71686-40-3

Upstream product

• 53669-33-3 4-acetoxy-3,5-dimethoxybenzaldehyde 
• 134-96-3 syringic aldehyde 
• 4206-58-0 (E)-sinapinaldehyde 
• 108-24-7 acetic anhydride 
• 52509-14-5 (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide 
• 39657-48-2 4-acetoxy-3,5-dimethoxycinnamic acid chloride 
• 6627-88-9 4-allyl-2,6-dimethoxyphenol 
• 29540-11-2 4-allyl-2,6-dimethoxyphenyl acetate 

Downstream Products

• 4206-58-0 (E)-sinapinaldehyde 
• 157096-52-1 (E)-3-(4-acetyloxy-3,5-dimethoxyphenyl)-2-propen-1-ol 
• 203179-62-8 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde 
• 154461-65-1 sinapyl aldehyde 4-O-β-D-glucopyranoside 
• 20675-96-1 trans-sinapyl alcohol 
• 213185-31-0 (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-3-(4-acetoxy-3,5-dimethoxy-phenyl)-allyl ester 
• 186023-58-5 (E)-3-(4-Hydroxy-phenyl)-acrylic acid (E)-3-(4-hydroxy-3,5-dimethoxy-phenyl)-allyl ester 

Relevant academic research and scientific papers

Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues

Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.

DDQ-mediated oxidation of allylarenes: Expedient access to cinnamaldehyde-containing phenylpropanoids

Phenylpropanoid natural products containing a cinnamaldehyde motif were easily synthesized from allylarenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation. Representative examples described herein are five types of 4-hydroxycinnamaldehyde derivatives from monolignols biosynthesis, Boropinal C, and 7-methoxywutaifuranal from plant extracts. Especially, simple synthesis of 7-methoxywutaifuranal was exploited through selective mono-oxidation and subsequent isomerization-ring-closing-metathesis strategy.

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.

Phase transfer Wittig reaction with 1,3-dioxolan-2-yl-methyltriphenyl phosphonium salts: An efficient method for vinylogation of aromatic aldehydes

Aldehydes were efficiently transformed into allylic dioxolanes by a Wittig-type reaction, using 1,3-dioxolan-2-yl-methyltriphenylphosphonium bromide under phase transfer conditions. The substituent kinetic effects were studied, and related to Hammett values and electrochemical potentials.

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.