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Journal articles on the topic 'Limonene epoxide'

Author: Grafiati

Published: 3 June 2025

Last updated: 1 August 2025

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1

Huang, Zi-Yi, Min-Ru Jiao, Xiu Gu, Zi-Ran Zhai, Jian-Qi Li, and Qing-Wei Zhang. "Asymmetric Synthesis of 1,2-Limonene Epoxides by Jacobsen Epoxidation." Pharmaceutical Fronts 03, no. 03 (2021): e113-e118. http://dx.doi.org/10.1055/s-0041-1740241.

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This study reported an asymmetric synthesis of 1,2-limonene epoxides. The absolute stereochemistry was controlled by a Jacobsen epoxidation of cis-1,2-limonene epoxide (with diastereomeric excess of 98%) and trans-1,2-limonene epoxide (with diastereomeric excess of 94%), which could be used as important raw materials for the preparation of related cannabinoid drugs.

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2

van der Werf, Mariët J., Karin M. Overkamp, and Jan A. M. de Bont. "Limonene-1,2-Epoxide Hydrolase fromRhodococcus erythropolis DCL14 Belongs to a Novel Class of Epoxide Hydrolases." Journal of Bacteriology 180, no. 19 (1998): 5052–57. http://dx.doi.org/10.1128/jb.180.19.5052-5057.1998.

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ABSTRACT An epoxide hydrolase from Rhodococcus erythropolisDCL14 catalyzes the hydrolysis of limonene-1,2-epoxide to limonene-1,2-diol. The enzyme is induced when R. erythropolis is grown on monoterpenes, reflecting its role in the limonene degradation pathway of this microorganism. Limonene-1,2-epoxide hydrolase was purified to homogeneity. It is a monomeric cytoplasmic enzyme of 17 kDa, and its N-terminal amino acid sequence was determined. No cofactor was required for activity of this colorless enzyme. Maximal enzyme activity was measured at pH 7 and 50°C. None of the tested inhibitors or m

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3

van der Werf, Mariët J., Henk J. Swarts, and Jan A. M. de Bont. "Rhodococcus erythropolis DCL14 Contains a Novel Degradation Pathway for Limonene." Applied and Environmental Microbiology 65, no. 5 (1999): 2092–102. http://dx.doi.org/10.1128/aem.65.5.2092-2102.1999.

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ABSTRACT Strain DCL14, which is able to grow on limonene as a sole source of carbon and energy, was isolated from a freshwater sediment sample. This organism was identified as a strain of Rhodococcus erythropolis by chemotaxonomic and genetic studies. R. erythropolis DCL14 also assimilated the terpenes limonene-1,2-epoxide, limonene-1,2-diol, carveol, carvone, and (−)-menthol, while perillyl alcohol was not utilized as a carbon and energy source. Induction tests with cells grown on limonene revealed that the oxygen consumption rates with limonene-1,2-epoxide, limonene-1,2-diol, 1-hydroxy-2-oxo

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4

Clerget, Mégane, Eric Gagnon, and Jerome P. Claverie. "Photopolymerization of Limonene Dioxide and Vegetable Oils as Biobased 3D-Printing Stereolithographic Formulation." Polymers 16, no. 7 (2024): 965. http://dx.doi.org/10.3390/polym16070965.

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Epoxidized vegetable oils and limonene dioxide, a bis-epoxide derived from the terpene limonene, are photo-copolymerized to yield highly crosslinked networks with high conversion of all epoxide groups at ambient temperature. However, the slow polymerization of such biobased formulation polymerizes is not compatible for a use in a commercial SLA 3D printer. Adding an acrylated epoxidized vegetable oil to the bis-epoxide leads to a decrease of curing time and an increase in LDO conversion to polymer. For example, in a 60:40 wt:wt mixture of LDO and epoxidized soybean oil, the conversions of both

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5

Fomenko, Vladislav V., Sergey S. Laev та Nariman F. Salakhutdinov. "Catalytic Epoxidation of 3-Carene and Limonene with Aqueous Hydrogen Peroxide, and Selective Synthesis of α-Pinene Epoxide from Turpentine". Catalysts 11, № 4 (2021): 436. http://dx.doi.org/10.3390/catal11040436.

