Journal articles: 'Citronellol'

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Chen, Qiu, Li Li Gu, and Zheng Hui Zhang. "The Binary Vapor-Liquid Phase Equilibrium of Citronella Oil under High Vacuum." Advanced Materials Research 772 (September 2013): 281–86. http://dx.doi.org/10.4028/www.scientific.net/amr.772.281.

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Citronellal, citronellol and geraniol are the main components of the natural plant citronella oil, and their vapor-liquid phase equilibrium relationship is the critical data to separate, purify the citronella oil and design rectifying column. Citronella oil is a thermo-sensitive material, so the separation under high vacuum conditions could lower its boiling point and maintain its quality. This paper adopts the precise vapor-liquid phase equilibrium instrument to collect the binary system of citronellal-citronellol, citronellal-geraniol and citronellol-geraniol with the absolute pressure of 1.2kPa. Meanwhile, the corresponding phase equilibrium diagrams are drawn, which provide data support for the distillation of citronella oil.

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Begha, Bruno Piotrovski, Carlos Henrique Antunes, and Julianne Milléo. "Coleopterofauna (Insecta: Coleoptera) coletada em armadilhas com óleo essencial de citronela ou seus componentes no município de Ponta Grossa, Paraná, Brasil." EntomoBrasilis 11, no. 2 (August 31, 2018): 85–94. http://dx.doi.org/10.12741/ebrasilis.v11i2.734.

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Resumo. Coleoptera é a ordem mais numerosa e diversificada de Insecta. Possuem diversos tipos de alimentação, sendo que os besouros herbívoros atacam cultivos agrícolas e plantas ornamentais causando prejuízos aos agricultores. Conhecer as espécies que afetam o cultivo local é uma forma de diminuir seu impacto e propor formas de manejo corretas. Os objetivos deste trabalho foram identificar os coleópteros coletados em armadilhas contendo o óleo de citronela ou seus componentes (citronelal, citronelol e geraniol) instaladas em Ponta Grossa, Paraná e, caracterizar a coleopterofauna através de diferentes análises ecológicas. Somente os coleópteros foram identificados e contabilizados. O programa ANAFAU analisou: índices de frequência, abundância, dominância e constância. Pelo PAST avaliou-se a diversidade, equitatividade e similaridade da comunidade atraída pelas armadilhas. Foram coletados 1269 coleópteros, distribuídos em 23 famílias. Diabrotica speciosa (Germar)foi a única espécie superdominante, superabundante, superfrequente e constante ao longo de toda a amostragem, correspondendo a 54,68% das coletas. Citronela 1% (25,22%), citronelol 1% (25,06%) representaram 50,28% das capturas. Citronela 1% teve a maior diversidade e riqueza de espécies e citronelol 0,5% a menor. O citronelal 1% e o citronelol 1% apresentaram maior similaridade entre as espécies capturadas nestas duas armadilhas. É possível inferir que a distribuição dos coleópteros capturados nos compostos ocorreu devido à presença de moléculas do atrativo também estarem presentes em seus feromônios. O elevado número de D. speciosa coletadas confirma o potencial atrativo dos compostos testados que podem vir a auxiliar na redução de pragas agrícolas, diminuindo o uso de agrotóxicos.Coleopterofauna (Insecta: Coleoptera) collected in traps with essential oil of citronella or its components in the city of Ponta Grossa, Paraná, BrazilAbstract. Coleoptera is the most numerous and diverse order of Insecta. They have various feeding behaviors, being that herbivorous beetles attack agricultural crops and ornamental plants, causing losses to farmers. Knowing the species that affect the local culture is a way to reduce its impact and to propose correct ways of handling them. The objectives of this research were to identify Coleoptera collected in traps containing citronella oil or its components (citronellal, citronellol and geraniol) installed in Ponta Grossa, Paraná, and to characterize the coleopterofauna through different ecological analysis. Only beetles were identified and counted. The ANAFAU program analyzed: indices of frequency, abundance, dominance and constancy. For PAST, the diversity, equity and similarity of the community attracted by the traps was evaluated. A total of 1269 beetles were collected, distributed in 23 families. Diabrotica speciosa (Germar) was the only superdominant, superabundant, superfrequent and constant species throughout the whole sampling, corresponding to 54.68% of the captures. Citronella 1% (25.22%) and citronellol 1% (25.06%) represented 50.28% of the catches. Citronella 1% had the highest diversity and species richness and citronellol 0.5% the lowest. Citronellal 1% and citronellol 1% showed greater similarity between the species captured in these two traps. It is possible that the distribution of the Coleoptera captured in the compounds occurred due to the presence of attractive molecules also being present in their pheromones. The high number of D. speciosa collected confirms the attractive potential of the tested compounds that may help to reduce agricultural pests, reducing the use of agrochemicals.

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Milléo, Julianne, Carlos Henrique Antunes, Elis Borges Pettres, Ricardo Antonio Ayub, and Paulo Vitor Farago. "Óleo essencial de citronela (Poaceae) e seus componentes para controle do brasileirinho (Coleoptera: Chrysomelidae) em olerícolas." EntomoBrasilis 12, no. 1 (April 30, 2019): 06–10. http://dx.doi.org/10.12741/ebrasilis.v12i1.782.

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Resumo. Este estudo teve como objetivo obter uma formulação atrativa à base de óleo de citronela e seus componentes voláteis para captura de Diabrotica speciosa (Germar). Três experimentos sequenciais foram realizados em culturas de abobrinha ou pepino. Os insetos foram coletados por armadilhas de garrafa PET com três aberturas laterais, contendo um volume de 200 ml de cada formulação, suspensas a 10 cm do nível do solo numa área experimental de 30 m2. No primeiro experimento foram testados óleo de citronela em 1, 2 e 4%. No segundo investigou-se também a ação de citronelal, citronelol e geraniol a 1%. E, o citronelol a 0,5, 1 e 2% foi testado no terceiro experimento. Como resultado observou-se que a formulação contendo citronelol a 0,5% foi estatisticamente superior às demais. Outros insetos foram capturados pelas armadilhas como coleópteros Diabrotica viridula (Fabricius)e Astylus variegatus (Germar), e também exemplares de Diptera, Hemiptera e Hymenoptera. Considerando a alta demanda por alimentos orgânicos e da preocupação com o ambiente e a saúde, a emulsão a base de citronelol em 0,5% cumpre adequadamente o seu objetivo, garantindo uma boa capacidade atrativa para D. speciosa. Esta formulação pode ser usada paralelamente com outros métodos alternativos para reduzir a presença desse inseto nas culturas.Citronella (Poaceae) essential oil and its components for the control of brasileirinho (Coleoptera: Chrysomelidae) in vegetable cropsAbstract. The present study aimed to get an attractive formulation of oil-based citronella and its volatile components to capture Diabrotica speciosa (Germar). Three sequential experiments were performed in zucchini or cucumber crops. The insects were collected in PET bottle traps with three lateral apertures, containing a volume of 200 ml of each formulation, suspended 10 cm above the ground level in an experimental area of 30 m2. In the first experiment citronella essential oil was tested at 1, 2 and 4%. In the second experiment the action of citronellal, citronellol and geraniol at 1% were investigated. Furthermore, citronellol at 0.5, 1 and 2% has been tested in the third experiment. As a result it was observed that the formulation containing 0.5% citronellol was statistically higher than the other tested formulations. Other insects were captured by the traps as the beetles of Diabrotica viridula (Fabricius)and Astylus variegates (Germar), and also copies of Diptera, Hemiptera and Hymenoptera. Considering the high demand for organic food, and concern for the environment and health, the citronellol emulsion at 0.5% adequately fulfilled its goal, ensuring a good attractive capacity for D. speciosa. This formulation can be used simultaneously with other alternative methods to reduce the presence of such insects in crops.

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Eden, Willy Tirza, Dante Alighiri, Kasmadi Imam Supardi, and Edy Cahyono. "The Mosquito Repellent Activity of the Active Component of Air Freshener Gel from Java Citronella Oil (Cymbopogon winterianus)." Journal of Parasitology Research 2020 (January 29, 2020): 1–5. http://dx.doi.org/10.1155/2020/9053741.

