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50118

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

≥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
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
329757568
NACRES:
NA.26
Beilstein/REAXYS Number:
4128096
MDL number:
MFCD07357252
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Product Name

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

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

296.6 °F

flash_point_c

147 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL2529
BCBX0042
BCBT8554
BCBR8852V
BCBN3504V

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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
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
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
Lucie Jetté et al.
Current opinion in investigational drugs (London, England : 2000), 10(4), 353-358 (2009-04-02)
The plant fenugreek has been used for centuries as a treatment for diabetes. This article presents evidence that the major isomer of 4-hydroxyisoleucine, an atypical branched-chain amino acid derived from fenugreek, is responsible for the effects of this plant on
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Global Trade Item Number

SKUGTIN
50118-50MG04061832719269

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