(S)-()-Ethyl 3-Hydroxybutyrate

2025年1月3日
产品资讯

(S)-()-Ethyl 3-Hydroxybutyrate

(S)-(+)-Ethyl 3-hydroxybutyrate is an organic compound that belongs to the class of chemicals known as esters. It is the ethyl ester of (S)-3-hydroxybutyric acid. The compound is characterized by the presence of a hydroxyl group (-OH) and an ester functional group (-COO-) in its structure.

Key Features:

  • Chemical Formula: C₆H₁₂O₃
  • Molecular Weight: 132.16 g/mol
  • Optical Activity: The (S)-(+) designation indicates that this compound is optically active and rotates plane-polarized light in a clockwise direction (+). The “S” refers to the specific spatial arrangement of the atoms around the chiral center, following the Cahn-Ingold-Prelog priority rules.

Structure:

The structure of (S)-(+)-Ethyl 3-hydroxybutyrate can be represented as follows:

   OH
    |
CH3-CH-CH2-COO-CH2-CH3

In this structure:

  • The chiral center is the carbon atom bonded to the hydroxyl group (-OH), the methyl group (CH₃), the hydrogen atom (H), and the rest of the molecule.
  • The ethyl group (CH₂-CH₃) is attached to the carbonyl carbon (C=O) of the ester functional group.

Applications:

(S)-(+)-Ethyl 3-hydroxybutyrate is often used in organic synthesis and as a chiral building block in the production of pharmaceuticals, agrochemicals, and fine chemicals. Its enantiomeric purity is crucial in these applications, as the biological activity of chiral compounds can vary significantly between enantiomers.

Synthesis:

The compound can be synthesized through the esterification of (S)-3-hydroxybutyric acid with ethanol in the presence of an acid catalyst. Alternatively, it can be obtained through asymmetric synthesis methods to ensure the desired enantiomeric purity.

Properties:

  • Boiling Point: The boiling point of (S)-(+)-Ethyl 3-hydroxybutyrate is typically around 180-185°C, though this can vary slightly depending on the specific conditions.
  • Solubility: It is generally soluble in organic solvents like ethanol, methanol, and ethyl acetate, but has limited solubility in water.

Safety:

As with many organic compounds, handling (S)-(+)-Ethyl 3-hydroxybutyrate should be done with appropriate safety precautions, including the use of gloves and eye protection, and working in a well-ventilated area or fume hood.

This compound is of interest in both academic and industrial research due to its chiral nature and potential applications in asymmetric synthesis.

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