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The epoxidation of turpentine (technical α-pinene), 3-carene, and limonene with aqueous hydrogen peroxide was studied in a new catalytic system employing manganese sulfate, salicylic acid, sodium bicarbonate, and acetonitrile, as a polar solvent. The proposed approach makes it possible to carry out a “chemical separation” of turpentine components, yielding valuable individual derivatives of monoterpenes without the need to isolate individual monoterpene reagents. Specific methods have been developed for the production of α-pinene epoxide, 3-carene epoxide, limonene diepoxide, as well as for tw

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6

Setzer, William N. "A Computational Examination of the Uncatalyzed Meinwald Rearrangement of Monoterpene Epoxides." Natural Product Communications 11, no. 9 (2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100901.

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Epoxides are relatively reactive compounds and may undergo decomposition or rearrangement reactions at elevated temperatures, and gas chromatographic analysis of essential oils may cause thermal decomposition or rearrangement of epoxide components at gas chromatographic temperatures. Density functional theory (DFT) calculations were carried out using the B3LYP functional at the 6-311++G**//6-31G* level of theory on the Meinwald rearrangements of α-pinene oxide (two different mechanisms leading to trans-pinocamphone and α-campholenal), cis-limonene oxide (leading to trans-dihydrocarvone), trans

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7

El Hammoumi, M. M., L. Ait Said, A. El Bachiri, and M. Khoukhi. "Kinetic Separation of cis-and trans-Limonene Epoxide: Reaction of Diastereomeric Mixture of Limonene Oxides with Secondary Amine and Carbamate." Asian Journal of Chemistry 33, no. 11 (2021): 2667–70. http://dx.doi.org/10.14233/ajchem.2021.23379.

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A simple kinetic separation of (1:1) diastereomeric mixture of limonene oxides was used to purify cis-and trans-diastereomers of (R)-(+)-limonene oxide. The epoxide ring of trans-isomer was selectively opened by (R)-N-methyl-(α-methyl-benzyl)amine. This secondary nucleophilic amine left cis-limonene oxide largely unreacted and was obtained up to 90% yield. In a diverse way, (R)-N-(α-methylbenzyl) ethyl carbamate, selectively catalyze hydrolysis of cis-limonene oxide to 1,2-limonene diol leaving trans-limonene oxide largely unreacted. The unreacted trans-limonene oxide was recovered in up to 75

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8

Sevalho, Elison de Souza, Elissandro Fonseca Dos Banhos, Antonia Queiroz Lima De Souza, and Afonso Duarte Leão De Souza. "Evaluation of the biotransformation of R-(+)-limonene to aroma compounds by Pestalotiopsis versicolor LabMicrA-478 isolated of Euterpe oleracea Martius." DELOS: DESARROLLO LOCAL SOSTENIBLE 16, no. 42 (2023): 75–85. http://dx.doi.org/10.55905/rdelosv16.n42-007.

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Fungal biotransformation is a pertinent strategy to overcome difficulties and problems arising from chemical synthesis and direct extraction from nature. This biotechnological approach is a relevant strategy to obtain high-added-value aroma compounds under environmentally friendly conditions. In order to understand the effect of an amazon endophytic fungus on the monoterpene substrate, this research work aims to investigate the biotransformation using cells cultivated of Pestalotiopsis versicolor LabMicrA-478 with R-(+)-limonene as a sole carbon and energy source. The main products of the limo

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9

Shafiezadeh, Fatemeh, Ali Javid, Rahele Zhiani, and Sadegh Allameh. "Ho₃Fe₅O₁₂ nanoparticles immobilized on FPS for production of a biopolymer from CO₂ and limonene epoxide." RSC Advances 14, no. 50 (2024): 37431–37. http://dx.doi.org/10.1039/d4ra05285d.

