Green synthesis of para-Menthane-3,8-diol from Eucalyptus citriodora: Application for repellent products

Drapeau, Jeremy; Rossano, Manon; Touraud, Didier; Obermayr, Ulla; Geier, Martin; Rose, Andreas; Kunz, Werner

doi:10.1016/j.crci.2011.02.008

Cited by 29 publications

(33 citation statements)

References 20 publications

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“…Para-menthane-3,8-diol is considered as the natural and safe topical repellent alternative to DEET (Diaz, 2016). Several studies have demonstrated the high repellent activity and longevity of PMD against Aedes, Anopheles, and Culex genera (Barnard and Xue, 2004;Carroll and Loye, 2006), similar to DEET (Carroll and Loye, 2006;Goodyer et al, 2010;Drapeau et al, 2011), while having low toxicity -except eye irritation which is observed for all non-toxic natural active ingredients -and no adverse effect reported (Reifenrath et al, 2009). For example, a 26% PMD formulation provided complete protection for 7-8 h against A. albopictus and Ochlerotatus triseriatus and for 3 h against Culex nigripalpus, which is comparable to a 7% DEET formulation (Barnard and Xue, 2004).…”

Section: Repellent Activity Of Pmdmentioning

confidence: 99%

Reflexion on Bio-Sourced Mosquito Repellents: Nature, Activity, and Preparation

et al. 2020

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Over the last decades, the geographical distribution of certain mosquito species carrying vector-borne diseases has considerably expanded. They represent a major health concern as they transmit pathogens causing alarming epidemics. In the absence of vaccines for most of the mosquito-borne diseases, the use of topical mosquito repellents is one of the main measures to prevent human-mosquito contacts. Synthetic repellents are the most used mosquito repellents. However, several concerns about their safety for consumers have led to a growing demand of natural alternatives. Here we present an overview of the most commonly used natural-based mosquito repellents: repellent activity, biological action, composition, stereochemical structure (when appropriate) and syntheses, paradoxically far from being eco-friendly. We discuss on future prospective that would combine sustainable chemical processes and synergistic effects promising for the development of natural, safe and efficient topical repellents.

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Section: Repellent Activity Of Pmdmentioning

confidence: 99%

Reflexion on Bio-Sourced Mosquito Repellents: Nature, Activity, and Preparation

et al. 2020

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“…Secara alami, PMD adalah suatu senyawa hasil sintesis dari sitronelal yang diisolasi dari minyak serai wangi. Selain itu, PMD juga dapat disintesis oleh reaksi Prins dari sitronelal (Drapeau et al 2011). Senyawa p-menthane-3, 8-diol juga ditemukan di dalam buah-buahan.…”

Section: Pendahuluanunclassified

The Effect of Essential Oil Formula and Para Menthane Diol on Mortality and Oviposition Deterrent of Brown Planthopper

