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

grade

analytical standard

assay

≥99.0% (sum of anomers, GC)

optical activity

[α]/D +18.8±2°, c = 8% in H2O (after 1 hr)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

impurities

≤0.5% water

mp

172-175 °C (lit.)

application(s)

clinical testing

format

neat

Quality Level

100

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Application

D-Glucuronic acid γ-lactone has been used as an analytical standard for the analysis of D-glucuronic acid γ-lactone as a component of microbial extracellular polysaccharides in biofilms by high performance liquid chromatography (HPLC) with pulsed amperometric detection (PAD) as well as diode array detection (DAD). D-(+)-Glucuronic acid γ-lactone has been used as a reference standard for the determination of D-(+)-glucuronic acid γ-lactone in energy drinks by ultra-high performance liquid chromatography-triple quadrupole
tandem mass spectrometry (UHPLC-MS/MS).

General description

D-Glucuronic acid γ-lactone is a normal human metabolite produced from glucose as starting material. It serves as a precursor for the synthesis of a number of deoxy sugars.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK8866
BCCG4316
BCCG4314
BCCB4124
BCCB3726

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Convenient syntheses of deoxypyranose sugars from glucuronolactone.
Stanford D and Stachulski, AV
Tetrahedron Letters, 48(13), 2361-2364 (2007)
Simultaneous determination of taurine, glucuronolactone and glucuronic acid in energy drinks by ultra high performance liquid chromatography-tandem mass spectrometry (triple quadrupole).
Ricciutelli M, et al.
Journal of Chromatography A, 1364, 303-307 (2014)
Analysis of microbial extracellular polysaccharides in biofilms by HPLC. Part I: development of the analytical method using two complementary stationary phases.
Meisen S, et al.
Analytical and Bioanalytical Chemistry, 391(3), 993-993 (2008)
Clotilde d'Errico et al.
Biotechnology and bioengineering, 112(5), 914-922 (2014-11-27)
Lignin-carbohydrate complexes (LCCs) are believed to influence the recalcitrance of lignocellulosic plant material preventing optimal utilization of biomass in e.g. forestry, feed and biofuel applications. The recently emerged carbohydrate esterase (CE) 15 family of glucuronoyl esterases (GEs) has been proposed

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