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Ho3Fe5O12@FPS was synthesized for the first time using an advanced and environmentally friendly method. Subsequently, Ho3Fe5O12@FPS was used as a long-lasting and reusable adsorbent for the reaction of carbon dioxide with limonene epoxide.

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10

Ait Said, Lyazid, Mohamed Merouane El Hammoumi, Chaimaa El Haimer, Abdelhadi El Bachiri та Mostafa Khoukhi. "Synthesis of limonene β-amino alcohol from (R)-(+)-α-methylbenzylamine and (+)-limonene 1,2-epoxide". Journal of Molecular Structure 1241 (жовтень 2021): 130691. http://dx.doi.org/10.1016/j.molstruc.2021.130691.

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11

Biondi, Daniela Maria, Claudia Sanfilippo, and Angela Patti. "Stereospecific Epoxidation of Limonene Catalyzed by Peroxygenase from Oat Seeds." Antioxidants 10, no. 9 (2021): 1462. http://dx.doi.org/10.3390/antiox10091462.

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Limonene is one of the most abundant naturally occurring cyclic monoterpenes and has recently emerged as a sustainable alternative to petroleum-based solvents as well as a chemical platform for the production of value-added compounds. The biocatalytic epoxidation of both enantiomers of limonene was carried out in the presence of a peroxygenase-containing preparation from oat (Avena sativa) flour. Different reaction profiles were observed depending on the starting enantiomer of limonene, but in both cases the 1,2-monoepoxide was obtained as the main product with excellent diastereoselectivity.

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12

Hopmann, Kathrin H., B. Martin Hallberg, and Fahmi Himo. "Catalytic Mechanism of Limonene Epoxide Hydrolase, a Theoretical Study." Journal of the American Chemical Society 127, no. 41 (2005): 14339–47. http://dx.doi.org/10.1021/ja050940p.

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13

Mosquera, Carina, and Aída Luz Villa. "Cycloaddition of limonene epoxide and CO2 over Zn/SBA-15 catalysts for limonene carbonate synthesis." Journal of CO2 Utilization 83 (May 2024): 102817. http://dx.doi.org/10.1016/j.jcou.2024.102817.

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14

Ali A. Taha. "Biotransformation of Natural Compounds by Free and Immobilized Fungal Laccase using Mediator Combinations in the LMS Reaction Model." Journal of Wasit for Science and Medicine 5, no. 1 (2022): 22–31. http://dx.doi.org/10.31185/jwsm.167.

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The ternary systems constructed on the basis of isotropic properties of various compositions of a hydrocarbon and a short chain alcohol in a low water content were used to carry out the oxidation of Mastic oil, d-limonene and α-Pinene at 30 °C using fungal laccase from Trametes versicolor in the presence of different concentrations and combinations of three mediators ,2,2'-azino-bis 3-methylbenzothiazoline-6-sulfonic acid(ABTS), 1-hydroxybenzotriazole (HBT) and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) in Laccase Mediator System (LMS) model . The biotransformation was conducted with the use

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15

Raupp, Yasmin S., Pia S. Löser, Silke Behrens, and Michael A. R. Meier. "Selective Catalytic Epoxide Ring-Opening of Limonene Dioxide with Water." ACS Sustainable Chemistry & Engineering 9, no. 23 (2021): 7713–18. http://dx.doi.org/10.1021/acssuschemeng.1c01788.

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16

van der Werf, Mariët J., Hugo Jongejan, and Maurice C. R. Franssen. "Resolution of limonene 1,2-epoxide diastereomers by mercury(II) ions." Tetrahedron Letters 42, no. 32 (2001): 5521–24. http://dx.doi.org/10.1016/s0040-4039(01)01037-1.

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17

Novakovic, Miroslav, Danka Bukvicki, Vlatka Vajs, et al. "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger." Natural Product Communications 13, no. 4 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300425.

