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Journal articles on the topic 'Methyl Methoxy'

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Published: 5 June 2025

Last updated: 15 July 2025

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1

Fischer, Alfred, George N. Henderson, and Sumit RayMahasay. "ipso Nitration. XXIX. Nitration of substituted 4-methylanisoles and phenols." Canadian Journal of Chemistry 65, no. 6 (1987): 1233–40. http://dx.doi.org/10.1139/v87-209.

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Nitration of 2-chloro-4-methylanisole (1a) in acetic anhydride gives (Z)-4-chloro-3-methoxy-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate (2a), 2-chloro-4-methyl-4-nitrocyclohexa-2,5-dienone (3a), and 2-chloro-4-methyl-6-nitroanisole (4a). Similarly 2-bromo-4-methylanisole (1b) gives (Z)-4-bromo-3-methoxy-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate (2b), 2-bromo-4-methyl-4-nitrocyclohexa-2,5-dienone (3b), and 2-bromo-4-methyl-6-nitroanisole (4b), whereas 4-methyl-2-nitroanisole (1c) gives (Z)-3-methoxy-6-methyl-4,6-dinitrocyclohexa-2,4-dienyl acetate (2c), (Z)-3-methoxy-6-methyl-2,6-dinitrocyc

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2

Perangin-angin, Sabarmin. "Synthesis Of 4-Alil-6- (Hydroxymethyl) -2-Methody Phenol Compounds from Eugenol Through Mannich Reaction Followed Methylation with Methyl Iodide and Subtitution Using NaOH." Journal of Chemical Natural Resources 1, no. 1 (2019): 75–85. http://dx.doi.org/10.32734/jcnar.v1i1.838.

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Eugenol derivative compound 4-allyl-6-hydroxymethyl-2-methoxy phenol was synthesized through Mannich reaction, methylation, dan nucleophilic substitution. Mannich reaction was carried out by reacting eugenol, formaldehyde 37%, and dimethylamine 40 % in reflux condition with n-heptane solvent at temperature 98o-100oC for 10 hours produced 4-allyl-6-(dimethylamino)methyl-2-methoxy phenol with yield of 83 %. The formation of dimethylaminomethyl group supported by C-N stretching vibration at 1246,16 cm-1 and ion molecule peak at 221 in GC-MS analysis. Methylation of 4-allyl-6-(dimethylamino)methyl

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3

Stefanovic, Olgica, Ivana Radojevic, and Ljiljana Comic. "Synthetic cinnamates as potential antimicrobial agents." Chemical Industry 69, no. 1 (2015): 37–42. http://dx.doi.org/10.2298/hemind130928014s.

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This study deals with synthesis of methyl cinnamate, butyl cinnamate, and p-methoxy methyl cinnamate and testing of their in vitro antimicrobial activity. Antimicrobial activity was examined towards 29 microorganisms using microdilution method. It is shown that antimicrobial activity of methyl cinnamate and p-methoxy methyl cinnamate was better than that of butyl cinnamate. Sarcina lutea, Bacillus subtilis ATCC 6633, B. subtilis and B. subtilis IP 5832 (probiotic) were the most sensitive bacteria. It is established that p-methoxy methyl cinnamate can be a new, potential anti-Staphylococcus aur

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4

Collins, DJ, GD Fallon, and CE Skene. "Synthesis of 6-Methoxy-2-methyl-2-[(1'-methyl-2',5'-dioxocyclopentyl)methyl]-3,4-dihydro-naphthalen-1(2H)-one: Its Novel Base-Catalyzed Rearrangement to a Hydrophenanthrene Keto Acid." Australian Journal of Chemistry 47, no. 4 (1994): 623. http://dx.doi.org/10.1071/ch9940623.

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Reaction of 2-dimethylaminomethyl-6-methoxy-3,4-dihydronaphthalen-1(2H)-one (7) with 2-methylcyclopentane-1,3-dione gave 64% of 6-methoxy-2-[(1′-methyl-2′,5′-dioxocyclopentyl)-methyl]-3,4-dihydronaphthalen-1(2H)-one(6a), which with 1 equiv. of ethylene glycol in refluxing benzene in the presence of 4-toluenesulfonic acid yielded a diastereomeric mixture of the 2′,2̶-ethylenedioxy derivatives (13a,b); the major diastereomer (13a) was shown to have 1′SR,2RS stereochemistry by X-ray crystallography. With an excess of ethylene glycol and prolonged reflux the triketone (6a) underwent aldol cyclizat

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5

Feld, Hildegard, David S. Rycroft, and Josef Zapp. "Chromenes and Prenylated Benzoic Acid Derivatives from the Liverwort Pedinophyllum interruptum." Zeitschrift für Naturforschung B 59, no. 7 (2004): 825–28. http://dx.doi.org/10.1515/znb-2004-0713.

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The chemical composition of a diethyl ether extract of the Scottish liverwort Pedinophyllum interruptum has been examined. Two new prenylated benzoic acid derivatives, methyl 2,6- dihydroxy-4-methoxy-3-(3’-methyl-2’-butenyl)benzoate and methyl 2,4,6-trihydroxy-3-(3’-methyl- 2’-butenyl)benzoate, two new chromenes, methyl 5,7-dihydroxy-2,2-dimethyl-2H-chromene-6- carboxylate and methyl 7-hydroxy-5-methoxy-2,2-dimethyl-2H-chromene-8-carboxylate, and the two known chromenes methyl 8-hydroxy-2,2-dimethyl-2H-chromene-6-carboxylate and methyl 8- methoxy-2,2-dimethyl-2H-chromene-6-carboxylate were iso

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6

Pimparkar, Sandeep, and Masilamani Jeganmohan. "Palladium-catalyzed cyclization of benzamides with arynes: application to the synthesis of phenaglydon and N-methylcrinasiadine." Chem. Commun. 50, no. 81 (2014): 12116–19. http://dx.doi.org/10.1039/c4cc05252h.

