4-Hydroxy Isoleucine - 10mM in Water , CAS No.781658-23-9

CAS: 781658-23-9 Cat. No.: H580281 Molecular Weight: 147.17 EC Number: 631-182-5

GRADE & PURITY 10mM in Water

Synonyms

4-?Hydroxy-?L-?isoleucine | 4-HYDROXY-L-ISOLEUCINE | (2S,3R)-2-amino-4-hydroxy-3-methylpentanoic acid | CCG-266183 | 4-ydroxy--soleucine | 4-Hydroxyisoleucine, United States Pharmacopeia (USP) Reference Standard | Rel-(2S,3R)-2-amino-4-hydroxy-3-methylpen

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Synonyms

4-?Hydroxy-?L-?isoleucine | 4-HYDROXY-L-ISOLEUCINE | (2S, 3R)-2-amino-4-hydroxy-3-methylpentanoic acid | CCG-266183 | 4-ydroxy--soleucine | 4-Hydroxyisoleucine, United States Pharmacopeia (USP) Reference Standard | Rel-(2S, 3R)-2-amino-4-hydroxy-3-methylpen

Specifications & Purity

10mM in Water

Biochemical and Physiological Mechanisms

A special amino acid extracted from the seeds of fenugreek, which has never been found in mammalian tissues, shows proinsulin activity; Effects on insulin secretion, plant-based treatment of metabolic syndrome.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CC(C(C)O)C(C(=O)O)N
• IUPAC Name: (2S,3R)-2-amino-4-hydroxy-3-methylpentanoic acid
• InChIKey: OSCCDBFHNMXNME-DSDZBIDZSA-N
• 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
• Isomeric SMILES: C[C@H]([C@@H](C(=O)O)N)C(C)O
• WGK Germany: 3
• Molecular Weight: 147.17
• Reaxy-Rn: 11036006
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11036006&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Isoleucine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Isoleucine and derivatives
• Alternative Parents: L-alpha-amino acids Short-chain hydroxy acids and derivatives Methyl-branched fatty acids Hydroxy fatty acids 1,3-aminoalcohols Secondary alcohols Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Isoleucine or derivatives - Alpha-amino acid - L-alpha-amino acid - Branched fatty acid - Hydroxy fatty acid - Methyl-branched fatty acid - Short-chain hydroxy acid - Fatty acyl - Fatty acid - 1,3-aminoalcohol - Amino acid - Secondary alcohol - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Primary amine - Primary aliphatic amine - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Amine - Organic oxygen compound - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as isoleucine and derivatives. These are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Flash Point(°F): 296.6 °F
• Flash Point(°C): 147 °C
• Molecular Weight: 147.170 g/mol
• XLogP3: -2.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 147.09 Da
• Monoisotopic Mass: 147.09 Da
• Topological Polar Surface Area: 83.600 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 126.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Emmanuel Osei Nkansah, Yunzhu Lan, Hui Zhang, Binbin Xu, Qiaodan Li, Mohammad Ishraq Zafar, Jian Xu.  (2025)  Potential role of 4-hydroxyisoleucine in enhancing fertility in male mice with diet-induced obesity.  Frontiers in Endocrinology,      [PMID:40917356] [10.3389/fendo.2025.1561543]