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. 2020 Nov 27;25(23):5582.
doi: 10.3390/molecules25235582.

Solubility and Thermal Degradation of Quercetin in CO2-Expanded Liquids

Larissa P Cunico  1 , Andrés Medina Cobo  1 , Said Al-Hamimi  1   2 , Charlotta Turner  1
Affiliations

Solubility and Thermal Degradation of Quercetin in CO2-Expanded Liquids

Larissa P Cunico et al. Molecules. .

Abstract

The solubility of quercetin and its thermal degradation was studied in CO2-expanded ethanol and ethyl lactate. An equipment setup was constructed that enabled the separation of the products of degradation while quantifying the solubility of quercetin. Three different conditions of temperature were analyzed (308, 323, and 343 K) at 10 MPa. Higher solubility and thermal degradation of quercetin were observed for CO2-expanded ethyl lactate in comparison with CO2-expanded ethanol. At the same time, as the amount of CO2 was increased in the CO2-expanded liquids mixtures, the thermal degradation of quercetin decreased for almost all the conditions of temperature considered in this work. The importance of considering thermal degradation while performing solubility measurements of compounds that are thermally unstable such as quercetin was highlighted.

Keywords: gas-expanded liquid; green solvent; quercetin; solubility; subcritical fluid; thermal degradation.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
A supercritical fluid chromatography separation method with diode array detection (SFC-DAD) chromatogram of the separation of quercetin (eluting at approximately 7 min) from two other compounds detected that could be possible products of degradation (in zoom). SFC-DAD method: Backpressure 12 MPa, temperature 323 K, flow rate 3 mL/min, gradient from 10 to 35 volume % of ethanol in 8 min and a holding time of 2 min, DAD wavelength 200 to 600 nm with quercetin quantification at 369 nm. For more information, see Section 3.3.
Figure 2
Figure 2
An ultrahigh performance liquid chromatography method with quadrupole time-of-flight detection (UHPLC-DAD-QTOF/MS) analysis of a treated sample of quercetin: (A) DAD chromatogram at 365 nm, (B) total ion current chromatogram in negative mode, (C) spectrum for the main peak, quercetin with some partly co-eluting degradation products, and (D) the spectrum for the other two peaks as degradation products of quercetin. The mass of m/z 400 is a background contamination, having also been detected in the blank injection solvent.
Figure 3
Figure 3
Thermal degradation kinetics of quercetin in: (A) CO2-expanded ethanol and (B) CO2-expanded ethyl lactate. For 308 K: ∆ 10% mol CO2, □ 30% mol CO2, and ○ 50% mol CO2. For 323 K: ▲ 10% mol CO2, ■ 30% mol CO2 and ● 50% mol CO2. For 343 K: ▲ 10% mol CO2, ■ 30% mol CO2, and ● 50% mol CO2. Mean values, n = 3.
See this image and copyright information in PMC

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