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Advisor(s)
Abstract(s)
Terpenes and terpenoids encompass one of the most extensive
and valuable classes of secondary metabolites. Their ten-carbon-containing
oxygenated representatives, monoterpenoids, are the main components of plant
essential oils, being widely exploited in the cosmetic, pharmaceutical, and food
industrial areas. Due to its widespread use, it is crucial to investigate their
environmental distribution. Thus, new water solubility data were obtained for
six monoterpenoids ((1R)-(+)-camphor, (S)-(+)-carvone, eucalyptol, (1R)-
(−)-fenchone, L-(−)-menthol, and (−)-menthone) at 298.2 and 313.2 K.
Furthermore, octanol−water partition coefficients of 12 monoterpenoids (the
six mentioned above plus carvacrol, (±)-β-citronellol, eugenol, geraniol, linalool,
and thymol) were measured at 298.2 K. The COSMO-RS thermodynamic
model and other more empirical approaches were evaluated for the description
of the solubilities and partition coefficients, showing reliable predictions. Lastly, the distribution of the monoterpenoids in the
different environmental compartments was assessed through an intuitive two-dimensional chemical space diagram based on the
physicochemical equilibrium information reported.
Description
Keywords
Essential oils Metabolites Solubility
Pedagogical Context
Citation
Vilas-Boas, Sérgio M.; Costa, Mariana C. Da; Coutinho, João A. P.; Ferreira, Olga; Pinho, Simão (2022). Octanol–water partition coefficients and aqueous solubility data of monoterpenoids: experimental, modeling, and environmental distribution. Industrial & Engineering Chemistry Research. ISSN 0888-5885. 61:8, p. 3154-3167
Publisher
ACS