357650-26-1

Basic information

• Product Name: (2E,5Z)-5,6,7-trimethylocta-2,5-dien-4-one
• Synonyms: (2E,5Z)-5,6,7-Trimethylocta-2,5-dien-4-one; 2,5-octadien-4-one, 5,6,7-trimethyl-, (2E,5Z)-
• CAS NO: 357650-26-1
• Molecular Formula: C₁₁H₁₈O
• Molecular Weight: 166.26
• Mol File: 357650-26-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 236.15°C at 760 mmHg
• Flash Point: 89.352°C
• Density: 0.855g/cm³
• Vapor Pressure: 0.048mmHg at 25°C
• Refractive Index: 1.455
• CAS DataBase Reference: (2E,5Z)-5,6,7-trimethylocta-2,5-dien-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,5Z)-5,6,7-trimethylocta-2,5-dien-4-one(357650-26-1)
• EPA Substance Registry System: (2E,5Z)-5,6,7-trimethylocta-2,5-dien-4-one(357650-26-1)

Safety Data

• Hazardous Substances Data: 357650-26-1(Hazardous Substances Data)

Usage

General Description

"(2E,5Z)-5,6,7-trimethylocta-2,5-dien-4-one" is a complex organic chemical compound in the family of monoterpene ketones. (2E,5Z)-5,6,7-trimethylocta-2,5-dien-4-one has a double bond stereochemistry and contains a series of functional groups such as alkene (carbon-carbon double bond), ketone (carbon-oxygen double bond with the carbon attached to two other carbons), and methyl groups (carbon atom bonded to three hydrogen atoms). Generally, it features eight carbon atoms alongside its multiple bonds and hydrogen atoms. This particular compound and similar structures are commonly found in essential oils and fragrant substances. However, specific applications or uses for (2E,5Z)-5,6,7-trimethylocta-2,5-dien-4-one are not readily documented.

Upstream product

• 13154-14-8 1-propenylmagnesium bromide 
• 6570-81-6 (2E/Z)-ethyl 2,3,4-trimethylpent-2-enoate 
• 563-80-4 3-methyl-butan-2-one 

Relevant articles and documents

5,6,7-Trimethylocta-2,5-dien-4-one - A suspected odorant with surprising olfactory properties

5,6,7-Trimethylocta-2,5-dien-4-one (3) was suspected of being a trace component smelling of damascone in a crude complex reaction product. Although this trace component eventually turned out to be the constitutional isomer 2-methyl-3-isopropylhepta-2,5-dien-4-one (4), the title compound 3 was found to possess even superior fruity, rosy odor characteristics, reminiscent of apples, plums, raisins and other dried fruits, and these odor characteristics are, surprisingly, due mainly to its (5Z)-isomer. The synthesis of 3 commenced with the preparation of 1-ethoxyprop-1-yne (11) from 2-chloro-1,1-diethoxyethane (9). Borontrifluoride-catalyzed addition of methyl isopropyl ketone (10) to 11 provided ethyl 2,3,4-trimethylpent-2-enoate (8), which was transformed into the target molecule 3 by Grignard reaction with propen-1-ylmagnesium bromide and in situ enolization. Further derivatives 13-16 provide more insight into the structure-odor correlation of damascone-type odorants, and the use of 3 in perfumery is illustrated by a composition formula of a demonstration perfume.