119207-19-1

Upstream product

• 23726-91-2 beta damascone 
• 945426-73-3 C₁₄H₂₂O₃ 
• 79-77-6 (E)-β-ionone 
• 945426-68-6 C₁₄H₂₄O₂ 
• 945426-65-3 4-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-2-methoxybutane 
• 945426-72-2 C₁₄H₂₄O₃ 
• 55093-47-5 (Z)-4-(2,6,6-trimethylcyclohex-2-enylidene)butan-2-ol 

Relevant academic research and scientific papers

Non-heme iron catalysis in CC, C-H, and CH2 oxidation reactions. Oxidative transformations on terpenoids catalyzed by Fe(bpmen)(OTf)2

The oxidation of terpene olefins with hydrogen peroxide in the presence of the non-hemo catalyst 5a afforded mixtures of epoxides whose composition was dependent upon the oxidation protocol used in each case. With terpenoid enones, the mixtures obtained evolved from clean epoxidation of α-ionone 23 to the clean allylic oxidation of damascone 28 due to the progressive deactivation of the electron density on the double bonds present in this series. The oxidation of bicyclic and tricyclic terpenoids afforded oxidation products coming from epoxidation, to olefin degradation, methyne and methylene activation products. Probably, the most attractive result was the synthesis of the Magnus lactone 46, from the tricyclic ether 45, with 88% yield and 100% conversion.

Selective oxygenation of ionones and damascones by fungal peroxygenases

Apocarotenoids are among the most highly valued fragrance constituents, being also appreciated as synthetic building blocks. This work shows the ability of unspecific peroxygenases (UPOs, EC1.11.2.1) from several fungi, some of them being described recently, to catalyze the oxyfunctionalization of α- and β-ionones and α- and β-damascones. Enzymatic reactions yielded oxygenated products such as hydroxy, oxo, carboxy, and epoxy derivatives that are interesting compounds for the flavor and fragrance and pharmaceutical industries. Although variable regioselectivity was observed depending on the substrate and enzyme, oxygenation was preferentially produced at the allylic position in the ring, being especially evident in the reaction with α-ionone, forming 3-hydroxy-α-ionone and/or 3-oxo-α-ionone. Noteworthy were the reactions with damascones, in the course of which some UPOs oxygenated the terminal position of the side chain, forming oxygenated derivatives (i.e., the corresponding alcohol, aldehyde, and carboxylic acid) at C-10, which were predominant in the Agrocybe aegerita UPO reactions, and first reported here.

New straightforward synthesis of β-damascenone and β-damascone derivatives from β-ionone via retro-α-ionol

β-Damascenone and β-damascone derivatives, important fragrant compounds, were directly obtained from β-ionone by a new way via retro-α-ionol. Copyright Taylor & Francis Group, LLC.

A DAMASCONE DERIVATIVE FROM NICOTIANA TABACUM

A new member of the damascone series, 4-hydroxy-β-damascone, was identified in the steam distillable oil from Virginia tobacco. Key Word Index - Nicotiana tabacum; Solanaceae; Virginia tobacco; norcarotenoids; damascones.

Butenoyl-cyclohexanones

Use of oxygenated alicyclic compounds, some of which are new, as perfuming and/or flavouring ingredients in the manufacture of perfumes and perfumed products and/or in the preparation of artificial flavours for foodstuffs, animal feeds, beverages, pharmac