| Identification | Back Directory | [Name]
4-HYDROXYISOLEUCINE | [CAS]
55399-93-4 | [Synonyms]
HIL
HYDROXYISOLEUCINE, 4-
HYDROXYISOLEUCINE, 4-(FG)
(4S)-4-Hydroxy-L-isoleucine
4-HYDROXYISOLEUCINE; 4-HYDROXY-L-ISOLEUCINE
[DISCONTINUED] Replaced by KIT-00008502-0HK
2-AMINO-2,3,5-TRIDEOXY-3-METHYL-D-XYLONIC ACID
L-Ribonic acid, 2-amino-2,3,5-trideoxy-3-methyl-
(2S,3R,4S)-2-Amino-4-hydroxy-3-methylpentanoic acid
(4S)-4-Hydroxy-L-isoleucine from fenugreek seed, >=98.0% (TLC)
(2S,3R,4S)-4-HYDROXYISOLEUCINE MAJOR ISOMER AND (2R,3R,4S)-4-HYDROXYISOLEUCINE MINOR ISOMER | [EINECS(EC#)]
2017-001-1 | [Molecular Formula]
C6H13NO3 | [MDL Number]
MFCD07357252 | [MOL File]
55399-93-4.mol | [Molecular Weight]
147.17 |
| Chemical Properties | Back Directory | [Melting point ]
223-224℃ | [Boiling point ]
331.6±32.0 °C(Predicted) | [density ]
1.181±0.06 g/cm3 (20 ºC 760 Torr) | [Fp ]
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 Rotation]
[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 |
| Hazard Information | Back Directory | [Description]
4-Hydroxyisoleucine is an amino acid that has been found in fenugreek (T. foenum graecum) seeds and has antidiabetic activity.1,2,3 It increases glucose-stimulated insulin release from isolated rat islets and isolated perfused rat pancreas when used at a concentration of 200 μM.1 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 (Item No. 11127) and streptozotocin (STZ; Item No. 13104) when administered at 25 mg/kg.2 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.3 | [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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