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This study examines the active component of Cymbopogon winterianus (Java citronella) oil, as a green mosquito repellent, obtained through a steam distillation method. Java citronella oil, which contains citronellol, citronellal, and geraniol, was isolated by batch vacuum fractional distillation, and their effect was tested against the dengue fever (DF) vector, known as Aedes aegypti. Furthermore, air freshener gels were formulated with Java citronella oil, carrageenan, gum, sodium benzoate, ethylene glycol, polysorbate 20, sodium chloride, and distilled water, at varying concentrations. The results show that formula I has the best controlled release evaporation for citronellal, citronellol, and geraniol, as well as the best storage time of 16.82 days and 12.77 days for geraniol and citronellol, respectively. The most significant specific gravity (0.0136) was recorded in formula V, while gel formula I exhibited the highest level of instability at 35°C, with a syneresis value of 77.11% in t=72 h and pH 5.33. In addition, formula IV at 5°C demonstrated the highest syneresis (75.34%) in t=72 h, with pH 7.04, while a peak viscosity of 100,958 cP was recorded in formula IV. The repellent activity of each active component was measured based on the period of protection conferred against the bites of Aedes aegypti within one hour, and the results showed geraniol and citronellol, with respective activity of 78.00%±4.83 and 77.34%±3.57, as the most effective.

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Widiyarti, Galuh, Firdayani Firdayani, Muhammad Hanafi, Soleh Kosela, and Emil Budianto. "Molecular Docking of Citronellol, Geraniol and Ester Derivatives as Pim 1 Kinase Inhibitor of Leukemia Cancer." Jurnal Kimia Valensi 5, no. 2 (November 30, 2019): 133–42. http://dx.doi.org/10.15408/jkv.v5i2.7195.

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The proviral insertion site in Moloney murine leukemia virus-1 (Pim1) kinase is overexpressed in many human cancer diseases. Inhibition of Pim1 kinase has been reported can suppress cell proliferation and induce apoptotic cell death, so that the protein could be chosen as drug target for the treatment of cancer. Citronellol and geraniol mainly contained in citronella oil that’s one of Indonesian natural products have bioactivity as antitumor agents, so that both of the compounds can be used as guiding compound to be developed as chemoprevention and chemotherapeutic agent compounds for cancer especially for leukemia cancer. In this research, sixteen citronellol and geraniol esters as an inhibitor of leukemia cancer designed were docked based on their interaction with leukemia receptor target of Pim1 kinase by using Molegro Virtual Docker (MVD). The result showed that the binding citronellol and geraniol esters to Pim1 kinase are more stable and better affinity than the binding between citronellol and geraniol, indicated by rerank score were lower than rerank score of citronellol/geraniolPim1 kinase. The docking resulted in the four top-ranked compounds, namely, citronellyl caproate, citronellyl caprylate, geranyl caproate and geranyl caprylate with rerank score value from -182.560 to -189.822 KJ/mol. These compounds have hydrogen bonding with amino acid residues of Lys 67 and Asp 186 of an active site of Pim1 kinase. Based on Lipinski’s rule of five, among of the four top-ranked compounds, citronellyl caproate and geranyl caproate were predicted have potency as new chemopreventive and chemotherapeutic agents for leukemia anticancer candidates.

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Ohashi, Yuka, Shuai Huang, and Isamu Maeda. "Biosyntheses of geranic acid and citronellic acid from monoterpene alcohols by Saccharomyces cerevisiae." Bioscience, Biotechnology, and Biochemistry 85, no. 6 (March 13, 2021): 1530–35. http://dx.doi.org/10.1093/bbb/zbab039.

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ABSTRACT Geraniol is one of the important aromatic ingredients in alcoholic beverages. Bioconversions of geraniol to other terpenoids and genes involved in the oxidation of geraniol were investigated. Geranic acid and citronellic acid were detected in yeast culture, where geraniol or nerol was added. Addition of citral, a mixture of geranial and neral, resulted in the production of geranic acid and citronellic acid, whereas the addition of citral or citronellal resulted in the production of citronellic acid, suggesting that citronellic acid might be produced through the conversion of citral to citronellal followed by the oxidation of citronellal. Consumption of geraniol and production of geranic acid, citronellic acid, and citronellol were affected in adh1Δ, adh3Δ, adh4Δ, and sfa1Δ yeast strains, which possess single deletion of a gene encoding alcohol dehydrogenase. This is the first report of the bioconversion of monoterpene alcohols, geraniol and nerol, to geranic acid and citronellic acid in yeast culture.

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Bhatnagar, Anju. "Composition variation of essential oil of Cymbopogon spp. growing in Garhwal region of Uttarakhand, India." Journal of Applied and Natural Science 10, no. 1 (March 1, 2018): 363–66. http://dx.doi.org/10.31018/jans.v10i1.1631.

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The present study was aimed to find out the chemical constituents of essential oils of cymbopogon species,viz. Cymbopogon martinii var motia, Cymbopogon flexuosus Nees., Cymbopogon winterianus Jowitt., growing in Garhwal region of Uttarakhand, India. The essential oils were obtained by hydro-distillationand subjected to detailed Gas Chromatography-Mass Spectroscopy (GC-MS) analysis in order to determine the variation in their volatile constituents. Twenty seven compounds are α-pinene, β-myrcene, Limonene, Cis-b-Ocimene, pCymene ,Terpinolene,6-Methyl hept-5-en-2-one, Citronellal, Linalool, Linalyl acetate, β-Elemene, β-Caryophyllene, Citronellyl acetate, Neral, α– Terpineol, Borneol,Gerainal, γ-Cadinene,Geranyl acetate, Citronellol,Nerol,Geraniol, Caryophyllene oxide,Germacrene—D-4-ol,Elemol, Epi-α-cadinol, δ-Cadinol representing 92.24 to 95.86% of the oil compositions as identified. While comparing the common constituents of three different species of cymbopogon taxa , the remarkable variation in compositions of essential oil was observed and it was in concentration of nearl (0.40;34.9;1.6), gerainal (nil;47.5;0.96) geraniol (82.5;4.5;20.15) , citronellol (T;0.2;12.39) , citronellal (0.1;0.5;36.19) , and linalool (0.8;1.6;0.96) for C.martini, C.flexuosus, C. winterianus respectively

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Ho, Yathsoeung, Nungruthai Suphrom, Krai Daowtak, Pachuen Potup, Yordhathai Thongsri, and Kanchana Usuwanthim. "Anticancer Effect of Citrus hystrix DC. Leaf Extract and Its Bioactive Constituents Citronellol and, Citronellal on the Triple Negative Breast Cancer MDA-MB-231 Cell Line." Pharmaceuticals 13, no. 12 (December 18, 2020): 476. http://dx.doi.org/10.3390/ph13120476.

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Triple negative breast cancer is one of the most aggressive breast cancer type with abilities of early metastasis and chemoresistance. The tropical plant Citrus hystrix DC. has been reported to promote many biological activities including anticancer. However, the effect of C. hystrix against triple negative breast cancer has not yet been identified. This study aimed to evaluate the anticancer properties of C. hystrix leaf extract and its bioactive constituents citronellol and citronellal against the triple negative breast cancer MDA-MB-231 cell line. C. hystrix leaves were powdered and sequentially macerated. The in vitro anticancer effects of C. hystrix leaf extracts, and its bioactive constituents (citronellol and citronellal) were evaluated against MDA-MB-231 cell line using cytotoxic MTT assay, cell proliferation, wound scratch migration, colony formation, cell cycle, apoptosis assay, Hoechst staining, RT-qPCR, and Western blot analysis. Results showed that crude hexane extract, citronellol, and citronellal significantly reduced cell proliferation, colony formation, and cell migration by inducing cell cycle arrest, while also inducing apoptosis in MDA-MB-231 cells through inhibition of anti-apoptotic Bcl-2 expression, leading to activation of the caspase-3-dependent pathway. This study is the first report to demonstrate the effect of C. hystrix, citronellol, and citronellal against triple negative breast cancer MDA-MB-231 cells.

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Jia, Yunpeng, Qizhou Wang, Jingjing Qiao, Binbin Feng, Xueting Zhou, Lijun Jin, Yingting Feng, Duxia Yang, Chenze Lu, and Xiangxian Ying. "Cascading Old Yellow Enzyme, Alcohol Dehydrogenase and Glucose Dehydrogenase for Selective Reduction of (E/Z)-Citral to (S)-Citronellol." Catalysts 11, no. 8 (July 30, 2021): 931. http://dx.doi.org/10.3390/catal11080931.