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A number of potentially useful compounds with various biological activities can be obtained from plant metabolites by microorganisms. In present research, essential oil of Calamintha glandulosa was subjected to the biotransformation process by mycromicete Aspergillus niger. GC/MS analyses of the original and biotransformed essential oil have revealed six (1–6) biotransformed compounds from one of the main component-limonene and one biotransformed product (7) originating from the less abundant component-thymol. Piperitone epoxide and piperitenone epoxide, the most abundant components of the ori

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18

Zapata, Rolando Barrera, Aída Luz Villa, and Consuelo Montes de Correa. "Measurement of activity coefficients at infinite dilution for acetonitrile, water, limonene, limonene epoxide and their binary pairs." Fluid Phase Equilibria 275, no. 1 (2009): 46–51. http://dx.doi.org/10.1016/j.fluid.2008.09.011.

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19

Wang, Ye, Lynette Lim, Lina Madilao, Ljerka Lah, Joerg Bohlmann, and Colette Breuil. "Gene Discovery for Enzymes Involved in Limonene Modification or Utilization by the Mountain Pine Beetle-Associated Pathogen Grosmannia clavigera." Applied and Environmental Microbiology 80, no. 15 (2014): 4566–76. http://dx.doi.org/10.1128/aem.00670-14.

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ABSTRACTTo successfully colonize and eventually kill pine trees,Grosmannia clavigera(Gs cryptic species), the main fungal pathogen associated with the mountain pine beetle (Dendroctonus ponderosae), has developed multiple mechanisms to overcome host tree chemical defenses, of which terpenoids are a major component. In addition to a monoterpene efflux system mediated by a recently discovered ABC transporter, Gs has genes that are highly induced by monoterpenes and that encode enzymes that modify or utilize monoterpenes [especially (+)-limonene]. We showed that pine-inhabiting Ophiostomale fungi

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20

KURATA, Takao, Takao KOSHIYAMA, and Hiroshi KAWASHIMA. "Isomerization of d-Limonene-1, 2-epoxide with Activated Carbon Catalyst." Journal of Japan Oil Chemists' Society 34, no. 12 (1985): 1032–34. http://dx.doi.org/10.5650/jos1956.34.1032.

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21

de Moraes, Josué, Antonia Almeida, Maria Brito, et al. "Anthelmintic Activity of the Natural Compound (+)-Limonene Epoxide against Schistosoma mansoni." Planta Medica 79, no. 03/04 (2013): 253–58. http://dx.doi.org/10.1055/s-0032-1328173.

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22

Ferrandi, Erica Elisa, Carlotta Marchesi, Celeste Annovazzi, Sergio Riva, Daniela Monti, and Roland Wohlgemuth. "Efficient Epoxide Hydrolase Catalyzed Resolutions of (+)- and (−)-cis/trans-Limonene Oxides." ChemCatChem 7, no. 19 (2015): 3171–78. http://dx.doi.org/10.1002/cctc.201500608.

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23

Jaime, Andrés Becerra Chalá, and Luz Villa Holguín Aída. "Separation of carvone by batch distillation from the mixture obtained from limonene oxidation." Revista Facultad de Ingeniería, Universidad de Antioquia, no. 104 (August 24, 2021): 118–28. https://doi.org/10.17533/udea.redin.20210848.

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Limonene is the main constituent of citrus oils whose oxidation produces a set of fine chemical compounds such as carvone, carveol, and limonene 1,2-epoxide. This contribution reports the results of the experimental evaluation and computational simulation of carvone separation by fractional distillation from the reaction mixture. Carvone was obtained from limonene oxidation over a perchlorinated iron phthalocyanine supported on modified silica catalyst (F eP cCl16 − NH2 − SiO2) and t-butyl hydroperoxide (TBHP) as oxidant. Both experimental and simulation results support that fracti

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24

Barbirato, Fabien, Jan C. Verdoes, Jan A. M. de Bont, and Mariët J. van der Werf. "TheRhodococcus erythropolisDCL14 limonene-1,2-epoxide hydrolase gene encodes an enzyme belonging to a novel class of epoxide hydrolases." FEBS Letters 438, no. 3 (1998): 293–96. http://dx.doi.org/10.1016/s0014-5793(98)01322-2.

