- Efficient demethylation of aromatic methyl ethers with HCl in water
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A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.
- Bomon, Jeroen,Bal, Mathias,Achar, Tapas Kumar,Sergeyev, Sergey,Wu, Xian,Wambacq, Ben,Lemière, Filip,Sels, Bert F.,Maes, Bert U. W.
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supporting information
p. 1995 - 2009
(2021/03/26)
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- Antibacterial mode of action of the daucus carota essential oil active compounds against campylobacter jejuni and efflux-mediated drug resistance in gram-negative bacteria
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Today, an alarming rise of bacterial gastroenteritis in humans resulting from consuming Campylobacter-tainted foods is being observed. One of the solutions for mitigating this issue may be the antibacterial activity of essential oils. In the present research, we propose to study the antibacterial activity against Campylobacter and other Gram-negative bacteria of Daucus carota essential oil and its active molecules. In addition, a few chemically synthesized molecules such as (E)-methylisoeugenol, Elemicin, and eugenol were also studied. The results showed that the essential oil itself and its most active component, (E)-methylisoeugenol, exhibited bactericidal effects. Similar effects were detected using purified and chemically synthesized molecules. Also, it was observed that the Daucus carota essential oil and its active molecules affected intracellular potassium and intracellular ATP contents in Campylobacter cells. Inhibition of the membrane bound FO F1-ATPase was also observed. Eventually, for the first time, the efflux mechanism of active molecules of Daucus carota essential oil was also identified in gamma proteobacteria and its specific antibacterial activity against Campylobacter jejuni was associated with the lack of this efflux mechanism in this species.
- Berti, Liliane,Bolla, Jean Michel,Brunel, Jean Michel,Dedieu, Luc,Lorenzi, Vanina,Muselli, Alain
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- Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates
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The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.
- Hui, Zi,Jiang, Songwei,Qi, Xiang,Ye, Xiang-Yang,Xie, Tian
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supporting information
(2020/05/18)
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- Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment
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Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.
- Cheng, Xi-Chuang,Guo, Xin-Ran,Liu, Hua-Min,Liu, Yu-Lan,Qin, Zhao,Wang, Xue-De
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p. 4348 - 4358
(2020/09/22)
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- Modular synthesis of (E)-cinnamaldehydes directly from allylarenes via a metal-free DDQ-mediated oxidative process
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An efficient synthesis of (E)-cinnamaldehydes by a metal-free DDQ-mediated oxidative transformation of allylarenes was developed. The protocol provides a practical method to prepare diverse (E)-cinnamaldehydes with broad functional group tolerance in good to excellent yields, including easy access to natural products randainal and geranyloxy sinapyl aldehyde from plant extracts. Finally, the mechanism of a single-electron transfer process was proposed.
- Xu, Ting-Ting,Jiang, Tao-Shan,Han, Xiao-Lan,Xu, Yuan-Hong,Qiao, Jin-Ping
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p. 5350 - 5358
(2018/08/03)
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- Lignin depolymerization to monophenolic compounds in a flow-through system
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A reductive lignocellulose fractionation in a flow-through system in which pulping and transfer hydrogenolysis steps were separated in time and space has been developed. Without the hydrogenolysis step or addition of trapping agents to the pulping, it is possible to obtain partially depolymerized lignin (21 wt% monophenolic compounds) that is prone to further processing. By applying a transfer hydrogenolysis step 37 wt% yield of lignin derived monophenolic compounds was obtained. Pulp generated in the process was enzymatically hydrolyzed to glucose in 87 wt% yield without prior purification.
- Kumaniaev, Ivan,Subbotina, Elena,S?vmarker, Jonas,Larhed, Mats,Galkin, Maxim V.,Samec, Joseph S.M.
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supporting information
p. 5767 - 5771
(2017/12/26)
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- Concise access toward chiral hydroxy phenylpropanoids: formal synthesis of virolongin B; kigelin; kurasoin A; 4-hydroxysattabacin, and actinopolymorphol A
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A simple, two step strategy consisting of Sharpless asymmetric dihydroxylation followed by regioselective breaking of [Formula presented] bond is utilized to target key chiral intermediates of natural products virolongin B, kigelin, kurasoin A, 4-hydroxy-sattabacin, and actinopolymorphol A. Derivatives of enantiopure hydroxy phenyl propanoids and α-hydroxy Weinreb amides are synthesized. The reductive cleavage of [Formula presented] bond in a regioselective manner is obtained using Pd/C in methanol.
- Patil, Sagar N.,Tilve, Santosh G.