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Citronellol is a kind of unsaturated alcohol with rose-like smell and its (S)-enantiomer serves as an important intermediate for organic synthesis of (-)-cis-rose oxide. Chemical methods are commonly used for the synthesis of citronellol and its (S)-enantiomer, which suffers from severe reaction conditions and poor selectivity. Here, the first one-pot double reduction of (E/Z)-citral to (S)-citronellol was achieved in a multi-enzymatic cascade system: N-ethylmaleimide reductase from Providencia stuartii (NemR-PS) was selected to catalyze the selective reduction of (E/Z)-citral to (S)-citronellal, alcohol dehydrogenase from Yokenella sp. WZY002 (YsADH) performed the further reduction of (S)-citronellal to (S)-citronellol, meanwhile a variant of glucose dehydrogenase from Bacillus megaterium (BmGDHM6), together with glucose, drove efficient NADPH regeneration. The Escherichia coli strain co-expressing NemR-PS, YsADH, and BmGDHM6 was successfully constructed and used as the whole-cell catalyst. Various factors were investigated for achieving high conversion and reducing the accumulation of the intermediate (S)-citronellal and by-products. 0.4 mM NADP+ was essential for maintaining high catalytic activity, while the feeding of the cells expressing BmGDHM6 effectively eliminated the intermediate and by-products and shortened the reaction time. Under optimized conditions, the bio-transformation of 400 mM citral caused nearly complete conversion (>99.5%) to enantio-pure (S)-citronellol within 36 h, demonstrating promise for industrial application.

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Batish, Daizy R., Harminder Pal Singh, Nidhi Setia, Shalinder Kaur, and Ravinder K. Kohli. "Chemical Composition and Inhibitory Activity of Essential Oil from Decaying Leaves of Eucalyptus citriodora." Zeitschrift für Naturforschung C 61, no. 1-2 (February 1, 2006): 52–56. http://dx.doi.org/10.1515/znc-2006-1-210.

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Abstract A study was undertaken to explore the content and composition of volatile oil from decaying leaves of lemon-scented eucalypt (Eucalyptus citriodora Hook.) not analyzed earlier. GC and GC-MS analysis of the oil (yield 0.6%) revealed the monoterpenoid nature with citronellal (52.2%), citronellol (12.3%) and isoisopulegol (11.9%) as the major constituents. Overall, 17 components were identified that accounted for over 94% of the decaying leaf oil. Surprisingly, the decaying leaf oil contained nearly 1.8% of trans-rose oxide, which is generally absent in eucalypt essential oil. Decaying leaf oil and its major 2 components (citronellal and citronellol) inhibited the germination and root elongation of two weeds D Cassia occidentalis (broad-leaved) and Echinochloa crus-galli (grassy weed). Based on the dose-response studies, I50 values were determined for decaying leaf oil and the effect was more on germination only of broad-leaved weed (C. occidentalis), whereas that of citronellal and citronellol were on germination as well as root length of E. crus-galli (grassy weed). Based on I50 values it was observed that citronellal was more phytotoxic and germination inhibiting in nature, whereas citronellol was a more potent root inhibitor, thereby indicating a possible different mode of action. The study concludes that decaying leaf oil hold a good commercial value for exploitation as weed management agent

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Chen, Qiu, and Lisha Feng. "Simulation Study of Citronellol-geraniol Rectification Tower Based on Aspen Plus Software." MATEC Web of Conferences 267 (2019): 02008. http://dx.doi.org/10.1051/matecconf/201926702008.

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Aspen Plus is a large-scale chemical simulation software based on steady-state chemical simulation, optimization, sensitivity analysis and economic evaluation. It can analyze the planning, research, development and technical reliability of chemical processes. High-purity citronellol and geraniol, the main high-value components of citronella oil, make the rectification and purification process difficult due to their boiling point and heat sensitivity, with high separation cost and poor effect, resulting in low economic benefits. This paper uses Aspen Plus software to estimate the physical properties of citronellol and geraniol system through known structural formula and room temperature boiling point; uses citronellol-geraniol vapor-liquid equilibrium experimental data to select physical properties analytical methods of Aspen Plus software; conducts process design and simulation of the high vacuum separation of citronellol and geraniol by using DSTWU simple simulation tower and RadFrac strict simulation tower respectively, gets the process parameters of citronellol and geraniol distillation tower, checks the separation process, and optimizes the separation conditions, which provide support for using industrial production in the high-purity separation of citronella oil system.

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Díaz-Pérez, A. L., A. N. Zavala-Hernández, C. Cervantes, and J. Campos-García. "The gnyRDBHAL Cluster Is Involved in Acyclic Isoprenoid Degradation in Pseudomonas aeruginosa." Applied and Environmental Microbiology 70, no. 9 (September 2004): 5102–10. http://dx.doi.org/10.1128/aem.70.9.5102-5110.2004.

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ABSTRACT Pseudomonas aeruginosa PAO1 mutants affected in the ability to degrade acyclic isoprenoids were isolated with transposon mutagenesis. The gny cluster (for geranoyl), which encodes the enzymes involved in the lower pathway of acyclic isoprenoid degradation, was identified. The gny cluster is constituted by five probable structural genes, gnyDBHAL, and a possible regulatory gene, gnyR. Mutations in the gnyD, gnyB, gnyA, or gnyL gene caused inability to assimilate acyclic isoprenoids of the citronellol family of compounds. Transcriptional analysis showed that expression of the gnyB gene was induced by citronellol and repressed by glucose, whereas expression of the gnyR gene had the opposite behavior. Western blot analysis of citronellol-grown cultures showed induction of biotinylated proteins of 70 and 73 kDa, which probably correspond to 3-methylcrotonoyl-coenzyme A (CoA) carboxylase and geranoyl-CoA carboxylase (GCCase) alpha subunits, respectively. The 73-kDa biotinylated protein, identified as the α-GCCase subunit, is encoded by gnyA. Intermediary metabolites of the isoprenoid pathway, citronellic and geranic acids, were shown to accumulate in gnyB and gnyA mutants. Our data suggest that the protein products encoded in the gny cluster are the β and α subunits of geranoyl-CoA carboxylase (GnyB and GnyA), the citronelloyl-CoA dehydrogenase (GnyD), the γ-carboxygeranoyl-CoA hydratase (GnyH), and the 3-hydroxy-γ-carboxygeranoyl-CoA lyase (GnyL). We conclude that the gnyRDBHAL cluster is involved in isoprenoid catabolism.

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Esmaeili, A., S. Rohany, S. Safaiyan, and Z. S. Amir. "Microbial transformation of citral by Aspergillus niger-PTCC 5011 and study of the pathways involved." Czech Journal of Food Sciences 29, No. 6 (November 28, 2011): 610–15. http://dx.doi.org/10.17221/237/2009-cjfs.

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Citronellol and hydroxy citronellal are fragrance ingredients used in decorative cosmetics and fine fragrances. They have many applications in flavourings, extracts, foods, and drugs manufacturing. Their use worldwide is in the range exceeding 1000 metric tons per annum. Previous studies investigated the biotransformation of citral by the free cell method and immobilised cell method with Saccharomyces cerevisae. In this research, the microbial transformation of citral by the sporulated surface cultures method with Aspergillus niger-PTCC 5011 was studied. In experiments, A. niger was inoculated on solid media in conical flasks. The transformation took place for the periods of time of 6 days and 15 days. The results were analysed by the theoretical study, Fourier transform infrared spectroscopy, gas chromatography, and gas chromatography-mass spectroscopy. The major compounds produced in 6 days were acetone (26.2%) and hydroxy citronellal (37.0%), while the major compounds after the 15-day period were acetone (15.0%) and citronellol (36.0%). As citronellol has numerous commercial applications, the 15-day biotransformation period was found to be preferable.

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Janssen, A. M., W. H. R. Tsai Sioe, J. J. C. Scheffer, and A. Baerheim Svendsen. "Citronellal and citronellol, a case of antimicrobial antagonism?" Flavour and Fragrance Journal 3, no. 3 (September 1988): 137–40. http://dx.doi.org/10.1002/ffj.2730030310.

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Sayekti, Endah, Imelda H. Silalahi, and Titin Anita Zaharah. "SUBSTITUTION REACTION OF HYDROXY OF CITRONELLOL WITH CHLORIDE USING A MIXTURE OF AMMONIUM CHLORIDE AND SULPHURIC ACID." ALCHEMY Jurnal Penelitian Kimia 11, no. 2 (September 27, 2016): 135. http://dx.doi.org/10.20961/alchemy.11.2.720.135-146.