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25

Hou, Q. Q., X. Sheng, J. H. Wang, Y. J. Liu, and C. B. Liu. "QM/MM study of the mechanism of enzymatic limonene 1,2-epoxide hydrolysis." Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 1824, no. 2 (2012): 263–68. http://dx.doi.org/10.1016/j.bbapap.2011.08.014.

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26

Bassanini, Ivan, Erica Elisa Ferrandi, Daniela Monti, and Sergio Riva. "Studies on the Catalytic Promiscuity of Limonene Epoxide Hydrolases in the Non‐hydrolytic Ring Opening of 1,2‐Epoxides." ChemBioChem 21, no. 13 (2020): 1868–74. http://dx.doi.org/10.1002/cbic.201900694.

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27

Sousa, Damião P. de, Genival A. S. Júnior, Luciana N. Andrade, et al. "Structure and Spasmolytic Activity Relationships of Monoterpene Analogues Found in Many Aromatic Plants." Zeitschrift für Naturforschung C 63, no. 11-12 (2008): 808–12. http://dx.doi.org/10.1515/znc-2008-11-1205.

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Abstract Rotundifolone, a monoterpene isolated from the essential oil of the leaves of Mentha x villosa, is a constituent of several essential oils and known to have spasmolytic activity. The present study aimed to investigate the correlation between structure and spasmolytic activity of rotundifolone and its analogues in ileum isolated from guinea-pig. Five of the seven tested analogues were found to have a spasmolytic effect more potent than rotundifolone itself, except for pulegone and (+)-limonene. The comparison between rotundifolone and limonene oxide showed that the absence of the keto

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28

Budić-Leto, Irena, Iva Humar, Jasenka Gajdoš Kljusurić, Goran Zdunić, and Emil Zlatić. "Free and Bound Volatile Aroma Compounds of ´Maraština´ Grapes as Influenced by Dehydration Techniques." Applied Sciences 10, no. 24 (2020): 8928. http://dx.doi.org/10.3390/app10248928.

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Dehydration or drying of grapes is one of the most important steps in the production of Croatian traditional dessert wine Prošek. The natural sun drying of grapes is the traditionally used method in Prošek production. Alternative methods, such as dehydration under controlled conditions, have been studied as safer and faster methods than the traditional sun drying but without precise knowledge of the effect on volatile compounds. The objective of this work was to study how dehydration of grapes carried out in a greenhouse and an environmentally controlled chamber impacts on the free and glycosi

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29

Elizabeth, Niño-Arrieta, Luz Villa-Holguín Aída, Alexis Alarcón-Durango Edwin, Talavera-López Alfonso, Antonio Gómez-Torres Sergio, and Ariel Fuentes-Zurita Gustavo. "Limonene epoxidation in aqueous phase over Ti/KIT-6." Revista Facultad de Ingeniería -redin-, no. 88 (September 4, 2018): 74–79. https://doi.org/10.17533/udea.redin.n88a08.

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Limonene epoxidation was carried out in the liquid phase using Ti/KIT-6 as the catalyst and tert-butyl hydroperoxide as oxidant. The best selectivity (60%) was obtained at 50 °C after 7 h of reaction, and the conversion was 23%. The main side products were carvone, carveol, 1,2-epoxylimonene diol, perillyl alcohol and p-mentha-2,8-dien-1-ol. The catalyst does not leach under reaction conditions and it can be reused after calcination at 550 ºC. The catalyst was characterized by atomic absorption, XRD, UV-vis and N2 adsorption isotherms.

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30

Bukvički, Danka, Ana Cirić, Marina Soković, et al. "Micromeria thymifolia Essential Oil Suppresses Quorum-sensing Signaling in Pseudomonas aeruginosa." Natural Product Communications 11, no. 12 (2016): 1934578X1601101. http://dx.doi.org/10.1177/1934578x1601101232.

