- The synthesis and evaluation of vanillin derivatives as the fruit fly attractant
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The present study was conducted to synthesize 4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone, a compound with similar structure to cue lure [4-(4-Acetyoxyphenyl)-2-butanone], using vanillin as a started material. The synthesis process was completed in two steps. The first step was the condensation reaction of Claisen Smidth between vanillin and acetone on alkaline conditions to produce 4-(4-hydroxyphenyl-3-methoxy)-3-buten-2-one, and the second step was the hydration reaction using zeolite catalysts activated by HCl, to produce 4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone. Characterization of the compounds was performed using IR and 1H-NMR spectroscopy. The evaluation of 4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone as fruit flies’ attractant was carried out in yard areas planted with guava and start fruit, in the Klidon village, Sukoharjo, Sleman Yogyakarta, with methyl eugenol as a standard. The observations were made for 24 hours. The synthesis product was obtained in the form of a white-orange solid with a melting point of 79-81oC and 60% yield.The field test showed that 4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone was potential as fruit flies’ attractant, indicated by the presence of lured fruit flies around the test location.
- Prabawati, Susy Yunita,Iskandar, Damayanti,Suci, Liimroati Purwo
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p. 2197 - 2202
(2018/09/13)
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- Traceless OH-Directed Wacker Oxidation-Elimination, an Alternative to Wittig Olefination/Aldol Condensation: One-Pot Synthesis of α,β-Unsaturated and Nonconjugated Ketones from Homoallyl Alcohols
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A new method for one-pot synthesis of β-substituted and β,β-disubstituted α,β-unsaturated methyl ketones from homoallyl alcohols by sequential PdCl2/CrO3-promoted Wacker process followed by an acid-mediated dehydration reaction has been developed. Remarkably, internal homoallyl alcohols delivered regioselectively nonconjugated unsaturated carbonyl compounds under the same protocol. A new starting material-based synthesis of α,β-unsaturated and nonconjugated methyl ketones is demonstrated.
- Bethi, Venkati,Fernandes, Rodney A.
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p. 8577 - 8584
(2016/09/28)
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- EFFICIENT SYNTHESIS OF AMINES AND AMIDES FROM ALCOHOLS AND ALDEHYDES BY USING CASCADE CATALYSIS
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The present invention relates generally to an eco-friendly methodology for the conversion of alcohols and aldehydes to amines and amides using an integrated enzyme cascade system with metal-and organocatalysis. More specifically, the present invention relates to synthesis of capsaicinoids starting from vanillin alcohol and using a combination of an enzyme cascade system and catalysts. Furthermore, the method also relates to synthesis of capsaicinoids derivatives starting from vanillin alcohol derivatives and using a combination of an enzyme cascade system and catalysts.
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- A photoswitchable organocatalyst based on a catalyst-imprinted polymer containing azobenzene
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An l-proline-catalyzed aldol reaction was photo-controlled using an l-proline-imprinted polymer containing azobenzene. Upon UV irradiation, azobenzene chromophores underwent trans → cis isomerization, thereby releasing l-proline to catalyze the aldol reac
- Liu, Hua-Dong,Zheng, An-Xun,Gong, Cheng-Bin,Ma, Xue-Bing,Hon-Wah Lam, Michael,Chow, Cheuk-Fai,Tang, Qian
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p. 62539 - 62542
(2015/08/06)
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- Total synthesis of capsaicin analogues from lignin-derived compounds by combined heterogeneous metal, organocatalytic and enzymatic cascades in one pot
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The total synthesis of capsaicin analogues was performed in one pot, starting from compounds that can be derived from lignin. Heterogeneous palladium nanoparticles were used to oxidise alcohols to aldehydes, which were further converted to amines by an enzyme cascade system, including an amine transaminase. It was shown that the palladium catalyst and the enzyme cascade system could be successfully combined in the same pot for conversion of alcohols to amines without any purification of intermediates. The intermediate vanillylamine, prepared with the enzyme cascade system, could be further converted to capsaicin analogues without any purification using either fatty acids and a lipase, or Schotten-Baumann conditions, in the same pot. An aldol compound (a simple lignin model) could also be used as starting material for the synthesis of capsaicin analogues. Using L-alanine as organocatalyst, vanillin could be obtained by a retro-aldol reaction. This could be combined with the enzyme cascade system to convert the aldol compound to vanillylamine in a one-step one-pot reaction.
- Anderson, Mattias,Afewerki, Samson,Berglund, Per,Cordova, Armando
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p. 2113 - 2118
(2014/07/07)
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- Side-chain length is important for shogaols in protecting neuronal cells from β-amyloid insult
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Ten shogaols were synthesized to evaluate the importance of the side-chain length in protecting cells from βA(1-42) insult using PC12 rat pheochromocytoma and IMR-32 human neuroblastoma cells. The compounds cell protectivity against βA insult was demonstrated using 3-[4,5- dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) reduction assay. The efficacy of cell protection from βA insult by these shogaols was shown to improve as the length of the side chain increase.
- Kim, Darrick S. H. L.,Kim, Jin Yung
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p. 1287 - 1289
(2007/10/03)
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