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7

Collins, DJ, GLP Choo та H. Obrist. "Preparation of β-Keto Ester Acetals by Reaction of Ortho Esters With Ketene Silyl Acetals in the Presence of Titanium Tetrachloride". Australian Journal of Chemistry 43, № 3 (1990): 617. http://dx.doi.org/10.1071/ch9900617.

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Reaction of 2-ethoxy-2-methyl-1,3-dioxolan (1c) with 1-methoxy-1-trimethylsilyloxyethene (4a) in dichloromethane in the presence of titanium tetrachloride gave 62% of methyl 2-(2′-methyl-1′,3′-dioxolan-2′-yl)acetate (5a). Similarly, reaction of (1c) with l-methoxy-1-trimethylsilyloxyprop-1-ene (4b) afforded 73% of methyl 2-(2′-methyl-1′,3′-dioxolan-2′-yl) propanoate (5b).

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8

SAVITRI, D. SRIVASTAVA, K. SRIVASTAVA SANTOSH, and SHRIVASTAVA SANDHYA. "New Coumarins from Murraya paniculata." Journal of Indian Chemical Society Vol. 73, Dec 1996 (1996): 666–68. https://doi.org/10.5281/zenodo.5928242.

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Department of Chemistry, Dr. H. S. Gour University, Sagar-470 003 <em>Manuscript received 15 December 1994, revised 18 April 1995, accepted 15 June 1995</em> An extract of the stem bark of Mrraya paniculata has yielded three new coumarins 8-(butenyl-3'-methyl)-7-<em>O</em>-β-D-galactopyranoside, 7 -methoxy-8-(2' -isovaleryloxy-3-butenyl-3-methyl)coumarin and marmesin-4'-<em>ο</em>-α-L-arabinopyranoside alongwith 3,5,6,7 ,8,3' ,4' ,5' -octamethoxyflavone, 7-methoxy-8-(3-butenyl-3-methyl-2-oxo)coumarin and 7-methoxy-8-(butenyl-3'-methyl)coumarin.

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9

Tsantrizos, Youla S., Kelvin K. Ogilvie, and Alan K. Watson. "Phytotoxic metabolites of Phomopsisconvolvulus, a host-specific pathogen of field bindweed." Canadian Journal of Chemistry 70, no. 8 (1992): 2276–84. http://dx.doi.org/10.1139/v92-286.

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Phomopsisconvolvulus is a host-specific pathogen which causes leaf spots and anthracnose lesions in the important perennial weed Convolvulusarvensis (field bindweed). Investigation of the metabolites produced by the fungus led to the isolation of the known fungal metabolites ergosterol (1) and ergosterol peroxide (2), in addition to four novel phytotoxins: the phthalides convolvulanic acid A (3), convolvulanic acid B (4), convolvulol (5), and the α-pyrone convolvulopyrone (6). The latter compounds were assigned the structures of 4-carboxy-3-hydroxy-7-methoxy-6-methyl-1(3H)-isobenzofuranone (3)

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10

Kopecký, Jaroslav, David Šaman, and Ladislav Novotný. "Methylation of substituted 1,4-benzoquinones." Collection of Czechoslovak Chemical Communications 52, no. 1 (1987): 228–32. http://dx.doi.org/10.1135/cccc19870228.

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Methylation of 1,4-benzoquinones I and Ia with diazomethane afforded methyl 15-(6-methoxy-3-methyl-1,4-benzoquinon-2-yl)pentadecanoate (IIa) and methyl 15-(3-methoxy-2,5-dioxobicyclo[4.1.0]hept-3-en-1-yl)pentadecanoate (IIIa), methylation of 1,4-benzoquinone IVa led to methyl 15-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)pentadecanoate (Va) and methyl 15-(3,4-dimethoxy-6-methyl-2,5-dioxobicyclo[4.1.0]hept-3-en-1-yl)pentadecanoate (VIa). Structure of the products was established by spectral methods.

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11

Capozzi, Maria Annunziata M., Giancarlo Terraneo та Cosimo Cardellicchio. "Structural insights into methyl- or methoxy-substituted 1-(α-aminobenzyl)-2-naphthol structures: the role of C—H...π interactions". Acta Crystallographica Section C Structural Chemistry 75, № 2 (2019): 189–95. http://dx.doi.org/10.1107/s2053229619001050.

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Aminobenzylnaphthols are a class of compounds containing a large aromatic molecular surface which makes them suitable candidates to study the role of C—H...π interactions. We have investigated the effect of methyl or methoxy substituents on the assembling of aromatic units by preparing and determining the crystal structures of (S,S)-1-{(4-methylphenyl)[(1-phenylethyl)amino]methyl}naphthalen-2-ol, C26H25NO, and (S,S)-1-{(4-methoxyphenyl)[(1-phenylethyl)amino]methyl}naphthalen-2-ol, C26H25NO2. The methyl group influenced the overall crystal packing even if the H atoms of the methyl group did not

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12

Šmidrkal, Jan, Jiří Holubek, and Jan Trojánek. "The synthesis of 2,3,7,8-bismethylenedioxy-11-methoxy-5-methylbenzo[c]phenanthridinium chloride." Collection of Czechoslovak Chemical Communications 50, no. 4 (1985): 984–90. http://dx.doi.org/10.1135/cccc19850984.

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Acylation of 3-methoxy-6,7-methylenedioxy-l-methylaminonaphthalene (VI) with 6-bromo-2,3-methylenedioxybenzoyl chloride gave N-(3-methoxy-6,7-methylenedioxynaphth-l-yl)-N-methylamide of 6-bromo-2,3-methylenedioxybenzoic acid (IIIa) the irradiation of which with ultraviolet light in acetonitrile and triethylamine gave N-methyl-2,3-methylenedioxy-l-(3'-methoxy-6',7'-methylenedioxynaphth-l-yl)benzamide (Xa) in low yield in addition to 2,3,7,8-bismethylenedioxy-11-methoxy-5-methyl-6-oxobenzo(c)phenanthridine (Va). The last compound was converted to dihydro derivative VIa from which 2,3,7,8-bismeth

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13

Liepa, AJ, AJ Liepa, JS Wilkie, et al. "Preparation of Bicyclic Herbicide Precursors by Intramolecular Stork-Danheiser Kinetic Alkylation Reactions of Methyl 1-(Haloalkyl)-3-methoxy-5-oxocyclohex-3-ene-1-carboxylate Derivatives." Australian Journal of Chemistry 45, no. 4 (1992): 759. http://dx.doi.org/10.1071/ch9920759.

