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781658-23-9

781658-23-9 Structure

781658-23-9 Structure
IdentificationMore
[Name]

4-Hydroxy-L-isoleucine
[CAS]

781658-23-9
[Synonyms]

4-HYDROXY-L-ISOLEUCINE
4-Hydroxyisoleucine
[EINECS(EC#)]

631-182-5
[Molecular Formula]

C6H13NO3
[MDL Number]

MFCD06799350
[Molecular Weight]

147.17
[MOL File]

781658-23-9.mol
Chemical PropertiesBack Directory
[Melting point ]

>200°
[Boiling point ]

332 ºC
[density ]

1.181
[Fp ]

147 ºC
[storage temp. ]

2-8°C
[form ]

powder
[pka]

2.41±0.25(Predicted)
[color ]

White
[optical activity]

[α]/D +34.0±2.0°, c = 1 in H2O
[Water Solubility ]

Soluble in water
[InChIKey]

OSCCDBFHNMXNME-UHFFFAOYSA-N
[CAS DataBase Reference]

781658-23-9(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26
[WGK Germany ]

3
[HS Code ]

2922505000
Hazard InformationBack Directory
[Chemical Properties]

4-Hydroxyisoleucine is Light Yellow Solid
[Uses]

4-Hydroxy-L-isoleucine is used as a treatment for type II diabetes.
[Definition]

ChEBI: 4-Hydroxy-L-isoleucine is an isoleucine derivative.
[Biochem/physiol Actions]

A peculiar amino acid extracted from fenugreek seeds and never found in mammalian tissues, exhibits interesting insulinotropic activity; effects on insulin secretion, plant-derived treatment for metabolic syndrome.
[in vivo]

4-Hydroxyisoleucine (50 mg/kg, p.o., daily, 8 weeks) inhibits the increase in serum glucose in the fructose-fed rat model of metabolic syndrome[1]. 4-Hydroxyisoleucine (200 mg/kg, p.o., 8 weeks) improves dyslipidemia and reduces lipid ectopic accumulation in C57BL/6 mice[4].
4-Hydroxyisoleucine (200 mg/kg, p.o., 8 weeks) decreases the expression of proinflammatory cytokine (IL-6, PAI-1, IL-1β, NF-κB, TNF-α, and MCP-1) and the proportion of proinflammatory M1 macrophages in C57BL/6 mice[4].
4-Hydroxyisoleucine (50 mg/kg, i.g., daily, 14 days) restores high levels of lipids (cholesterol, HDL, LDL and triglycerides) and uric acid in type 1 diabetic rat to that of nondiabetic controls level[5].

Animal Model:Fructose-fed rat[1]
Dosage:50 mg/kg
Administration:Oral gavage (p.o.), daily, 8 weeks
Result:Decreased the levels of glucose and ALT.
Reduced 80% of fructosehe-induced AST release to 151 ± 45 U/mL.
Animal Model:Type 2 diabetic rat[1]
Dosage:50 mg/kg
Administration:i.g., daily, 14 days
Result:Restored the level of HDL-cholesterol to levels comparable to controls.
Animal Model:Male C57BL/6 mice[4]
Dosage:50-200 mg/kg
Administration:Oral gavage (p.o.), 8 weeks
Result:Decreases the body weights of mice in a dose-dependent manner.
Decreased blood glucose levels and fasting plasma insulin content in mice.
Decreased the expression of TLR4, inhibited the phosphorylation of JNK, and increased the production of IκB-α.
Animal Model:Type 1 diabetic rat[5]
Dosage:50 mg/kg
Administration: i.g., daily, 14 days
Result:Improved appearance and heavy ocular vascularization.
Reduced the blood glucose from 500 mg/dl to 330 mg/dl.
Decreased the levels of lipid markers (TG, LDL and HDL) and uric acid.
Didn’t increase the level of inculin compared with untreated diabetic controls.
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