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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

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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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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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
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)
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)
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
S Ritter et al.
Brain research, 856(1-2), 37-47 (2000-03-10)
Feeding and blood glucose responses to local injection of nanoliter volumes of 5-thio-D-glucose (5TG), a potent antimetabolic glucose analogue, were studied at 142 hindbrain and 61 hypothalamic cannula sites. A site was considered positive if 5TG elicited at least 1.5
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