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Reductive alkylation of methyl 3,5-dimethoxybenzoate with the dibromoalkane and the bromochloroalkane derivatives (4a-d) and (4e-g) afforded, after acid hydrolysis, the corresponding methyl 1-( haloalkyl )-3-methoxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (6a-g). Reaction of (6a-c) with lithium diisopropylamide afforded methyl 3-methoxy-5-oxobicyclo[4.2.0]oct-3-ene- 1-carboxylate (2a), methyl 5-methoxy-7-oxo-1,2,3,4,7,7a-hexahydro-3aH-indene-3a-carboxylate (2b) and methyl 6-methoxy-8-oxo-1,3,4,5,8,8a-hexahydronaphtha1ene-4a(2 H)- carboxylate (2c), respectively. Compounds (2b) and (2c) we

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14

Khalid, Rozida Mohd, Md Lip Jabit, Faridah Abas, Johnson Stanslas, Khozirah Shaari, and Nordin H. Lajis. "Cytotoxic Xanthones from the Leaves of Garcinia Urophylla." Natural Product Communications 2, no. 3 (2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200309.

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Two new xanthones, 7-hydroxydesoxymorellin (1) and isocaledonixanthone D (2), and four known ones, gaudichaudione H, 1,7-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, 1,5-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, and 1,3,7-trihydroxy-2-(3-methyl-2-butenyl)xanthone, as well as lupeol were isolated from the leaves of Garcinia urophylla (Guttiferae). Their structures were determined using a combination of 1D (1H NMR, 13C NMR, DEPT) and 2D (COSY, gHSQC, gHMBC) NMR spectroscopic techniques. Among the isolates, 7-hydroxydesoxymorellin (1), gaudichaudione H, 1,5-dihydroxy-3-methoxy-2-

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15

Gottschling, Stephen E., Michael C. Jennings, and Kim M. Baines. "The addition of alkynes to a tetrasilyldisilene Evidence for a biradical intermediate." Canadian Journal of Chemistry 83, no. 9 (2005): 1568–76. http://dx.doi.org/10.1139/v05-169.

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The addition of two newly developed mechanistic probes, (trans,trans-2-methoxy-3-phenylcyclopropyl)ethyne (1) and (trans,trans-2-methoxy-1-methyl-3-phenylcyclopropyl)ethyne (2), to tetrakis(tert-butyldimethylsilyl)disilene (3) has been investigated. The addition of 1 to 3 gave 1-[2-(cis-2-methoxy-3-phenylcyclopropylidene)vinyl]-1,1,2,2-tetrakis(tert-butyldimethylsilyl)disilane (5) as the major product; whereas addition of alkyne 2 to the disilene gave three stereoisomers of 1,1,2,2-tetrakis(tert-butyldimethylsilyl)-6-methoxy-5-methyl-7-phenyl-1,2-disilacyclohepta-3,4-diene (79) and 1,1,2,2- t

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16

Halim, Shimaa Abdel, and Magdy A. Ibrahim. "Synthesis, spectral analysis, quantum studies, NLO, and thermodynamic properties of the novel 5-(6-hydroxy-4-methoxy-1-benzofuran-5-ylcarbonyl)-6-amino-3-methyl-1H-pyrazolo[3,4-b] pyridine (HMBPP)." RSC Advances 12, no. 21 (2022): 13135–53. http://dx.doi.org/10.1039/d2ra01469f.

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Ring opening followed by ring closure reactions of 4-methoxy-5-oxo-5H-furo[3,2-g] chromene-6-carbonitrile with 5-amino-3-methyl-1H-pyrazole gave the novel 5-(6-hydroxy-4-methoxy-1-benzofuran-5-ylcarbonyl)-6-amino-3-methyl-1H-pyrazolo[3,4-b] pyridine.

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17

Elix, JA, DA Venables, and L. Brako. "New Chlorine-Containing Depsidones From the Lichen Phyllopsora corallina var. ochroxantha." Australian Journal of Chemistry 43, no. 11 (1990): 1953. http://dx.doi.org/10.1071/ch9901953.

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The depsidones phyllopsorin (2-chloro-4,6-diformyl-3-hydroxy-8-methoxy- 1,9-dimethyl-11H-dibenzo[ b,e ][1,4]dioxepin-11-one (3), chlorophyllopsorin (2,7-dichloro-4,6-diformyl-3-hydroxy-8-methoxy-1,9- dimethyl-11H-dibenzo[ b,e ][1,4]dioxepin-11-one) (4), methyl 2,7- dichloro-psoromate (methyl 2,7-dichloro-4-formyl-3-hydroxy-8-methoxy- 1,9-dimethyl-11-oxo-11H-dibenzo[ b,e ][1,4]dioxepin-6-carboxylate) (5) and methyl 2,7-dichloronorpsoromate (methyl 2,7-dichloro-4-formyl-3,8- dihydroxy-1,9-dimethyl-11-oxo-11H-dibenzo[ b,e ][1,4]dioxepin-6-carb- oxylate ) (6) have been isolated from the lichen Phy

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18

Elix, JA, KL Gaul, PW James, and OW Purvis. "Three New Lichen Depsidones." Australian Journal of Chemistry 40, no. 2 (1987): 417. http://dx.doi.org/10.1071/ch9870417.

