69017-41-0

Upstream product

• 50906-12-2 4-acetoxy-3-methoxycinnamoyl chloride 
• 881-68-5 vanillin acetate 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 
• 458-36-6 trans-coniferyl aldehyde 

Downstream Products

• 458-35-5 coniferal alcohol 
• 213185-30-9 (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-3-(4-acetoxy-3-methoxy-phenyl)-allyl ester 
• 113349-27-2 3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside 
• 65401-83-4 (E)-2-methoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate 
• 67638-41-9 (E)-3-(4-Hydroxy-phenyl)-acrylic acid (E)-3-(4-hydroxy-3-methoxy-phenyl)-allyl ester 

Relevant academic research and scientific papers

A selective and mild glycosylation method of natural phenolic alcohols

Several bioactive natural p-hydroxyphenylalkyl β-D-glucopyranosides, such as vanillyl β-D-glucopyranoside, salidroside and isoconiferin, and their glycosyl analogues were prepared by a simple reaction sequence. The highly efficient synthetic approach was achieved by utilizing acetylated glycosyl bromides as well as aromatic moieties and mild glycosylation promoters. The aglycones, p-O-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2-trans-O-glycosylation methods were studied, including the DDQ-iodine or ZnO-ZnCl2 catalyst combination. Among them, ZnO-iodine has been identified as a new glycosylation promoter and successfully applied to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.

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; selective deacetylation, without cinnamate ester hydrolysis, was accomplished with neat pyrrolidine.

A mild synthesis of coumaryl, coniferyl, sinapyl aldehydes and alcohols

Acetylconiferyl aldehyde is obtained from acetylvanillin by a Wittig reaction under phase-transfer conditions; basic hydrolysis gives coniferyl aldehyde, or after reduction with sodium borohydride affords coniferyl alcohol. This method is extended to the sinapyl and coumaryl series.

BIOSYNTHESIS OF LIGNANS IN FORSYTHIA INTERMEDIA

Feeding experiments with young shoots of Forsythia intermedia have shown that phenylalanine and ferulic acid are good precursors of the dibenzylbutyrolactone lignan arctigenin and the furofuran lignans phillygenin and epipinoresinol.Although matairesinol was incorporated into arctigenin, and epipinoresinol into phillygenin, in accord with late methylation steps in the biosynthetic pathway, some incorporation of label from one lignan class into the other was observed, particularly from epipinoresinol into arctigenin.This may indicate a high degree of catabolic activity followed by non-specific incorporation. Coniferyl alcohol was incorporated into all three lignans with a significant increase in the 3H:14C isotopic ratio.This supports the hypothesis that the lignans arise by oxidative coupling of two coniferyl alcohol units, rather than from two ferulic acid or coniferaldehyde units.The observed increase in isotopic ratio probably results from a primary isotope effect in the reversible oxidation-reduction reactions interrelating cinnamic acids and cinnamyl alcohols.A similar increase in isotopic ratio was measured during biosynthesis of the aryltetralin lactone lignan podophyllotoxin in Podophyllum hexandrum.