- Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols
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Formyloxyacetoxyphenylmethane, symmetric 1,1-diacylals and mixed 1-pivaloxy-1-acyloxy-1-phenylmethanes have been used as moisture stable O-formylating and O-acylating reagents for primary and secondary alcohols, allylic alcohols and phenols under solvent/catalyst free conditions to afford their corresponding esters in good yield.
- Chapman, Robert S.L.,Francis, Molly,Lawrence, Ruth,Tibbetts, Joshua D.,Bull, Steven D.
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p. 6442 - 6452
(2018/10/02)
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- Perilla alcohol derivative and its preparation and use
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The invention belongs to the technical field of medicine, and relates to a series of perilla alcohol derivatives disclosed as Formula I, and preparation and application thereof. The invention also relates to pharmaceutically acceptable salts and solvates of the perilla alcohol derivatives, and a pharmaceutical composition containing the perilla alcohol derivatives or pharmaceutically acceptable salts thereof as active components, which can be used for treating cancers. The perilla alcohol derivatives and pharmaceutical salts thereof have favorable anticancer activity. The preparation method is simple and feasible, and is easy to operate.
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- Heteropoly acid catalysts for the synthesis of fragrance compounds from bio-renewables: Acetylation of nopol and terpenic alcohols
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The cesium salt of tungstophosphoric heteropoly acid, Cs2.5H0.5PW12O40, is an active and environmentally friendly heterogeneous catalyst for the liquid-phase acetylation of nopol and several biomass-derived terpenic alcohols (i.e., α-terpineol, nerol, geraniol, linalool, menthol, isoborneol, perillyl alcohol, carveol, isopulegol, carvacrol and nerolidol) with acetic anhydride. The resulting flavor and fragrance acetic esters, which are widely used in perfumery, household and food products, are obtained in good to excellent yields. The reactions occur at room temperature with low catalyst loadings without substantial catalyst leaching and can be performed with stoichiometric amounts of an acetylating agent in solvent free systems.
- Costa, Vinicius V.,Da Silva Rocha, Kelly A.,Oliveira, Luiz C. A.,Kozhevnikova, Elena F.,Kozhevnikov, Ivan V.,Gusevskaya, Elena V.
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p. 43217 - 43222
(2016/05/24)
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- Synthesis and antiproliferative effects of amino-modified perillyl alcohol derivatives
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Two series of amino-modified derivatives of (S)-perillyl alcohol were designed and synthesized using (S)-perillaldehyde as the starting material. These derivatives showed increased antiproliferative activity in human lung cancer A549 cells, human melanoma A375-S2 cells and human fibrosarcoma HT-1080 cells comparing with that of (S)-perillyl alcohol. Among these derivatives, compounds VI5 and VI7 were the most potent agents, with the IC50s below 100 μM. It was demonstrated that the antiproliferative effect of VI5 was mediated through the induction of apoptosis in A549 cells.
- Hui, Zi,Zhang, Meihui,Cong, Lin,Xia, Mingyu,Dong, Jinhua
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p. 6671 - 6682
(2014/06/10)
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- Synthesis of (+)-perillyl alcohol from (+)-limonene
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(+)-Perillyl alcohol (1) has been synthesised in four steps and 39% overall yield from commercially available limonene oxide (4). The sequence features, as its key step, a palladium(0)-mediated transformation of a secondary allylic acetate (6) into its primary isomer (7). An application of (+)-perillyl alcohol (1) in a formal synthesis of naturally occurring (-)-mesembrine (2) and (-)-mesembranol was demonstrated.
- Geoghegan, Kimberly,Evans, Paul
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p. 1431 - 1433
(2014/03/21)
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- Preparation and utilization of perillyl acetate
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Perillyl acetate is a fragrance compound that was prepared by the reaction of β-pinenoxide with acetic anhydride and using acetic acid as an acid catalyst. Several selected catalysts were tested (homogenous: phosphoric acid, boric acid, acetic acid, and citric acid; heterogeneous: zeolite USY, SSA, and montmorillonite K-10) and the reaction conditions optimized for this reaction. The yield 78.7 % of perillyl acetate was obtained. Mayol (4- isopropylcyclohexylmethanol), a valuable fragrance compound, was further obtained by a two-step synthesis from perillyl acetate. Firstly, perillyl acetate was saponified to perillyl alcohol. The yield of alcohol was 94.4 %. The last step of the entire preparation was the hydrogenation of perillyl alcohol to Mayol. The yield of the desired product of this reaction was 94.6 %. Springer Science+Business Media B.V. 2012.