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supporting information
p. 3371 - 3375
(2016/07/11)
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- NOVEL 1-PHENYLMONO- OR -POLYHYDROXYPROPANE COMPOUNDS, COMPOSITIONS AND COSMETIC USES THEREOF
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The present invention relates to novel compounds of formula (I) to compositions comprising same, and also to the use thereof for preventing and/or cosmetically treating the signs of aging of the skin.
- -
-
Page/Page column 29; 31; 32
(2017/04/04)
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- Asymmetric glycolate alkylation approach towards total synthesis of 8-O.6′ and 8-O.4′-neolignans
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The glycolate alkylation approach for the total synthesis of 8-O.6′ and 8-O.4′-neolignans has been optimized affording the natural products with high overall yields and excellent stereoselectivity. The developed approach can be further utilized towards the synthesis of many natural and unnatural neolignans. This is the first approach for the synthesis of neolignans using asymmetric glycolate alkylation approach.
- Gangar, Mukesh,Chouhan, Mangilal,Goyal, Sandeep,Harikrishnan,Chandran,Ittuveetil, Avinash,Nair, Vipin A.
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supporting information
p. 5931 - 5934
(2016/12/09)
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- Three new polyphenolic acids from the leaves of Eucalyptus citriodora with antivirus activity
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Six polyphenolic acids (1-6), including the three new compounds citriodolic acids A, B, and C (1-3), were isolated from the leaves of Eucalyptus citriodora. Their structures were elucidated by spectroscopic methods including one dimensional (1D)- and 2D-NMR, high-resolution electrospray ionization (HR-ESI)-MS, and circular dichroism (CD). The potential antivirus activity against respiratory syncytial virus (RSV) of all the isolated compounds was evaluated.
- Lin, San-Qing,Zhou, Zhong-Liu,Yin, Wen-Qing
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p. 1641 - 1646
(2016/11/09)
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- Allyl/propenyl phenol synthases from the creosote bush and engineering production of specialty/commodity chemicals, eugenol/isoeugenol, in Escherichia coli
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The creosote bush (Larrea tridentata) harbors members of the monolignol acyltransferase, allylphenol synthase, and propenylphenol synthase gene families, whose products together are able to catalyze distinct regiospecific conversions of various monolignols into their corresponding allyl- and propenyl-phenols, respectively. In this study, co-expression of a monolignol acyltransferase with either substrate versatile allylphenol or propenylphenol synthases in Escherichia coli established that various monolignol substrates were efficiently converted into their corresponding allyl/propenyl phenols, as well as providing proof of concept for efficacious conversion in a bacterial platform. This capability thus potentially provides an alternate source to these important plant phytochemicals, whether for flavor/fragrance and fine chemicals, or ultimately as commodities, e.g.; for renewable energy or other intermediate chemical purposes. Previous reports had indicated that specific and highly conserved amino acid residues 84 (Phe or Val) and 87 (Ile or Tyr) of two highly homologous allyl/propenyl phenol synthases (circa 96% identity) from a Clarkia species mainly dictate their distinct regiospecific catalyzed conversions to afford either allyl- or propenyl-phenols, respectively. However, several other allyl/propenyl phenol synthase homologs isolated by us have established that the two corresponding amino acid 84 and 87 residues are not, in fact, conserved.
- Kim, Sung-Jin,Vassao, Daniel G.,Moinuddin, Syed G.A.,Bedgar, Diana L.,Davin, Laurence B.,Lewis, Norman G.
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- A concise asymmetric synthesis of (-)-virolin, (-)-surinamensin,(-)- raphidecursinol B and (-)-polysphorin
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Highly concise and general asymmetric syntheses of biologically important natural (-)-8,4-oxyneolignans [(-)-virolin, (-)-surinamensin, (-)-raphidecursinol B, and (-)-polysphorin] are reported. The key step in the synthesis is the Evan's syn-aldol reaction to achieve the adducts with the desired stereochemistry. The four biologically important plant metabolites were synthesized using two common intermediates. Georg Thieme Verlag Stuttgart · New York.
- Nagaraju, Manda,Chandra, Rajesh,Gawali, Bhimrao B.
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supporting information; experimental part
p. 1485 - 1488
(2012/07/28)
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- Asymmetric synthesis of the natural erythro-(1R,2S)-8-O-4′-neolignan myrislignan
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An efficient and practical asymmetric synthesis of erythro-(1R,2S)-8-O- 4′-neolignan myrislignan was achieved by using vanillin and pyrogallic acid as the starting materials. Two key steps are involved: preparation of an enantiopure threo alcohol of predictable stereochemistry by dihydroxylation with AD-mix-β, and inversion of the absolute configuration from the threo to the erythro isomer using a Mitsunobu reaction. The route illustrates a new methodology for the synthesis of erythro-8-O-4′-neolignan. Graphical abstract: [Figure not available: see fulltext.]