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The depsidones α- acetylconstictic acid (5-acetoxymethyl-1,4-dihydroxy-10-methoxy-8-methyl-3,7-dioxo-1,3-dihydro-7 H- isobenzofuro [4,5- b][l,4] benzodioxepin-ll-carbaldehyde ) (6), substictic acid (1,4-dihydroxy-10-methoxy-8-methy1-3,7-dioxo- 1,3-dihydro-7 H- isobenzofuro [4,5-b][1,4]benzodioxepin-11-carbaldehyde) (7) and conphysodalic acid (9-acetoxymethyl-3,8-dihydroxy-4-hydroxymethyl-1,6-dimethyl-11-oxo-11 H- dibenzo [ b,e ][l,4]dioxepin-7-carboxylic acid) (12) have been identified in lichens and characterized.

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19

Banville, Jacques, Philippe Lapointe, Bernard Belleau та Marcel Menard. "Nuclear analogs of β-lactam antibiotics. Synthesis of 6,6-disubstituted acylaminopenems". Canadian Journal of Chemistry 66, № 6 (1988): 1390–99. http://dx.doi.org/10.1139/v88-225.

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The preparation of 6α-methyl-2-methyl-6β-phenoxyacetamidopenem-3-carboxylate, 6α-methoxy-2-methyl-6β-phenoxyacetamidopenem-3-carboxylate, and 6α-methoxy-2-methyl-6β-phenylmalonylamidopenem-3-carboxylate from penicillin V and 6-aminopenicillanic acid is described. These penems have been isolated and characterized as their sodium or potassium salt. The chemical stability of the above compounds was determined as their half-life in aqueous buffer. In this way, it was found that the 6α-methyl analog was more stable than the parent 6-monosubstituted acylaminopenem while the remaining analogs were of

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20

Prince, P., F. R. Fronczek, and R. D. Gandour. "Methyl 7-methoxy-2-naphthoate." Acta Crystallographica Section C Crystal Structure Communications 47, no. 10 (1991): 2226–27. http://dx.doi.org/10.1107/s010827019100361x.

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21

Popovski, Emil, Kristina Mladenovska, and Ana Poceva Panovska. "Methyl 4-[(Benzoylamino)methoxy]benzoate." Molbank 2011, no. 1 (2010): M712. http://dx.doi.org/10.3390/m712.

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22

Inagaki, Junko, Airi Nakano, Omer Faruk Hatipoglu, et al. "Potential of a Novel Chemical Compound Targeting Matrix Metalloprotease-13 for Early Osteoarthritis: An In Vitro Study." International Journal of Molecular Sciences 23, no. 5 (2022): 2681. http://dx.doi.org/10.3390/ijms23052681.

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Osteoarthritis is a progressive disease characterized by cartilage destruction in the joints. Matrix metalloproteinases (MMPs) and a disintegrin and metalloproteinase with thrombospondin motifs (ADAMTSs) play key roles in osteoarthritis progression. In this study, we screened a chemical compound library to identify new drug candidates that target MMP and ADAMTS using a cytokine-stimulated OUMS-27 chondrosarcoma cells. By screening PCR-based mRNA expression, we selected 2-(8-methoxy-2-methyl-4-oxoquinolin-1(4H)-yl)-N-(3-methoxyphenyl) acetamide as a potential candidate. We found that 2-(8-metho

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23

Silva, Ana L. R., Gastón P. León, and Maria D. M. C. Ribeiro da Silva. "Energetic Effects in Methyl- and Methoxy-Substituted Indanones: A Synergistic Experimental and Computational Study." Applied Sciences 13, no. 18 (2023): 10262. http://dx.doi.org/10.3390/app131810262.

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This experimental and computational study on the energetic properties of 2-methyl-, 3-methyl-, 4-methoxy- and 5-methoxy-indanones has been carried out using mostly calorimetric techniques and a suitable computational approach. The combustion and sublimation/vaporization enthalpies were determined via combustion calorimetry and Calvet microcalorimetry, respectively, allowing for the calculation of the standard molar enthalpies of formation in the gaseous phase. The enthalpy of sublimation of 5-methoxy-indanone was also derived via Knudsen effusion. Additionally, the gas-phase standard molar ent

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24

Oramahi, Hasan Ashari, Tirsa Maurisa, Nurhaida Nurhaida, Herlina Darwati, and Slamet Rifanjani. "Optimization and Characterization of Liquid Smoke Produced by Terminalia catappa Wood Pyrolysis and its In Vitro Antifungal Activity." Science and Technology Indonesia 9, no. 1 (2024): 207–14. http://dx.doi.org/10.26554/sti.2024.9.1.207-214.

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This research utilized response surface methodology (RSM) to explore how the yield of liquid smoke obtained from ketapang wood (Terminalia catappa) is influenced by the size of wood particles and the temperature of pyrolysis. Gas chromatography-mass spectrometry (GC-MS) was used to characterize the liquid smoke. To assess liquid smoke’s antifungal effects, a petri dish bioassay was conducted using 1.0-4.0% (v/v) concentrations against Schizophyllum commune. RSM was applied to optimize vinegar from T. catappa by varying the wood particle size and the pyrolysis temperature. The optimal yield, 24

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25

Melese Damtew, Asfaw. "Chemical composition of olive stems essential oil from Ethiopia." Journal of Plant Science and Phytopathology 6, no. 2 (2022): 057–61. http://dx.doi.org/10.29328/journal.jpsp.1001075.

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In this article, the chemical compounds, antimicrobial and antioxidant activity of the volatile oil from leaves of Olea Europaea L. cultivar from Ethiopia has been studied. The essential oil was provided with a dry distillation apparatus and analyzed by GC-MS/FID. This analysis leads to the detection of 128 compounds representing 89.4% of the total oil. The major constituents were methyl ester hexadecanoic acid (4.10%), 2,4-dimethoxyphenolAa (4.05%), 2-methoxy-phenol (3.25%), 3,5-dimethoxy-4-hydroxytoluene (3.20%), 2-methoxy-5-methyl phenol (3.19%), 1,2,3-trimethoxy-5-methyl benzene (2.93%), 2

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26

Sokol, Wojciech, and John Warkentin. "Synthesis and thermolysis rate constants of diastereomeric oxadiazoline sources of acetoxy(methoxy)carbene — Reaction of acetoxy(methoxy)carbene with isocyanates." Canadian Journal of Chemistry 84, no. 7 (2006): 927–33. http://dx.doi.org/10.1139/v06-109.