- ?tekrová, Martina,Paterová-Dudková, Iva,Vysko?ilová-Leitmannová, Eli?ka,?erveny, Libor
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p. 2075 - 2084
(2013/02/22)
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- Reactions of epoxides prepared from some monoterpenes with acetic anhydride on aluminosilicate catalysts
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Reactions of epoxides prepared from α-, β-pinenes and camphene with acetic anhydride on aluminosilicate catalysts (clay K-10, zeolite β) were investigated affording various products of skeleton rearrangements: mono- and diacetates with five- and six-membered rings, and also with norbornane and pinane cores.
- Tatarova,Korchagina,Volcho,Salakhutdinov,Barkhash
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p. 1076 - 1082
(2007/10/03)
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- Pd-containing catalytic system for oxidative acetoxylation of alkenes
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Four-substituted cyclohexenes were used as examples for revealing the substituent effect on composition of products obtained by oxidative acetoxylation of alkenes catalyzed with Pd(II) acetate. The distribution of products is rationalized on assumption of relative stability of allylic anions and steric strains in (π-allyl)palladium intermediates. Stereoselective yield of trans-substituted endo-acetates is due to stabilizing effect of lower unoccupied orbital of the forming C-OAc bond and occupied orbitals of pseudoaxial C-H bonds at the cycle in the transition states. The substrates capable of this reaction are limited to alkenes with insignificant steric shielding of the double bond. The study of the influence on the process of the characteristics of oxidant used in the catalytic system revealed that the most significant difference is observed between catalysts prepared as homogeneous oxidative systems and those containing heterogeneous oxidant MnO2 or TiO2 as additive. 1998 MAHK "Hayka/Interperiodica".
- Romanenko,Tormyshev,Shteingarts
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p. 1549 - 1562
(2007/10/03)
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- 7,9-dihydroxy-1,8-cineole and 2α,7-dihydroxy- 1,8-cineole: Two new possum urinary metabolites
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Chemical syntheses for 7,9-dihydroxy-1,8-cineole (8a) and 2α,7-dihydroxy-1,8-cineole (9a) are reported. These products are identical with the urinary metabolites isolated from brushtail possums fed 1,8-cineole (1) and 2α-hydroxy-1,8-cineole (4) respectively.
- Carman, Raymond M.,Garner, A. Christopher
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p. 741 - 749
(2007/10/03)
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- Reactions of d-Limonene with t-Butyl Hypochlorite
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Investigation of the title reaction under different conditions of temperature, solvents and catalysis has led to its optimisation with respect to the yield of (-)-trans-carvyl chloride (2).Other products formed in the reaction have been identified as 1,2-dichloro-p-menth-8-ene (5), 10-chloro-p-mentha-1,8-diene (6), 2-chloro-p-mentha-1(7)8-diene (10) and 6,10-dichloro-p-mentha-1,8-diene (11).The reaction proceeds almost entirely by electrophilic halogenation with no evidence of competition from a radical mechanism.
- Ravindranath, B.,Srinivas, P.
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p. 163 - 165
(2007/10/02)
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- Synthese von (-)-Spathulenol
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In reference to the famous synthesis of (-)-aromadendrene, the synthesis of (-)-spathulenol (31) and (-)-7-epi-spathulenol (32) from (-)-β-pinene via (-)-perillaaldehyde and the intermediates 7, 19 and 25 is described.
- Surburg, Horst,Mondon, Albert
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p. 118 - 131
(2007/10/02)
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- Alicyclic compounds, their use and process for preparing same
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Use of alicyclic compounds, some of which are new, as odor-modifying ingredients for manufacturing perfumes, perfumed products or synthetic essential oils, and as flavor-modifying ingredients for the manufacture of artificial flavors or for the aromatization of foodstuffs, animal feeds, pharmaceutical preparations or tobacco products. Process for preparing said alicyclic compounds.
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