135754-92-6

Upstream product

• 37746-78-4 4-bromo-trans-crotonic acid ethyl ester 
• 123-08-0 4-hydroxy-benzaldehyde 
• 103582-08-7 methyl (2E,4E)-5-(4-hydroxyphenyl)penta-2,4-dienoate 

Downstream Products

• 249938-84-9 2,4-dinitrophenyl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoate 
• 313048-02-1 2,5-dinitrophenyl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoate 
• 313048-04-3 4-chloro-2-nitrophenyl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoate 
• 313048-03-2 2-chloro-4-nitrophenyl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoate 
• 313048-05-4 4-nitrophenyl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoate 
• 313048-06-5 4-cyanophenyl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoate 

Relevant academic research and scientific papers

COSMETIC OR PHARMACEUTICAL USE OF AVENANTHRAMIDE L

The present invention relates generally to: the cosmetic or pharmaceutical use of avenanthramide L or an oat extract comprising avenanthramide L; avenanthramide L or an oat extract comprising avenanthramide L as a neurokinin-1 receptor NK1R antagonist; and a method for preparing of preparing avenalumic acid and/or avenanthramide L.

An effective strategy to develop active cinnamic acid-directed antioxidants based on elongating the conjugated chains

To optimize antioxidant activity and lipophilicity of cinnamic acid derivatives (CAs) including ferulic acid, sinapic acid, 3,4-dimethoxycinnamic acid, and p-hydroxycinnamic acid, four analogs bearing an additional double bond between their aromatic ring and propenoic acid moiety were designed and synthesized based on the conjugated chain elongation strategy. The antioxidant performance of the CAs were investigated by 2,2′-diphenyl-1-picrylhydrazyl (DPPH)-scavenging, ferric reducing/antioxidant power, cyclic voltammetry, DNA strand breakage-inhibiting and anti-haemolysis activity assays. It was found that CAs with elongation of conjugated chains display increased DPPH --scavenging, DNA strand breakage-inhibiting and anti-haemolysis activities as compared to their parent molecules, due to their improved hydrogen atom-donating ability and lipophilicity. Overall, this work highlights an effective strategy to develop potential CA-directed antioxidants by elongating their conjugated chain.

Occurrence of an elongated p-oxo ketene intermediate in the dissociative alkaline hydrolysis of aryl (2E,4E)-5-(4'-hydroxyphenyl)pentadienoates

The alkaline hydrolysis of title esters possessing acidic leaving groups follows an E1cB mechanism involving the participation of an 'extra extended' p-oxo ketene intermediate. For the hydrolysis of the 2,4-dinitrophenyl ester kinetic data, activation parameters and trapping of the intermediate clearly indicate that the dissociative pathway carries the reaction flux. Break in the Bronsted plot of the apparent second-order rate constants versus the pK(a) of the leaving group suggests that the reaction mechanism changes from E1cB to B(Ac)2 for esters having pK(a) higher than about 6.

A new, "elongated" oxo ketene intermediate in the dissociative hydrolysis of 2,4-dinitrophenyl (2E,4E)-5-(4′-hydroxyphenyl)pentadienoate

(matrix presented) Reactivity comparison, Arrhenius parameters, and trapping of the above-depicted unsaturated intermediate strongly suggest that the alkaline hydrolysis of the title ester follows a mechanism of the E1cB type. This is the first observation of the occurrence of a dissociative route in the hydrolysis of an acyl derivative with three π-systems interposed between the hydroxyl group (the internal nucleophile upon ionization) and the reaction center. Comparison with the hydrolysis of 2,4-dinitrophenyl 4′-hydroxybenzoate shows that interposition of the vinylenic groups is beneficial to the dissociative route.