Trans-cinnamyl Alcohol Research Articles

Crystal Structure of Inclusion Compounds Based on Porous Trans-Thienothiophendicarboxylate of Europium(III) with Norbornadiene and Trans-Cinnamyl Alcohol

Crystal Structure of Inclusion Compounds Based on Porous Trans-Thienothiophendicarboxylate of Europium(III) with Norbornadiene and Trans-Cinnamyl Alcohol

Pandatonkinosides A and B: two new phenolic glycosides from the roots of Pandanus tonkinensis and their nitric oxide production inhibitory activities

Two new phenolic glycosides, 4-(3-hydroxypropyl)-2,6-dimethoxyphenol β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (1), trans-cinnamyl alcohol 9-O-(6′-O-β-D-apiofuranosyl)-β-D-glucopyranoside (2), together with nine known phenolic glycosides (3-11) were isolated from the roots of Pandanus tonkinensis. Their structures were determined by extensive analysis of HRESIMS and NMR spectral data, as well as by comparison of their spectral data (including CD spectra) with those reported in the literature. Compounds 1-4 and 6-11 inhibited NO production in LPS-activated RAW264.7 cells with IC50 values in the range from 0.80 ± 0.06 µM to 43.38 ± 3.92 µM, whereas compound 5 was inactive. The NO production inhibitory activities of compounds 1, 4, 8, and 10 with IC50 values of 10.16 ± 1.05, 0.80 ± 0.06, 1.10 ± 0.13, and 2.79 ± 0.21 µM, respectively, are as potent as that of the positive control of N G-monomethyl-L-arginine acetate (L-NMMA) with an IC50 value of 9.80 ± 0.78 µM.

Attraction effectiveness of funnel traps in tones of blue and different heights together with a light source against apricot pests [Tropinota hirta (Poda, 1761) (Coleoptera: Cetoniidae)

This study was conducted in order to determine the effects of different traps, attractants and food traps parameters against to Trophinota hirta (Poda, 1761) (Coleoptera: Ciconiidae) in the apricot orchards in Baskil district of Elazig province in 2018. For this purpose; By hanging funnel traps containing attractive capsules including Trans-cinnamyl alcohol + Trans-anethol + Methoxyphenethyl alcohol mixtures in apricot orchards, the effect of mass trapping of the pest at different height and combination of light sources was investigated. Another parameter used in the study was the number of adults captured in funnel traps, in which wine-bearing traps were placed at a ratio of 1/1. As a result of the research; It has been determined that the most successful experiment in mass trapping experiments against T. hirta in apricot orchards was the funnel-trap combination with Trans-cinnamyl alcohol+Trans-anethol+Methoxyphenethyl alcohol mixed with illuminated 3 and 1 m high. In this trap parameter; It was determined that statistically more T. hirta individuals were captured compared to other trap parameters. Statistically; In the examination of the average values; the highest number of individuals was captured with an average of 70.35 at 1 m high with 3 lights, the second at 1 m with 60.45 lights, and the third and the most at 1 m with 59.05 without light. It was determined that it was also

Oxidation of alcohols by TBHP in the presence of sub-stoichiometric amounts of MnO2

Abstract Commercially available activated MnO2 has been investigated as a catalyst for the oxidation of alcohols (phenylethanol, 4-methyl- and 4-methoxybenzyl alcohol, trans-cinnamyl alcohol, cyclohexanol, menthol, perillyl alcohol and myrtenol) by TBHP/decane or TBHP/water in MeCN. The activity is highest for benzylic and allylic alcohols. Secondary alcohols yield ketones with good selectivities, while the aldehydes generated from primary alcohols are further oxidized. The process competes with the TBHP catalyzed decomposition. It thus requires the use of excess TBHP and high catalyst loadings to achieve high conversions. However, the low cost of the reagents makes this new protocol convenient for the oxidation of reactive secondary alcohols. The study also suggests that MnO2 should be proscribed as a reagent to quench excess TBHP in oxidative processes when the synthetic target contains easily oxidizable alcohol functions and when carrying our detailed kinetic monitoring of oxidation processes.