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The chemical composition, antimicrobial and antiquorum sensing activity of the essential oil of Micromeria thymifolia (Scop.) Fritsch were investigated. Limonene, piperitone epoxide and piperitenone epoxide were found as the main constituents using a gas chromatography-mass spectrometry technique. In vitro antimicrobial activity of the oil was tested against six bacterial and seven fungal strains and high antimicrobial potential was noticed. Minimum inhibitory concentration varied from 0.031 mg/mL to 0.5 mg/mL for bacterial and 0.062 mg/mL to 0.5 mg/mL for fungal strains. The antiquorum proper

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31

Cubillos, Jairo, Edwing Grajales, Santiago Vásquez, and Consuelo Montes de Correa. "Immobilization of Jacobsen type catalysts on modified silica." Revista Facultad de Ingeniería Universidad de Antioquia, no. 57 (February 28, 2013): 38–48. http://dx.doi.org/10.17533/udea.redin.14642.

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Several immobilized Jacobsen type catalysts were covalently anchored on modified SiO2 using 3-aminopropyltriethoxysilane (3-APTES) as a reactive surface modifier. Characterization of the heterogeneous catalysts, as well as their precursors, by FTIR, DR UV-VIS, TGA and AAS confirms the successful immobilization of chiral Mn(III) salen complexes. These catalysts were examined for the diastereoselective epoxidation of R-(+)-limonene with in situ generated dimethyldioxirane (DMD) as oxidizing agent, yielding 1,2-epoxide as the main product. When compared to homogeneous catalysts, under similar exp

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32

Arand, M. "Structure of Rhodococcus erythropolis limonene-1,2-epoxide hydrolase reveals a novel active site." EMBO Journal 22, no. 11 (2003): 2583–92. http://dx.doi.org/10.1093/emboj/cdg275.

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33

Rinaldi, Silvia, Marc W. Van der Kamp, Kara E. Ranaghan, Adrian J. Mulholland, and Giorgio Colombo. "Understanding Complex Mechanisms of Enzyme Reactivity: The Case of Limonene-1,2-Epoxide Hydrolases." ACS Catalysis 8, no. 7 (2018): 5698–707. http://dx.doi.org/10.1021/acscatal.8b00863.

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34

Lind, Maria E. S., and Fahmi Himo. "Quantum Chemistry as a Tool in Asymmetric Biocatalysis: Limonene Epoxide Hydrolase Test Case." Angewandte Chemie 125, no. 17 (2013): 4661–65. http://dx.doi.org/10.1002/ange.201300594.

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35

de Almeida, Antonia Amanda Cardoso, Renan Oliveira Silva, Lucas Antonio Duarte Nicolau, et al. "Physio-pharmacological Investigations About the Anti-inflammatory and Antinociceptive Efficacy of (+)-Limonene Epoxide." Inflammation 40, no. 2 (2017): 511–22. http://dx.doi.org/10.1007/s10753-016-0496-y.

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36

Lind, Maria E. S., and Fahmi Himo. "Quantum Chemistry as a Tool in Asymmetric Biocatalysis: Limonene Epoxide Hydrolase Test Case." Angewandte Chemie International Edition 52, no. 17 (2013): 4563–67. http://dx.doi.org/10.1002/anie.201300594.

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37

Rolim, Thaís de Souza, André Luiz Franco Sampaio, José Luiz Mazzei, Davyson Lima Moreira, and Antonio Carlos Siani. "Synthesis, Bioproduction and Bioactivity of Perillic Acid—A Review." Molecules 30, no. 3 (2025): 528. https://doi.org/10.3390/molecules30030528.

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Perillic acid (PA) is a limonene derivative in which the exocyclic methyl is oxidized to a carboxyl group. Although endowed with potential anticancer activity, PA has been much less explored regarding its biological properties than analogous compounds such as perillyl alcohol, perillaldehyde, or limonene itself. PA is usually described in mixture with alcohols and ketones produced in the oxidation of monoterpenes, with relatively few existing reports focusing on the PA molecule. This study provides a comprehensive review of PA, addressing its origin, the processes of obtaining it through organ

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38

Sousa, Damião P. de, Edison V. M. Júnior, Fernando S. Oliveira, Reinaldo N. de Almeida, Xirley P. Nunes, and José M. Barbosa-Filho. "Antinociceptive Activity of Structural Analogues of Rotundifolone: Structure-Activity Relationship." Zeitschrift für Naturforschung C 62, no. 1-2 (2007): 39–42. http://dx.doi.org/10.1515/znc-2007-1-207.

