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

Description

(Z,E)-4-(2-butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one, also known as piperitorine, is a natural sesquiterpene alkaloid compound found in black pepper. It exhibits various pharmacological properties, such as anti-inflammatory, analgesic, and antiplatelet activities, and has 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.

Uses

Used in Pharmaceutical Industry:
Piperitorine is used as a therapeutic agent for its anti-inflammatory, analgesic, and antiplatelet properties, making it a potential candidate for the development of drugs targeting inflammation, pain, and blood clotting disorders.
Used in Neuroprotective Applications:
Piperitorine is used as a neuroprotective agent due to its potential to protect neurons from damage and degeneration, which could be beneficial in the treatment of neurodegenerative diseases.
Used in Anti-cancer Applications:
Piperitorine is used as an anti-cancer agent, as it has shown potential in inhibiting the growth and progression of cancer cells. Further research is needed to explore its full potential in cancer therapy.
Used in Nutraceutical Industry:
Piperitorine can be used as a nutraceutical ingredient for its health-promoting properties, such as its anti-inflammatory and analgesic effects, which can contribute to overall wellness and support a healthy lifestyle.

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

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