Synthesis of ionones and carvone analogues: olfactory properties and preliminary toxicity assays

Anzaldi, Maria; Sottofattori, Enzo; Dusatti, Fabiola; Ferro, Margherita; Pani, M.; Balbi, Alessandro

doi:10.1016/s0223-5234(00)00181-1

Cited by 9 publications

(1 citation statement)

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“…The in vitro assays of compound 36, which was evaluated on human keratinocyte NCT 2544 cell line and three different in vitro studies, showed higher cytotoxicity compared with its corresponding aromatized analogue. Cyclohexadienal 36 shows similar IC 50 values compared with SDS (sodium dodecyl sulfate), IC 50 = 0.12 mM and IC 50 = 0.13 mM, respectively, and thus it can be considered a strong irritant [101].…”

Section: Biological Activities Of 13-cyclohexadien-1-carboxaldehydementioning

confidence: 95%

1,3-Cyclohexadien-1-Als: Synthesis, Reactivity and Bioactivities

et al. 2021

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In synthetic organic chemistry, there are very useful basic compounds known as building blocks. One of the main reactions wherein they are applied for the synthesis of complex molecules is the Diels–Alder cycloaddition. This reaction is between a diene and a dienophile. Among the most important dienes are the cyclic dienes, as they facilitate the reaction. This review considers the synthesis and reactivity of one of these dienes with special characteristics—it is cyclic and has an electron withdrawing group. This building block has been used for the synthesis of biologically active compounds and is present in natural compounds with interesting properties.

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Section: Biological Activities Of 13-cyclohexadien-1-carboxaldehydementioning

confidence: 95%

1,3-Cyclohexadien-1-Als: Synthesis, Reactivity and Bioactivities

et al. 2021

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High Regioselective Diels--Alder Reaction of Myrcene with Acrolein Catalyzed by Zinc-Containing Ionic Liquids

Li¹,

Li²,

Tao³

et al. 2005

Advanced Synthesis & Catalysis

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The ambient zinc-containing ionic liquids, MX-ZnCl 2 , functioning as both Lewis acid catalyst and green solvent, are employed for a high regioselective Diels-Alder reaction of myrcene with acrolein for the first time, where MX is either 1-butyl-3-methylimidazolium chloride (BmimCl), 1-ethyl-3-methylimidazolium bromide (EmimBr), N-butylpyridinium bromide (BPyBr), or N-ethylpyridinium bromide (EtPyBr). Compared with the analogous reaction performed over a ZnCl 2 catalyst in the conventional solvent dichloromethane, higher regioselectivity of the para cycloadduct and excellent yield were achieved at shorter reaction time in these ionic liquids with optimized molar compositions of MX and ZnCl 2 . These moisture-insensitive ionic liquids can be easily separated from reaction products after simple washing with hexane, allowing their reuse with no obvious loss in activity.

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