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Substitution reaction of hydroxy of citronellol with chloride using a mixture of ammonium chloride (NH4Cl) and sulphuric acid (H2SO4) has been conducted. The citronellol was obtained from the reduction of citronellal using sodium borohydride (NaBH4) at room temperature for 30 minutes. Substitution of hydroxy of citronellol with chloride ion was carried out at 80 oC and molarity ratio of citronellol and NH4Cl 1:1, 1:2; 1:3; and 1:4 respectively. Identification of the product by gas chromatography-mass spectrometry (GC-MS) showed that the substitution reaction produced 2-isopropyl-5-methyl-1-chlorocyclohexane compound with rendemen 64,49 % in mol ratio of 1:4. The infra red (IR) analysis showed that there was a vibration at wave number 763 cm-1 which is a typical C-Cl vibrations.

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Sayekti, Endah, Imelda H. Silalahi, and Titin Anita Zaharah. "SUBSTITUTION REACTION OF HYDROXY OF CITRONELLOL WITH CHLORIDE USING A MIXTURE OF AMMONIUM CHLORIDE AND SULPHURIC ACID." ALCHEMY Jurnal Penelitian Kimia 11, no. 2 (September 27, 2016): 135. http://dx.doi.org/10.20961/alchemy.v11i2.720.

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Substitution reaction of hydroxy of citronellol with chloride using a mixture of ammonium chloride (NH4Cl) and sulphuric acid (H2SO4) has been conducted. The citronellol was obtained from the reduction of citronellal using sodium borohydride (NaBH4) at room temperature for 30 minutes. Substitution of hydroxy of citronellol with chloride ion was carried out at 80 oC and molarity ratio of citronellol and NH4Cl 1:1, 1:2; 1:3; and 1:4 respectively. Identification of the product by gas chromatography-mass spectrometry (GC-MS) showed that the substitution reaction produced 2-isopropyl-5-methyl-1-chlorocyclohexane compound with rendemen 64,49 % in mol ratio of 1:4. The infra red (IR) analysis showed that there was a vibration at wave number 763 cm-1 which is a typical C-Cl vibrations.

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Fauzi, Nurulwahidah, and Juliana Jumal. "Cymbopogon Nardus From Malay Society Tradition Perspectives: An Analysis of Chemical Composition Using Steam Distillation From Scientific Finding." Ulum Islamiyyah 31 (August 2, 2020): 19–34. http://dx.doi.org/10.33102/uij.vol31no.106.

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Cymbopogon nardus (C. nardus) or fragrance lemongrass is a member of Gramineae family which is well known for its citronella oil content that is commonly used as a natural fragrant oil, in insect repellents, as well as in beauty, household and perfumery products. C. nardus is one of the unique herbs that has been widely discussed in Malay Medical Manuscript and has been consumed by Malay practitioner as it possesses various anti biological activities such as anti fungal, anti bacteria and anti-inflammatory. In traditional system of medicine among Malay traditional people, C. nardus has been used for the treatment of fever, muscle pain, and many kinds of illness. Various uses shown by this herb and the tendency of high application of the herb among Malay society has led us to study C. nardus according to the scientific perspective. Therefore, the objectives of this study are to identify the morphology of C. nardus and its application from Malay traditional’s perspectives, as well as to determine the active compounds present in the herb through scientific findings. Two different parts of leaves and stems of C. nardus were extracted using steam distillation method for 2 hours. The chemical composition of citronella oil was determined by Gas Chromatography-Mass Spectrometry (GC-MS). An amount of 0.55 % and 0.024 % of citronella oil were extracted from leaves and stems parts, respectively. The main compositions of oil extracted from the leaves part are citronellol (41.4 %), methyleugenol (80.2 %), citronellal (39.7 %), D- limonene (40 %) and geraniol (36.5 %). Meanwhile, the extraction from the stems composed of α-Himachalene (45.34%), Citronellol acetate (48.2 %), cis-Geraniol (57.8 %) and endo- Borneol (26.2 %). Thus, it can be concluded that C. nardus leaves extraction yield higher citronella oil content as compared to stems and consist of different main chemical compositions between the two parts.

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Chen, Hai, Kai Yang, Chun You, Shu Du, Qian Cai, Qing He, Zhu Geng, and Zhi Deng. "Chemical constituents and biological activities against Tribolium castaneum (Herbst) of the essential oil from Citrus wilsonii leaves." Journal of the Serbian Chemical Society 79, no. 10 (2014): 1213–22. http://dx.doi.org/10.2298/jsc140227037c.

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The essential oil obtained from Citrus wilsonii Tanaka leaves with hydrodistillation was investigated by GC and GC-MS. The main components of the essential oil were identified to be citronellol (16.94%), nerol acetate (10.35%), ?-terpinen (9.85%), citronellal (9.36%) and ?-pinene (6.72%). Among them, the four active constituents, predicted with a bioactivity-test, were isolated and identified as citronellol, ?-terpinene, nerol (neryl) acetate and ?-pinene. It was found that the essential oil of C. wilsonii leaves and isolated compounds possessed fumigant and contact toxicity against Tribolium castaneum adults. The essential oil and ?-terpinen showed strong fumigant toxicity against T. castaneum (LC50 = 8.18 and 4.09 mg L-1). Repellency of the crude oil and active compounds was also determined. Citronellol, neryl acetate and ?-pinene were strongly repellent (100%, 86% and 92%, respectively, at 78.63 nL cm-2, after 2 h treatment) against T. castaneum. The essential oil and citronellol exhibited the same level of repellency compared with the positive control, DEET. The results indicate that the essential oil of C. wilsonii leaves and its active compounds had the potential to be developed as natural fumigants, insecticides and repellents for control of T. castaneum.

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NINAGAWA, Yoichi. "Citronellol." Journal of Synthetic Organic Chemistry, Japan 49, no. 1 (1991): 71–72. http://dx.doi.org/10.5059/yukigoseikyokaishi.49.71.

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Niculau, Edenilson dos Santos, Péricles Barreto Alves, Paulo Cesar de Lima Nogueira, Luciane Pimenta Cruz Romão, Graziele da Costa Cunha, Arie Fitzgerald Blank, and Anderson de Carvalho Silva. "Chemical Profile and Use of the Peat as an Adsorbent for Extraction of Volatile Compounds from Leaves of Geranium (Pelargonium graveolens L’ Herit)." Molecules 25, no. 21 (October 24, 2020): 4923. http://dx.doi.org/10.3390/molecules25214923.

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Volatile organic compounds (VOCs) from leaves of geranium (Pelargonium graveolens L’ Herit) were extracted by dynamic headspace using Porapak Q (HSD-P) as adsorbent and peat, a novel adsorbent in the extraction of plant volatiles, analyzed by gas chromatography–mass spectrometry (GC/MS) and gas chromatography–flame ionization (GC/FID), and the results were compared with those obtained by hydrodistillation (HD). The yield volatiles changed with the extraction method. HD was more efficient for extracting linalool (11.19%) and citronellyl formate (9.41%). Citronellol (28.06%), geraniol (38.26%) and 6,9-guaiadiene (9.55%) and geranyl tiglate (8.21%) were the major components identified by dynamic headspace using peat (HSD-T), while citronellol (16.88%), geraniol (13.63%), 6,9-guaiadiene (16.98%) and citronellyl formate (6.95%) were identified by dynamic headspace using Porapak Q (HSD-P). Furthermore, this work showed, for the first time, that in natura peat is useful to extract VOCs from leaves of geranium.

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Songkro, Sarunyoo, Narissara Hayook, Jittarat Jaisawang, Duangkhae Maneenuan, Thitima Chuchome, and Nattha Kaewnopparat. "Investigation of inclusion complexes of citronella oil, citronellal and citronellol with β-cyclodextrin for mosquito repellent." Journal of Inclusion Phenomena and Macrocyclic Chemistry 72, no. 3-4 (May 21, 2011): 339–55. http://dx.doi.org/10.1007/s10847-011-9985-7.

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Iijima, Miu, Hiromichi Kenmoku, Hironobu Takahashi, Jung-Bum Lee, Masao Toyota, Yoshinori Asakawa, Fumiya Kurosaki, and Futoshi Taura. "Characterization of 12-Oxophytodienoic Acid Reductases from Rose-scented Geranium (Pelargonium graveolens)." Natural Product Communications 11, no. 12 (December 2016): 1934578X1601101. http://dx.doi.org/10.1177/1934578x1601101201.