Fumigant and contact toxicity of 22 wooden essential oils and their major components against Drosophila suzukii (Diptera: Drosophilidae)

Fumigant and contact toxicities of 22 plant essential oils (EOs) from 14 families and their constituents against the adult spotted wing drosophila (SWD), Drosophila suzukii were examined. Analyses by GC, GC-MS, and NMR led to the identification of 2, 16, 13, 4, 6, 9, and 10 compounds from Gaultheria fragrantissima, Croton anistatum, Illicium verum, Liquidamabar orientalis, Cinnamomum cassia, Rosa damasena, and Santalum album, respectively. In fumigant toxicity test, G. fragrantissima, C. anistatum, and I. verum exhibited 100, 93.8, and 95.8, and 100, 70.0, and 80.0% mortalities against the adult male and female SWD at 4.41mg/L air, respectively. LC50 values (mg/L air) of G. fragrantissima, C. anistatum, and I. verum were 3.46, 3.67, and 3.16 against male, and 3.48, 4.31, and 4.01 against female SWD. LC50 values (mg/L air) of methyl salicylate and trans-anethole were 2.17 and 1.75 against male and 2.65 and 3.00 against female SWD, respectively. In contact toxicity tests, L. orientalis, C. cassia, R. damasena, and S. album showed insecticidal activity with LD50 values (μg/fly) of 2.64, 1.84, 3.40 and 2.18 against male SWD and of 3.74, 2.24, 8.91 and 5.61 against female SWD, respectively. 2-Phehy-1-ethanol, 3-phenyl-1-propanol, trans-cinnamaldehyde, trans-cinnamyl alcohol, and α-santalol also exhibited insecticidal activity with LD50 values of 9.79, 5.52, 2.39, 3.02 and 2.37 against male SWD and of 11.77, 7.04, 2.94, 3.32, and 3.99 against female SWD, respectively. trans-Cinnamaldehyde exhibited the highest AChE inhibition but its inhibition is likely due to a non-specific chemical inhibition. Our results indicate that wooden EOs and their components can be used as fumigants or spray-type control agents against SWD

An alternate synthesis of appetite suppressant (R)-2-benzylmorpholine employing Sharpless asymmetric epoxidation strategy

An alternate synthesis of (R)-2-benzylmorpholine 1, an appetite suppressant agent has been accomplished starting from readily available trans-cinnamyl alcohol employing Sharpless asymmetric epoxidation strategy as a key step, with an overall yield of 24%.

Cinnamyl Alcohol, Benzyl Alcohol, and Flavonoid Glycosides from Sanchezia nobilis

Further phytochemical investigation of Sanchezia nobilis Hook.f. (Acanthaceae) has afforded nine compounds, the cinnamyl alcohol glycosides: 9-O-β-glucopyranosyl trans-cinnamyl alcohol (1), 9-O-β-xylopyranosyl-(1→6)-O-β-glucopyranosyl-(1→6)-O-β-glucopyranosyl trans-cinnamyl alcohol (2), and syringin (3); the neolignan glucoside: 4-O-β-glucopyranosyl dehydrodiconiferyl alcohol (4); the benzyl alcohol glycosides: 7-O-β-glucopyranosyl benzyl alcohol (5) and 7-O-β-apiofuranosyl-(1→6)-O-β-glucopyranosyl benzyl alcohol (6), together with the flavonoid glycosides: apigenin-7-O-β-glucopyranoside (7), apigenin-7-Ogentiobioside (8), and apigenin-7-O-β-glucuronopyranoside (9). Compound 2 is isolated here for the first time from a natural source, compounds 1, 3, 4, and 8 have been isolated for the first time from the family Acanthaceae, while compounds 5–7 and 9 are reported for the first time from the genus Sanchezia.

Fumigant toxicity of Oriental sweetgum (Liquidambar orientalis) and valerian (Valeriana wallichii) essential oils and their components, including their acetylcholinesterase inhibitory activity, against Japanese termites (Reticulitermes speratus).

