5471-51-2Relevant articles and documents
Neurotrophic and anti-neuroinflammatory constituents from the aerial parts of Coriandrum sativum
Cha, Joon Min,Yoon, DaHye,Kim, Sun Yeou,Kim, Chung Sub,Lee, Kang Ro
, (2020)
In the course of our continuing search for biologically active compounds from medicinal sources, we investigated the MeOH extract of the aerial parts of Coriandrum sativum Linn. An extended phytochemical investigation of the aerial parts of C. sativum led to the isolation and identification of seven compounds (1–7) including two new isocoumarin glycosides (1–2) and a new phenolic glycoside (5). The chemical structures of the new compounds (1, 2, and 5) were elucidated by analysis of 1D and 2D NMR (1H and 13C NMR, COSY, HSQC, and HMBC) and HRESIMS data as well as by using chemical methods. All the isolates were evaluated not only for their potential neurotrophic activity by means of induction of nerve growth factor (NGF) in C6 glioma cells but also for production of nitric oxide (NO) levels in lipopolysaccharide (LPS)-activated murine microglia BV-2 cells to assess their anti-neuroinflammatory activity. Compounds 1–3 and 7 were stimulants of NGF release, with levels of NGF stimulated at 127.23 ± 1.89%, 128.22 ± 5.45%, 121.23 ± 6.66%, and 120.94 ± 3.97%, respectively. Furthermore, the aglycones of 1 and 2 (1a and 2a) showed more potent NGF secretion activity and anti-neuroinflammatory effect than did their glycosides (1a: 130.81 ± 5.45% and 2a: 134.44 ± 5.45%).
Stereochemistry of the double bond saturation in the formation in Baker's yeast of 4-(4-hydroxyphenyl)-2-butanone (raspberry ketone)
Fronza, Giovanni,Fuganti, Claudio,Mendozza, Monica,Rallo, Roberta S.,Ottolina, Gianluca,Joulain, Daniel
, p. 4041 - 4052 (1996)
Yeast extract-mediated reduction of 4-(4-hydroxyphenyl)-but-3-en-2-one 3 to raspberry ketone 1 occurs with transfer β to the carbonyl group of H(R) from NADPH and of an hydrogen atom from the solvent at α position, as indicated by experiments with (4R) and (4S) [4-2H]-NADPH and with deuterated solvent. The same extract converts 3 in 1 in the presence of NADH, but much less efficiently. In this latter case H(S) and not H(R) is transferred from the reduced cofactor to position 4 of 1. Horse liver alcohol dehydrogenase-mediated reduction of 1, bearing deuterium labelling at positions 1, 3 and 4 and obtained from 3 using the whole-cell system in the presence of D2O, gave an S carbinol possessing 0.95 ee, shown by 2H NMR studies onto the diacetate 7 to contain an excess of the (3S,4S) diastereoisomer, thus suggesting a prevalent β re-face,syn addition of hydrogen across the double bond of 3 in the whole-cell mediated conversion into 1.
Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides
Colas, Kilian,Kohlhepp, Stefanie V.,Mendoza, Abraham,V. D. dos Santos, A. Catarina
supporting information, (2022/02/02)
The synthesis of ketones through addition of organometallic reagents to aliphatic carboxylic acids is a straightforward strategy that is limited to organolithium reagents. More desirable Grignard reagents can be activated and controlled with a bulky aniline-derived turbo-Hauser base. This operationally simple procedure allows the straightforward preparation of a variety of aliphatic and perfluoroalkyl ketones alike from functionalized alkyl, aryl and heteroaryl Grignard reagents.
8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
Xing, Gang,Zhi, Zhengxing,Yi, Ce,Zou, Jitian,Jing, Xuefeng,Yiu-Ho Woo, Anthony,Lin, Bin,Pan, Li,Zhang, Yuyang,Cheng, Maosheng
, (2021/07/19)
β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.
Efficient demethylation of aromatic methyl ethers with HCl in water
Bomon, Jeroen,Bal, Mathias,Achar, Tapas Kumar,Sergeyev, Sergey,Wu, Xian,Wambacq, Ben,Lemière, Filip,Sels, Bert F.,Maes, Bert U. W.
supporting information, p. 1995 - 2009 (2021/03/26)
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.
Synthetic method of high-purity raspberry ketone
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Paragraph 0043-0049, (2021/11/21)
The invention belongs to the technical field of perfumes and fine chemical engineering. The invention specifically relates to a synthesis method of high-purity raspberry ketone. To the synthesis method, 2 and 6 - di-tert-butyl phenol are used as raw materials, and the butanone or a-hydroxybutanone is subjected to alkylation reaction under the catalysis condition of the acid catalyst 4 - to generate 2 and 6 - b di-tert-butyl -4 -hydroxybenzyl acetone. To the invention, 2, 6 -position occupying-protected phenol 2 and 6 - di-tert-butyl phenol are used as raw materials, and the butanone or 4 -hydroxybutanone alkylation reaction can 100% position in the para position, and the obtained 2 and 6 - di-tert-butyl -4 -hydroxybenzyl acetone. Yield. A tert-butyl process is performed, so that high-yield and high-purity raspberry ketone is obtained. The method is simple in process, short in reaction time, high in product purity, recyclable in reaction byproducts, recyclable in catalyst, low in cost and suitable for industrial production.
