539-70-8

Basic information

• Product Name: 2-methyl-6-methylideneocta-2,7-dien-4-one
• Synonyms: 1Y1& U1V1YU1& 1U1; 2,7-Octadien-4-one, 2-methyl-6-methylene-; 2-Methyl-6-methyleneocta-2,7-dien-4-one; 2-Methyl-6-methylideneocta-2,7-dien-4-one; 539-70-8; Myrcenon; Myrcenone
• CAS NO: 539-70-8
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.2176
• Mol File: 539-70-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 218.5°C at 760 mmHg
• Flash Point: 83.7°C
• Density: 0.862g/cm³
• Vapor Pressure: 0.125mmHg at 25°C
• Refractive Index: 1.458
• CAS DataBase Reference: 2-methyl-6-methylideneocta-2,7-dien-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-6-methylideneocta-2,7-dien-4-one(539-70-8)
• EPA Substance Registry System: 2-methyl-6-methylideneocta-2,7-dien-4-one(539-70-8)

Safety Data

• Hazardous Substances Data: 539-70-8(Hazardous Substances Data)

Usage

Description

2-methyl-6-methylideneocta-2,7-dien-4-one is a member of the class of monoterpene ketones, characterized by its unique structure with a carbonyl group and a methylidene group at positions 2 and 6, respectively. This organic compound is derived from the larger family of monoterpenes, which are known for their diverse range of applications and properties.

Uses

Used in Flavor and Fragrance Industry:
2-methyl-6-methylideneocta-2,7-dien-4-one is used as a key compound in the flavor and fragrance industry for its distinctive aroma and taste. Its unique chemical structure contributes to the creation of various scents and flavors, making it a valuable ingredient in the development of perfumes, colognes, and other scented products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-methyl-6-methylideneocta-2,7-dien-4-one is utilized as an intermediate in the synthesis of various drugs and medicinal compounds. Its versatile chemical properties allow for its use in the development of new medications, potentially leading to advancements in the treatment of various diseases and conditions.
Used in Chemical Synthesis:
2-methyl-6-methylideneocta-2,7-dien-4-one serves as a valuable building block in the synthesis of a wide range of organic compounds. Its unique structure makes it a useful starting material for the production of various chemicals, including dyes, plastics, and other specialty chemicals.
Used in Research and Development:
Due to its unique chemical properties, 2-methyl-6-methylideneocta-2,7-dien-4-one is often employed in research and development settings. Scientists and researchers use this compound to study its reactivity, explore new synthetic pathways, and develop novel applications in various industries.

Synthesis Reference(s)

Tetrahedron Letters, 20, p. 429, 1979 DOI: 10.1016/S0040-4039(01)93524-5

Upstream product

• 58193-39-8 8-chloro-2,6-dimethyl-octa-2,6-dien-4-one 
• 14434-41-4 ipsdienol 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 187800-99-3 Dimethyl-(2-methylene-but-3-enyl)-phenyl-silane 
• 78-79-5 isoprene 
• 6994-89-4 (E)-2-methyl-6-methylene-3,7-octadiene-2-ol 
• 18913-31-0 2,3-butadien-1-ol 
• 114846-91-2 4-methyl-3-penten-2-one dimethyl ketal 
• 4786-24-7 3,3-dimethylacrylonitrile 
• 23691-13-6 2-(bromomethyl)buta-1,3-diene 
• 19860-70-9 2-(2-methylene-but-3-enyl)-2-(2-methyl-propenyl)-[1,3]dithiane 
• 70901-64-3 trimethyl(2-methylenebut-3-enyl)silane 

Downstream Products

• 60894-97-5 (R)-(-)-2-Methyl-6-methylene-2,7-octadien-4-ol 
• 35628-00-3 (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol 
• 502-33-0 trans-ocimenone 
• 14434-41-4 ipsdienol 

Relevant articles and documents

METHOD FOR PRODUCING MONOTERPENE AND MONOTERPINOID COMPOUNDS AND USE THEREOF

In various embodiments, the present disclosure provides a method and enzyme for forming various compounds, such as monoterpenes and monoterpenoid compounds. In a specific example, the present disclosure provides a method for producing one or more of (?)-ipsdienol, (?)-ipsenol, ipsenone, and ipsdienone. The present disclosure also provides methods of using compounds formed from the disclosed method and enzyme.

Claisen Rearrangements with Mesityl Oxide Dimethyl Ketal. Synthesis of Ipsdienone, E- and E-Ocimenone, 2,6-Dimethyl-2,7-octadien-4-one and 2,6-Dimethyl-2,7-octadien-4-ol

4-Methyl-3-penten-2-one (mesityl oxide) dimethyl ketal was synthesized and utilizied in Claisen rearrangements with 2,3-butadien-1-ol and 2-buten-1-ol to form ipsdienone and 2,6-dimethyl-2,7-octadien-4-one, from which the ocimenones and 2,6-dimethyl-2,7-octadien-4-ol were prepared.

CONDENSATION DES NITRILES AVEC LES ORGANOZINCIQUES ALLYLIQUES. APPLICATIONS EN SERIE TERPENIQUE

The reaction of 3-bromomethyl-2,5-dihydrothiophen-1,1-dioxide 6 and 2-bromomethyl-1,3-butadiene 7 with nitriles in the presence of the zinc-silver couple leads to a mixture of ketones 8,9, the pyrolysis of which give the ketones 10 and 11, corresponding respectively to acylation of isoprene at its methyl group from 8, and at C-3 from 9.The reaction of bromide 7 with nitriles leads also to the formation of ketones 10 which by acid isomerisation give the ketones 12 corresponding to an acylation at C-1 of isoprene.In the same way the reaction of 2-(1'-methyl-4'-cyclohexenyl)-3-bromo propene 13 with 3,3-dimethyl acrylonitrile give β- atlantone 14 which is isomerised in acidic medium to α-atlantone 15. 10,11-dihydro α and β-atlantone 16, 17 are obtained by the same procedure from 13 and 3-methyl butyronitrile.