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88635

Sigma-Aldrich

5-Thio-D-glucose

≥98.0% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C6H12O5S
CAS Number:
20408-97-3
Molecular Weight:
196.22
Beilstein:
1865193
EC Number:
243-798-8
MDL number:
MFCD00006663
UNSPSC Code:
12352201
PubChem Substance ID:
57653273
NACRES:
NA.25

Assay

≥98.0% (HPLC)

form

powder

optical activity

[α]/D 220.0±5.0°, c = 1 in 0.1 M HCl

color

white to off-white

mp

135-138 °C (lit.)

SMILES string

OC[C@H]1S[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C6H12O5S/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6+/m1/s1

InChI key

KNWYARBAEIMVMZ-DVKNGEFBSA-N

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Application

5-Thio-D-glucose (Glc-5S), a thiosugar hexokinase inhibitor, is used to control/reduce the rate of glycolysis in vivo.

Biochem/physiol Actions

Potent, competitive inhibitor of the cellular transport of D-glucose and of D-glucose mediated insulin release. Inhibitor of spermatogenesis.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

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)

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B He et al.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 217(2), 168-172 (1998-02-06)
5-Thioglucose (5-TG) has been shown to increase food intake after acute administration. To determine the longer-term effects of 5-TG on feeding and body composition, thirty-four female Sprague-Dawley rats were cannulated into the fourth ventricle and infused with artificial CSF and
D P Figlewicz et al.
Stress (Amsterdam, Netherlands), 5(3), 217-226 (2002-08-21)
Hypoglycemia-associated autonomic failure (HAAF) is a syndrome of acute adaptation to a metabolic stressor, in which neuroendocrine responses to repetitive hypoglycemic bouts are blunted. The CNS mechanisms that contribute to HAAF are unknown. In the present study, we modeled HAAF
A M Altizer et al.
Physiology & behavior, 65(4-5), 685-690 (1999-03-12)
Previous research has shown that glucoprivic and lipoprivic metabolic challenges selectively augment the performance of appetitive responses conditioned to carbohydrate- and fat-associated cues, respectively. The present experiment investigated whether intracerebroventricular (i.c.v.) infusion of neuropeptide Y (NPY) has a similar selective
Ambrose A Dunn-Meynell et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 29(21), 7015-7022 (2009-05-29)
Although several studies implicate small declines in blood glucose levels as stimulus for spontaneous meal initiation, no mechanism is known for how these dips might initiate feeding. To assess the role of ventromedial hypothalamus (VMH) (arcuate plus ventromedial nucleus) glucosensing
K D Brady et al.
The Journal of heredity, 72(5), 347-350 (1981-09-01)
5-thio-D-glucose at 40 mg/kg body weight was administered daily by intraperitoneal injections to male C3H mice. The animals were studied via direct counts of the spermatogenic cells in histologic sections of the testes. These revealed the selective loss or injury
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