- Xia,Wang, Wei
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scheme or table
p. 93 - 96
(2011/10/01)
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- Synthesis of (1R,2S)-2-(4'-allyl-2',6'-dimethoxyphenoxyl)-1-(4''-hydroxy- 3'', 5''-dimethoxyphenyl)propan-1-ol
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The asymmetric synthesis of the natural neolignan (1R,2S)-2-(4'-allyl-2', 6'-dimethoxyphenoxyl)-1-(4''-hydroxy-3'',5''- dimethoxyphenyl)propan-1-ol based on an asymmetric dihydroxylation as a key reaction using AD-mix-β to preparing the chiral threo-(1R,2R)-glycerol. The reaction, threo-alcohols were inverted by an SN2 reaction into erythro-(1R,2S)-isomers.
- Ding, Junwei,Qi, Rongwei,Zhou, Haitang,Jiao, Bin,Xia, Yamu
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scheme or table
p. 519 - 521
(2011/11/29)
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- A new shortcut synthesis route for (±)raphidecursinol
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The new shortcut synthesis route of (±)raphidecursinol 1, a racemic 8,4′-oxyneolignan compound, can be more easily achieved by the synthesis route, starting from readily available inexpensive 3,4,5-trimethoxy-benzaldehyde and 1,2,3-trihydroxybenzene. All structures were confirmed by 1H NMR, IR and MS.
- Yuan, Hua Jie,Cheng, Yao Yao,Qian, Shan,Xiao, Xiang,Wu, Yong
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scheme or table
p. 127 - 130
(2010/11/18)
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- Comparing the stereoselective biooxidation of cyclobutanones by recombinant strains expressing bacterial baeyer - Villiger monooxygenases
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Microbial Baeyer - Villiger oxidation of representative prochiral ketones with a cyclobutanone structural motif was investigated using a collection of eight monooxygenases of different bacterial origin. This platform of enzymes is able to perform stereoselective biotransformations on an array of structurally diverse substrates. With several ketone precursors, biooxidations yielded enantiocomplementary butyrolactones as key intermediates for the synthesis of natural products and bioactive compounds. The microbial Baeyer - Villiger oxidation allows a facile and rapid entry to several compound classes in a desymmetrization reaction upon de novo generation of chirality.
- Rudroff, Florian,Rydz, Joanna,Ogink, Freek H.,Fink, Michael,Mihovilovic, Marko D.
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p. 1436 - 1444
(2008/09/17)
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- UDCaT-5: A novel and efficient solid superacid catalyst for Claisen rearrangement of substituted allyl phenyl ethers
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The Claisen rearrangement of allyl phenyl ethers is a fundamental reaction in organic synthesis with a variety of applications in perfumes, flavors, pharmaceuticals, agrochemicals, polymers, fine chemicals, and intermediate industries. The development of environmentally benign processes using solid acid catalysts is becoming an area of growing interest. It was accomplished in an efficient, economical, environmentally friendly manner and is 100% selective toward alllyl phenols by employing UDCaT-5 as solid acid catalyst. Copyright Taylor & Francis Group, LLC.
- Yadav, Ganapati D.,Lande, Sharad V.
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p. 941 - 946
(2007/10/03)
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- Bismuth(III) triflate: Novel and efficient catalyst for Claisen and Fries rearrangements of allyl ethers and phenyl esters
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Bismuth(III) triflate catalyzed Claisen and Fries rearrangements of allyl phenyl ethers and phenyl acetates have been presented. The reaction proceeds smoothly and yields corresponding rearranged products in good yields. The bismuth triflate displays higher activity over the corresponding La, Yb, and Sc triflates.
- Sreedhar,Swapna,Sridhar
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p. 1433 - 1440
(2007/10/03)
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- First enantioselective synthesis of the neolignans Rhaphidecursinol A and Virolongin B
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The enantioselective synthesis of the neolignans Rhaphidecursinol A and Virolongin B is reported for the first time. The key reactions in the synthesis were Sharpless asymmetric dihydroxylation and Mitsunobu reaction. The absolute configuration of Rhaphidecursinol A was confirmed.
