31853-85-7Relevant academic research and scientific papers
Microbial production of 4-vinylguaiacol from ferulic acid by Bacillus cereus SAS-3006
Mishra, Shashank,Sachan, Ashish,Vidyarthi, Ambarish Sharan,Sachan, Shashwati Ghosh
, p. 259 - 266 (2014)
Ferulic acid is an abundant cinnamic acid derivative found in the plant kingdom. It is a commercially available substrate utilized to produce flavor compounds such as 4-vinylguaiacol (4-VG), vanillin, and vanillic acid. The isolate Bacillus cereus SAS-3006 was screened and selected based on its ability to produce 4-VG upon ferulic acid biotransformation. It was identified based on morphological and physiochemical characteristics and its 16S ribosomal DNA sequence (GenBank accession number: KF699134). A maximum amount (79.4 mg/L) of 4-VG accumulation was observed on the 5th day of incubation when the culture was grown on 2.5 mM ferulic acid as sole carbon source. Further conversion of 4-VG to other intermediates such as vanillin, vanillic acid, protocatechuic acid, acetovanillone, and vanillyl alcohol was not observed. In-vitro conversion of ferulic acid to 4-VG was also studied with cell extracts of B. cereus SAS-3006. The present study provides the first evidence for production of 4-VG as the sole product using B. cereus SAS-3006.
Synthesis of styrenes through the biocatalytic decarboxylation of trans-cinnamic acids by plant cell cultures
Takemoto,Achiwa
, p. 639 - 641 (2001)
A novel method for producing styrenes from trans-cinnamic acids was developed. When trans-cinnamic acid was incubated with plant cell cultures at room temperature, styrene was obtained. 4-Hydroxy-3-methoxystyrene (2a), 3-nitrostyrene (2f) and furan (2g) were synthesized quantitatively.
Bioinspired Selective Synthesis of Heterodimer 8-5′ or 8- O-4′ Neolignan Analogs
Dong, Kui,Zhao, Chuang-Yuan,Wang, Xiao-Ju,Wu, Li-Zhu,Liu, Qiang
, p. 2816 - 2820 (2021)
The bioinspired synthesis of heterodimer neolignan analogs is reported by single-electron oxidation of both alkenyl phenols and phenols individually, followed by a combination of the resultant radicals. This oxidative radical cross-coupling strategy can afford heterodimer 8-5′ or 8-O-4′ neolignan analogs selectively with the use of air as the terminal oxidant and copper acetate as the catalyst at room temperature.
The bio-based phthalocyanine resins with high Tg and high char yield derived from vanillin
Wang, Caiyun,Shi, Manling,Fang, Linxuan,Dai, Menglu,Huang, Gang,Sun, Jing,Fang, Qiang
, (2021)
The conversion of bio-based vanillin into the heat-resistant polymers is investigated. Firstly, converting the aldehyde group of vanillin into a vinyl group obtained 2-methoxy-4-vinylphenol (S1), which was then treated with nitro-phthalonitrile to give 4-(2-methoxy-4-vinylphenoxy)phthalonitrile (S2). Secondly, thermal polymerization between S1 and S2 in a different molar ratio gave a series of vanillin–based phthalocyanine (V-PN) resins that display high char yield and high Tg. The best result was obtained when the molar ratio between S1 and S2 was 1–50 and the obtained V-PN resin displayed a char yield of up to 76%, a Tg over 400 °C. These data are much better than those of the widely used petroleum-based phthalocyanine resins, suggesting that these bio-based functional monomers derived from vanillin are suitable as the precursors for the fabrication of the ablation-resistant materials in the application of the aerospace industry.
Rapid transformation of ferulic acid to 4-vinyl guaiacol by Bacillus pumilus S-1
Hua, Dong-Liang,Liang, Xiao-Hui,Zhang, Xiao-Dong,Zhang, Jie,Xu, Hai-Peng,Li, Yan,Xu, Ping
, p. 615 - 617 (2013)
A Bacillus pumilus strain S-1, earlier reported to efficient in converting of isoeugenol to vanillin, was found to have the biotransformation ability of ferulic acid. This strain rapidly dissimilated 1 g L-1 ferulic acid within 3 h and 4-vinyl guaiacol was identified as the main product. The highest concentration of 4-vinyl guaiacol, 0.72 g L-1, was obtained with a molar yield of 93.1 %. Different from former reports, 4-vinyl guaiacol was not further metabolized and no other vanilla flavour compounds were found.
