20408-97-3

Basic information

• Product Name: 5-THIO-D-GLUCOSE
• Synonyms: 5-Thio-α-D-glucopyranose;α-D-Glucothiopyranose;5-Thio-D-glucose,predominantly &-anomer;5-Thio-D-glucose, alpha-anomer;5-Thio-D-glucose ,98%;NSC 204984;(2R,3R,4S,5R)-2,3,4,6-Tetrahydroxy-5-mercaptohexanal;-2,3,4,6-Tetrahydroxy-5-mercaptohexanal
• CAS NO: 20408-97-3
• Molecular Formula: C₆H₁₂O₅S
• Molecular Weight: 196.22
• EINECS: 243-798-8
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Sulfur & Selenium Compounds;Biochemicals and Reagents;Carbohydrates;Monosaccharide
• Mol File: 20408-97-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 135-138 °C(lit.)
• Boiling Point: 303.11°C (rough estimate)
• Flash Point: 234 °C
• Appearance: White/Powder
• Density: 1.271 (estimate)
• Vapor Pressure: 4.09E-08mmHg at 25°C
• Refractive Index: 1.5060 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in Water (up to 15 mg/ml)
• PKA: 9.11±0.10(Predicted)
• Water Solubility: Miscible with water.
• Stability: Stable for 2 years as supplied. Solutions in distilled water may be stored at -20°C for up to 2 months.
• Merck: 13,9408
• BRN: 1865193
• CAS DataBase Reference: 5-THIO-D-GLUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-THIO-D-GLUCOSE(20408-97-3)
• EPA Substance Registry System: 5-THIO-D-GLUCOSE(20408-97-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: LZ7500000
• F: 3-10-23
• Hazardous Substances Data: 20408-97-3(Hazardous Substances Data)

Usage

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

Wang et al. (1995) Glucose transporter 2 expression: prevention of streptozotocin-induced reduction in beta-cells with 5-thio-D-glucose; Clin. Endocrinol. Diabetes, 103 83 Suppl.2 Shah et al. (2019), Recurrent glucose deprivation leads to the preferential use of lactate by neurons in the ventromedial hypothalamus; J. Physiol. Endocrinol. Metab., 316 E948 Li et al. (2014), Stimulation of feeding by three different glucose-sensing mechanisms requires hindbrain catecholamine neurons; J. Physiol. Regul. Integr. Comp. Physiol., 306 R257 Salkovic-Petrisic et al. (2006), Alzheimer-like changes in protein kinase B and glycogen synthase kinase-3 in rat frontal cortex and hippocampus after damage to the insulin signaling pathway; J. Neurochem., 96 1005 Lane et al. (2000), 5-thio-D-glucose elevates renal transforming growth factor beta-1 at a dose that does not prevent streptozotocin diabetes in rats; Endocrinology, 141 3337

InChI:InChI=1/C6H12O5S/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6+/m1/s1