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Rotundifolone, a monoterpene isolated from the essential oil of the leaves of Mentha x villosa, is a constituent of several essential oils and known to have antinociceptive activity. Our recent study demonstrated that the analogues of rotundifolone showed also a significant antinociceptive effect. In the present report, to investigate the correlation between the structure and antinociceptive activity, rotundifolone and its analogues were evaluated in the acetic acid-induced writhing test in mice. All compounds showed to be more antinociceptive than rotundifolone against the pain response induc

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39

Gomes, Diana M., Patrícia Neves, Margarida M. Antunes, António J. S. Fernandes, Martyn Pillinger, and Anabela A. Valente. "Post-Synthesis Strategies to Prepare Mesostructured and Hierarchical Silicates for Liquid Phase Catalytic Epoxidation." Catalysts 12, no. 12 (2022): 1513. http://dx.doi.org/10.3390/catal12121513.

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Olefin epoxidation is an important transformation for the chemical valorization of olefins, which may derive from renewable sources or domestic/industrial waste. Different post-synthesis strategies were employed to introduce molybdenum species into mesostructured and hierarchical micro-mesoporous catalysts of the type TUD-1 and BEA, respectively, to confer epoxidation activity for the conversion of relatively bulky olefins (e.g., biobased methyl oleate, DL-limonene) to epoxide products, using tert-butyl hydroperoxide as an oxidant. The influences of (i) the type of metal precursor, (ii) type o

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40

Malkov, Andrei V., and Pavel Kočovský. "Tetrahydrocannabinol Revisited: Synthetic Approaches Utilizing Molybdenum Catalysts." Collection of Czechoslovak Chemical Communications 66, no. 8 (2001): 1257–68. http://dx.doi.org/10.1135/cccc20011257.

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∆9-Tetrahydrocannabinol 1 and its isomers were synthesized via domino-type methodology. The first approach, leading to (±)-1, relies on the Mo(IV)-catalyzed, one-pot cascade reaction of citral (4) with olivetol (15), affording (±)-∆9-tetrahydrocannabinol as a 69 : 31 mixture of the trans- (natural) and cis-isomers in 20% yield. The alternative approach, leading to natural (-)-1, commenced with epoxidation of (+)-limonene (R)-(+)-16; opening of the resulting cis-epoxide 17 with PhSeNa, followed by elimination, afforded tertiary alcohol 21, whose acetate 22 was treated with olivetol 15 in the pr

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de Almeida, Antonia Amanda Cardoso, Rusbene Bruno Fonseca de Carvalho, Oskar Almeida Silva, Damião Pergentino de Sousa, and Rivelilson Mendes de Freitas. "Potential antioxidant and anxiolytic effects of (+)-limonene epoxide in mice after marble-burying test." Pharmacology Biochemistry and Behavior 118 (March 2014): 69–78. http://dx.doi.org/10.1016/j.pbb.2014.01.006.

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Ferrandi, Erica Elisa, Christopher Sayer, Michail N. Isupov, et al. "Discovery and characterization of thermophilic limonene-1,2-epoxide hydrolases from hot spring metagenomic libraries." FEBS Journal 282, no. 15 (2015): 2879–94. http://dx.doi.org/10.1111/febs.13328.

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Almeida, Antonia Amanda Cardoso de, José Roberto de Oliveira Ferreira, Rusbene Bruno Fonseca de Carvalho, et al. "Non-clinical toxicity of (+)-limonene epoxide and its physio-pharmacological properties on neurological disorders." Naunyn-Schmiedeberg's Archives of Pharmacology 393, no. 12 (2020): 2301–14. http://dx.doi.org/10.1007/s00210-020-01943-w.