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Oxidation of the methoxycarbonylhydrazone of p-methoxyacetophenone affords both the cis- and trans-2-acetoxy-2-methoxy-5-(p-methoxyphenyl)-5-methyl-Δ3-1,3,4-oxadiazolines (also known as corresponding 2,5-dihydro-1,3,4-oxadiazoles) as well as methyl 1-acetoxy-1-(p-methoxyphenylethyl)diazenecarboxylate. The three isomers were separated and identified by spectroscopic means. Methyl 1-acetoxy-1-(p-methoxyphenylethyl)diazenecarboxylate is the major product from oxidation in dichloromethane. Oxidation in acetic acid did not afford the oxadiazolines but gave the diazenecarboxylate and, in addition, 1

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27

Purwono, Bambang, Chairil Anwar, and Ahmad Hanapi. "Syntheses of Azo-Imine Derivatives from Vanillin as an Acid Base Indicator." Indonesian Journal of Chemistry 13, no. 1 (2013): 1–6. http://dx.doi.org/10.22146/ijc.21318.

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Preparations of azo, imine and azo-imine derivatives from vanillin as an indicator of acid-base titration have been carried out. The azo derivative of 4-hydroxy-3-methoxy-5-(phenylazo)benzaldehyde 2 was produced by diazotitation reaction of vanillin in 37.04% yield. The azo product was then refluxed with aniline in ethanol to yield azo-imine derivatives, 2-methoxy-6-(phenylazo)-4-((phenylimino)methyl)phenol 1 in 82.21% yield. The imine derivative, 2-methoxy-4-((phenylimino)methyl)-phenol 3 was obtained by refluxing of vanillin and aniline mixture in ethanol solvent and produced 82.17% yield. T

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28

Frick Neto, Francisco, Frida Maciel Pagliosa, and Maria Elizabeth do Canto Vinadé. "Neolignanas de uma Embuia do Rio Grande do Sul, Brasil." Ciência e Natura 10, no. 10 (1988): 89. http://dx.doi.org/10.5902/2179460x25486.

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The n-hexane of the bark of Ocotea porosa fractioned by chromatographic tecniques, afforded there neolignanas of benzofuranoid, type: porosin, (2R,3a,3aR,5R)-3a-allyl-3-methyl-5-methoxy- 2- (3' ,4', dimethoxyphenyl )-6-oxo-2 ,3 ,3a ,4,5,6 hexahydrobenzofuran; II, rel (2R,3S,3aR,5R,6S,7 a S)-3a-allyl-6-7a-dihydroxi-3-methyl-5-methoxy-2- (3' ,4', dimethoxyphenyl )-2-3-3a ,4,5,6,7 ,7a-octahidrobenzofuran, and Il, reI (2R,3S,3aR,5R,6R,7 a S)-3a-allyl-6,7a-dihidroxy-3.;methyl-5-methoxy-2-(3' ,4', dimethoxyphenyl )-2,3,3a,5,6,7,7a-octahydrobenzofuran. The structures of isolated neolignanas were iden

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29

Elix, JA, JA Elix, DA Venables, DA Venables, M. Wedin, and M. Wedin. "New Dibenzofurans and Depsides From the Lichen Bunodophoron patagonicum." Australian Journal of Chemistry 47, no. 7 (1994): 1335. http://dx.doi.org/10.1071/ch9941335.

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The lichen Bunodophoron patagonicum has been shown to contain five new dibenzo -furans: ascomatic acid (3,7-dimethoxy-1,9-dimethyldibenzofuran-2-carboxylic acid) (2) and the corresponding methyl ester (3); 7-O-methylnorascomatic acid (3-hydroxy-7-methoxy-1,9-dimethyldibenzofuran-2-carboxylic acid) (4) and the corresponding methyl ester (5); and norascomatic acid (3,7-dihydroxy-1,9-dimethyldibenzofuran-2-carboxylic acid) (6). The lichen also contains two new depsides : patagonic acid [2-hydroxy-4-(2′-hydroxy-4′-methoxy-6′-methyl-benzoyloxy)-6-(2′-oxononyl)benzoic acid] (10) and isopatagonic aci

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30

Amorim, Magali S., Alessandra F. Serain, Marcos José Salvador, and Maria Élida A. Stefanello. "Chemical Constituents of Sinningia hatschbachii." Natural Product Communications 12, no. 11 (2017): 1934578X1701201. http://dx.doi.org/10.1177/1934578x1701201128.

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A new naphthoquinone, 6-hydroxy-7-methoxy-2- O-methylduniol (1), was isolated from the tubers of Sinningia hatschbachii Chautems (Gesneriaceae), together with 10 known compounds: 7-hydroxy-α-dunnione, 7-hydroxy-6-methoxy-α-dunnione, 2,4,4’,6-tetramethoxydihydrochalcone, 4’-hydroxy-2,4,6-trimethoxydihydrochalcone, 4’,2-dihydroxy-4,6-dimethoxydihydrochalcone, methyl 1-hydroxy-4-methoxy-2-naphthoate, methyl 1,4-dimethoxy-2-naphthoate, methyl 4-hydroxybenzoate, calceolarioside B, and conandroside. All compounds were identified by spectroscopic techniques, and comparison with literature. Extracts i

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31

Pashko, Mykhailo O., and Yurii L. Yagupolskii. "Introduction of the Difluoro(methoxy)methyl Group into the Aromatic Ring and the Study of Its Electronic Properties." Journal of Organic and Pharmaceutical Chemistry 22, no. 4 (2024): 10–16. https://doi.org/10.24959/ophcj.24.321167.

