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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/REAXYS Number:
1865193
EC Number:
243-798-8
MDL number:
MFCD00006663
UNSPSC Code:
12352201
PubChem Substance ID:
57653273
NACRES:
NA.25

Quality Level

100

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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Related Categories

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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I Tahirovic et al.
Journal of neural transmission. Supplementum, (72)(72), 235-240 (2007-11-07)
It is believed that oxidative stress plays a central role in the pathogenesis of metabolic diseases like diabetes mellitus (DM) and its complications (like peripheral neuropathy) as well as in neurodegenerative disorders like sporadic Alzheimer's disease (sAD). Representative experimental models
Shayne F Andrew et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 292(5), R1792-R1798 (2007-01-16)
Glucose is required for brain energy metabolism. Decerebration, aqueduct occlusion, and cannula mapping studies have established that glucose-sensing cells capable of eliciting feeding and adrenal medullary responses to glucoprivation are localized in the hindbrain. Glucoprivation also evokes corticosterone and glucagon
Xiaoyin Wu et al.
Journal of neurophysiology, 91(4), 1734-1747 (2003-12-03)
Circulating glucose levels significantly affect vagal neural activity, which is important in the regulation of pancreatic functions. Little is known about the mechanisms involved. This study investigates the neural pathways responsible for hypoglycemia-induced vagal efferent signaling to the pancreas and
The pancreatic beta-cell recognition of insulin secretagogues. 3. Effects of substituting sulphur for oxygen in the D-glucose molecule.
B Hellman et al.
Biochemical pharmacology, 22(1), 29-35 (1973-01-01)
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
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