A Practical and Efficient Synthesis of <i>p</i>-Menthane-3,8-diols

Tsuruta, and Haruki; Yuasa, Yoko

doi:10.1021/op9901036

Cited by 35 publications

(39 citation statements)

References 6 publications

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“…[19][20][21] We confirmed this experimentally: in addition to minor products 3a-d, a mixture of four stereoisomeric p-menthane-3,8-diols (4) is observed as the major class of products. Once formed, 4 may undergo condensation with 2 to generate pmenthane-3,8-diol citronellal acetal stereoisomers (5).…”

Section: Introductionsupporting

confidence: 58%

Selective Monoterpene-like Cyclization Reactions Achieved by Water Exclusion from Reactive Intermediates in a Supramolecular Catalyst

et al. 2012

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A polyanionic supramolecular assembly (1) is shown to catalytically cyclize the monoterpene citronellal and two homologues. In contrast to cyclization in acidic aqueous solution, the hydrophobic interior of 1 prevents the capture of reactive intermediates by water. This effect was also observed in the gold-catalyzed cycloisomerization of an enyne. Due to the steric confinement of the catalyst's interior, Prins cyclizations in 1 proceed cleanly both for substrates containing and lacking gem-dimethyl substitution. Encapsulation in 1 consequently imposes a degree of mechanistic control that, similar to enzyme catalysis, is not observed in bulk aqueous solution.

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Section: Introductionsupporting

confidence: 58%

Selective Monoterpene-like Cyclization Reactions Achieved by Water Exclusion from Reactive Intermediates in a Supramolecular Catalyst

et al. 2012

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“…Diol (−)‐ 8a was prepared by enzyme‐mediated resolution of the corresponding racemic material, which was in turn obtained by hydroboration of commercial isopulegol 17 . Racemic diol 8b was obtained by cyclization of citronellal 18 . Diols 8c and 8d were prepared starting from (+)‐pulegone 19 and racemic piperitone 20 , respectively, by means of the combined use of known methods or by slight modification of the same (see below).…”

Section: Methodsmentioning

confidence: 99%

p‐Menthandiol‐vanillin acetals: synthesis and study of their chemo‐sensorial properties

Serra

Cominetti

Gatti

et al. 2013

Flavour & Fragrance J

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A study on the synthesis of a number of p‐menthandiols‐vanillin(isovanillin) acetals derivatives is reported here. Properties of the compounds prepared were crudely investigated by tasting and by focusing on their chemesthetic effect. In particular some of these acetals showed a definite warming effect. In order to investigate correlation between chemical structure and biological activity, a large number of the aforementioned acetals were prepared by means of the targeted modification of the p‐menthane framework. This approach revealed that structural modifications considerably affect the chemesthetic properties of these compounds, allowing the identification of two kinds of sensorially active chemical frameworks. The potential of these findings in the design of new food additives featuring a warming/tingling effect is discussed. Copyright © 2013 John Wiley & Sons, Ltd.

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“…Citronellal was also used as a control standard. [19,20] Consumers could be conditioned to the lemon odour for a repellent product, even though citronellal shows a short-lasting protection from mosquitoes.…”

Section: Hedonic Dimensionmentioning

confidence: 99%

Repellent studies with Aedes aegypti mosquitoes and human olfactory tests on 19 essential oils from Corsica, France

Drapeau

Fröhler²,

Touraud

et al. 2009

Flavour & Fragrance J

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In order to reduce the risk of getting infected with any epidemic disease transmitted by mosquitoes, repellent products are often used to protect populations at risk. The repellent potential of 19 essential oils from the island of Corsica, France, was evaluated in a bio-assay with the mosquito Aedes aegypti, in order to assess the 'space repellent' properties of these oils. Lavendula stoechas, Helichrysum italicum (leaves) and Laurus nobilis oils showed a capability of reducing the attractivity of a human finger for yellow fever mosquitoes in a Y-tube olfactometer. In addition to the behavioural studies on mosquitoes, two tests on the olfactory perception of these 19 oils were performed, involving 25 female and 25 male human volunteers. The aspects studied were the 'hedonic dimension' of these oils and their acceptance as a final fragrance for a repellent formulation. The experiments yielded promising results concerning both aspects for three oils, from Calamintha nepeta, Laurus nobilis and Rosmarinus officinalis, with minor differences between male and female participants. Laurus nobilis oil was the only oil tested fulfilling both properties: a spatial repellent effect on Aedes aegypti and acceptance by the volunteers for its integration in a repellent product. Thermogravimetric analysis showed that Calamintha nepeta oil has a slower evaporation rate in comparison to the Laurus nobilis and Rosmarinus officinalis oils.

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A Practical and Efficient Synthesis of p-Menthane-3,8-diols

Cited by 35 publications

References 6 publications

Selective Monoterpene-like Cyclization Reactions Achieved by Water Exclusion from Reactive Intermediates in a Supramolecular Catalyst

Selective Monoterpene-like Cyclization Reactions Achieved by Water Exclusion from Reactive Intermediates in a Supramolecular Catalyst

p‐Menthandiol‐vanillin acetals: synthesis and study of their chemo‐sensorial properties

Repellent studies with Aedes aegypti mosquitoes and human olfactory tests on 19 essential oils from Corsica, France

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