An efficient method for the synthesis of lignans

SUMMARY:A novel antioxidant, butylated caffeic acid (BCA) was rationally designed by adding a tertbutyl group to caffeic acid, which was synthesized at a high yield (36.2%) from 2-methoxy-4-methylphenol (1) by a four-step reaction including Friedel-Crafts alkylation, bromine oxidation, ether bond hydrolysis and Knoevenagel condensation. Its antioxidant capacity was much stronger than common commercial antioxidant tert-butyl hydroquinone (TBHQ) and its mother compound, caffeic acid, in both rancimat and deep frying tests. When investigated via the DPPH method, the antioxidant capacity of BCA was almost equal to TBHQ, but lower than caffeic acid. BCA could be a potentially strong antioxidant, especially for food processing at high temperatures such as deep frying and baking. KEYWORDS: Antioxidant capacity; Butylated caffeic acid; Deep fryingRESUMEN: Ácido cafeico butilado: un nuevo y eficaz antioxidante. Se diseñó razonadamente un nuevo antioxidante, el ácido cafeico butilado (BCA) mediante la adición de un grupo terc-butilo al ácido cafeico, que se sintetizó con un alto rendimiento (36,2%) a partir de 2-metoxi-4-metilfenol, reacción de Friedel-Crafts, oxidación de bromo, hidrólisis del enlace éter y condensación de Knoevenagel. Su capacidad antioxidante fué mucho más fuerte que la del antioxidante comercial mas común el terc-butil hidroquinona (TBHQ) y la de su compuesto madre el ácido cafeico, tanto en rancimat como en pruebas de fritura. Cuando se investigó mediante el método DPPH, la capacidad antioxidante de BCA fue casi igual a TBHQ, pero menor que la del ácido cafeico. BCA podría ser un fuerte antioxidante potencial, especialmente para el procesamiento de alimentos a alta temperatura, tales como freír y hornear.

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“…The compounds 2-4 were prepared according to earlier methods (Saiz-Poseu et al, 2012;Wang et al, 2006) with slight modifications (Scheme 1).…”

Section: General Synthesis Of Bcamentioning

confidence: 99%

Butylated caffeic acid: An efficient novel antioxidant

et al. 2017

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“…The NMR data agree with those in the literature. 11) meso-4,4 0 -Dihydroxy-3,3 0 -dimethoxylignane-7,7 0 -dione (meso-ODGA). A reaction mixture of 10 (66 mg, 0.12 mmol) and 5% Pd/C (0.12 g) in EtOAc (20 ml) was stirred at ambient temperature under H 2 gas for 2 h before filtration.…”

Section: Meso-44mentioning

confidence: 99%

Antimicrobial Activity of Stereoisomers of Butane-Type Lignans

Kawaguchi¹,

Yamauchi²,

Masuda³

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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“…The large scale isolation of vanillin from lignin is a demonstrated commercial process, [6] and the straightforward hydrogenation of vanillin has been shown to produce 1 in 99 % yield. [7] The condensation of 1 with short-chain aldehydes has the potential to produce bisphenols that can be converted to resins with tunable physical characteristics, which include melting point, hydrophobicity, and toughness. The methyl group in 1 effectively blocks the position para to the hydroxyl group, while the methoxy and phenol groups direct coupling to the 5-and 6-positions, respectively (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Renewable Bisphenols from Creosol

2011

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A series of renewable bisphenols has been synthesized from creosol (2-methoxy-4-methylphenol) through stoichiometric condensation with short-chain aldehydes. Creosol can be readily produced from lignin, potentially allowing for the large scale synthesis of bisphenol A replacements from abundant waste biomass. The renewable bisphenols were isolated in good yields and purities without resorting to solvent-intense purification methods. Zinc acetate was shown to be a selective catalyst for the ortho-coupling of formaldehyde, but was unreactive when more sterically demanding aldehydes were used. Dilute HCl and HBr solutions were shown to be effective catalysts for the selective coupling of aldehydes in the position meta to the hydroxyl group. The acid solutions could be recycled and reused multiple times without decrease in activity or yield.

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An efficient method for the synthesis of lignans

Cited by 51 publications

References 35 publications

Butylated caffeic acid: An efficient novel antioxidant

Butylated caffeic acid: An efficient novel antioxidant

Antimicrobial Activity of Stereoisomers of Butane-Type Lignans

Synthesis of Renewable Bisphenols from Creosol

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