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A simple and efficient method for synthesizing aromatic compounds with a difluoro(methoxy)methyl fragment (CF2OCH3) by the fluorodesulfurization of thionoesters has been developed. Systematic screening identified SnCl4/DAST as the optimal reagent combination, providing excellent selectivity and high yields of target products. A series of aromatic difluoro(methoxy)methyl compounds was synthesized under these conditions. Further studies of the electronic properties of the difluoro(methoxy)methyl group using 19F NMR allowed us to determine its Hammett constants for inductive (σI) and resonance (σ

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32

Carvalho, CF, and MV Sargent. "Naturally-Occurring Dibenzofurans. VIII. The Synthesis of Isodidymic Acid." Australian Journal of Chemistry 39, no. 11 (1986): 1765. http://dx.doi.org/10.1071/ch9861765.

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The synthesis of the lichen dibenzofuran isodidymic acid (2)(3-hydroxy- 7-methoxy-9-pentyl-1-propyldibenzofuran-2-carboxylic acid) by intramolecular Ullmann coupling of methyl 3-iodo-4-(2′-iodo-5′-methoxy- 3′-pentylphenoxy)-6-methoxy-2-propylbenzoate (22), and further transformations, is described.

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33

Griesbaum, Karl, Gilbert Kiesel, Henri Mertens, Petra Krieger-Beck, and Henning Henke. "Acid-catalyzed reactions of six- and seven-membered cyclic hemiperacetals and peracetals and of related bicyclic ozonides." Canadian Journal of Chemistry 72, no. 11 (1994): 2198–204. http://dx.doi.org/10.1139/v94-280.

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HCl-catalyzed reactions of the hemiperacetals 3-methoxy-3-methyl-7-hydroxy-1,2-dioxepane (1a) and 3-methoxy-3-methyl-6-hydroxy-1,2-dioxane (1b) and of the related ozonides 1-methyl-6,7,8-trioxabicyclo[3.2.1]octane (2a) and 1-methyl-5,6,7-trioxabicyclo[2.2.1]heptane (2b) gave peroxidic monocyclic (11—13), bicyclic (14), and (or) tricyclic (15) products. By contrast, reactions of the peracetals corresponding to 1a and 1b, viz., 3-methyl-3,7-dimethoxy-1,2-dioxepane (13a) and 3-methyl-3,6-dimethoxy-1,2-dioxane (13b) gave only non-peroxidic products. Reactions of the persubstituted peracetals 3,6-d

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34

la Parra, Mario Gonzalez-de, Carlos Ramos-Mundo, Manuel Jimenez-Estrada, et al. "A Germination Bioassay as a Toxicological Screening System for Studying the Effects of Potential Prodrugs of Naproxen." Alternatives to Laboratory Animals 26, no. 5 (1998): 635–47. http://dx.doi.org/10.1177/026119299802600509.

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A germination bioassay with radish (Raphanus sativus L.) seeds was developed as a toxicological screening system for assessing the effects of new potential prodrugs of naproxen, as an alternative to animals and animal cell toxicity screens. Both enantiomers of naproxen (6-methoxy-α-methyl-2-naphthaleneacetic acid) and naproxol (6-methoxy-β-2-naphthaleneethanol), and their racemic mixtures, inhibited the radicle growth of R. sativus at a concentration of 1mM, while only ( R)-(+)-naproxol and racemic naproxol inhibited the hypocotyl growth of R. sativus at the same concentration. Four novel comb

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35

Nitai, Chand Sinha. "Excellent chemoselective synthesis of α,β-unsaturated ester moiety in introducing side chain in coumarin". Journal of Indian Chemical Society Vol. 87, Mar 2010 (2010): 379–84. https://doi.org/10.5281/zenodo.5784016.

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Department of Chemistry, Sarat Centenary College, Dhaniakhali-712 302, Hooghly, West Bengal, India <em>Manuscript received 28 January 2009, revised 16 July 2009, accepted 7 August 2009</em> Organomagnesium reagents failed to divulge any degree of chemoselectivity towards on 7-methoxy-4-methyl-8-coumarinyl methyl ketone 1 and 7-methoxy-4-methyl-8-formyleoumarin 2 but the carbanion triethyl phosphonoester shows excellent chemoselectivity together with high stereoselectivity during the synthesis of β-coumarinylacrylates 13, 14 .and β-coumarinylcrotonates 15 and 16.

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36

Blaser, D., J. Gunzinger, H. Stoeckli-Evans та R. Tabacchi. "Structure of 2-methoxy methyl β-orcinol carboxylate (methyl 4-hydroxy-2-methoxy-3,6-dimethylbenzoate)". Acta Crystallographica Section C Crystal Structure Communications 48, № 6 (1992): 1126–27. http://dx.doi.org/10.1107/s010827019101274x.

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37

BEENA, RAWAT, and S. RAMA H. "Kinetics of Hydrolysis of Methyl Hydroxy and Methyl Methoxy Benzoates using Aquo-organic Solvents." Journal of Indian Chemical Society Vol. 71, Feb 1994 (1994): 103–5. https://doi.org/10.5281/zenodo.5893992.

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<em>Department of Chemistry, Faculty of Science, M.S. Umversity of Baroda, Baroda-390 002 Manuscript received 14 October 1992, revised 29 March 1993, accepted 13 April 1993</em> Kinetics of Hydrolysis of Methyl Hydroxy and Methyl Methoxy Benzoates using Aquo-organic Solvents.

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38

Lin, Myat T., Alexander A. Shubin, Rimma I. Samoilova, et al. "Exploring by Pulsed EPR the Electronic Structure of Ubisemiquinone Bound at the QH Site of Cytochrome bo3 from Escherichia coli with in Vivo13C-Labeled Methyl and Methoxy Substituents." Journal of Biological Chemistry 286, no. 12 (2011): 10105–14. http://dx.doi.org/10.1074/jbc.m110.206821.

