Chemo-enzymatic synthesis and screening
of a library of renewable
saturated and unsaturated bis- and trisphenols deriving from p-hydroxycinnamic acids (i.e., p-coumaric
acid, ferulic acid, and sinapic acid) and biobased diols/triol (i.e.,
isosorbide, 1,4-butanediol, glycerol) showed that these compounds
were potent antioxidants/antiradicals. To optimize their antiradical
activities, we assessed the structure–activity relationships
(SAR) of these phenolics focusing on the internal diol/triol linker,
the degree of methoxylation on the aromatic rings, and the CC
double bond of the α,β-unsaturated esters. We found that
methoxylation degree and the unsaturation were critical for antiradical
activity while the nature of the diol had a small impact. Indeed,
SAR revealed that, for saturated compounds, the higher the methoxylation
degree, the higher the antiradical activity; on the other hand, unexpectedly,
the presence of the unsaturation had a negative impact on the activity.
The antiradical activities of these bis- and trisphenols were then
compared to that of Irganox 1010, a widely used antioxidant additive
in polypropylene. The optimized compounds, i.e. those deriving from
sinapic acid and with saturated esters, proved as effective while
being 100% biobased and obtained through a more sustainable synthetic
pathway. Thermal analyses (TGA) demonstrated that these bis- and trisphenols
exhibit high thermal stability and that their T
d5% can be easily tailored by playing with the structure of
the bisphenol core. p-Hydroxycinnamic acids-based
bis- and trisphenols are thus promising easily accessible, eco-friendly,
and biocompatible antiradical additives for a sustainable approach
to the stabilization of polymers in packaging and other applications.
An experimental design based on Response Surface Methodology (RSM) was used for the formulation of a growth medium based on sugar beet and wheat processing coproducts adapted to the cultivation of Lactobacillus reuteri (L. reuteri) DSM17938. The strain was cultivated on 30 different media varying by the proportions of sugar beet and wheat processing coproducts, and the concentration of yeast extract, tween 80 and vitamin B12. The media were used in a two-step process consisting of L. reuteri cultivation followed by the bioconversion of glycerol into 3-hydroxypropionic acid by resting cells. The efficiency of the formulations was evaluated according to the maximal optical density at the end of the growth phase (∆OD 620nm ) and the ability of the resting cells to convert glycerol into 3-hydroxypropionic acid, a platform molecule of interest for the plastic industry. De Man, Rogosa, and Sharpe medium (MRS), commonly used for the cultivation of lactic bacteria, was used as the control medium. The optimized formulation allowed increasing the 3-HP production.
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