Preparation method of raspberry ketone
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Paragraph 0038-0076, (2021/08/07)
The invention relates to a preparation method of raspberry ketone. The preparation method comprises the step of reacting phenol with butanone alcohol under the action of an organic acid catalyst and a crown ether cocatalyst to obtain the target product raspberry ketone. The raspberry ketone prepared by the method is high in yield, the molar yield can reach up to 91.96% (according to the consumption molar number of butanone alcohol), meanwhile, the dosage of the organic acid catalyst in the preparation method is small, the generation of three wastes can be effectively reduced, and the method has great economic benefits and environmental protection benefits.
Deracemization and Stereoinversion of Alcohols Using Two Mutants of Secondary Alcohol Dehydrogenase from Thermoanaerobacter pseudoethanolicus
Hamdan, Samir M.,Musa, Musa M.,Nafiu, Sodiq A.,Takahashi, Etsuko,Takahashi, Masateru
, (2020/07/24)
We developed a one-pot sequential two-step deracemization approach to chiral alcohols using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). This approach relies on consecutive non-stereospecific oxidation of alcohols and stereoselective reduction of their prochiral ketones using two mutants of TeSADH with poor and good stereoselectivities, respectively. More specifically, W110G TeSADH enables a non-stereospecific oxidation of alcohol racemates to their corresponding prochiral ketones, followed by W110V TeSADH-catalyzed stereoselective reduction of the resultant ketone intermediates to enantiopure (S)-configured alcohols in up to > 99 percent enantiomeric excess. A heat treatment after the oxidation step was required to avoid the interference of the marginally stereoselective W110G TeSADH in the reduction step; this heat treatment was eliminated by using sol-gel encapsulated W110G TeSADH in the oxidation step. Moreover, this bi-enzymatic approach was implemented in the stereoinversion of (R)-configured alcohols, and (S)-configured alcohols with up to > 99 percent enantiomeric excess were obtained by this Mitsunobu-like stereoinversion reaction.
Indigo Formation and Rapid NADPH Consumption Provide Robust Prediction of Raspberry Ketone Synthesis by Engineered Cytochrome P450 BM3
Rousseau, Olivier,Ebert, Maximilian C. C. J. C.,Quaglia, Daniela,Fendri, Ali,Parisien, Adem H.,Besna, Jonathan N.,Iyathurai, Saathanan,Pelletier, Joelle N.
, p. 837 - 845 (2019/12/15)
Natural raspberry ketone has a high value in the flavor, fragrance and pharmaceutical industries. Its extraction is costly, justifying the search for biosynthetic routes. We hypothesized that cytochrome P450 BM3 (P450 BM3) could be engineered to catalyze the hydroxylation of 4-phenyl-2-butanone, a naturally sourceable precursor, to raspberry ketone. The synthesis of indigo by variants of P450 BM3 has previously served as a predictor of promiscuous oxidation reactions. To this end, we screened 53 active-site variants of P450 BM3 using orthogonal high-throughput workflows to identify the most streamlined route to all indigo-forming variants. Among the three known and 13 new indigo-forming variants, eight hydroxylated 4-phenyl-2-butanone to raspberry ketone. Previously unreported variant A82Q displayed the highest initial rates and coupling efficiencies in synthesis of indigo and of raspberry ketone. It produced the highest total concentration of raspberry ketone despite producing less total indigo than previously reported variants. Its productivity, although modest, clearly demonstrates the potential for development of a biocatalytic route to raspberry ketone. In addition to validating indigo as a robust predictor of this promiscuous activity, we demonstrate that monitoring rapid NADPH consumption serves as an alternative predictor of a promiscuous reactivity in P450 BM3.
Raspberry ketone reaction device and raspberry ketone continuous preparation method
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, (2019/01/14)
The invention discloses a raspberry ketone reaction device and a raspberry ketone continuous prepration method. A 4-formyl sodium phenate solution and acetone are taken as raw materials, water is taken as a solvent, and continuous aldehyde ketone condensation reaction is performed in a micro reactor to obtain an aqueous solution of 4-(3-oxo-1-butene) sodium phenolate; an intermediate solution is not separated and is added with a catalyst to continuously react with hydrogen gas in a tubular reactor with a pusher airscrew, so that olefin is selectively reduced to obtain the aqueous solution of raspberry ketone sodium salt, and the aqueous solution is subjected to after-treatment operation such as neutralization and crystallization to obtain raspberry ketone. In a synthesis process, water isonly used as the solvent, so that separating safety of the catalyst is improved, and product selectivity is as high as 99%, and raspberry alcohol generated by excessive reduction is less than 0.2%. the reaction system is free of amplifying effect, has good stability of continuous reaction, has the advantages of simple and convenient operation, short production period, simple production process, less pollution, low energy consumption, and the like, and is suitable for industrialized production.
