Facile Synthesis of 4-Hydroxycinnamyl p-Coumarates

Facile Synthesis of 4-Hydroxycinnamyl p-Coumarates

Coniferyl p-coumarate (4-hydroxy-3-methoxycinnamyl 4-hydroxycinnamate) and sinapyl p-coumarate (3,5-dimethoxy-4-hydroxycinnamyl 4-hydroxycinnamate) were synthesized in high overall yield. In this improved method acetate was used as the phenol protecting group instead of 2,4-dinitrophenyl ether; sele...

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Veröffentlicht in:Journal of agricultural and food chemistry 1998-08, Vol.46 (8), p.2911-2913
Hauptverfasser: Lu, Fachuang, Ralph, John
Format: Artikel
Sprache:eng
Schlagworte:
ACIDE COUMARIQUE
ACIDOS CUMARICOS
ACYLATION
CHEMICAL REACTIONS
Chemistry
CONIFERYL P-COUMARIC ACID
COUMARIC ACIDS
CROP YIELD
DEACETYLATION
Exact sciences and technology
FITOALEXINA
GRAMINEAS
GRAMINEE
GRASSES
LIGNINAS
LIGNINE
LIGNINS
Noncondensed benzenic compounds
Organic chemistry
P-COUMARIC ACID
PHYTOALEXINE
PHYTOALEXINS
PRECURSORS
Preparations and properties
REACCIONES QUIMICAS
REACTION CHIMIQUE
RENDEMENT DES CULTURES
RENDIMIENTO DE CULTIVOS
SINAPYL P-COUMARIC ACID
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Zusammenfassung:Coniferyl p-coumarate (4-hydroxy-3-methoxycinnamyl 4-hydroxycinnamate) and sinapyl p-coumarate (3,5-dimethoxy-4-hydroxycinnamyl 4-hydroxycinnamate) were synthesized in high overall yield. In this improved method acetate was used as the phenol protecting group instead of 2,4-dinitrophenyl ether; selective deacetylation, without cinnamate ester hydrolysis, was accomplished with neat pyrrolidine. Keywords: Coniferyl p-coumarate; sinapyl p-coumarate; lignin; acylation; grasses; radical coupling; deacetylation
ISSN:0021-8561
1520-5118
DOI:10.1021/jf980440y