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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

InChI key

LPTITAGPBXDDGR-LJIZCISZSA-N

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

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

assay

99%

optical activity

[α]20/D ≥+98°, c = 1 in ethanol

mp

109-111 °C (lit.)

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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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)
E Olivares et al.
Cell biochemistry and function, 16(4), 233-237 (1998-12-19)
The esterification of several monosaccharides, such as D-glucose, D-mannoheptulose and 2-deoxy-D-glucose was recently reported to increase their biological efficiency as either nutrient or antimetabolic agent. In the present study, however, the tetraacetate ester of streptozotocin was unexpectedly found to be
Directed assembly of sub-nanometer thin organic materials with programmed-size nanopores.
Delia C Danila et al.
Angewandte Chemie (International ed. in English), 47(37), 7036-7039 (2008-08-05)
K Louchami et al.
International journal of molecular medicine, 3(2), 181-184 (1999-01-26)
The anomers of both D-glucose pentaacetate and L-glucose pentaacetate were recently found to display insulinotropic potential. In order to progress in understanding the mode of action of these esters in islet cells, we have now investigated whether they mimic the
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