4-HYDROXYISOLEUCINE 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)

pka

2.41±0.25(Predicted)

form 

Solid

color 

White to Off-White

biological source

fenugreek seeds

optical activity

[α]/D +32.5±2.0°, c = 1 in H2O

BRN 

4128096

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

4-HYDROXYISOLEUCINE 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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