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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

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.

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This Item
49549I275258879
(4S)-4-Hydroxy-L-isoleucine from fenugreek seeds, ≥98.0% (TLC)

Sigma-Aldrich

50118

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

4-Hydroxy-L-isoleucine ≥98.0% (TLC)

Sigma-Aldrich

49549

4-Hydroxy-L-isoleucine

L-Isoleucine reagent grade, ≥98% (HPLC)

Sigma-Aldrich

I2752

L-Isoleucine

L-Isoleucine BioUltra, ≥99.5% (NT)

Sigma-Aldrich

58879

L-Isoleucine

form

powder or flakes

form

-

form

powder

form

powder or crystals

assay

≥98.0% (TLC)

assay

≥98.0% (TLC)

assay

≥98% (HPLC)

assay

≥99.5% (NT), ≥99.5% (TLC)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

optical activity

[α]/D +32.5±2.0°, c = 1 in H2O

optical activity

[α]/D +34.0±2.0°, c = 1 in H2O

optical activity

-

optical activity

[α]20/D +41.0±1°, c = 5% in 6 M HCl

color

white to almost white

color

white to off-white

color

white

color

white

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

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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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
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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Global Trade Item Number

SKUGTIN
50118-50MG04061832719269

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