((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate
[CAS# 144256-11-1]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: ((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate
• Synonyms: [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-(4-hydroxyphenyl)propanoate
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32
• CAS Registry Number: 144256-11-1
• EC Number: 689-773-9
• SMILES: CC1(OC[C@H](O1)COC(=O)CCC2=CC=C(C=C2)O)C

Properties

• Density: 1.156±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.515, Calc.^*
• Boiling Point: 409.2±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 147.9±19.4 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate is a chemical compound that combines the features of a chiral dioxolane ring system with a hydroxyphenylpropanoate moiety. The structure consists of a dioxolane ring with a methyl group attached to the carbon adjacent to the oxygen atoms, and the ester group features a hydroxyphenylpropanoate structure that imparts unique properties to the compound. This compound has been of interest due to its potential biological activities and its utility in synthetic chemistry.

The discovery of ((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate can be traced to efforts in designing chiral molecules that exhibit specific interactions with biological targets. Chiral compounds are often more selective in their activity, which makes them valuable in the pharmaceutical industry. In this case, the chiral center at the 2-position of the dioxolane ring likely influences the compound’s interactions with biological systems, giving it potential advantages over non-chiral or racemic analogs.

The presence of the hydroxyphenylpropanoate group suggests that ((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate could have significant applications in the development of drugs with anti-inflammatory, antioxidant, or anticancer properties. Hydroxyphenylpropanoates are well known for their biological activities, especially their ability to scavenge free radicals and modulate enzyme activity related to inflammation. The dioxolane ring may contribute to the stability and solubility of the compound, enhancing its pharmacokinetic properties.

Given the chiral nature of the molecule, ((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate may exhibit stereoselective interactions with specific receptors or enzymes, making it a candidate for the development of drugs targeting particular pathways. The compound could be investigated for its potential as an anti-inflammatory agent, or as a modulator of metabolic pathways involved in oxidative stress, a key factor in various chronic diseases, including cardiovascular disease, cancer, and neurodegenerative disorders.

In addition to its potential therapeutic applications, ((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate could serve as an intermediate in the synthesis of more complex molecules. Its functional groups offer opportunities for further modification, allowing researchers to explore analogs with enhanced potency, selectivity, and bioavailability. The ability to modify the ester, hydroxy group, or even the dioxolane ring could open up new avenues for drug discovery.

In summary, ((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate is a promising compound with potential biological activities, particularly in the fields of anti-inflammatory and anticancer research. Its chiral structure, along with its functional groups, makes it a valuable candidate for further study in the design of novel therapeutics.