- Ren, Xinfeng,She, Xuegong,Peng, Kun,Su, Ying,Xie, Xingang,Pan, Xinfu,Zhang, Hongbin
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p. 969 - 974
(2007/10/03)
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- Total synthesis of six natural products of benzodioxane neolignans
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(±)-Eusiderin E, (±)-Eusiderin F, (±)-Eusiderin K, (±)-Eusiderin J, (±)-Eusiderin M and (±)-Eusiderin G were first synthesized from pyrogallol, in which the Claisen Rearrangement was used to afford two important C6-C3 units.
- Jing, Xiao-Bi,Wang, Li,Han, Ying,Shi, Yao-Cheng,Liu, Yong-Hong,Sun, Jing
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p. 1001 - 1004
(2007/10/03)
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- First enantioselective synthesis of Rhaphidecursinol A
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The enantioselective synthesis of Rhaphidecursinol A was reported for the first time and the absolute configuration of Rhaphidecursinol A was confirmed.
- Ren, Xinfeng,She, Xuegong,Peng, Kun,Su, Ying,Xie, Xingang,Pan, Xinfu
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p. 358 - 359
(2007/10/03)
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- Total synthesis of (±)-Eusiderin G and (±)-Eusiderin M
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(±)-Eusiderin G and (±)-Eusiderin M were first synthesized from pyrogallol, in which the Claisen Rearrangement was used to afford two important C6-C3 units.
- Jing, Xiaobi,Gu, Wenxin,Ren, Xinfeng,Bie, Pingyan,Pan, Xinfu
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- Total synthesis of (±)-Eusiderin K and (±)-Eusiderin J
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(±)-Eusiderin K and (±)-Eusiderin J were first synthesized from pyrogallol, in which the Claisen Rearrangement was used to afford two important C6-C3 units.
- Jing, Xiaobi,Gu, Wenxin,Bie, Pingyan,Ren, Xinfeng,Pan, Xinfu
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p. 861 - 867
(2007/10/03)
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- Evaluation of acute toxicity and genotoxicity of liquid products from pyrolysis of Eucalyptus grandis wood
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Slow pyrolysis of Eucalyptus grandis wood was performed in an oven laboratory, and smoke was trapped and condensed to yield liquid products. Polycyclic aromatic hydrocarbons (PAHs) and phenolic fractions were isolated from the former liquid products using adsorption column chromatography (ACC) and identified by GC/MS. Concentrations of PAH and phenolic fractions in total pyrolysis liquids were respectively 48.9 μg/g and 8.59% (w/w). Acute toxicity of total samples of pyrolysis liquids and the phenolic fraction was evaluated by means of two bioassays, namely, 24-h immobilization bioassay with Daphnia magna and Microtox(TM) bioassays, the latter employing the luminescent bacteria Photobacterium phosphoreum. Total pyrolysis liquids and the PAH fraction were evaluated for genotoxicity by the Microtox(TM) bioassay conducted using rehydrated freeze-dried dark mutant of the luminescent bacteria Vibrio fisheri strain M169. Total pyrolysis liquids and the phenolic fraction, respectively, in concentrations of 170 and 68 mg/L were able to immobilize 50% (EC50) of the D. magna population following 24-h exposure. Concentrations of 19 and 6 mg/L, respectively, for total pyrolysis liquids and phenolic fraction were the effective concentrations that resulted in a 50% (EC50) reduction in light produced by bacteria in the Microtox(TM) bioassay. Accordingly, the Microtox(TM) bioassay was more sensitive to toxic effects of both kind of samples than the D. magna bioassay, particularly for the phenolic fraction. Regarding to the genotoxicity evaluation, the results achieved by Microtox(TM) bioassay showed that total pyrolysis liquids had no genotoxic effects with and without exogenous metabolic activation using rat liver homogenate (S9). However, the PAH fraction showed toxic effects with rat liver activation and had a dose-response number (DRN) equal to 1.6, being in this way suspected genotoxic. The lowest detected concentration (LDC) of the PAH fraction able to cause genotoxic effects was 375 μg/L.
- Pimenta,Bayona,Garcia,Solanas
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p. 169 - 175
(2007/10/03)
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- Evolution of products in the combustion of scrap tires in a horizontal, laboratory scale reactor
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A horizontal laboratory reactor was used to study the evolution of byproducts from the combustion of scrap tires at five nominal temperatures (ranging from 650 to 1050 °C) and different oxygen:sample ratios A model was used to calculate the bulk air ratio (λ), and the oxygen consumption was discussed considering this ratio λ. More than 100 volatile and semivolatile compounds were identified and quantified by gas chromatography mass spectrometry, plotting their yields vs the bulk air ratio and temperature. Five different behaviors considering the bulk air ratio and the temperature were identified.