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Pelargonium graveolens L'Hér, also referred to as rose geranium, is a popular herbal plant with typical rosy fragrance largely based on the blend of monoterpenoid constituents. Among them, citronellol, which is biosynthesized from geraniol via double bond reduction, is the most abundant scent compound. In this study, three 12-oxophytodienoic acid reductases (PgOPR1–3) have been cloned from P. graveolens, as possible candidates for the double-bond reductase involved in citronellol biosynthesis. The bacterially expressed recombinant PgOPRs did not reduce geraniol to citronellol, but stereoselectively converted citral into ( S)-citronellal in the presence of NADPH. Thus, the α,β-unsaturated carbonyl moiety in the substrate is essential for the catalytic activity of PgOPRs, as reported for OPRs from other plants and structurally related yeast old yellow enzymes. PgOPRs promiscuously accepted linear and cyclic α,β-unsaturated carbonyl substrates, including methacrolein, a typical reactive carbonyl compound. The possible biotechnological applications for PgOPRs in plant metabolic engineering, based on their catalytic properties, are discussed herein.

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Manaf, Mastura Abd, Junaidah Jai, Ana Najwa Mustapa, Rafeqah Raslan, and Istikamah Subuki. "Water Based Paint with Java Citronella Oil as Mosquito Repellent Agent." Applied Mechanics and Materials 625 (September 2014): 860–63. http://dx.doi.org/10.4028/www.scientific.net/amm.625.860.

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Active compounds ofCymbopogon winterianius(Java Serai Wangi) which consists of citronella oil (CO), has been reported to has mosquito repellent compounds; citronellol, citronellal, and geraniol. Limitation on the use of natural mosquito repellent has driven this work to incorporate the CO in commercial water-based paint. In this work, the CO-paint was formulated and its ability to repel mosquito was determined. The optimum composition of CO was determined by three standard paint analyses which were volatile organic compound (VOC), viscosity and adhesion. The best composition of CO in paint was found to be 20% vol. where it able to repelAedes aegyptiwith 80% efficiency. It is envisioned that the formulated CO-paint is effectively function as mosquito-repellent thus as an alternative way to reduce the mosquito-borne diseases.

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Aldhayan, Daifallah, Květa Kalíková, Mohammed Rafi Shaik, Mohammed Rafiq H. Siddiqui, and Jan Přech. "Selective Oxidation of Citronellol over Titanosilicate Catalysts." Catalysts 10, no. 11 (November 5, 2020): 1284. http://dx.doi.org/10.3390/catal10111284.

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Citronellol is one of the most widely used fragrances for bouquetting purposes and it is a starting material for synthesis of several other terpenoids. Nevertheless, few data have been reported on citronellol selective oxidation. Accordingly, we report our findings on the selective oxidation of citronellol with hydrogen peroxide using a set of titanosilicate catalysts with different morphologies and textural properties—conventional titanium silicalite 1 (TS-1), mesoporous TS-1, layered TS-1 and silica-titania pillared TS-1 and also studying the effect of the solvent used. Epoxidation of C6=C7 double bond was the main primary reaction in this system and trace signals of C5 allylic oxidation products were observed without formation of citronellal. Due to the presence of post-synthesis introduced additional Ti sites, the silica-titania pillared TS-1 (TS-1-PITi) provided the highest conversion among the tested catalysts; nevertheless, citronellol was oxidized over all the studied catalysts including conventional TS-1; therefore, showing that it penetrates even into MFI micropores (0.55 nm in diameter). When using acetonitrile as a solvent, the conversion was proportional to the titanium content of the catalyst. When studying the effect of the solvent, acetonitrile provided the highest epoxide selectivity (55%) while in methanol, 2-propanol and 1,4-dioxane, ring opening reactions caused epoxide decomposition.

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Ambari, Yani, and Ni Made Dharma Shantini Suena. "UJI STABILITAS FISIK FORMULASI LOTION ANTI NYAMUK MINYAK SEREH." Jurnal Ilmiah Medicamento 5, no. 2 (September 30, 2019): 111–15. http://dx.doi.org/10.36733/medicamento.v5i2.844.

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Nyamuk adalah penyebar berbagai penyakit. Nyamuk adalah sumber transmisi demam berdarah, malaria, Chikungunya, dan ekstremitas (filariasis). Salah satu bahan alam yang memiliki potensi sebagai anti nyamuk adalah minyak Citronella (Citronella oil). Minyak Citronella mengandung minyak esensial dengan komponen geraniol (20-40%), citronellal (25-50%), dan citronellol (10-15) yang menimbulkan aroma, sehingga dapat digunakan sebagai repellent atau pengusir nyamuk. Minyak Citronella adalah insektisida alami murah dan efektif, juga dapat digunakan dengan aman dan praktis, sehingga dapat dikembangkan menjadi lotion anti nyamuk. Untuk menjaga stabilitas minyak Citronella dalam bentuk lotion, perlu formulasi lotion anti nyamuk yang tepat. Tujuan dari penelitian ini adalah untuk mengetahui formulasi lotion dari bahan aktif dari oleum Citronella dan untuk mengetahui hasil evaluasi dilakukan pada Lotion Citronella. Metode yang digunakan dalam pembuatan lotion Citronella adalah metode peleburan. Evaluasi dilakukan seminggu setelah pembuatan sediaan lotion, yaitu uji organoleptik, uji pH, uji bobot jenis, uji homogenitas, uji daya sebar, dan uji ukuran partikel. Hasil evaluasi sediaan lotion minyak Citronella, antara lain, pada uji organoleptis lotion tidak berubah, tetap berwarna putih, memiliki bau khas Citronella dan tekstur lembut. Hasil pemeriksaan pH, lotion tidak mengalami berubah pH yaitu tetap pH 7. Dalam uji daya sebar, lotion Citronella pada konsentrasi 18% menyebar merata atau homogen. Hasil uji homogenitas, lotion Citronella pada konsentrasi 18% tidak menunjukkan butiran kasar pada kaca transparan. Pada uji bobot jenis menggunakan alat Piknometer, diperoleh bobot jenis lotion Citronella adalah 23, 8 g/ml. Terakhir pada uji ukuran partikel, lotion Citronella memiliki ukuran partikel yang seragam.

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Santos, Renata C., Jhersyka S. Paes, Arthur V. Ribeiro, Abraão A. Santos, and Marcelo C. Picanço. "Toxicity of Corymbia citriodora essential oil compounds against Ascia monuste (Linnaeus, 1764) (Lepidoptera: Pieridae) and Plutella xylostella (Linnaeus, 1758) (Lepidoptera: Plutellidae)." Entomological Communications 2 (July 28, 2020): ec02013. http://dx.doi.org/10.37486/2675-1305.ec02013.

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Essential oils (EO’s) have been investigated as a safe alternative to pest management. The toxicity of an EO can vary due to abiotic and biotic factors. The individual compounds of different EO’s have shown promise to insect control and they may present toxicity similar to or greater than the EO’s. In this study, we determined the toxicity of Corymbia citriodora EO compounds against Ascia monuste (Linnaeus, 1764) and Plutella xylostella (Linnaeus, 1758). Citronellal, trans-caryophyllene, and citronellol (LD50 = 23.24, 24.17 and 27.84 μg/mg, respectively) were the most toxic compounds to A. monuste. On the other hand, α-pinene and β-pinene presented low toxicity to this pest. For P. xylostella, citronellol and citronellal were the most toxic compounds (LD50 = 22.36 and 25.53 μg/mg, respectively). The other compounds presented lower toxicity with similar doses. Thus, the individual compounds of C. citriodora EO can be an alternative for A. monuste and P. xylostella control.

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Pinheiro, Patrícia Fontes, Vagner Tebaldi de Queiroz, Vando Miossi Rondelli, Adilson Vidal Costa, Tiago de Paula Marcelino, and Dirceu Pratissoli. "Insecticidal activity of citronella grass essential oil on Frankliniella schultzei and Myzus persicae." Ciência e Agrotecnologia 37, no. 2 (April 2013): 138–44. http://dx.doi.org/10.1590/s1413-70542013000200004.

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The thrips, Frankliniella schultzei, and green peach aphid, Myzus persicae, cause direct damage to plants of economic importance and transmit phytoviruses, causing large economic losses. Chemical constituents of essential oils present a wide range of biological activities. The aim of this work was to evaluate insecticidal activity of essential oil from citronella grass, Cymbopogon winterianus, on F. schultzei and M. persicae. This essential oil was obtained by steam distillation and components were identified by GC/FID and GC/MS. A Potter spray tower was used to spray insects with the essential oil. The major constituents are geraniol (28.62%), citronellal (23.62%) and citronellol (17.10%). Essential oil of C. winterianus at 1% (w v-1) causes mortality in F. schultzei and M. persicae at 34.3% and 96.9%, respectively. The LC50 value for M. persicae was 0.36% and LC90 0.66%. Thus, citronella grass essential oil at 1% (w v-1) is more toxic to M. persicae than F. schultzei. This essential oil shows promise for developing pesticides to manage M. persicae.

