92500-17-9

Basic information

• Product Name: 1-(4-HYDROXY-3-PIPERIDIN-1-YLMETHYL-PHENYL)-ETHANONE
• Synonyms: Acetophenone,4'-hydroxy-3'-(piperidinomethyl)- (7CI);1-[4-Hydroxy-3-[(piperidin-1-yl)methyl]phenyl]ethanone
• CAS NO: 92500-17-9
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 0
• Mol File: 92500-17-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 396.6°Cat760mmHg
• Flash Point: 193.6°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 7.4E-07mmHg at 25°C
• CAS DataBase Reference: 1-(4-HYDROXY-3-PIPERIDIN-1-YLMETHYL-PHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-HYDROXY-3-PIPERIDIN-1-YLMETHYL-PHENYL)-ETHANONE(92500-17-9)
• EPA Substance Registry System: 1-(4-HYDROXY-3-PIPERIDIN-1-YLMETHYL-PHENYL)-ETHANONE(92500-17-9)

Safety Data

• Hazardous Substances Data: 92500-17-9(Hazardous Substances Data)

Usage

Appearance

White crystalline solid

Odor

Sweet, floral

Uses

a. Production of fragrances and flavorings
b. Precursor in the synthesis of pharmaceuticals and agrochemicals

Biological activities

a. Potential anti-inflammatory properties
b. Potential antioxidant properties

Natural occurrence

Present in some plants and insects as a pheromone or defensive chemical

Synthesis

Derived from safrole, a substance found in certain essential oils, through a series of chemical reactions

Importance

Versatile chemical compound in the fields of chemistry, pharmaceuticals, and natural products research

InChI:InChI=1/C14H19NO2/c1-11(16)12-5-6-14(17)13(9-12)10-15-7-3-2-4-8-15/h5-6,9,17H,2-4,7-8,10H2,1H3/p+1

Upstream product

• 110-89-4 piperidine 
• 24085-05-0 1-(3-chloromethyl-4-hydroxyphenyl)ethanone 
• 50-00-0 formaldehyd 
• 99-93-4 4-Hydroxyacetophenone 

Downstream Products

• 93344-85-5 Thiophosphoric acid O-(4-acetyl-2-piperidin-1-ylmethyl-phenyl) ester O',O''-diethyl ester 

Relevant articles and documents

2-Benzyloxynaphthalene aminoalkylated chalcone designed as acetylcholinesterase inhibitor: Structural characterisation, in vitro biological activity and molecular docking studies

The design of an acetylcholinesterase inhibitor with multifunctional properties became the perspective for the development of an effective drug against Alzheimer's disease. Towards this target, 1-{4-hydroxy-3-[(piperidin-1-yl)methyl]phenyl}ethan-1-one (chalcone 3) was prepared and studied as an acetylcholinesterase inhibitor. The novel chalcone 3 was synthesised via Claisen-Schmidt condensation reaction with 84percent yield and characterized using 1D and 2D NMR spectroscopy. The in vitro bioactivity studies of chalcone 3 demonstrated excellent inhibitory activity against AChE (IC50 1.0 nM) showing 33-fold better inhibition than donepezil, biometal chelating ability and moderate antioxidant activity. Chalcone 3 with these fascinating multifunctional proprieties can be a good candidate for the development of AD treatments. A molecular modelling investigation revealed that chalcone 3 showed dual binding inhibition of AChE enzyme. XRD shows short intra- and inter-molecular interactions with two chalcone 3 molecules per cell. Interesting Hirshfeld Surface Analysis (HSA) was conducted showing explicit agreement with the XRD analysis.

Synthesis and Insecticidal Activity of Some New 3-Substituted 4-Hydroxyacetophenones

A number of 3-(N,N-dialkylaminomethyl)-4-hydroxy acetophenones (4-10) and their thiophosphorylated compounds (11-16) have been synthesised and screened for their insecticidal activity.Only thiophosphorylated compounds are found to possess significant activity.The intramolecular hydrogen bonding in these compounds has also been discussed.