850786-96-8

Upstream product

• 22280-95-1 4-allyloxy-3-methoxybenzaldehyde 
• 121-33-5 vanillin 
• 115375-24-1 (E)-3-(4-(allyloxy)-3-methoxyphenyl)acrylic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 

Downstream Products

• 1384546-10-4 methyl 1-O-feruloyl-3-O-caffeoyl-muco-quinate 
• 1384545-96-3 C₄₂H₅₀O₁₄ 
• 1384546-04-6 methyl 3-feruloyl-muco-quinate 
• 1384546-12-6 methyl 1-O-caffeoyl-3-O-feruloyl-muco-quinate 
• 1384546-15-9 3-O-feruloyl-muco-quinic acid 
• 1384546-00-2 C₂₄H₃₂O₁₁ 
• 1384545-88-3 C₂₇H₃₆O₁₁ 
• 1384545-92-9 C₄₀H₄₈O₁₄ 
• 1384546-08-0 methyl 1,3-di-O-feruloyl-muco-quinate 
• 110978-95-5 2-(4-hydroxyphenyl)ethyl 6-O-(E)-(3-methoxy-4-hydroxy)cinnamoyl β-D-glucopyranoside 

Relevant academic research and scientific papers

A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives

A thorough study on the (E) to (Z) photoisomerization of ferulic acid derivatives (esters, amides of all types, and ketones) was carried out. At the photostationary state, only aliphatic or benzylic tertiary amides reach a nearly complete conversion of (E) isomers into the (Z) ones, whereas for esters, primary and secondary amides or aromatic tertiary amides mixtures of (Z)/(E) ranging from 7 : 93 to 72 : 28 are observed. Ketones show rather limited photoisomerization. However, (Z) ketones may be obtained by the reaction of organometal compounds with an isomerized (Z) Weinreb amide.

Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D

Starting from readily available vanillin and α-D-acetobromo glucose, two natural acylated phenolic glycosides vitexnegheteroin A and ovatoside D were synthesized for the first time in 4 steps with overall yields of 54% and 65%, respectively. The key steps involve the directly regioselective O-6 acylation of vanillin β-D-glucopyranoside with acyl chlorides, and simultaneous removal of the allyl protecting groups on the phenolic acid moiety and reduction of the aldehyde in the aglycon moiety by using Pd(PPh)3-NaBH4 system in one pot.

First diastereoselective synthesis of methyl caffeoyl- and feruloyl-muco-quinates

We report on a diastereoselective synthesis of six derivatives of caffeoyl- and feruloyl-muco-quinic acids. All the muco-quinic acid derivatives were obtained in excellent yield in five steps starting from quinic acid, caffeic acid and ferulic acid. Allyl ether protection of trans-hydroxy cinnamic acids was here introduced to chlorogenic acids synthesis. We show that muco-quinic acid derivatives, which are formally diastereoisomers of chlorogenic acids, can be readily distinguished by their tandem mass spectra. The Royal Society of Chemistry 2012.