4-HYDROXYISOLEUCINE
Synonym(s):(2S,3R,4S)-2-Amino-4-hydroxy-3-methylpentanoic acid;4-HYDROXYISOLEUCINE;HIL
- CAS NO.:55399-93-4
- Empirical Formula: C6H13NO3
- Molecular Weight: 147.17
- MDL number: MFCD07357252
- EINECS: 2017-001-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 08:26:49
What is 4-HYDROXYISOLEUCINE?
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.
Occurrence
4-hydroxyisoleucine has been extracted and purified from fenugreek seeds, which are known in traditional medicine for their antidiabetic properties.
The Uses of 4-HYDROXYISOLEUCINE
(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.
Properties of 4-HYDROXYISOLEUCINE
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 |
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 |
Safety information for 4-HYDROXYISOLEUCINE
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 4-HYDROXYISOLEUCINE
InChIKey | OSCCDBFHNMXNME-YUPRTTJUSA-N |
SMILES | C(O)(=O)[C@@H](N)[C@@H](C)[C@H](C)O |
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