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50118

Sigma-Aldrich

(4S)-4-Hydroxy-L-isoleucine

≥98.0% (TLC)

Synonyme(s) :

4-HYDROXYISOLEUCINE, HIL, (2S,3R,4S)-2-Amino-4-hydroxy-3-methylpentanoic acid

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About This Item

Formule empirique (notation de Hill):
C6H13NO3
Numéro CAS:
55399-93-4
Poids moléculaire :
147.17
Numéro Beilstein :
4128096
Numéro MDL:
MFCD07357252
Code UNSPSC :
12352209
eCl@ss :
32160406
ID de substance PubChem :
329757568
Nomenclature NACRES :
NA.26

product name

(4S)-4-Hydroxy-L-isoleucine, from fenugreek seeds, ≥98.0% (TLC)

Source biologique

fenugreek seeds

Niveau de qualité

100

Pureté

≥98.0% (TLC)

Forme

powder or flakes

Activité optique

[α]/D +32.5±2.0°, c = 1 in H2O

Couleur

white to almost white

Température de stockage

2-8°C

Chaîne SMILES 

C[C@H](O)[C@H](C)[C@H](N)C(O)=O

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

Clé InChI

OSCCDBFHNMXNME-YUPRTTJUSA-N

Actions biochimiques/physiologiques

(4S)-4-Hydroxy-L-isoleucine (HIL) is a non-proteinogenic α amino acid produced by the activity of bacterial isoleucine dioxygenase(s). (2S,3R,4S)-HIL is being studied to understand its insulinotropic (anti-diabetic) and anti-obesity effects.
4-Hydroxyisoleucine (HIL) from fenugreek (Trigonella foenum-graecum) seeds is a potential insulinotropic (anti-diabetic) and anti-obesity amino acid. HIL stimulates glucose-dependent insulin secretion from pancreatic cells. HIL activates insulin receptor substrate-associated phosphoinositide 3 (PI3) kinase activity. HIL reduces plasma levels of triglycerides, free fatty acids and cholesterol.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

296.6 °F

Point d'éclair (°C)

147 °C

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Mohammad Reza Haeri et al.
Phytotherapy research : PTR, 23(1), 61-64 (2008-08-06)
Fenugreek (Trigonella foenum graecum L) is a plant traditionally used for the treatment of diabetes. It contains an unusual amino acid, 4-hydroxyisoleucine, demonstrated to have insulinotropic and antidiabetic properties in animal models. Here we examine the effect of 4-hydroxyisoleucine on
Makoto Hibi et al.
Applied and environmental microbiology, 77(19), 6926-6930 (2011-08-09)
We determined the enzymatic characteristics of an industrially important biocatalyst, α-ketoglutarate-dependent l-isoleucine dioxygenase (IDO), which was found to be the enzyme responsible for the generation of (2S,3R,4S)-4-hydroxyisoleucine in Bacillus thuringiensis 2e2. Depending on the amino acid used as the substrate
Jun Ogawa et al.
Applied microbiology and biotechnology, 89(6), 1929-1938 (2010-11-12)
4-Hydroxyisoleucine (HIL) found in fenugreek seeds has insulinotropic and anti-obesity effects and is expected to be a novel orally active drug for insulin-independent diabetes. Here, we show that the newly isolated strain Bacillus thuringiensis 2e2 and the closely related strain
Tadigoppula Narender et al.
Bioorganic & medicinal chemistry letters, 16(2), 293-296 (2005-10-26)
Trigonella foenum-graecum, commonly known as fenugreek, is an annual herbaceous plant. From the seeds of T. foenum-graecum an unusual amino acid, 4-hydroxyisoleucine 5, has been isolated, which significantly decreased the plasma triglyceride levels by 33% (P<0.002), total cholesterol (TC) by
Y Sauvaire et al.
Diabetes, 47(2), 206-210 (1998-03-31)
We report the characterization of a new insulinotropic compound, 4-hydroxyisoleucine. This amino acid has been extracted and purified from fenugreek seeds, which are known in traditional medicine for their antidiabetic properties. 4-Hydroxyisoleucine increases glucose-induced insulin release, in the concentration range
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