5492-79-5

Basic information

• Product Name: (Z,E)-4-(2-butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one
• Synonyms: (Z,E)-4-(2-butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one;4-[(1Z,2E)-2-Buten-1-ylidene]-3,5,5-trimethyl-2-cyclohexen-1-one;(4Z)-4-[(E)-but-2-enylidene]-3,5,5-trimethylcyclohex-2-en-1-one
• CAS NO: 5492-79-5
• Molecular Formula: C₁₃H₁₈O
• Molecular Weight: 190.28142
• EINECS: 226-825-8
• Mol File: 5492-79-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z,E)-4-(2-butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z,E)-4-(2-butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one(5492-79-5)
• EPA Substance Registry System: (Z,E)-4-(2-butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one(5492-79-5)

Safety Data

• Hazardous Substances Data: 5492-79-5(Hazardous Substances Data)

Usage

General Description

(Z,E)-4-(2-butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one, also known as piperitorine, is a natural chemical compound found in black pepper. It is a sesquiterpene alkaloid that possesses various pharmacological properties, including anti-inflammatory, analgesic, and antiplatelet activities. Piperitorine has also been studied for its potential as a neuroprotective and anti-cancer agent. Its unique chemical structure and biological activities make piperitorine a promising compound for further research and potential therapeutic applications.

InChI:InChI=1/C13H18O/c1-5-6-7-12-10(2)8-11(14)9-13(12,3)4/h5-8H,9H2,1-4H3/b6-5+,12-7+

Upstream product

• 149457-34-1 6-Bromo-8-but-3-enyl-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-7-ene 
• 14203-64-6 7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one 
• 149457-31-8 8-(But-3-enyl)-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-ol 

Relevant articles and documents

Novel synthesis of degradation products of carotenoids, megastigmatrienone analogues and blumenol-A

Synthesis of 4-alkylidene-3,5,5-trimethylcyclohex-2-enones 7 has been achieved utilising 1,4-conjugate dehydrobromination of allylic bromides 5 as a key step. This chemical transformation is applied to the synthesis of degradation products of carotenoids: megastigmatrienones 7e/1-4,4-methylene-3,5,5-trimethylcyclohex-2-enone 7a, 4-(3-hydroxybutylidene)-3,5,5-trimethylcyclohex-2-enone 9,1,3,7,7-tetramethyl-2-oxabicyclo[4.4.0]dec-5-en-9-one 10a-b and 3,4,7,8-tetrahydro-4,4,7-trimethylnaphthalen-2(6H)-one 15. A novel photoisomerisation of 4-[(Z)-3-acetoxybut-2-enyl]-4-hydroxy-3,5,5-trimethylcyclohex-2-enone 19 to 4-[(E)-3-acetoxybut-2-enyl]-4-hydroxy-3,5,5-trimethylcyclohex-2-enone 20 enables us to synthesise blumenol-A 21.