ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Isoleucine derivatives 4-Hydroxyisoleucine

4-Hydroxyisoleucine

Product Name4-Hydroxyisoleucine
CAS55399-93-4
MFC6H13NO3
MW147.17
EINECS2017-001-1
MOL File55399-93-4.mol

Chemical Properties

Melting point	223-224℃
Boiling point	331.6±32.0 °C(Predicted)
Density	1.181±0.06 g/cm3 (20 ºC 760 Torr)
Flash point	147℃
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
solubility	Methanol (Slightly), Water (Slightly)
form	Solid
pka	2.41±0.25(Predicted)
color	White to Off-White
biological source	fenugreek seeds
optical activity	[α]/D +32.5±2.0°, c = 1 in H2O
BRN	4128096
Cosmetics Ingredients Functions	SKIN CONDITIONING HUMECTANT
InChI	InChI=1S/C6H13NO3/c1-3(4(2)8)5(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t3-,4-,5-/m0/s1
InChIKey	OSCCDBFHNMXNME-YUPRTTJUSA-N
SMILES	C(O)(=O)[C@@H](N)[C@@H](C)[C@H](C)O

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Description

4-Hydroxyisoleucine is an amino acid that has been found in fenugreek (T. foenum graecum) seeds and has antidiabetic activity. It increases glucose-stimulated insulin release from isolated rat islets and isolated perfused rat pancreas when used at a concentration of 200 μM. In vivo, 4-hydroxyisoleucine increases PI3K activity in muscle and liver in rats when administered at a dose of 18 mg/kg and in muscle in a rat model of type 2 diabetes induced by nicotinamide and streptozotocin (STZ; ) when administered at 25 mg/kg. 4-Hydroxyisoleucine (50 mg/kg per day for four weeks) decreases plasma glucose, triglyceride, LDL, HDL, and cholesterol levels in an STZ-induced rat model of type 1 diabetes.

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from fenugreek seeds.

Occurrence

4-hydroxyisoleucine has been extracted and purified from fenugreek seeds, which are known in traditional medicine for their antidiabetic properties.

Uses

(4S)-4-Hydroxy-L-isoleucine is 4S isomer of 4-Hydroxyisoleucine, which is used as a treatment for type II diabetes.

Definition

ChEBI: An L-isoleucine derivative that is L-isoleucine bearing a (4S)-hydroxy substituent.

Biological Activity

4-Hydroxyisoleucine increases glucose-induced insulin release, in the concentration range of 100 micromol/l to 1 mmol/l, through a direct effect on isolated islets of Langerhans from both rats and humans.

References

[1] CHRISTOPHE BROCA . 4-Hydroxyisoleucine: effects of synthetic and natural analogues on insulin secretion[J]. European journal of pharmacology, 2000, 390 3: Pages 339-345. DOI: 10.1016/s0014-2999(00)00030-3
[2] CHRISTOPHE BROCA. Insulinotropic agent ID-1101 (4-hydroxyisoleucine) activates insulin signaling in rat.[J]. American journal of physiology. Endocrinology and metabolism, 2004, 287 3: E463-71. DOI: 10.1152/ajpendo.00163.2003
[3] MOHAMMED R. HAERI . Non-insulin dependent anti-diabetic activity of (2S, 3R, 4S) 4-hydroxyisoleucine of fenugreek (Trigonella foenum graecum) in streptozotocin-induced type I diabetic rats[J]. Phytomedicine, 2012, 19 7: Pages 571-574. DOI: 10.1016/j.phymed.2012.01.004

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