| Identification | Back Directory | [Name]
5-THIO-D-GLUCOSE | [CAS]
20408-97-3 | [Synonyms]
d-glucos
NSC 204984
THIOGLUCOSE
5-Thioglucose
5-THIO-D-GLUCOSE
GLUCOTHIOPYRANOSE
α-D-Glucothiopyranose
5-Thio-D-glucose ,98%
5-Thio-α-D-glucopyranose
alpha-d-glucothiopyranose
5-O-Thia-α-D-glucopyranose
5-Deoxy-5-mercapto-D-glucose
5-thio-alpha-d-glucopyranose
5-THIO-D -GLUCOSE CRYSTALLINE
5-Thio-D-glucose, alpha-anomer
5-Thio-D-glucose,predominantly &-anomer
-2,3,4,6-Tetrahydroxy-5-mercaptohexanal
5-THIO-D-GLUCOSE, 96%, PREDOMINANTLY ALP HA-ANOMER
(2R,3R,4S,5R)-2,3,4,6-Tetrahydroxy-5-mercaptohexanal
(2S)-6β-(Hydroxymethyl)tetrahydro-2H-thiopyran-2α,3α,4β,5α-tetraol | [EINECS(EC#)]
243-798-8 | [Molecular Formula]
C6H12O5S | [MDL Number]
MFCD00148892 | [MOL File]
20408-97-3.mol | [Molecular Weight]
196.22 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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 |
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