7028-27-5

Usage

Chemical classification

Ketone

Structure

Long-chain with an attached phenyl group

Odor

Strong and distinctive

Applications

Perfumes and fragrances, flavoring agent in the food industry, scent enhancer in personal care products

Industry relevance

Fragrance and flavor industry, pharmaceuticals, organic synthesis

Aroma characteristics

Intense and long-lasting

Usage

Widely used in the production of perfumes and fragrances due to its strong and long-lasting aroma

Regulatory status

Generally recognized as safe (GRAS) by the US Food and Drug Administration (FDA) for use as a flavoring agent

Synonyms

β-10-Undecen-1-one, β-10-Phenylundecanone, 1-Phenylundecan-1-one, and β-Phenylundecanone

Upstream product

• 38460-95-6 undec-10-enoyl chloride 
• 2674-04-6 diphenyl cadmium 
• 109-99-9 tetrahydrofuran 
• 100-58-3 phenylmagnesium bromide 
• 112-45-8 10-Undecenal 
• 112-38-9 10-undecenoic acid 
• 102613-04-7 N-methyl-N-methoxyundec-10-enamide 

Downstream Products

• 7203-77-2 2-Methyl-13-oxo-13-phenyl-tridecanoic acid 

Relevant academic research and scientific papers

Rhodium-Catalyzed Remote Isomerization of Alkenyl Alcohols to Ketones

We develop herein an efficient rhodium-catalyzed remote isomerization of aromatic and aliphatic alkenyl alcohols into ketones. This catalytic process, with a commercially available catalyst and ligand ([RhCl(cod)]2 and Xantphos), features high efficiency, low catalyst loading, good functional group tolerance, a broad substrate scope, and no (sub)stoichiometric additive. Preliminary mechanistic studies suggest that this transformation involves an iterative dissociative β-hydride elimination-migration insertion process.

Chemoselective reduction of aldehydes: Via a combination of NaBH4 and acetylacetone

A bench-stable combination of NaBH4-acetylacetone was developed for the efficient chemoselective reduction of aldehydes in the presence of ketones. This method offers a useful synthetic protocol for distinguishing carbonyl reaction sites, and its synthetic utility is reflected by its moisture tolerance and high efficiency in a variety of complex settings.

Aerobic Acetoxyhydroxylation of Alkenes Co-catalyzed by Organic Nitrite and Palladium

An aerobic acetoxyhydroxylation of alkenes cooperatively catalyzed by organic nitrite and palladium at room temperature using clean and cheap air as the sole oxidant has been developed. Various vicinal diols, diacetoxyalkanes, and dihalogenoalkanes have been synthesized. The gram-scale synthesis has also been approached. Vicinal difluorination and dichlorolation products have also been achieved via this reaction.

Direct Ni° mediated synthesis of ketones from acyl bromides and Grignard reagents

A catalytic amount of NidppeCl2 converts an acyl bromide directly into ketones at 0°C in THF in the presence of a Grignard reagent. The described procedure represents a useful way to afford dialkyl, diaryl or alkyl aryl ketones as well as 1,2-diketones. In the adopted reaction conditions double bonds, esters and ketones are unaffected.