4-Hydroxy-L-isoleucine
4-Hydroxy-L-isoleucine Basic information
- Product Name:
- 4-Hydroxy-L-isoleucine
- Synonyms:
-
- 4-HYDROXY-L-ISOLEUCINE
- (2S,3R)-2-aMino-4-hydroxy-3-Methylpentanoic acid
- L-4- hydroxyl isoleucine
- (4S)-4-Hydroxy-L-isoleucine from fenugre
- L-Isoleucine, 4-hydroxy-
- 4-Hydroxy-L-isoleucine USP/EP/BP
- 4-Hydroxyisoleucine (1327319)
- Hydroxy L-isoleucine
- CAS:
- 781658-23-9
- MF:
- C6H13NO3
- MW:
- 147.17
- EINECS:
- 631-182-5
- Product Categories:
-
- Amino Acids & Derivatives
- Aliphatics
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Mol File:
- 781658-23-9.mol
4-Hydroxy-L-isoleucine Chemical Properties
- Melting point:
- >200°
- Boiling point:
- 332 ºC
- Density
- 1.181
- Flash point:
- 147 ºC
- storage temp.
- 2-8°C
- pka
- 2.41±0.25(Predicted)
- form
- powder
- 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)
4-Hydroxy-L-isoleucine Usage And Synthesis
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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