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McDaniel, C. J., B. J. Dunn, and P. J. Weldon. "Citronellol and Citronellyl Esters from the Paracloacal Glands of the Broad-Snouted Caiman, Caiman latirostris (Crocodylia, Reptilia)." Zeitschrift für Naturforschung C 53, no. 9-10 (October 1, 1998): 932–34. http://dx.doi.org/10.1515/znc-1998-9-1026.

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The secretions of the paracloacal glands of an adult male broad-snouted caiman (Caiman latirostris) were analyzed by GC/MS. 3,7-Dimethyl-6-octen-1-ol (citronellol) and four citronellyl esters, with acid moieties ranging from two to five carbons, were identified. Squalene, β-farnesene, and straight-chain esters also were observed.

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Hammid, Syaliza Abdul, and Fasihuddin Ahmad. "Chemotype of Litsea cubeba Essential Oil and Its Bioactivity." Natural Product Communications 10, no. 7 (July 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000741.

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The essential oils from different parts of Litsea cubeba, collected from the highlands of Sarawak, were isolated and their chemical compositions analyzed. This study demonstrated significant variations in the chemical compositions and the chemical profiles of the volatiles and could provide valuable supplementary information on the geographical variations of the species. The fruit essential oil was dominated by citronellal, d-limonene and citronellol, while the leaf oil was high in eucalyptol and α-terpineol. High concentrations of citronellal and citronellol in both the root and bark oils were identified. In the stem, the oil was dominated by eucalyptol, d-limonene and α-terpineol. The activity of the oils against brine shrimp larvae, bacteria, yeast and fungi was determined. The oils were toxic against brine shrimp larvae with LC50 values ranging from 25.1 – 30.9 μL/mL. The oils also demonstrated a wide spectrum of inhibition against microorganisms with inhibition zones between 19.5 – 46.7 mm against Gram-positive bacteria and 10.5 – 90.0 mm against yeast and fungi. However, the oils were not active against Gram-negative bacteria.

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Sudiyarmanto, S., I. B. Adilina, R. R. Aditya, D. Sukandar, and S. Tursiloadi. "Catalytic conversion of citronellal to citronellol over skeletal Ni catalyst." Journal of Physics: Conference Series 1442 (January 2020): 012047. http://dx.doi.org/10.1088/1742-6596/1442/1/012047.

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Wang, Fa Song, Yun He Li, Dong Hai Huang, and Jia Gui Xiang. "Chemical Composition of the Root Bark Oil of Litsea mollis from China." Advanced Materials Research 997 (August 2014): 132–35. http://dx.doi.org/10.4028/www.scientific.net/amr.997.132.

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The essential oil from the Root Bark of Litsea mollis was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by gas chromatography–mass spectrometry (GC-MS). A total of 31 compounds were identified, representing 95.22% of the oil. The main components identified were (R)-citronellal (39.9%), (R)-citronellol (13.63%), (Z)-citral (11.5%) and β-caryophyllene (5.78%).

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Lopez-Romero, Julio Cesar, Humberto González-Ríos, Anabela Borges, and Manuel Simões. "Antibacterial Effects and Mode of Action of Selected Essential Oils Components againstEscherichia coliandStaphylococcus aureus." Evidence-Based Complementary and Alternative Medicine 2015 (2015): 1–9. http://dx.doi.org/10.1155/2015/795435.

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Bacterial resistance has been increasingly reported worldwide and is one of the major causes of failure in the treatment of infectious diseases. Natural-based products, including plant secondary metabolites (phytochemicals), may be used to surpass or reduce this problem. The objective of this study was to determine the antibacterial effect and mode of action of selected essential oils (EOs) components: carveol, carvone, citronellol, and citronellal, againstEscherichia coliandStaphylococcus aureus. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were assessed for the selected EOs components. Moreover, physicochemical bacterial surface characterization, bacterial surface charge, membrane integrity, andK+leakage assays were carried out to investigate the antimicrobial mode of action of EOs components. Citronellol was the most effective molecule against both pathogens, followed by citronellal, carveol, and carvone. Changes in the hydrophobicity, surface charge, and membrane integrity with the subsequentK+leakage fromE. coliandS. aureuswere observed after exposure to EOs. This study demonstrates that the selected EOs have significant antimicrobial activity against the bacteria tested, acting on the cell surface and causing the disruption of the bacterial membrane. Moreover, these molecules are interesting alternatives to conventional antimicrobials for the control of microbial infections.

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Uchiyama, Takeo, Masayoshi Suzuki, Masurou Numata, Sounosuke Naitou, and Tsutomu Hoshino. "Biotransformation of Citronellal to Citronellol by Cultured tissues of Mentha Plant." Plant tissue culture letters 8, no. 1 (1991): 9–13. http://dx.doi.org/10.5511/plantbiotechnology1984.8.9.

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Orzeszko, Andrzej, Dorota Melon-Ksyta, Ewa Kowalczyk, and Krzysztof Czupryński. "Synthesis and Liquid Crystalline Properties of Novel Imides and Thioimides with Chiral Aliphatic Tails." Zeitschrift für Naturforschung B 58, no. 10 (October 1, 2003): 1015–20. http://dx.doi.org/10.1515/znb-2003-1013.

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Three chiral compounds (R)-octan-2-ol, (S)-citronellol and (S)-citronellyl bromide were used for the synthesis of novel ester imides with biphenyl moieties as mesogenic units. Observations by means of polarising microscopy as well as DSC measurements revealed the presence of SmC* and/or SmA phases for all the compounds examined. It was found that the biphenyl units with long chiral alkoxy substituents induce smectic C phases.

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Koch, Wolf-Gerald, and Volker Sinnwell. "Isopulegol from Liquid Cultures of the Fungus Ceratocystis coerulescens (Ascomycotina)." Zeitschrift für Naturforschung C 42, no. 1-2 (February 1, 1987): 159–61. http://dx.doi.org/10.1515/znc-1987-1-227.

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Abstract Ceratocystis coerulescens RWD 451 (Ascomycetes) was cultivated on defined synthetic culture medium containing glucose (3.0% ), asparagine (0.1% ), mineral salts and thiamine. 6 weeks oid cultures produced methyl heptenyl compounds, citronellol. citronellyl acetate, dihydro-farnesol and a hitherto unknown monoterpene alcohol. By GC/MS, 1H and 13C NMR spectroscopy, this alcohol could be identified as ( -)isopulegol. So far, this monocyclic monoterpene alcohol has not been described as a fungal metabolite.

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Yu, Weiyong, Hanfan Liu, Manhong Liu, and Zhijie Liu. "Selective hydrogenation of citronellal to citronellol over polymer-stabilized noble metal colloids." Reactive and Functional Polymers 44, no. 1 (April 2000): 21–29. http://dx.doi.org/10.1016/s1381-5148(99)00073-5.

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Sharma, Ruchi, Rekha Rao, Sunil Kumar, Sheefali Mahant, and Sarita Khatkar. "Therapeutic Potential of Citronella Essential Oil: A Review." Current Drug Discovery Technologies 16, no. 4 (December 11, 2019): 330–39. http://dx.doi.org/10.2174/1570163815666180718095041.

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Mosquito-borne diseases such as malaria, filariasis, chikunguniya, yellow fever, dengue and Japanese encephalitis are the major cause of remarkable morbidity and mortality in livestock and humans worldwide. Since ancient times, aromatic plants are used for their medicinal value. Essential oils derived from these plants may be used as effective alternatives/adjuvants in pharmaceuticals, biomedical, cosmetic, food, veterinary and agriculture applications. These oils have also gained popularity and interest for prevention and treatment of various disorders. However, several reports on adverse effects including skin eruption, contact artricaria or toxic encephalopathy in children are available for synthetic repellent in the literature. Thus, natural insect repellents like essential oils have been explored recently as an alternative. One such essential oil studied widely, is citronella oil, extracted mainly from Cymbopogon nardus. This essential oil has exhibited good efficacy against mosquitoes. It is a mixture of components including citronellal, citronellol, geraniol as major constituents contributing to various activities (antimicrobial, anthelmintic, antioxidant, anticonvulsant antitrypanosomal and wound healing), besides mosquito repellent action. Citronella essential oil is registered in US EPA (Environmental protection agency) as insect repellent due to its high efficacy, low toxicity and customer satisfaction. However, poor stability in the presence of air and high temperature limits its practical applications. Since specific knowledge on properties and chemical composition of oil is fundamental for its effective application, the present review compiles and discusses biological properties of citronella oil. It also sheds light on various formulations and applications of this essential oil.