Mardiningsih¹,

Rismayani²,

Ma'mun³

2020

bul. littro

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Minyak cengkih, serai wangi, dan serai dapur dikenal sebagai insektisida nabati. Formula campuran minyak atsiri dan senyawa tunggal minyak atsiri diharapkan dapat meningkatkan keefektifan insektisida nabati. Percobaan ini bertujuan untuk menguji efek dari campuran minyak atsiri dan formula para-menthane-3,8-diol (PMD) dalam menghambat kemampuan bertelur dan mortalitas wereng cokelat. Penelitian dilakukan di rumah kaca Balai Penelitian Tanaman Rempah dan Obat, Bogor. Formula yang diuji adalah minyak cengkih + serai wangi (1: 1), minyak cengkih + serai dapur (1: 1), minyak atsiri tunggal, bahan pembawa formula minyak atsiri (campuran tween 80, terpentin, dan surfaktan), serta formula PMD dan bahan pembawa (pengemulsi, alkohol 96 %, dan surfaktan). Aplikasi formula dilakukan secara kontak pada serangga uji. Parameter pengamatan adalah jumlah telur yang diletakkan dan mortalitas wereng cokelat dewasa dan nimfa. Hasil penelitian menunjukkan bahwa formula insektisida nabati yang diaplikasikan secara kontak terhadap larva dan wereng cokelat dewasa menyebabkan tingkat kematian yang tidak berbeda secara signifikan dibanding kontrol dan insektisida sintetis. Uji residu tanaman, mortalitas nimfa pada perlakuan minyak atsiri tidak berbeda nyata dari kontrol dan insektisida. Formula minyak cengkih + serai wangi yang disemprotkan langsung pada serangga dan melalui tanaman tidak berbeda nyata dibandingkan dengan perlakuan insektisida sintetik, walaupun efektivitas formula minyak cengkih + serai wangi lebih lambat. Kemanjuran formula minyak cengkih + serai wangi terhadap peletakan telur berbeda nyata dibandingkan dengan perlakuan insektisida sintetis, yaitu lebih sedikit telur yang diletakkan. Formuka PMD kurang efektif dari formula minyak cengkih + serai wangi terhadap nimfa dan kematian dewasa wereng cokelat. Perlu penelitian lebih lanjut untuk mengevaluasi aktivitas formula minyak cengkih + serai wangi di lapangan. Kata kunci: Insektisida botani; minyak cengkih; minyak serai dapur; minyak serai wangi; Nilaparvata lugens StalEssential oils such as clove, lemongrass, and citronella are known as botanical insecticides. Mixed-essential oils and a single compound of the oil itself may increase its efficacy. The experiment aimed to examine the effect of the essential oil mixture and para-menthane-3,8-diol (PMD) formulas in inhibiting of the egg-laying and mortality of brown planthopper. The study conducted at the greenhouse of Indonesian Spices and Medicinal Crops Research Institute, Bogor. The formula tested were clove+citronella oils (1:1), clove+lemongrass oils (1:1), the single essential oil, solvent materials (a mixture of tween 80, Turpentine, and surfactant), alcohol 96%, and surfactant). A contact application was applied to the insect. Observation parameters were egg numbers laid and brown planthopper adult and nymph mortalities. The result of the insect contact application method showed that adult mortality was not significantly different compare with control and synthetic insecticide. Based on the plant residue test, nym...

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“…The terpene, citronellal (3,7-dimethyl-6-octenal, 1 ) is widely used as a feedstock material in the synthesis of fine chemicals such as menthol ( 2 ) and para -menthane-3,8-diol ( 3 ) [1–2]. These chemical derivatives have a wide range of uses in pharmaceuticals, cosmetics, toothpastes, insect repellents, cleaning agents and other products [3].…”

Section: Introductionmentioning

confidence: 99%

“…This chemical derivative is well-known as an active insect repellent and can be found naturally as a minor component of citriodora oil [2]. Considering the chemical structure of 3 , two reactive hydroxy groups are present which can undergo an organic transformation, such as acylation, to yield natural bio-based compounds.…”

Section: Introductionmentioning

confidence: 99%

Solvent-free synthesis of novel para-menthane-3,8-diol ester derivatives from citronellal using a polymer-supported scandium triflate catalyst

Mafu

Zeelie

Watts

2016

Beilstein J. Org. Chem.

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SummaryThe use of natural resources as a chemical feedstock for the synthesis of added-value products is gaining interest; as such we report an environmentally friendly method for the synthesis of para-menthane-3,8-diol from natural citronellal oil in 96% yield, under solvent free aqueous conditions. The acylation of para-menthane-3,8-diol with various acid anhydrides over polymer-supported scandium triflate (PS-Sc(OTf)3) catalyst was subsequently developed, where both hydroxy groups of para-menthane-3,8-diol could be simultaneous acylated under mild reaction conditions to form the corresponding diesters in good yields. The advantages of this method include a simple procedure from natural resources, using solvent-free reaction conditions.

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Green synthesis of para-Menthane-3,8-diol from Eucalyptus citriodora: Application for repellent products

Cited by 29 publications

References 20 publications

Reflexion on Bio-Sourced Mosquito Repellents: Nature, Activity, and Preparation

Reflexion on Bio-Sourced Mosquito Repellents: Nature, Activity, and Preparation

The Effect of Essential Oil Formula and Para Menthane Diol on Mortality and Oviposition Deterrent of Brown Planthopper

Solvent-free synthesis of novel para-menthane-3,8-diol ester derivatives from citronellal using a polymer-supported scandium triflate catalyst

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