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50118

Sigma-Aldrich

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

from fenugreek seeds, ≥98.0% (TLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H13NO3
CAS Number:
55399-93-4
Molecular Weight:
147.17
Beilstein:
4128096
MDL number:
MFCD07357252
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
329757568
NACRES:
NA.26

biological source

fenugreek seeds

Quality Level

100

Assay

≥98.0% (TLC)

form

powder or flakes

optical activity

[α]/D +32.5±2.0°, c = 1 in H2O

color

white to almost white

storage temp.

2-8°C

SMILES string

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

InChI key

OSCCDBFHNMXNME-YUPRTTJUSA-N

Related Categories

Biochem/physiol Actions

(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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

296.6 °F

Flash Point(C)

147 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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
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