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Oda, Shinobu, Takeshi Sugai, and Hiromichi Ohta. "Syntheses of Optically Active Citronellol, Citronellal, and Citronellic Acid by Microbial Oxidation and Double Coupling System in an Interface Bioreactor." Bulletin of the Chemical Society of Japan 73, no. 12 (December 2000): 2819–23. http://dx.doi.org/10.1246/bcsj.73.2819.

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Chaimovitsh, David, Alona Shachter, Mohamad Abu-Abied, Baruch Rubin, Einat Sadot, and Nativ Dudai. "Herbicidal Activity of Monoterpenes Is Associated with Disruption of Microtubule Functionality and Membrane Integrity." Weed Science 65, no. 1 (November 4, 2016): 19–30. http://dx.doi.org/10.1614/ws-d-16-00044.1.

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Aromatic plants and their volatile compounds affect seed germination and plant growth, and therefore hold potential for agriculture uses as plant growth regulators and bioherbicides. In the present study 17 major monoterpenes were selected, and their mechanisms of plant toxicity were elucidated using transgenicArabidopsis thalianaat various growth stages. Microtubulin and the plant cell membrane were identified as the focal targets through which phytotoxicity and herbicidal activity acted. Variability in monoterpene mechanisms was observed. Limonene and (+)-citronellal had strong antimicrotubule efficacy, whereas citral, geraniol, (−)-menthone, (+)-carvone, and (−)-citronellal demonstrated moderate antimicrotubule efficacy. Pulegone, (−)-carvone, carvacrol, nerol, geranic acid, (+)/(−)-citronellol, and citronellic acid lacked antimicrotubule capacity. An enantioselective disruption of microtubule assembly was recorded for (+)/(−)-citronellal and (+)/(−)-carvone. The (+) enatiomers were more potent than their (−) counterparts. Citral, limonene, carvacrol, and pulegone were also tested for phytotoxicity and herbicidal activity. Pulegone had no detectable effect on microtubules or membranes. Citral disrupted microtubules but did not cause membrane damage. Carvacrol lacked a detectable effect on microtubules but incited membrane leakage, and limonene disrupted microtubules and membrane leakage. Therefore, only limonene was herbicidal at the tested concentrations.In plantaquantification of residues revealed that citral was biotransformed into nerol and geraniol, and limonene was converted into carvacrol, which could explain its dual capacity with respect to microtubules and membrane functionality. The results obtained are an important added value to commercial efforts in selecting appropriate aromatic plants to be sources of bioherbicidal compounds for sustainable weed management with a limited potential for herbicide resistance evolution in weed populations.

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Bergman, Matthew E., Ángel Chávez, Albert Ferrer, and Michael A. Phillips. "Distinct metabolic pathways drive monoterpenoid biosynthesis in a natural population of Pelargonium graveolens." Journal of Experimental Botany 71, no. 1 (August 31, 2019): 258–71. http://dx.doi.org/10.1093/jxb/erz397.

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Abstract Pelargonium graveolens is a wild predecessor to rose-scented geranium hybrids prized for their essential oils used as fragrances and flavorings. However, little is known about their biosynthesis. Here we present metabolic evidence that at least two distinct monoterpene biosynthetic pathways contribute to their volatile profiles, namely, cyclic p-menthanes such as (−)-isomenthone and acyclic monoterpene alcohols such as geraniol and (−)-citronellol and their derivatives (referred to here as citronelloid monoterpenes). We established their common origin via the 2C-methyl-d-erythritol-4-phosphate pathway but found no indication these pathways share common intermediates beyond geranyl diphosphate. Untargeted volatile profiling of 22 seed-grown P. graveolens lines demonstrated distinct chemotypes that preferentially accumulate (−)-isomenthone, geraniol, or (−)-citronellol along with approximately 85 minor volatile products. Whole plant 13CO2 isotopic labeling performed under physiological conditions permitted us to measure the in vivo rates of monoterpenoid accumulation in these lines and quantify differences in metabolic modes between chemotypes. We further determined that p-menthane monoterpenoids in Pelargonium are likely synthesized from (+)-limonene via (+)-piperitone rather than (+)-pulegone. Exploitation of this natural population enabled a detailed dissection of the relative rates of competing p-menthane and citronelloid pathways in this species, providing real time rates of monoterpene accumulation in glandular trichomes.

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Silva, Daniele, Hermes Diniz-Neto, Laísa Cordeiro, Maria Silva-Neta, Shellygton Silva, Francisco Andrade-Júnior, Maria Leite, et al. "(R)-(+)-β-Citronellol and (S)-(−)-β-Citronellol in Combination with Amphotericin B against Candida Spp." International Journal of Molecular Sciences 21, no. 5 (March 5, 2020): 1785. http://dx.doi.org/10.3390/ijms21051785.

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The enantiomers (R)-(+)-β-citronellol and (S)-(−)-β-citronellol are present in many medicinal plants, but little is understood about their bioactivity against Candida yeasts. This study aimed to evaluate the behavior of positive and negative enantiomers of β-citronellol on strains of Candida albicans and C. tropicalis involved in candidemia. The minimum inhibitory concentration (MIC) and minimum fungicide concentration (MFC) were determined. The evaluation of growth kinetics, mechanism of action, and association studies with Amphotericin B (AB) using the checkerboard method was also performed. R-(+)-β-citronellol and S-(−)-β-citronellol presented a MIC50% of 64 µg/mL and a MFC50% of 256 µg/mL for C. albicans strains. For C. tropicalis, the isomers exhibited a MIC50% of 256 µg/mL and a MFC50% of 1024 µg/mL. In the mechanism of action assay, both substances displayed an effect on the fungal membrane but not on the fungal cell wall. Synergism and indifference were observed in the association of R-(+)-β-citronellol and AB, while the association between S-(−)-β-citronellol and AB displayed synergism, additivity, and indifference. In conclusion, both isomers of β-citronellol presented a similar profile of antifungal activity. Hence, they can be contemplated in the development of new antifungal drugs providing that further research is conducted about their pharmacology and toxicity.

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42

Yuan, Yuan, Ye Sun, Yanchun Zhao, Chungui Liu, Xiulan Chen, Fengtong Li, and Jianzhong Bao. "Identification of Floral Scent Profiles in Bearded Irises." Molecules 24, no. 9 (May 7, 2019): 1773. http://dx.doi.org/10.3390/molecules24091773.

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Bearded irises are ornamental plants with distinctive floral fragrance grown worldwide. To identify the floral scent profiles, twenty-seven accessions derived from three bearded iris, including Iris. germanica, I. pumila and I. pallida were used to investigate the composition and relative contents of floral scent components by headspace solid-phase microextraction (HS-SPME) and gas chromatography–mass spectrometry (GC-MS). A total of 219 floral scent components were detected in blooming flowers. The scent profile varied significantly among and within the three investigated species. Principal component analysis (PCA) indicated that terpenes, alcohols and esters contributed the most to the floral scent components and 1-caryophyllene, linalool, citronellol, methyl cinnamate, β-cedrene, thujopsene, methyl myristate, linalyl acetate, isosafrole, nerol, geraniol were identified as the major components. In a hierarchical cluster analysis, twenty-seven accessions could be clustered into six different groups, most of which had representative scent components such as linalool, citronellyl acetate, thujopsene, citronellol, methyl cinnamate and 1-caryophyllene. Our findings provide a theoretical reference for floral scent evaluation and breeding of bearded irises.

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43

Xu, Brittany M., George L. Baker, Paul J. Sarnoski, and Renée M. Goodrich-Schneider. "A Comparison of the Volatile Components of Cold Pressed Hamlin and Valencia (Citrus sinensis (L.) Osbeck) Orange Oils Affected by Huanglongbing." Journal of Food Quality 2017 (2017): 1–20. http://dx.doi.org/10.1155/2017/6793986.