This study investigated the fumigant toxicity of oriental sweetgum (Liquidambar orientalis) and valerian (Valeriana wallichii) essential oils and their components against the Japanese termite (Reticulitermes speratus). The fumigant toxicity of oriental sweetgum and valerian oil differed significantly according to exposure time. Oriental sweetgum showed toxicity at short exposure times (2 days), and the toxicity of valerian oil was high 7 days after treatment. The main constituents of oriental sweetgum and valerian oils were tested individually for their fumigant toxicity against Japanese termites. Among the test compounds, benzyl alcohol, acetophenone, 1-phenyl-1-ethanol, hydrocinnamyl alcohol, trans-cinnamyl aldehyde, trans-cinnamyl alcohol, cis-asarone, styrene, and cis-ocimene showed toxicity against Japanese termites 7 days after treatment. Hydrocinnamyl alcohol and trans-cinnamyl alcohol were found to be the major contributors to the fumigant antitermitic toxicity of oriental sweetgum oil. The acetylcholinesterase (AChE) inhibition activity of two oils and their constituents was tested to determine their mode of action. Only cis-ocimene showed strong AChE inhibition activity with an IC50 value of 0.131 mg/mL. Further studies are warranted to determine the potential of these essential oils and their constituents as fumigants for termite control.

Mavi Renkli Huni Tuzaklarda Kullanılan Farklı Cezbedicilerin Kiraz Çiçeklerinde Beslenen Tropinota hirta (Poda) (Coleoptera: Scarabaeidae) Erginlerinin Yakalanması Üzerine Etkisi

This study was conducted to capture Tropinota hirta (Poda) (Coleoptera: Scarabaeidae) adults, which cause economic damage on flowers of cherry trees, using mixtures of different floral attractants in 2013 and 2014 in Isparta province, Turkey. In field trials, the commercial trap, namely VARb3k, was also included to compare the efficacy of this trap with other traps used in this study. The mixtures of floral attractants were tested Trans-Cinnamyl alcohol+Anethol (CA), TransCinnamyl alcohol+Anethol+Geraniol (CAG), Trans-Cinnamyl alcohol+Anethol+ Eugenol (CAE), Trans-Cinnamyl alcohol +Anethol+4-Methoxyphenethyl alcohol (CAM). The study was carried out on cherry orchards as ten replications. Based on the results of this study, the highest number of insects (260) was captured by plastic cone-type traps containing CA and CAG attractants in 2013, while the lowest number of insects (24) was captured in commercial cone-type traps loaded with CA attractant. In contrast, the highest number of insects (1126) was caught in plastic cone traps with CAM attractant at 1.5 m height above the ground in 2014

The synthesis of (R,S)-reboxetine employing a tandem cyclic sulfate rearrangement—opening process

(R,S)-Reboxetine was synthesized in nine steps and with 43% overall yield starting from trans-cinnamyl alcohol. Following silylation and AD steps, the two hydroxyl groups at C-1 and C-2 were simultaneously activated to the cyclic sulfate. A series of tandem reactions initiated by desilylation transposed the activation to C-3, then to C-1, where nucleophilic displacements took place in succession. During this process, the configuration at C-2 was inverted while that at C-1 was retained through a double inversion.

The use of environmental metrics to evaluate green chemistry improvements to the synthesis of (S,S)-reboxetine succinate

The Pfizer Green Chemistry metrics program is described and exemplified with a case history involving the synthesis of (S,S)-reboxetine succinate. The initial route used a classical resolution approach and generated high levels of waste. This route was replaced by an enantiospecific synthesis which used Sharpless epoxidation chemistry, an enzymatic process to selectively protect a primary alcohol and a new efficient method of chiral morpholine construction as key steps. These improvements reduced the levels of waste produced by the synthesis by more than 90%. Detailed metrics starting from a common starting material (trans-cinnamyl alcohol) for all routes of synthesis are presented.

Stereoselective synthesis of (S)-dapoxetine starting from trans-cinnamyl alcohol

A novel stereoselective synthesis of (S)-dapoxetine starting from commercially available transcinnamyl alcohol is described. Sharpless Asymmetric Epoxidation (SAE) is utilized as the key step in this synthetic strategy.