- Fullana,Font,Conesa,Blasco
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p. 2092 - 2099
(2007/10/03)
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- Methoxyphenols from burning of Scandinavian forest plant materials
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Semivolatile compounds in smoke from gram-scale incomplete burning of plant materials were assessed by gas chromatography and mass spectrometry. Gas syringe sampling was shown to be adequate by comparison with adsorbent sampling. Methoxyphenols as well as 1,6-anhydroglucose were released in amounts as large as 10 mg kg-1 of dry biomass at 90% combustion efficiency. Wood, twigs, bark and needles from the conifers Norway spruce and Scots pine emitted 12 reported 2-methoxyphenols in similar proportions. Grass, heather and birchwood released the same 2-methoxyphenols but also the corresponding 2,6-dimethoxyphenols which are characteristic of angiosperms. The methoxyphenols are formed from lignin and differ in structure by the group in para position relative to the phenolic OH group. Prominent phenols were those with trans-l-propenyl and ethenyl groups in that position. Vanillin, 4- hydroxy-3-methoxybenzaldehyde, was a prominent carbonyl compound from the conifer materials. (C) 2000 Elsevier Science Ltd.
- Kjaellstrand, Jennica,Ramnaes, Olle,Petersson, Goeran
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p. 735 - 741
(2007/10/03)
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- Facile Total Synthesis of Isopregomisin
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Isopregomisin, a diarylbutane-lignan, has been synthesized by a short and efficient route starting from pyrogallol; the synthesis involves a novel selective demethylation reaction and the coupling reaction of the Grignard reagent produced from an aryl bromopropane with (E)-2-tert-butyl-3-phenyloxaziridine.
- Mingyi, Wang,Hongfang, Yang,Anxin, Wu,Xinfu, Pan
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p. 158 - 159
(2007/10/03)
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- A new convenient synthetic procedure for 4-allyl-2,6-dimethoxyphenol
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4-Allyl-2,6-dimethoxyphenol was synthesized from 4-hydroxy-2,6-dimethoxybenzoic acid and allylbromide by condensation under basic condition and by subsequent Claisen rearrangement.
- Li, Guoqing,Li, Zhan,Fang, Xiuhua
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p. 2569 - 2572
(2007/10/03)
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- Synthesis and Reactivity of Vinyl Quinone Methides
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Vinyl quinone methides 4a and 4b were obtained in high yields by Ag2O oxidation of eugenol (3a) and of 2,6-dimethoxy-4-(2-propenyl)phenol (3b).Vinyl quinone methides (VQMs) reacted with alcohols, with phenols, and with acetic acid giving compounds 5 and 6.As the former rearranged to the latter in the reaction medium, the addition of the reported substrates to VQMs turned out to be wholly regioselective toward the formation of coniferyl and sinapyl derivatives 6.In contrast, addition of carbon nucleophiles (acetylacetone and EtNO2) to VQMs gave both compounds 7 and 8.By reaction of the acetates 6a and 6b (CR=CH3CO) with LiAlH4 it was possible to perform a novel synthesis of coniferyl and sinapyl alcohols (1a and 1b).Treatment of the same acetates with an aqueous solution of NaHCO3 reproduced VQMs 4, which by subsequent reduction with NaBH4, gave propenylphenols 2 and allylphenols 3.Formation of the latter compounds from coniferyl and sinapyl acetates via VQM is here proposed as a possible biosynthetic pathway.
- Zanarotti, Antonio
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p. 941 - 945
(2007/10/02)
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- PREPARATION AND REACTIVITY OF 2,6-DIMETHOXY-4-ALLYLIDENE-2,5-CYCLOHEXADIEN-1-ONE (VINYL QUINONE METHIDE) A NOVEL SYNTHESIS OF SINAPYL ALCOHOL
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Title compound (3b), prepared in concentrated CHCl3 or benzene solution and spectroscopically characterized, is shown to be an useful intermediate for the synthesis of sinapyl alcohol (1b) and its derivatives.
- Zanarotti, A.
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p. 3815 - 3818
(2007/10/02)
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- RETRO-DIELS-ALDER REACTION OF ASATONE: SYNTHESIS OF HETEROTROPANONE AND ISOHETEROTROPANONE
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Two novel neolignans, heterotropanone and isoheterotropanone, have been synthesized by retro-Diels-Alder reaction of asatone in 1-allyl-3,4,5-trimethoxybenzene.These two neolignans have also been obtained on thermal reaction of asatone followed by methylation.
- Yamamura, Shosuke,Niwa, Masatake
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p. 625 - 626
(2007/10/02)
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