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Agudelo, Yeison, and Rolando Barrera Zapata. "Simulation and model-validation of batch distillation processes in Aspen Batch Modeler: Limonene epoxide distillation." Ingeniería y Desarrollo 34, no. 1 (2016): 204–24. http://dx.doi.org/10.14482/inde.34.1.7954.

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Sá, Stone de, Tatiana de Sousa Fiuza, Leonardo Luiz Borges, Luiz Carlos da Cunha, Jerônimo Raimundo de Oliveira Neto, and José Realino de Paula. "Variability of Volatile Oils Composition, Tannins, and Phenols from Campomanesia adamantium (CAMBESS.) O. Berg." Fronteiras: Journal of Social, Technological and Environmental Science 11, no. 4 (2022): 206–23. http://dx.doi.org/10.21664/2238-8869.2022v11i4.p206-223.

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Campomanesia adamantium (Myrtaceae), known as "guabiroba-do-campo", is a native Cerrado shrub popularly used as anti-inflammatory, antidiarrheal, urinary tract antiseptics. The aims of this study were evaluate the seasonal variability of total phenols and tannins and chemical compounds of the volatile oils of C. adamantium leaves in a period of 12 months. The leaves and flowers were collected in Bela Vista, Goiás, Brazil. The volatile oils were obtained by hydrodistillation in a Clevenger apparatus and analyzed by GC/MS. The determination of total phenols and tannins was performed by the metho

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de Carvalho, Carla C. R., Frederik van Keulen, M. Manuela, and R. da Fonseca. "Production and Recovery of Limonene-1,2-Diol and Simultaneous Resolution of a Diastereomeric Mixture of Limonene-1,2-Epoxide with whole Cells ofRhodococcus ErythropolisDCL14." Biocatalysis and Biotransformation 18, no. 3 (2000): 223–35. http://dx.doi.org/10.3109/10242420009015246.

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Zheng, Huabao, and Manfred T. Reetz. "Manipulating the Stereoselectivity of Limonene Epoxide Hydrolase by Directed Evolution Based on Iterative Saturation Mutagenesis." Journal of the American Chemical Society 132, no. 44 (2010): 15744–51. http://dx.doi.org/10.1021/ja1067542.

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de Almeida, Antonia Amanda C., Jéssica Pereira Costa, Rusbene Bruno F. de Carvalho, Damião Pergentino de Sousa, and Rivelilson Mendes de Freitas. "Evaluation of acute toxicity of a natural compound (+)-limonene epoxide and its anxiolytic-like action." Brain Research 1448 (April 2012): 56–62. http://dx.doi.org/10.1016/j.brainres.2012.01.070.

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Paninho, Ana B., Ana N. Mustapa, Kamran T. Mahmudov, et al. "A Bio-Based Alginate Aerogel as an Ionic Liquid Support for the Efficient Synthesis of Cyclic Carbonates from CO2 and Epoxides." Catalysts 11, no. 8 (2021): 872. http://dx.doi.org/10.3390/catal11080872.

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In this work, the ionic liquid [Aliquat][Cl] was supported into alginate and silica aerogel matrices and applied as a catalyst in the cycloaddition reaction between CO2 and a bio-based epoxide (limonene oxide). The efficiency of the alginate aerogel system is much higher than that of the silica one. The method of wet impregnation was used for the impregnation of the aerogel with [Aliquat][Cl] and a zinc complex. The procedure originated a well-defined thin solvent film on the surface of support materials. Final materials were characterised by Fourier Transform Infrared Spectroscopy, N2 Adsorpt

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KURATA, Takeo, Takao KOSHIYAMA та Hiroshi KAWASHIMA. "Reaction of α-Pinene-2, 3-epoxide, d-Limonene-1, 2-epoxide, and Styrene Oxide by Molecular Sieve Catalyst Coated with Potassium Permanganate". Journal of Japan Oil Chemists' Society 36, № 3 (1987): 206–9. http://dx.doi.org/10.5650/jos1956.36.206.

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