Nematicidal Activity of Plant Essential Oils and Components from Coriander (Coriandrum sativum), Oriental Sweetgum (Liquidambar orientalis), and Valerian (Valeriana wallichii) Essential Oils against Pine Wood Nematode (Bursaphelenchus xylophilus)

Commercial essential oils from 28 plant species were tested for their nematicidal activities against the pine wood nematode, Bursaphelenchus xylophilus. Good nematicidal activity against B. xylophilus was achieved with essential oils of coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii). Analysis by gas chromatography-mass spectrometry led to the identification of 26, 11, and 4 major compounds from coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii) oils, respectively. Compounds from each plant essential oil were tested individually for their nematicidal activities against the pine wood nematode. Among the compounds, benzaldehyde, trans-cinnamyl alcohol, cis-asarone, octanal, nonanal, decanal, trans-2-decenal, undecanal, dodecanal, decanol, and trans-2-decen-1-ol showed strong nematicidal activity. The essential oils described herein merit further study as potential nematicides against the pine wood nematode.

Green procedure for the preparation of scented alcohols from carbonyl compounds

Several alcohols--interesting as cosmetic fragrances whose main preparative route on an industrial scale or in the research laboratory is the reduction of the corresponding carbonyl compound--were obtained by a solvent-free methodology in a green chemistry context. The process involves the simple mixing of the carbonyl compound with sodium borohydride dispersed in wet alumina in the solid state; the conversions of the carbonyl compounds were obtained in good yields within short reaction times, without energy consumption. The following carbinols were studied: octan-3-ol, 2-cineolylols (endo-exo mixture), alpha-ionol, 4-methylbenzyl alcohol, 1-phenylethanol, trans-cinnamyl alcohol, p-anisyl alcohol, 4-phenyl-3-buten-2-ol.

Cyclohexanones Derived from Dihydrocarvone as Precursor of Chiral Dioxiranes for Epoxidation of Olefins.

ChemInformVolume 36, Issue 13 Preparative Organic Chemistry Cyclohexanones Derived from Dihydrocarvone as Precursor of Chiral Dioxiranes for Epoxidation of Olefins. Arlette Solladie-Cavallo, Arlette Solladie-Cavallo Lab. Stereochim. Organomet., CNRS, Univ. Louis Pasteur, F-67008 Strasbourg, Fr.Search for more papers by this authorLoic Jierry, Loic Jierry Lab. Stereochim. Organomet., CNRS, Univ. Louis Pasteur, F-67008 Strasbourg, Fr.Search for more papers by this authorPaolo Lupattelli, Paolo Lupattelli Lab. Stereochim. Organomet., CNRS, Univ. Louis Pasteur, F-67008 Strasbourg, Fr.Search for more papers by this authorPaolo Bovicelli, Paolo Bovicelli Lab. Stereochim. Organomet., CNRS, Univ. Louis Pasteur, F-67008 Strasbourg, Fr.Search for more papers by this authorRoberto Antonioletti, Roberto Antonioletti Lab. Stereochim. Organomet., CNRS, Univ. Louis Pasteur, F-67008 Strasbourg, Fr.Search for more papers by this author Arlette Solladie-Cavallo, Arlette Solladie-Cavallo Lab. Stereochim. Organomet., CNRS, Univ. Louis Pasteur, F-67008 Strasbourg, Fr.Search for more papers by this authorLoic Jierry, Loic Jierry Lab. Stereochim. Organomet., CNRS, Univ. Louis Pasteur, F-67008 Strasbourg, Fr.Search for more papers by this authorPaolo Lupattelli, Paolo Lupattelli Lab. Stereochim. Organomet., CNRS, Univ. Louis Pasteur, F-67008 Strasbourg, Fr.Search for more papers by this authorPaolo Bovicelli, Paolo Bovicelli Lab. Stereochim. Organomet., CNRS, Univ. Louis Pasteur, F-67008 Strasbourg, Fr.Search for more papers by this authorRoberto Antonioletti, Roberto Antonioletti Lab. Stereochim. Organomet., CNRS, Univ. Louis Pasteur, F-67008 Strasbourg, Fr.Search for more papers by this author First published: 02 March 2005 https://doi.org/10.1002/chin.200513033Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume36, Issue13March 29, 2005 RelatedInformation

Cyclohexanones derived from dihydrocarvone as precursor of chiral dioxiranes for epoxidation of olefins

