5-THIO-D-GLUCOSE Chemical Properties

Melting point:

135-138 °C(lit.)

Boiling point:

303.11°C (rough estimate)

Density 

1.271 (estimate)

refractive index 

1.5060 (estimate)

storage temp. 

2-8°C

solubility 

Soluble in Water (up to 15 mg/ml)

form 

Powder

pka

9.11±0.10(Predicted)

color 

White

optical activity

[α]/D 220.0±5.0°, c = 1 in 0.1 M HCl

Water Solubility 

Miscible with water.

Merck 

13,9408

BRN 

1865193

Stability:

Stable for 2 years as supplied. Solutions in distilled water may be stored at -20°C for up to 2 months.

CAS DataBase Reference

20408-97-3

EPA Substance Registry System

D-Glucose, 5-thio- (20408-97-3)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

LZ7500000

F 

3-10-23

Toxicity

mouse,LD50,intraperitoneal,5500mg/kg (5500mg/kg),International Journal of Radiation Oncology, Biology, Physics. Vol. 8, Pg. 589, 1982.

5-THIO-D-GLUCOSE Usage And Synthesis

Description

5-Thio-D-glucose (20408-97-3) is a potent competitive inhibitor of the cellular transport of glucose and glucose-mediated insulin release.1 May be used to induce a state of glucose deprivation in laboratory animals.2 Stimulates feeding in rat models.3? Induces Alzheimer-like changes in frontal cortex and hippocampus in rats.4? Elevates renal TGF-b1 at a dose that does not prevent streptozotocin diabetes in rats.5

Uses

5-Thio-D-glucose (cas# 20408-97-3) is a compound useful in organic synthesis.

References

[1] Z WANG  H G. Glucose transporter 2 expression: prevention of streptozotocin-induced reduction in beta-cells with 5-thio-D-glucose.[J]. Experimental and Clinical Endocrinology & Diabetes, 1995, 103 Suppl 2: 83-97. DOI:10.1055/s-0029-1211400
[2] MAITREYEE SHAH. Recurrent glucose deprivation leads to the preferential use of lactate by neurons in the ventromedial hypothalamus.[J]. American journal of physiology. Endocrinology and metabolism, 2019, 316 5: E948-E955. DOI:10.1152/ajpendo.00468.2018
[3] AI-JUN LI. Stimulation of feeding by three different glucose-sensing mechanisms requires hindbrain catecholamine neurons.[J]. American journal of physiology. Regulatory, integrative and comparative physiology, 2014, 306 4: R257-64. DOI:10.1152/ajpregu.00451.2013
[4] MELITA SALKOVIC-PETRISIC. Alzheimer-like changes in protein kinase B and glycogen synthase kinase-3 in rat frontal cortex and hippocampus after damage to the insulin signalling pathway[J]. Journal of Neurochemistry, 2006, 96 4: 1005-1015. DOI:10.1111/j.1471-4159.2005.03637.x
[5] LANE P. 5-thio-D-glucose elevates renal transforming growth factor beta-1 at a dose that does not prevent streptozocine diabetes in rats.[J]. Endocrinology, 2000, 26 1: 3337-3342. DOI:10.1210/en.141.9.3337

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