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Merck
CN

G2354

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
UNSPSC Code:
12164502
NACRES:
NA.22
PubChem Substance ID:
24895094
EC Number:
210-073-2
Beilstein/REAXYS Number:
98852
MDL number:
MFCD00064071

Key Documents

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Quality Level

200

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

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.

signalword

Warning

hcodes

H317

pictograms

Exclamation mark
GHS07

Hazard Classifications

Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB7249
SDBB6186
SDBB0977
STBL0150
STBK3789

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Acetate groups as probes of the stereochemistry of carbohydrates: a vibrational circular dichroism study
PK Bose
Carbohydrate Research, 322, 135-141 (1999)
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)
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
Monosaccharide esters: new tools in biomedical research.
W J Malaisse
Molecular genetics and metabolism, 65(2), 129-142 (1998-10-27)
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
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Global Trade Item Number

SKUGTIN
G2354-100G04061833628812
G2354-25G04061833317730

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