88635
5-Thio-D-glucose
≥98.0% (HPLC)
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About This Item
Empirical Formula (Hill Notation):
C6H12O5S
CAS Number:
Molecular Weight:
196.22
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
EC Number:
243-798-8
Beilstein/REAXYS Number:
1865193
MDL number:
Product Name
5-Thio-D-glucose, ≥98.0% (HPLC)
InChI key
KNWYARBAEIMVMZ-DVKNGEFBSA-N
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
SMILES string
OC[C@H]1S[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O
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.)
Quality Level
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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
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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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
Studies on oxidative phosphorylation. XVI. Sulfhydryl involvement in the energy-transfer pathway.
C K Kurup et al.
Biochemistry, 7(12), 4483-4491 (1968-12-01)
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)
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