1083200-79-6

Basic information

• Product Name: 1,7-Bis(4-hydroxyphenyl)hept-1-en-3-one
• Synonyms: 1,7-Bis(4-hydroxyphenyl)hept-1-en-3-one
• CAS NO: 1083200-79-6
• Molecular Formula: C19H20O3
• Molecular Weight: 296.3603
• Mol File: 1083200-79-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,7-Bis(4-hydroxyphenyl)hept-1-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,7-Bis(4-hydroxyphenyl)hept-1-en-3-one(1083200-79-6)
• EPA Substance Registry System: 1,7-Bis(4-hydroxyphenyl)hept-1-en-3-one(1083200-79-6)

Safety Data

• Hazardous Substances Data: 1083200-79-6(Hazardous Substances Data)

Usage

General Description

1,7-Bis(4-hydroxyphenyl)hept-1-en-3-one, also known as DPHO, is a chemical compound with the formula C19H18O3. It is classified as a phenol and a ketone, with two hydroxyphenyl groups attached at either end of a heptenone chain. This means it has two phenol groups, which consist of a benzene ring with an attached hydroxyl (-OH) group, and a ketone group characterized by a carbon double-bonded to an oxygen atom. Furthermore, its heptenone chain denotes the presence of seven carbon atoms. DPHO is less common and less extensively studied than other phenolic compounds. Potential applications or uses of this compound are not well-documented in scientific literature. Although chemical compounds with similar structures have been studied for their potential antioxidant and anticancer activities.

Upstream product

• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 84184-57-6 (E)-3-[4-(methoxymethoxy)phenyl]acrylaldehyde 
• 84184-56-5 (E)-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-ol 
• 7400-08-0 p-Coumaric Acid 

Downstream Products

• 130233-83-9 1,7-bis(4'-hydroxyphenyl)-3-heptanone 

Relevant articles and documents

Synthesis of natural and non-natural curcuminoids and their neuroprotective activity against glutamate-induced oxidative stress in HT-22 cells

A strategy for the synthesis of natural and non-natural 5-deoxy-6,7-dihydrocurcuminoids (diarylheptanoids) was developed for the preparation of 14 compounds with varying aromatic substituent patterns and a different functionality in the aliphatic seven-carbon chain. The in vitro protective activity against glutamate-induced neuronal cell death was examined in the murine hippocampal cell line HT-22 to find structural motifs responsible for neuroprotective effects in vitro. Among the tested compounds the ferulic acid-like unit, present in the structures of (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-en-3-one (5) and (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hept-1-en-3-one (7), appeared to be an important feature for protection against glutamate-induced neurotoxicity. Both compounds demonstrated significant neuroprotective activity in a concentration range between 1 and 25 ～M without showing toxic effects in a cytotoxicity assay with HT-22 cells. Furthermore, (E)-1,7-bis(3,4-dihydroxyphenyl)hept-1-en-3-one (9), exhibiting a caffeic acid-like structural motif, displayed a neuroprotective activity at a nontoxic concentration of 25 ～M. In contrast, (1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione (4, di-O-demethylcurcumin) showed mainly cytotoxic effects. A corresponding single-ring analogue that contains the ferulic acid-like unit as an enone was not active.