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Physicochemical Properties of 4-(4-Hydroxyphenyl)-butan-2-one ("Raspberry Ketone") Evaluated Using a Computational

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Raspberry ketone (RK) is a natural compound used in supplements. This study calculated its thermodynamic properties, revealing its chemical reactivity and solubility, which align with its metabolic profile in mammals.

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Area of Science:

  • Computational Chemistry
  • Biochemistry
  • Physical Chemistry

Background:

  • Raspberry ketone (RK) is a natural phenylpropanoid derivative.
  • RK is valued as a flavoring agent and nutritional supplement for purported fat metabolism benefits.

Purpose of the Study:

  • To computationally evaluate the thermodynamic properties of Raspberry Ketone.
  • To predict physicochemical properties like pKa, logD, and solubility.
  • To analyze the chemical reactivity of RK using theoretical methods.

Main Methods:

  • Utilized the ccCA-CBS-2 approach for enthalpy of formation calculations.
  • Employed TPSS/def2-TZVP and M06-2X/def2-TZVPP levels of theory for geometry optimization and single-point energies.
  • Applied conceptual density functional theory (DFT) for reactivity analysis.

Main Results:

  • Calculated enthalpy of formation (ΔfH°) as -299.4 ± 0.17 kJ·mol⁻¹.
  • Predicted pKa of 9.95 and logD of 1.84.
  • Estimated aqueous solubility of 2.5 mg·mL⁻¹ and an electrode potential of 1.29 V at pH 7.4.
  • HOMO-LUMO energy gap of ~7.8 eV suggests moderate reactivity, with predicted nucleophilic attack at the carbonyl carbon and electrophilic addition on the benzene ring.

Conclusions:

  • The calculated thermodynamic and physicochemical properties of RK are consistent with experimental and chemometric predictions.
  • Theoretical reactivity analysis correlates with observed mammalian metabolite profiles.
  • Provides a foundational computational understanding of Raspberry Ketone's behavior.