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The cytochrome bo3 ubiquinol oxidase from Escherichia coli resides in the bacterial cytoplasmic membrane and catalyzes the two-electron oxidation of ubiquinol-8 and four-electron reduction of O2 to water. The one-electron reduced semiquinone forms transiently during the reaction, and the enzyme has been demonstrated to stabilize the semiquinone. The semiquinone is also formed in the D75E mutant, where the mutation has little influence on the catalytic activity, and in the D75H mutant, which is virtually inactive. In this work, wild-type cytochrome bo3 as well as the D75E and D75H mutant protei

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39

Supriya, Singh, and Singh Janhavi. "A bianthraquinone and anthraquinone from Cassia javanica heart wood." Journal of Indian Chemical Society Vol. 85, Nov 2008 (2008): 1159–62. https://doi.org/10.5281/zenodo.5820589.

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Department of Chemistry, Udai Pratap Autonomous College, Varanasi-221 002, Uttar Pradesh, India <em>E-mail</em> : jnh_singh@yahoo.co.in, supriya singh@rediffmail.com <em>Manuscript received 9 April 2008, accepted 7 August 2008</em> Phytochemical study of <em>Cassia javanica</em> stem bark has resulted in the isolation of one new bianthraquinone, 4,4' -bis(1,5-dihydroxy-7-hydroxymethyl-2-methyl-3-methoxy) anthraquinone, along with known compounds anthraquinone, 1,3,5,8-tetrahydroxy-6-methoxy-2-methyl anthraquinone and I ,2-dihydro-I ,3-dihydroxy-6,8-dimethoxy-2-methyl anthraquinone.

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40

Rocha, Michelle Rodrigues e., Carolina Passos Da Cunha, Raimundo Braz Filho, and Ivo J. Curcino Vieira. "A Novel Alkaloid Isolated from Spiranthera Atlantica (Rutaceae)." Natural Product Communications 11, no. 3 (2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100318.

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A novel alkaloid 3-hydroxy-4-(2-hydroxyethyl)-4′-methoxy-7′ H-quinolino[2,1- b]quinazolin-7′-one, named atlanticol (1), was isolated from Spiranthera atlantica (Rutaceae), along with five known compounds: lupeol (3), γ-fagarine (4), skimmianine (5), 7-methoxy-1-methyl-2-phenyl-4-quinolone (6) and 8-methoxy-1-methyl-2-phenyl-4-quinolone (7). Compound 6 was isolated from the Spiranthera genus for the first time. These compounds were characterized based on their spectral data, mainly through one and two-dimensional NMR and mass spectra, but also involving comparison with literature data.

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41

Chen, Jialuo, Lili Duan, Kunming Liu, and Jin-Biao Liu. "A Convenient Synthesis towards 2-Bromo-2-(methoxy(phenyl)methyl)malononitrile and 2-Iodo-2-(methoxy(phenyl)methyl)malononitrile." Molbank 2022, no. 2 (2022): M1373. http://dx.doi.org/10.3390/m1373.

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This short note elaborates a concise protocol for the synthesis of two novel vicinal haloethers bearing a malonontrile group, 2-bromo-2-(methoxy(phenyl)methyl)malononitrile (1) and 2-iodo-2-(methoxy(phenyl)methyl)malononitrile (2). The structures of the synthesized compounds were confirmed by 1H, 13C-NMR spectroscopy. The final products indicate that methanol not only acts as solvent but also participates in and dominates the reaction result.

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42

Hasegawa, Toshio, Haruna Seimiya, Takashi Fujihara, Noriko Fujiwara, and Hideo Yamada. "Aroma Profile of Star Anise and the Structure-odor Relationship of Anethole." Natural Product Communications 9, no. 2 (2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900230.

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Star anise is an important fragrance material that has a characteristic anise-like odor. Although the main component of star anise is ( E)-anethole, which accounts for over 90% of the constituents, the odor of ( E)-anethole is different from that of the material itself. Here, we examined the aroma profile of star anise. GC-MS analysis of star anise extracts showed that it contains many compounds with structures similar to ( E)-anethole. Our results indicate that ( E)-anethole is the key compound in the odor of star anise, but structurally similar compounds play an important role in creating it

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43

Lippold, Tim, Jörg M. Neudörfl, and Axel Griesbeck. "New Acridone- and (Thio)Xanthone-Derived 1,1-Donor–Acceptor-Substituted Alkenes: pH-Dependent Fluorescence and Unusual Photooxygenation Properties." Molecules 26, no. 11 (2021): 3305. http://dx.doi.org/10.3390/molecules26113305.

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A synthetic route to new heterocyclic 1,1-donor–acceptor-substituted alkenes starting with N-methyl-acridone, xanthone, and thioxanthone was investigated, leading to the acridone- and xanthone-derived products methyl 2-methoxy-2-(10-methylacridin-9 (10H)-ylidene)acetate (7) and methyl 2-methoxy-2-(9H-xanthen-9-ylidene)acetate (10) in low yields with the de-methoxylated product methyl 2-(10-methylacridin-9 (10H)-ylidene)acetate (8) and the reduced compound methyl 2-methoxy-2-(9H-xanthen-9-yl)acetate (11) as the major products from N-methyl acridone and xanthone. From thioxanthone, only the rear

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44

Li, Ruipeng, Zhenren Liu, Liang Chen, Jing Pan, and Weicheng Zhou. "Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine." Beilstein Journal of Organic Chemistry 14 (June 11, 2018): 1421–27. http://dx.doi.org/10.3762/bjoc.14.119.

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In order to prepare asymmetrically (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (3a), a key intermediate of dezocine, 17 cinchona alkaloid-derived catalysts were prepared and screened for the enantioselective alkylation of 1-methyl-7-methoxy-2-tetralone with 1,5-dibromopentane, and the best catalyst (C7) was identified. In addition, optimizations of the alkylation were carried out so that the process became practical and effective.

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45

Bourke, David G., and David J. Collins. "The Conversion of Steroidal Ring B Lactones into Ortho Esters: Preparation of 7,7-Dimethoxy-6-oxaestra-1,3,5(10)-triene Derivatives." Australian Journal of Chemistry 51, no. 11 (1998): 1003. http://dx.doi.org/10.1071/c97179.

