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Key Documents

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:
Molecular Weight:
390.34
Beilstein:
98852
EC Number:
MDL number:
UNSPSC Code:
12164502
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Signal Word

Warning

Hazard Statements

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

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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)
W J Malaisse
International journal of molecular medicine, 2(4), 383-388 (1998-12-19)
The two anomers of L-glucose pentaacetate were recently found to stimulate insulin release. The insulinotropic action of these esters cannot be attributed to the catabolism in islet cells of their glucidic or acetic moieties. The present review deals with an
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)

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