New ketones having an axial α-fluorine atom and substituents other than fluorine at C8, derived from commercially available (+)-dihydrocarvone, have been prepared and used for epoxidations of trans stilbene, trans methyl p-methoxy cinnamate, trans cinnamyl alcohol and derivatives. It was found that replacement of the H at C8 by a substituent containing an oxygen atom increases the enantioselectivities in all cases. It was also shown that protic substituents (hydroxyl groups) provide a decrease in enantioselectivity in the case of cinnamates probably because of H-bonding dioxirane-substrate. It is noted that the absolute configurations of the various epoxides obtained hold with the usual model involving a spiro-approach on the dioxirane conformation C1 having the α-fluorine axial. Moreover, sub-stoichiometric amounts (0.3 equiv) of ketone can be used in all cases as these ketones do not undergo Baeyer-Villiger oxidation and are recovered.

Rosavin as a product of glycosylation by Rhodiola rosea (roseroot) cell cultures

The paper discusses glycosylation of trans-cinnamyl alcohol to obtain the biologically active compound rosavin and possibly other cinnamoylglycosides. Cell suspension cultures of Rhodiola rosea were established from callus of leaf origin cultured under light in a modified Murashige and Skoog medium. Under these conditions, no rosavin was formed. However, when trans-cinnamyl alcohol (2.5 mM; in MeOH) was added to the medium, after 72 h incubation cells transformed over 90% of the cinnamyl alcohol into a number of unidentified products. The structure of potential rosavin accumulated in intracellular spaces was elucidated as [3-phenyl-2-propenyl-O-(6'-O-α-L-arabinopyranosyl) -β-D-glucopyranoside] by means of chemical and spectral analysis using TLC, HPLC, UV, LSIMS and NMR methods. Rosavin yields of 0.03–1.01% dry weight were obtained. The actual amount depended on the cell strain cultured and the biotransformation period.

Migration of aryl groups from silicon to carbon in α, β-epoxysilanes. A new model for hypervalent silicon study

The reaction of (2 R,3 R)-3-(triphenylsilyl)glycidol ( 1) with n-Bu 4NF·3H 2O in THF, followed by treatment of the product with p-nitrobenzoyl chloride yields (2 S)-glycidol p-nitrobenzoate ( 4) and trans-cinnamyl p-nitrobenzoate ( 6) in a ratio of 1:1.5. The reaction of ( R)Si-( 2R,3R)- or ( R)Si-( 2S,3 S)-3-[(methyl)(phenyl)(1-naphthyl)silyl]-glycidols, 7 or 8 respectively, with n-Bu 4NF·3H 2O affords mixtures of the respective glycidol, trans-cinnamyl alcohol and 3-(1-naphthyl)allyl alcohol. No significant difference in the product distribution in reaction of these two diasteromers was observed.

Stereoselective Synthesis of a Key Precursor of Halicholactone and Neohalicholactone.

An efficient synthesis of a known precursor of halicholactone (1a) and neohalicholactone (1b) has been developed using the strategically functionalized key cyclopropane intermediate 2, which in turn has been synthesized via stereoselective cyclopropanation of trans-cinnamyl alcohol in the presence of the chiral dioxaborolane ligand 4. Elaboration of the above bifunctional cyclopropane to the target molecule was achieved in a relatively short reaction sequence and in good overall yield, representing a formal synthesis of the title compounds.

Cleavage of sulfonamides with phenyldimethylsilyllithium

The toluene-p-sulfonamides of secondary amines and indoles are cleaved by treatment with phenyldimethylsilyllithium to give the secondary amines. Aziridine toluene-p-sulfonamides, however, are opened by attack of the silyllithium reagent on carbon to give β-silylethyl sulfonamides. The aziridine toluene-p-sulfonamide 22 derived from norbornene is different in giving the 2-[dimethyl(phenyl)silyl]-4-methylbenzenesulfonamide 23 of exo-norbornylamine. The aziridine toluene-p-sulfonamides 26, 28 and 30, derived from methyl cinnamate, methyl acrylate and cinnamyl acetate, are also anomalous, giving 3-[N-(p-tolylsulfonyl)amino]-3-phenylpropionic acid 27, {3-[N-(p-tolylsulfonyl)amino]propionyl}dimethyl(phenyl)silane 29 and trans-cinnamyl alcohol 31, respectively, each derived by opening of the aziridine ring followed by loss of the silyl group.