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G2354

Sigma-Aldrich

α-D(+)-Glucose pentaacetate

99%

Synonym(s):

1,2,3,4,6-Penta-O-acetyl-α-D-glucopyranose

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About This Item

Empirical Formula (Hill Notation):
C16H22O11
CAS Number:
604-68-2
Molecular Weight:
390.34
Beilstein:
98852
EC Number:
210-073-2
MDL number:
MFCD00064071
UNSPSC Code:
12164502
PubChem Substance ID:
24895094
NACRES:
NA.22

Assay

99%

optical activity

[α]20/D ≥+98°, c = 1 in ethanol

mp

109-111 °C (lit.)

SMILES string

CC(=O)OC[C@H]1O[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI

1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15-,16+/m1/s1

InChI key

LPTITAGPBXDDGR-LJIZCISZSA-N

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General description

α-D(+)-Glucose pentaacetate also known as 1,2,3,4,6-penta-O-acetyl-α-D-glucopyranose, is an acetylated sugar that has wide applications in organic synthesis.

Application

α-D(+)-Glucose pentaacetate is used as a model compound to study the stereochemistry of carbohydrates through spectroscopic techniques such as Vibrational circular dichroism (VCD). Additionally, it has been used as a standard in the analysis of monosaccharide and polysaccharide components by gas chromatography.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1A

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Analysis of polysaccharides and monosaccharides in the root mucilage of maize (Zea mays L.) by gas chromatography
HI Osborn
Journal of Chromatography A, 831, 267-276 (1999)
Acetate groups as probes of the stereochemistry of carbohydrates: a vibrational circular dichroism study
PK Bose
Carbohydrate Research, 322, 135-141 (1999)
Somayeh Keshtkar et al.
Stem cells international, 2020, 8857457-8857457 (2021-01-01)
Protection of isolated pancreatic islets against hypoxic and oxidative damage-induced apoptosis is essential during a pretransplantation culture period. A beneficial approach to maintain viable and functional islets is the coculture period with mesenchymal stem cells (MSCs). Hypoxia preconditioning of MSCs
W J Malaisse et al.
The American journal of physiology, 275(6 Pt 1), E993-E1006 (1998-12-09)
The metabolism of beta-L-glucose pentaacetate and its interference with the catabolism of L-[U-14C]glutamine, [U-14C]palmitate, D-[U-14C]glucose, and D-[5-3H]glucose were examined in rat pancreatic islets. Likewise, attention was paid to the effects of this ester on the biosynthesis of islet peptides, the
Shaji K Chacko et al.
Journal of applied physiology (Bethesda, Md. : 1985), 104(4), 944-951 (2008-01-12)
We report a new method to measure the fraction of glucose derived from gluconeogenesis using gas chromatography-mass spectrometry and positive chemical ionization. After ingestion of deuterium oxide by subjects, glucose derived from gluconeogenesis is labeled with deuterium. Our calculations of
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