(3S)-3-(4-Hydroxyphenyl)-4-hexynoic acid
[CAS# 865233-35-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: (3S)-3-(4-Hydroxyphenyl)-4-hexynoic acid
• Molecular Formula: C₁₂H₁₂O₃
• Molecular Weight: 204.22
• CAS Registry Number: 865233-35-8
• SMILES: CC#C[C@@H](CC(=O)O)C1=CC=C(C=C1)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.590, Calc.^*
• Boiling Point: 398.2±37.0 ºC (760 mmHg), Calc.^*
• Flash Point: 208.8±23.0 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

(3S)-3-(4-Hydroxyphenyl)-4-hexynoic acid is a chiral organic compound featuring a hydroxyl group (-OH) on a phenyl ring attached to a hexynoic acid backbone. Its distinct structure, with a triple bond in the hexynoic acid chain and a hydroxyl-substituted phenyl group, gives it notable reactivity and biological relevance, making it useful in pharmaceutical and biochemical research. The (3S) stereochemistry indicates that the compound possesses specific spatial arrangement, which can influence its interactions with biological molecules and systems.

The discovery of compounds like (3S)-3-(4-Hydroxyphenyl)-4-hexynoic acid can be attributed to the search for bioactive molecules that could modulate biological pathways or serve as building blocks for more complex drug candidates. The introduction of hydroxyl groups onto aromatic rings, combined with unsaturated aliphatic chains such as hexynoic acid, provides a platform for investigating the compound's potential as a modulator of enzyme activities, receptor interactions, or as a precursor in synthetic chemistry. This specific compound is often synthesized through stereoselective chemical reactions, ensuring the desired (3S) configuration, which is critical for its potential biological effects.

In terms of application, (3S)-3-(4-Hydroxyphenyl)-4-hexynoic acid has gained attention in pharmaceutical research due to its structural similarity to other phenolic compounds that play key roles in modulating physiological processes. The hydroxyl group on the phenyl ring allows for hydrogen bonding interactions, which can enhance its binding to biological targets, including enzymes and receptors. These properties make it a potential lead compound in the design of new therapeutics, especially in areas such as enzyme inhibition, receptor modulation, or as a scaffold for drug design.

In addition, this compound is useful as an intermediate in organic synthesis, where its combination of aromatic hydroxyl and acetylenic functionalities provides diverse possibilities for chemical modifications. The alkyne group offers a reactive site for further derivatization through well-known organic reactions, such as click chemistry or Sonogashira coupling, facilitating the creation of more complex molecules with potential applications in medicinal chemistry or materials science.

Given its unique structural attributes and biological potential, (3S)-3-(4-Hydroxyphenyl)-4-hexynoic acid continues to be a compound of interest in both academic and industrial settings. Its role as a starting material or intermediate in complex synthesis and its promise in therapeutic applications underscore its significance in modern chemical research.