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Volatiles from huanglongbing (HLB) symptomatic and asymptomatic cold pressed orange oils from Florida Hamlin and Valencia fruit were assessed. Qualitative gas-liquid chromatography studies showed the presence of several compounds (β-longifolene, perillene, and 4-decenal) which are not commonly identified in Citrus sinensis (L.) Osbeck oils. Oils derived from huanglongbing symptomatic fruit had lower concentrations of linalool, decanal, citronellol, neral, geranial, carvone, dodecanal, and 2-decenal and higher concentrations of citronellal compared to asymptomatic fruit. A comparison to historic literature of orange oil investigations before HLB was of issue in Florida orange crops showed lower levels of linalool, decanal, neral, and geranial in Hamlin peel oil samples, as well as higher levels of dodecanal. Valencia peel oil samples showed lower concentrations of linalool and increased concentration of citronellol and dodecanal. As a result of huanglongbing (HLB) phenomena, the concentrations of several important volatiles found in Hamlin and Valencia peel oil profiles have changed compared to historic values. Differences in volatile concentrations of symptomatic and asymptomatic HLB affected peel oil compounds in orange fruit are identified.

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Kaur, Shalinder, Shivani Rana, Harminder Pal Singh, Daizy Rani Batish, and Ravinder Kumar Kohli. "Citronellol Disrupts Membrane Integrity by Inducing Free Radical Generation." Zeitschrift für Naturforschung C 66, no. 5-6 (June 1, 2011): 260–66. http://dx.doi.org/10.1515/znc-2011-5-609.

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Citronellol, an oxygenated monoterpene, is found naturally in the essential oils of several aromatic plants and has been reported to exhibit growth inhibitory and pesticidal activities. However, its mechanism of action is largely unexplored. We investigated the effect of citronellol, which is lipophilic in nature on membrane integrity in terms of lipid peroxidation, conjugated dienes content, membrane permeability, cell death, and activity of the enzyme lipoxygenase in roots of hydroponically grown wheat. Citronellol (50 - 250 μM) caused a significant inhibition of root and shoot growth. Furthermore, exposure to citronellol enhanced the solute leakage, increased the malondialdehyde content and lipoxygenase activity, and decreased the conjugated diene content. This indicates that citronellol induces generation of reactive oxygen species (ROS) resulting in lipid peroxidation and membrane damage. This was confirmed by in situ histochemical studies indicating cell death and disruption of membrane integrity. We conclude from this study that citronellol inhibits the root growth by ROS-mediated membrane disruption.

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45

Huang, Dong Hai, Fa Song Wang, Yun He Li, and Jia Gui Xiang. "Chemical Composition of the Twig Oil of Litsea mollis from China." Advanced Materials Research 997 (August 2014): 136–39. http://dx.doi.org/10.4028/www.scientific.net/amr.997.136.

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The essential oil from the twig of Litsea mollis was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by gas chromatography–mass spectrometry (GC-MS). A total of 39 compounds were identified, representing 89.27% of the oil. Among the twig oil compounds, oxygenated monoterpenes (39.06%) and sesquiterpene hydrocarbons (36.62%) were predominant (75.68% in total). Among the oxygenated monoterpenes, eucalyptol (9.9%), (R)-citronellol (7.23%), (R)-citronellal (7.0%), and (Z)-citral (5.03%) were the major compounds. Of the sesquiterpene hydrocarbons, β-caryophyllene (7.96%), (-)-α-panasinsene (6.31) and à-Caryophyllene (6.28%) were the main components.

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Oda, Shinobu, Yūichi Inada, Akio Kato, Naotoshi Matsudomi, and Hiromichi Ohta. "Production of (S)-citronellic acid and (R)-citronellol with an interface bioreactor." Journal of Fermentation and Bioengineering 80, no. 6 (January 1995): 559–64. http://dx.doi.org/10.1016/0922-338x(96)87731-2.

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47

Batish, Daizy R., Harminder P. Singh, Nidhi Setia, Shalinder Kaur, and Ravinder K. Kohli. "Chemical Composition and Phytotoxicity of Volatile Essential Oil from Intact and Fallen Leaves of Eucalyptus citriodora." Zeitschrift für Naturforschung C 61, no. 7-8 (August 1, 2006): 465–71. http://dx.doi.org/10.1515/znc-2006-7-801.

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A total of 23 volatile constituents was identified and characterized by GC and GC-MS in the volatile essential oil extracted from intact (juvenile and adult) and fallen (senescent and leaf litter) leaves of lemon-scented eucalyptus (Eucalyptus citriodora Hook.). The leaves differed in their pigment, water and protein content, and C/N ratio. The oils were, in general, monoterpenoid in nature with 18 monoterpenes and 5 sesquiterpenes. However, a great variability in the amount of essential oils and their individual constituents was observed in different leaf tissues. The amount was maximum in the senescent leaves collected from the floor of the tree closely followed by that from juvenile leaves. In all, 19 constituents were identified in oil from juvenile and senescent leaves compared to 23 in adult leaves and 20 in leaf litter, respectively. Citronellal, a characteristic monoterpene of the oil reported hitherto was found to be more (77D78%) in the juvenile and senescent leaves compared to 48 and 54%, respectively, in the adult leaves and leaf litter. In the adult leaves, however, the content of citronellol - another important monoterpene - was very high (21.9%) compared to other leaf types (7.8-12.2%). Essential oil and its two major monoterpenes viz. citronellal and citronellol were tested for their phytotoxicity against two weeds (Amaranthus viridis and Echinochloa crus-galli) and two crops (Triticum aestivum and Oryza sativa) under laboratory conditions. A difference in the phytotoxicity, measured in terms of seedling length and dry weight, of oil from different leaves and major monoterpenes was observed. Oil from adult leaves was found to be most phytotoxic although it occurs in smaller amount (on unit weight basis). The different toxicity of different oil types was due to the relative amount of individual monoterpenes present in the oil, their solubility and interactive action. The study concludes that oil from senescent and juvenile leaves being rich in citronellal could be used as commercial source of citronellal whereas that from adult leaves for weed management programmes as it was the most phytotoxic.

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48

Staudt, Amanda, Henrik Terholsen, Jasmin Kaur, Henrik Müller, Simon P. Godehard, Ivaldo Itabaiana, Ivana C. R. Leal, and Uwe T. Bornscheuer. "Rational Design for Enhanced Acyltransferase Activity in Water Catalyzed by the Pyrobaculum calidifontis VA1 Esterase." Microorganisms 9, no. 8 (August 23, 2021): 1790. http://dx.doi.org/10.3390/microorganisms9081790.

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Biocatalytic transesterification is commonly carried out employing lipases in anhydrous organic solvents since hydrolases usually prefer hydrolysis over acyl transfer in bulk water. However, some promiscuous acyltransferases can catalyze acylation in an aqueous solution. In this study, a rational design was performed to enhance the acyltransferase selectivity and substrate scope of the Pyrobaculum calidifontis VA1 esterase (PestE). PestE wild type and variants were applied for the acylation of monoterpene alcohols. The mutant PestE_I208A is selective for (–)-menthyl acetate (E-Value = 55). Highly active acyltransferases were designed, allowing for complete conversion of (–)-citronellol to citronellyl acetate. Additionally, carvacrol was acetylated but with lower conversions. To the best of our knowledge, this is the first example of the biocatalytic acylation of a phenolic alcohol in bulk water. In addition, a high citronellol conversion of 92% was achieved with the more environmentally friendly and inexpensive acyl donor ethyl acetate using PestE_N288F as a catalyst. PestE_N288F exhibits good acyl transfer activity in an aqueous medium and low hydrolysis activity at the same time. Thus, our study demonstrates an alternative synthetic strategy for acylation of compounds without organic solvents.

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49

Hostýnek, Jurij J., and Howard I. Maibach. "Sensitization Potential of Citronellol." Exogenous Dermatology 3, no. 6 (2004): 307–12. http://dx.doi.org/10.1159/000092445.

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50

Dugelay, Isabelle, Ziya Günata, Jean-Claude Sapis, Raymond L. Baumes, and Claude L. Bayonove. "Etude de l'origine du citronellol dans les vins." OENO One 26, no. 3 (September 30, 1992): 177. http://dx.doi.org/10.20870/oeno-one.1992.26.3.1193.

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La formation du citronellol à partir du géraniol et du nérol au cours de la fermentation de moûts synthétiques et naturels de raisin par différentes souches de levures a été étudiée. Le géraniol et le nérol sont transformés en citronellol par la levure, ceci de façon plus marquée avec le géraniol. La quantité de citronellol formé dépend de la souche de levure utilisée. D'autres monoterpènes, comme les acétates de géranyle et de néryle et l'α-terpinéol, sont aussi formés au cours de la fermentation. La préparation enzymatique utilisée n'a pas montré d'activités réductases vis-à-vis du géraniol et du nérol pour former du citronellol.

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Journal articles on the topic 'Citronellol'

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