1246948-10-6

Basic information

• Product Name: (E)-3-(2,4-dihydroxyphenyl)-1-(piperidin-1-yl)prop-2-en-1-one
• Synonyms: (E)-3-(2,4-dihydroxyphenyl)-1-(piperidin-1-yl)prop-2-en-1-one
• CAS NO: 1246948-10-6
• Molecular Weight: 247.294
• Mol File: 1246948-10-6.mol

Chemical Properties

• CAS DataBase Reference: (E)-3-(2,4-dihydroxyphenyl)-1-(piperidin-1-yl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(2,4-dihydroxyphenyl)-1-(piperidin-1-yl)prop-2-en-1-one(1246948-10-6)
• EPA Substance Registry System: (E)-3-(2,4-dihydroxyphenyl)-1-(piperidin-1-yl)prop-2-en-1-one(1246948-10-6)

Safety Data

• Hazardous Substances Data: 1246948-10-6(Hazardous Substances Data)

Upstream product

• 13246-46-3 2,4-dibenzyloxybenzaldehyde 
• 1356601-48-3 ethyl 3-(2,4-dibenzyloxyphenyl)-2-propenoate 
• 95-01-2 2,4-Dihydroxybenzaldehyde 

Relevant articles and documents

Design, synthesis and anti-melanogenic effect of cinnamamide derivatives

Pigmentation disorders are attributed to excessive melanin which can be produced by tyrosinase. Therefore, tyrosinase is supposed to be a vital target for the treatment of disorders associated with overpigmentation. Based on our previous findings that an (E)-β-phenyl-α,β-unsaturated carbonyl scaffold can play a key role in the inhibition of tyrosinase activity, and the fact that cinnamic acid is a safe natural substance with a scaffolded structure, it was speculated that appropriate cinnamic acid derivatives may exhibit potent tyrosinase inhibitory activity. Thus, ten cinnamamides were designed, and synthesized by using a Horner-Emmons olefination as the key step. Cinnamamides 4 (93.72% inhibition), 9 (78.97% inhibition), and 10 (59.09% inhibition) with either a 2,4-dihydroxyphenyl, or 4-hydroxy-3-methoxyphenyl substituent showed much higher mushroom tyrosinase inhibition at 25 μM than kojic acid (18.81% inhibition), used as a positive control. Especially, the two cinnamamides 4 and 9 having a 2,4-dihydroxyphenyl group showed the strongest inhibition. Docking simulation with tyrosinase revealed that these three cinnamamides, 4, 9, and 10, bind to the active site of tyrosinase more strongly than kojic acid. Cell-based experiments carried out using B16F10 murine skin melanoma cells demonstrated that all three cinnamamides effectively inhibited cellular tyrosinase activity and melanin production in the cells without cytotoxicity. There was a close correlation between cellular tyrosinase activity and melanin content, indicating that the inhibitory effect of the three cinnamamides on melanin production is mainly attributed to their capability for cellular tyrosinase inhibition. These results imply that cinnamamides having the (E)-β-phenyl-α,β-unsaturated carbonyl scaffolds are promising candidates for skin-lighting agents.

Base generator

A photosensitive resin composition which is excellent in resolution, low in cost, and usable in a wide range of structures of polymer precursors each of which is reacted into a final product by a basic substance or by heating in the presence of a basic su