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17β-t-Butyldimethylsilyloxy-3-methoxy-6-oxaestra-1,3,5(10)-trien-7-one (1), prepared in three steps from 17b-hydroxy-3-methoxy-6-oxaestra-1,3,5(10),8-tetraen-7-one (5a), was converted via the corresponding phenolic acid into 1β-t-butyldimethylsilyloxy-5β-(2′-t-butyldimethylsilyloxy-4′-methoxyphenyl)-N,7aβ-dimethyl-N-phenyl-2,3,3aα,4,5,6,7,7a-octahydro-1H-indene-4α-carboxamide (17c). Subjection of (17c) to a reaction sequence with methyl trifluoromethanesulfonate, sodium methoxide/methanol, and then dry methanol/acetic acid gave a low yield (12%) of the ortho ester 3,7,7,17β-tetramethoxy- 6-oxa

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46

Maddi, N. V. D. Harikiran, Srinivas Garaga, Ambati V. Raghava Reddy, Paul Douglas Sanasi, and Raghubabu Korupolu. "Synthesis and characterization of related substances of Azilsartan Kamedoxomil." Current Issues in Pharmacy and Medical Sciences 30, no. 1 (2017): 31–35. http://dx.doi.org/10.1515/cipms-2017-0007.

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Abstract Azilsartan Kamedoxomil is an AT1-subtype angiotensin II receptor blocker (ARB). During the laboratory synthesis of Azilsartan Kamedoxomil, four related substances of Azilsartan Kamedoxomil were observed and identified. These were 2-Ethoxy-3-[[4-[2- [4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-5-oxo-1,2,4-oxadiazol-3-yl]phenyl]phenyl] methyl] benzimidazole-4-carboxylic acid (azilsartan N-medoxomil, 9), (5-methyl-2-oxo- 1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-[4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-5- oxo-1,2,4-oxadiazol-3-yl]phenyl]phenyl] methyl] benzimidazole-4-carboxylate (azils

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47

Aye, Mya Mu, Hnin Thanda Aung, Zaw Min Thu, et al. "Constituents of the Rhizomes of Sansevieria cylindrica." Natural Product Communications 13, no. 9 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300908.

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A new sappanin-type 3-benzyl chroman-4-one (homoisoflavanone), (3 S)-3-(4'-methoxybenzyl)-3,5-dihydroxy-7-methoxy-6-methyl chroman-4-one (1), together with known congeners (3 S)-3-(4'-methoxybenzyl)-3,5-dihydroxy-7-methoxy chroman-4-one (2), (3 S)-3-(4'-hydroxybenzyl)-3,5-dihydroxy-7-methoxy-6-methyl chroman-4-one (3), (3 S)-3-(4'-hydroxybenzyl)-3,5-dihydroxy-7-methoxy chroman-4-one (4), 3-(3’,4'-methyledioxybenzyl)-7-hydroxy-8-methoxy chroman-4-one (5), and stigmasterol and ergosterol peroxide have been isolated from the rhizomes of Sansevieria cylindrica, collected in Myanmar. Moreover, the

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48

Kolmakov, Kirill A., and A. Jerry Kresge. "Synthesis of possible o-thioquinone methide precursors." Canadian Journal of Chemistry 86, no. 2 (2008): 119–23. http://dx.doi.org/10.1139/v07-142.

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Investigating the synthetic accessibility of o-thioquinone methide precursors containing electron donating groups, we prepared four methyl- and methoxy-substituted 2H-benzo[b]thiete derivatives by means of flash vacuum pyrolysis of the corresponding benzooxathiinone species. Methyl- and methoxy-substituted substrates proved to be compatible with the pyrolysis protocol. The pyrolysis can be performed at considerably lower temperatures and with higher yields than in previously reported syntheses of nonsubstituted 2H-benzo[b]thiete. Under proper conditions the reaction products can be isolated in

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49

Domínguez-Villegas, Valeri, Vanessa Domínguez-Villegas, María Luisa García, Ana Calpena, Beatriz Clares-Naveros, and María Luisa Garduño-Ramírez. "Anti-inflammatory, Antioxidant and Cytotoxicity Activities of Methanolic Extract and Prenylated Flavanones Isolated from Leaves of Eysehardtia platycarpa." Natural Product Communications 8, no. 2 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800211.

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From the methanolic extract of Eysenhardtia platycarpa (leaves), were isolated the prenylated flavanones: 5,7-dihydroxy-6-methyl-8-prenylflavanone (1), 5,7-dihydroxy-6-methyl-8-prenyl-4′-methoxy-flavanone (2), 5,7-dihydroxy-6-prenylflavanone (3), 5-dihydroxy-7-methoxy-6-prenylflavanone (4), 5,7-dihydroxy-8-prenyl-4′-methoxy-flavanone (5). Methanolic extract of E. platycarpa (leaves) and flavanones (5), (2) and (3) showed anti-inflammatory activity according to tested quantities. In addition, flavanone (5) revealed the best percentage reduction of free radical DPPH. Finally, after cytotoxic act

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50

Gianini, Aline S., Maria Rita Marques, Nádia Cristina P. Carvalho, and Neli K. Honda. "Activities of 2,4-Dihydroxy-6-n-pentylbenzoic Acid Derivatives." Zeitschrift für Naturforschung C 63, no. 1-2 (2008): 29–34. http://dx.doi.org/10.1515/znc-2008-1-206.

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Esters of 2-hydroxy-4-methoxy-6-n-pentylbenzoic acid (2−8) (methyl, ethyl, butyl, pentyl, isopropyl, sec-butyl and benzyl), olivetol (9), methyl, ethyl, butyl perlatolates (10−12), 2,4- dihydroxy-6-n-pentylbenzoic acid (15), and methyl and ethyl esters of (15) were prepared through structural modifications of perlatolic acid (1) with the aim to detect new antifungal and antibacterial substances and also to evaluate the toxicity by the brine shrimp lethality assay against Artemia salina. The antifungal assays were carried out against the fungus Cladosporium sphaerospermum through the bioautogra

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