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D-(+)-Glucuronic acid γ-lactone

analytical standard

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Synonym(s):
D-(+)-Glucurono-6,3-lactone, D-Glucurone, D-Glucurono-6,3-lactone, Glucuronolactone
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:
85151701
PubChem Substance ID:
329748094
NACRES:
NA.24

grade

analytical standard

Quality Level

100

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

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 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.

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).

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Convenient syntheses of deoxypyranose sugars from glucuronolactone.
Stanford D and Stachulski, AV
Tetrahedron Letters, 48(13), 2361-2364 (2007)
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)
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)
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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