709007-50-1

Basic information

• Product Name: 2-Propenoic acid, 3-(3,4,5-trihydroxyphenyl)-, (2E)-
• CAS NO: 709007-50-1
• Molecular Formula: C9H8O5
• Mol File: 709007-50-1.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(3,4,5-trihydroxyphenyl)-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(3,4,5-trihydroxyphenyl)-, (2E)-(709007-50-1)
• EPA Substance Registry System: 2-Propenoic acid, 3-(3,4,5-trihydroxyphenyl)-, (2E)-(709007-50-1)

Safety Data

• Hazardous Substances Data: 709007-50-1(Hazardous Substances Data)

Upstream product

• 530-59-6 sinapinic acid 
• 13677-79-7 gallaldehyde 
• 6093-59-0 trans-3-(3,4,5-trihydroxyphenyl)-2-propenoic acid 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 141-82-2 malonic acid 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 110-89-4 piperidine 
• 331-39-5 caffeic acid 
• 7400-08-0 p-Coumaric Acid 

Downstream Products

• 7560-49-8 3,4,5-trimethoxycinnamic acid methyl ester 

Relevant articles and documents

Semi-synthesis and Structure–Activity Relationship of Neuritogenic Oleanene Derivatives

(3S,4R)-23,28-Dihydroxyolean-12-en-3-yl (2E)-3-(3,4-dihydroxyphenyl)acrylate (1 a), which possesses significant neuritogenic activity, was isolated from the traditional Chinese medicine (TCM) plant, Desmodium sambuense. To confirm the structure and to assess biological activity, we semi-synthesized 1 a from commercially available oleanolic acid. A series of novel 1 a derivatives was then designed and synthesized for a structure–activity relationship (SAR) study. All synthetic derivatives were characterized by analysis of spectral data, and their neuritogenic activities were evaluated in assays with PC12 cells. The SAR results indicate that the number and position of the hydroxy groups on the phenyl ring and the triterpene moiety, as well as the length of the (saturated or unsaturated) alkyl chain that links the phenyl ring with the triterpene critically influence neuritogenic activity. Among all the tested compounds, 1 e [(3S,4R)-23,28-dihydroxyolean-12-en-3-yl (2E)-3-(3,4,5-trihydroxyphenyl)acrylate] was found to be the most potent, inducing significant neurite outgrowth at 1 μm.

Biology-oriented development of novel lipophilic antioxidants with neuroprotective activity

Hydroxycinnamic derivatives based on ferulic and caffeic acids were designed to meet the pharmacokinetic requirements to cross the blood-brain barrier and to display neuroprotective activity within the central nervous system. Biological screening included

Novel flavonol glycosides from the aerial parts of lentil (Lens culinaris)

While the phytochemical composition of lentil (Lens culinaris) seeds is well described in scientific literature, there is very little available data about secondary metabolites from lentil leaves and stems. Our research reveals that the aerial parts of lentil are a rich source of flavonoids. Six kaempferol and twelve quercetin glycosides were isolated, their structures were elucidated using NMR spectroscopy and chemical methods. This group includes 16 compounds which have not been previously described in the scientific literature: quercetin 3-O-P-D-glucopyranosyl(1→2)-β-D-galactopyranoside-7-O-β-D-glucuropyranoside (1), kaempferol 3-O-β-D-glucopyranosyl(1→2)-β-D-galactopyranoside-7-O-β-D-glucuropyranoside (3), their derivatives 4-10,12-15,17,18 acylated with caffeic, p-coumaric, ferulic, or 3,4,5-trihydroxycinnamic acid and kaempferol 3-O-{[(6-O-E - p-coumaroyl)-β-D-glucopyranosyl(1→2)]-α-L-rhamnopyranosyl(1-6)}-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (11). Their DPPH scavenging activity was also evaluated. This is probably the first detailed description of flavonoids from the aerial parts of lentil.