Host attractants for red weevil, Rhynchophorus ferrugineus: Identification, electrophysiological activity, and laboratory bioassay
Gunawardena, Neelakanthi E.,Kern, Friedrich,Janssen, Edelgard,Meegoda, Chandana,Schaefer, Doris,Vostrowsky, Otto,Bestmann, Hans Juergen
, p. 425 - 437 (1998)
A steam distillate from the freshly cut young bark of coconut palm Cocos nucifera was analyzed by gas chromatography, combined gas chromatography-electroantennographic detection (GC-EAD) and GC-MS to detect host attractants for the curculionid weevil Rhynchophorus ferrugineus, one of the major coconut pests in Sri Lanka. A twin FID peak consisting of a minor and a major component was shown to possess electrophysiological (EAG) activity. The minor peak was identified as γ-nonanoic lactone 2, while the major peak was identified as 4-hydroxy-3-methoxystyrene 2. In an EAG assay the synthetic racemic nonanoic lactone 1 did not elicit a considerable response in the antenna of R. ferrugineus, whereas the laboratory synthesized 2 showed activity. In a laboratory bioassay using a Y-type olfactometer, synthetic 1 and 2 elicited moderate attractant properties to R. ferrugineus, whereas a 1:1 mixture of the compounds showed increased attraction over that of the individual compounds.
Synthesis, Surface Properties and Effect of an Amino Acid Head Group of 11-(2-Methoxy-4-vinylphenoxy)undecanoicacid-Based Anionic Surfactants
Darapureddi, Prabhakara Rao,Nayak, Rati Ranjan
, p. 1133 - 1142 (2016)
Our present research describes the surface properties of three biobased anionic surfactant synthesized from vinylguaiacol and 11-bromo undecanoic acid. To further improve its hydrophobicity and bioavailability, amino acid head group incorporation was carried out. All these synthesized compounds were thoroughly characterized using NMR and mass spectroscopy. The performance properties such as foaming, wetting, emulsification value and calcium tolerance were evaluated. The studied surfactants possess excellent emulsion stability and moderate calcium tolerance as compared to commercially available surfactant sodium lauryl sulfate (SLS). The micelle formation and the thermodynamics involved at the air–water interface were estimated from surface tension measurements. These surfactants showed a higher tendency towards adsorption at the air–water interface than micellization. Dynamic light scattering and steady state fluorescence anisotropy study were carried out to shed light on the bulk micellization properties of the synthesized surfactant. Along with spherical micelles of?5?nm size, larger aggregates (35–84?nm) were observed with higher anisotropy values. FESEM images further confirmed the larger spherical micelles formed by these surfactants. The surfactants formed chiral aggregates above the critical micelle concentration as indicated by circular dichroism spectra. These surfactants may be suitable candidates for additives to detergents to improve their calcium tolerance especially in the case of hard water. Furthermore, a low foaming ability along with high emulsion stability may find these surfactants to be better replacement of the conventional surfactant used as emulsifiers in many industrial applications.
Synthesis of Lipophilic Antioxidants by a Lipase-B-Catalyzed Addition of Peracids to the Double Bond of 4-Vinyl-2-methoxyphenol
Zago, Erika,Durand, Erwann,Barouh, Nathalie,Lecomte, Jér?me,Villeneuve, Pierre,Aouf, Chahinez
, p. 9069 - 9075 (2015)
4-Vinyl guaiacol (2) was lipophilized through the electrophilic addition of peracids to its vinylic double bond. Those peracids were formed in situ, by the Candida antarctica lipase-B-assisted perhydrolysis of carboxylic acids ranging from C2 to C18, in hydrogen peroxide solution. The addition of peracids with 4-8 carbons in their alkyl chains led to the formation of two regioisomers, with the prevalence of hydroxyesters bearing a primary free hydroxyl (4c-4e). This prevalence became more pronounced when peracids with longer alkyl chains (C10-C18) were used. In this case, only isomers 4f-4h were formed. The antioxidant activity of the resulting hydroxyesters was assessed by means of the conjugated autoxidizable triene (CAT) assay, and it was found out that the 4-vinyl guaiacol antioxidant activity was significantly increased by grafting alkyl chains with 2-8 carbons.
Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- And Alkynylnaphthoquinones and Derivatives
Demidoff, Felipe C.,Rodrigues Filho, Eduardo José P.,De Souza, Andréa Luzia F.,Netto, Chaquip D.,De Carvalho, Leandro L.
supporting information, p. 4097 - 4109 (2021/08/31)
Functionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free Cu I -mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.
Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates
Zhao, Mingtao,Hong, Xulin,Abdullah,Yao, Ruilian,Xiao, Yi
, p. 838 - 847 (2021/02/09)
Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.
