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49549

Sigma-Aldrich

4-Hydroxy-L-isoleucine

≥98.0% (TLC)

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Synonym(s):
(2S,3R)-2-Amino-4-hydroxy-3-methylpentanoic acid
Empirical Formula (Hill Notation):
C6H13NO3
CAS Number:
781658-23-9
Molecular Weight:
147.17
MDL number:
MFCD06799350
UNSPSC Code:
12352204
eCl@ss:
32160406
PubChem Substance ID:
329757475
NACRES:
NA.32

Quality Level

100

Assay

≥98.0% (TLC)

optical activity

[α]/D +34.0±2.0°, c = 1 in H2O

color

white to off-white

storage temp.

2-8°C

SMILES string

CC(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-DSDZBIDZSA-N

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Biochem/physiol Actions

A peculiar amino acid extracted from fenugreek seeds and never found in mammalian tissues, exhibits interesting insulinotropic activity; effects on insulin secretion, plant-derived treatment for metabolic syndrome.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

296.6 °F

Flash Point(C)

147 °C

Certificates of Analysis (COA)

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C Broca et al.
European journal of pharmacology, 390(3), 339-345 (2000-03-10)
4-Hydroxyisoleucine, a peculiar amino acid extracted from fenugreek seeds and never found in mammalian tissues, exhibits interesting insulinotropic activity. To investigate the structural requirements for this stimulating effect, the insulinotropic activity of the major isomer (2S,3R,4S) of 4-hydroxyisoleucine, in the
Choong Tat Keng et al.
Gut, 65(10), 1744-1753 (2015-07-08)
HCV infection affects millions of people worldwide, and many patients develop chronic infection leading to liver cancers. For decades, the lack of a small animal model that can recapitulate HCV infection, its immunopathogenesis and disease progression has impeded the development
Anna Maria Herzner et al.
PloS one, 6(7), e22389-e22389 (2011-08-04)
Lantibiotics are small peptide antibiotics that contain the characteristic thioether amino acids lanthionine and methyllanthionine. As ribosomally synthesized peptides, lantibiotics possess biosynthetic gene clusters which contain the structural gene (lanA) as well as the other genes which are involved in
Jasmin Dischinger et al.
PloS one, 4(8), e6788-e6788 (2009-08-27)
Lantibiotics are small microbial peptide antibiotics that are characterized by the presence of the thioether amino acids lanthionine and methyllanthionine. Lantibiotics possess structural genes which encode inactive prepeptides. During maturation, the prepeptide undergoes posttranslational modifications including the introduction of rare
Zhi Zhang et al.
PloS one, 8(4), e62909-e62909 (2013-05-03)
Natural populations of the fruit fly, Drosophila melanogaster, segregate genetic variation that leads to cardiac disease phenotypes. One nearly isogenic line from a North Carolina peach orchard, WE70, is shown to harbor two genetically distinct heart phenotypes: elevated incidence of
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