128301-02-0Relevant articles and documents
Lipophilic constituents from aerial and root parts of Mercurialis perennis L
Lorenz, Peter,Hradecky, Marc,Berger, Melanie,Bertrams, Julia,Meyer, Ulrich,Stintzing, Florian C.
, p. 234 - 245 (2010)
Introduction - Dog's mercury (Mercurialis perennis L.) is a perennial herb used in remedies for medicinal purposes. The plant is supposed to contain potentially active substances but its constituents have only been rarely studied. Objective - Detailed studies on the phytochemical composition are of great interest to broaden the knowledge on the chemotaxonomy and pharmacognosy of M. perennis. Methodology - Chloroform and hexane extracts from roots and aerial parts were investigated using GC/MS and LC/MS. Results - The whole plant exhihited a broad spectrum of structurally diverse constituents, mainly alkaloids, terpenes, sterols and simple aromatic compounds. Closer inspection of the piperidine alkaloid hermidin revealed its inherent instability towards air oxygen. To obtain quantitative data on these alkaloids the synthesis of the more stable reference compound 4-methoxy-1-methylpyridine-2,6(1H,3H)-dione (MMPD) was required. In this study, MMPD was detected for the fi rst time as a genuine compound in Mercurialis. Hermidine quinone and hermidin dimers originating from hermidin via a free anionic radical reaction were also confi rmed by GC/MS. Moreover, volatile compounds such as benzylalcohol, 2-phenylethanol, 4-methoxy- and 3,4-dimethoxyphenol, (-)-cis- and (+)-trans-myrtanol, (-)-cis-myrtanal as well as squalene were predominantely present in Mercurialis roots. In contrast, aerial parts mainly contained phytol derivatives, sterols and tocopherols. By changing solvent polarity, lipid and wax-containing fractions were obtained. LC/MS-studies on hexane extracts showed the presence of several mixed triglycerides constituted by linolenic, linoleic, oleic, stearic and palmitic acids, as well as lutein, carotenes and pheophytins. Conclusions - The phytochemical data presented complement our knowledge on the rarely studied plant M. perennis and may broaden its use in future phytotherapy. Copyright
Photocaged Hydrocarbons, Aldehydes, Ketones, Enones, and Carboxylic Acids and Esters that Release by the Norrish II Cleavage Protocol and Beyond: Controlled Photoinduced Fragrance Release
Griesbeck, Axel G.,Porschen, Bj?rn,Kropf, Christian,Landes, Agnieszka,Hinze, Olga,Huchel, Ursula,Gerke, Thomas
, p. 539 - 553 (2017/01/25)
Five families of caged fragrance compounds that allow the storage and release of the following small volatile organic molecules are described: terpene hydrocarbons, aldehydes, ketones, Michael-type α,β-unsaturated enones, and carboxylic acids and esters. These caged molecules are released by photoexcitation via carbonyl-directed hydrogen-transfer processes and subsequent C-C bond cleavage (Norrish Type II) or by didenitrogenation of diazirines.
Non-heme iron catalysis in CC, C-H, and CH2 oxidation reactions. Oxidative transformations on terpenoids catalyzed by Fe(bpmen)(OTf)2
Clemente-Tejeda, David,López-Moreno, Alejandro,Bermejo, Francisco A.
, p. 2977 - 2986 (2013/03/29)
The oxidation of terpene olefins with hydrogen peroxide in the presence of the non-hemo catalyst 5a afforded mixtures of epoxides whose composition was dependent upon the oxidation protocol used in each case. With terpenoid enones, the mixtures obtained evolved from clean epoxidation of α-ionone 23 to the clean allylic oxidation of damascone 28 due to the progressive deactivation of the electron density on the double bonds present in this series. The oxidation of bicyclic and tricyclic terpenoids afforded oxidation products coming from epoxidation, to olefin degradation, methyne and methylene activation products. Probably, the most attractive result was the synthesis of the Magnus lactone 46, from the tricyclic ether 45, with 88% yield and 100% conversion.
Convenient preparation of carbonyl compounds from 1,2-diols utilizing Mitsunobu conditions
Barrero, Alejandro F.,Alvarez-Manzaneda, Enrique J.,Chahboun
, p. 1959 - 1962 (2007/10/03)
1,1-Disubstituted 1,2-diols are efficiently converted into carbonyl compounds by reaction with triphenylphosphine and diethyl azodicarboxylate. (C) 2000 Elsevier Science Ltd.
Selective aerobic oxidation of primary alcohols catalyzed by a Ru(PPh3)3Cl2/hydroquinone system
Hanyu, Atsushi,Takezawa, Eiichiro,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 5557 - 5560 (2007/10/03)
Aerobic oxidation of primary alcohols to aldehydes was efficiently performed using a Ru(PPh3)3Cl2/hydroquinone system under atmospheric oxygen at 60 °C. A primary alcohol even in the presence of a secondary one was selectively oxidized to the corresponding aldehyde in high yield.
Chemistry of Silyl Thioketones. Part 7. Synthesis, Cycloaddition and Oxidation of Cycloalkyl Silyl Thioketones and Desilylation of the Reaction Products
Bonini, Bianca F.,Busi, Filippo,Laet, Roland C. de,Mazzanti, Germana,Thuring, Jan-Willem J. F.,et al.
, p. 1011 - 1018 (2007/10/02)
Cycloalkyl silyl thioketones 3, achiral as well as chiral at carbon, have been synthesized by thionation of the corresponding acyl silanes 2.During thionation of 2a, 2d and 2f unexpected products were observed.Cycloaddition reactions of cycloalkyl silyl thioketones 3 with buta-1,3-diene have been performed.A diastereoisomeric excess (d.e.) of 80percent was obtained in the case of chiral thione 3e.Desilylation of the cycloadducts was only possible at the stage of the corresponding α-silyl sulfones 11.Oxidation of compounds 3 led to the corresponding (E)-silyl sulfines 13 which by stereospecific fluorodesilylation gave (Z)-thioaldehyde S-oxides 14.Compound 14e is the first example of enantiomerically pure mono-substituted sulfine (thioaldehyde S-oxide).
