6053-02-7Relevant articles and documents
Monitoring hydroxycinnamic acid decarboxylation by lactic acid bacteria using high-throughput UV-Vis spectroscopy
García-Cano, Israel,Giusti, M. Monica,Jiménez-Flores, Rafael,Miyagusuku-Cruzado, Gonzalo,Rocha-Mendoza, Diana
, (2020/08/24)
Hydroxycinnamic acid (HCA) decarboxylation by lactic acid bacteria (LAB) results in the production of 4-vinylplenols with great impact on the sensorial characteristics of foods. The determination of LAB decarboxylating capabilities is key for optimal strain selection for food production. The activity of LAB strains from the Ohio State University-Parker Endowed Chair (OSU-PECh) collection potentially capable of synthesizing phenolic acid decarboxylase was evaluated after incubation with HCAs for 36 h at 32 °C. A high-throughput method for monitoring HCAs decarboxylation was developed based on hypsochromic shifts at pH 1.0. Out of 22 strains evaluated, only Enterococcus mundtii, Lactobacillus plantarum and Pediococcus pentosaceus were capable of decarboxylating all p-coumaric, caffeic and ferulic acids. Other strains only decarboxylated p-coumaric and caffeic acid (6), only p-coumaric acid (2) or only caffeic acid (1), while 10 strains did not decarboxylate any HCA. p-Coumaric acid had the highest conversion efficiency, followed by caffeic acid and lastly ferulic acid. Results were confirmed by HPLC-DAD-ESI-MS analyses, showing the conversion of HCAs into their 4-vinylphenol derivatives. This work can help improve the sensory characteristics of HCA-rich foods where fermentation with LAB was used during processing.
Bio-based vinylphenol family: Synthesis via decarboxylation of naturally occurring cinnamic acids and living radical polymerization for functionalized polystyrenes
Takeshima, Hisaaki,Satoh, Kotaro,Kamigaito, Masami
, (2019/08/20)
A series of bio-based vinylphenols or hydroxystyrenes is prepared by simple decarboxylation of various naturally occurring cinnamic acids such as o-, m-, and p-coumaric; caffeic; ferulic; and sinapinic acids, which possess hydroxy groups and other substituents at different positions on the aromatic ring. After protection of the phenolic moieties with trialkylsilyl groups, reversible addition–fragmentation chain-transfer polymerization is accomplished with cumyl dithiobenzoate to afford various bio-based hydroxyl-protected polystyrenes with controlled molecular weights and narrow molecular weight distributions. Subsequent deprotection of the silyl groups under mild conditions results in a series of well-defined functionalized polystyrenes possessing different numbers (mono-, di-, tri-) of hydroxy groups at different positions (o, m, p). The obtained functionalized polystyrenes show unique thermal properties depending on the substituents, and those with phenol and catechol groups serve as reducing agents for silver ions.
Preparation method of 3,4-diacetoxystyrene
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, (2018/07/06)
The invention relates to a preparation method of 3,4-diacetoxystyrene. The method comprises the steps of allowing 3,4-dihydroxy benzaldehyde and malonic acid to react in the presence of at least one organic solvent and a catalyst at 60-70 DEG C to generate a first reaction mixture containing 3,4-dihydroxy cinnamic acid, heating up to 80-90 DEG C to allow the first reaction mixture to continue reaction to generate a second reaction mixture containing 3,4-dyhydroxy styrene, allowing 3,4-dyhydroxy styrene to react with an acetylation reagent to generate a third reaction mixture containing 3,4-diacetoxystyrene, and purifying the third reaction mixture to form 3,4-diacetoxystyrene. The invention further provides a preparation method of an acetylation derivative of styrene. The method has the benefits that raw materials for preparation are easy to obtain; the cost is low; a synthesis condition is mild; a technology is simple and convenient; a post-treatment procedure is quick; and industrialization is easy to achieve.
