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285943

Sigma-Aldrich

β-D-Glucose pentaacetate

98%

Synonym(s):

beta-D-Glucose pentaacetate, 1,2,3,4,6-Penta-O-acetyl-β-D-glucopyranose

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About This Item

Empirical Formula (Hill Notation):
C16H22O11
CAS Number:
604-69-3
Molecular Weight:
390.34
Beilstein:
98851
EC Number:
210-074-8
MDL number:
MFCD00006597
UNSPSC Code:
12352201
PubChem Substance ID:
24857226
NACRES:
NA.22

Quality Level

100

Assay

98%

form

powder

optical activity

[α]20/D +4.2°, c = 1 in chloroform

mp

130-132 °C (lit.)

SMILES string

CC(O)O[C@@H]1[C@@H](COC(C)=O)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-IBEHDNSVSA-N

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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F Ponticelli et al.
Carbohydrate research, 330(4), 459-468 (2001-03-28)
We describe the synthesis of some 3-tert-butyl-4-hydroxyphenyl D-glycopyranosides by reaction of tert-butylhydroquinone with beta-D-pentaacetyl-glucose, beta-D-pentaacetyl-galactose, 2-acetamido- and 3,4,6-tri-O-acetyl-2-butanamido-2-deoxy-beta-D-glucopyranosyl chlorides as well as the formation of anomeric 3-tert-butyl-4-hydroxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-eno-pyranosides by reaction between tert-butylhydroquinone and 3,4,6-tri-O-acetyl-D-glucal. All compounds, except 3-tert-butyl-4-hydroxyphenyl alpha- and
W J Malaisse
Acta clinica Belgica, 57(2), 49-52 (2002-08-03)
The first report dealing with the use of monosaccharide esters as new tools in biomedicine was published in 1997 (1). This topic was first reviewed in 1998 (2). The major aim of the present report is to briefly evoke the
A Bastida et al.
Bioorganic & medicinal chemistry letters, 9(4), 633-636 (1999-03-31)
Penta-O-acetyl-alpha-D-glucopyranose was selectively deacetylated in aqueous media by lipases from Candida cilindracea (CCL) adsorbed on octyl-agarose support. Enzymatic hydrolyses was regioselective at the 4-position under neutral pH and towards the 6 position under acidic conditions. This enzymatic approach allows 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
W J Malaisse et al.
Archives of biochemistry and biophysics, 381(1), 61-66 (2000-10-06)
Hepatocytes from fed rats were incubated for 120 min in the presence of alpha-D-[1,2-13C]glucose pentaacetate (1.7 mM), both D-[1,2-13C]glucose (1.7 mM) and acetate (8.5 mM), alpha-D-glucose penta[2-13C]acetate (1.7 mM), or D-[1,2-13C]glucose (8.3 mM). The amounts of 13C-enriched L-lactate and D-glucose
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