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About This Item
Empirical Formula (Hill Notation):
C6H12O5S
CAS Number:
Molecular Weight:
196.22
Beilstein:
1865193
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25
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Quality Level
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
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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
L M Raamsdonk et al.
Yeast (Chichester, England), 18(11), 1023-1033 (2001-08-02)
In previous studies it was shown that deletion of the HXK2 gene in Saccharomyces cerevisiae yields a strain that hardly produces ethanol and grows almost exclusively oxidatively in the presence of abundant glucose. This paper reports on physiological studies on
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
Role of the binuclear manganese(II) site in xylose isomerase.
R Bogumil et al.
Metal ions in biological systems, 37, 365-405 (2000-02-29)
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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