- 1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents
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The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.
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- Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents
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The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.
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- Anaerobic nitroxide-catalyzed oxidation of alcohols using the NO +/NO· redox pair
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A new method for alcohol oxidation using TEMPO or AZADO in conjunction with BF3·OEt2 or LiBF4 as precatalysts and tert-butyl nitrite as a stoichiometric oxidant has been developed. The system is based on a NO+/NO· pair for nitroxide reoxidation under anaerobic conditions. This allows the simple, high-yielding conversion of various achiral and chiral alcohols to carbonyl compounds without epimerization and no formation of nonvolatile byproducts.
- Holan, Martin,Jahn, Ullrich
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supporting information
p. 58 - 61
(2014/01/23)
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- A detailed identification study on high-temperature degradation products of oleic and linoleic acid methyl esters by GC-MS and GC-FTIR
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GC-MS and GC-FTIR were complementarily applied to identify oxidation compounds formed under frying conditions in methyl oleate and linoleate heated at 180 °C. The study was focused on the compounds that originated through hydroperoxide scission that remain attached to the glyceridic backbone in fats and oils and form part of non-volatile molecules. Twenty-one short-chain esterified compounds, consisting of 8 aldehydes, 3 methyl ketones, 4 primary alcohols, 5 alkanes and 1 furan, were identified. In addition, twenty non-esterified volatile compounds, consisting of alcohols, aldehydes and acids, were also identified as major non-esterified components. Furanoid compounds of 18 carbon atoms formed by a different route were also identified in this study. Overall, the composition of the small fraction originated from hydroperoxide scission provides a clear idea of the complexity of the new compounds formed during thermoxidation and frying.
- Berdeaux, Olivier,Fontagné, Stéphanie,Sémon, Etienne,Velasco, Joaquin,Sébédio, Jean Louis,Dobarganes, Carmen
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experimental part
p. 338 - 347
(2012/06/29)
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- Synthesis of naturally occurring diene and trienes by Te/Li exchange on (1Z,3Z)-butyltelluro-4-methoxy-1,3-butadiene
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(1Z,3Z)-Butyltelluro-4-methoxy-1,3-butadiene 2 was obtained by the hydrotelluration of (Z)-1-methoxy-but-1-en-3-ynes 1. The butadienyllithium 3 obtained by the Te/Li exchange reaction in the (1Z,3Z)-1-butyltelluro-4-methoxy-1,3-butadiene 2 reacted with aldehydes to form the corresponding alcohols 4a-d with total retention of configuration. The alcohols formed undergo hydrolysis, resulting in the α,β,γ,δ-unsaturated aldehydes of (E,E) configuration, which are precursors of trienes obtained from natural sources. The products of this reaction were employed in the synthesis of methyl-(2E,4E)-decadienoate 7, which is a component of the flavor principles of ripe Bartlett pears. Performing the Wittig reaction of the methyl triphenylphosphorane with the deca-(2E,4E)-dienal 5a, we were able to synthesize the undeca-(1,3E,5E)-triene 6a. This compound is a sex-pheromone component of the marine brown algae Fucus serratus, Dictyopteris plagiograma, and Dictyopteris australis. Performing the Wittig reaction of methyl triphenylphosphorane with the octa-(2E,4E)-dienal 5c, the nona-(1,3E,5E)-triene 6b was synthesized. The compound obtained is a sex-pheromone component of the marine brown alga Sargassum horneri. The octa-(1,3E,5E)-triene 6c was easily obtained from hepta-(2E,4E)-dienal 5d by the Wittig reaction with methyl triphenylphophorane. This compound is a sex-pheromone component of the marine brown alga Fucus serratus.
- Dabdoub, Miguel J.,Dabdoub, Vania B.,Baroni, Adriano C.M.,Hurtado, Gabriela R.,Barbosa, Sandro L.
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experimental part
p. 1666 - 1670
(2010/05/19)
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- Catalytic enantioselective allylation of dienals through the intermediacy of unsaturated π-allyl complexes
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(Chemical Equation Presented) The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester [allylB(pin)] to >,β,γ,δ-unsaturated aldehydes is described. This reaction results in a remarkable inversion of substrate olefin geometry, providing the Z,E-configured reaction product in good enantioselectivity and olefin stereoselectivity. The reaction appears to proceed by conversion of the dienal to an unsaturated B-allyl complex followed by reductive elimination via transition state II. Enantioselectivities range from 73-94% ee for a range of δ-substituted dienals when chiral ligand L3 is employed.
- Zhang, Ping,Morken, James P.
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supporting information; scheme or table
p. 12550 - 12551
(2010/01/30)
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- Aggregation behavior of tetraenoic fatty acids in aqueous solution
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(Chemical Equation Presented) Why so blue? Unique blue-shifted UV absorptions were used to follow the aggregation of C24 tetraene fatty acids in aqueous solution. Aggregation takes place through three distinct states (i.e. K→T1→T2; see picture). It is suggested that all of these aggregates are lamellar-type in a local sense but differ in the packing mode of the fatty acid backbone.
- Wang, Yonghui,Ma, Jianguo,Cheon, Hwan-Sung,Kishi, Yoshito
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p. 1333 - 1336
(2008/04/05)
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- Synthesis and biological activity of α,β,γ,δ-unsaturated aldehydes from diatoms
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α,β,γ,δ-Unsaturated aldehydes have gained increasing attention since 2,4-decadienal and 2,4,7-decatrienal were isolated from the diatom Thalassiosira rotula and characterized as cell antiproliferative metabolites. Structurally related α,β,γ,δ-unsaturated aldehydes were found in this alga as well as in other diatom species. We present a short and universal synthesis of this compound class along with a structure-activity study of the potential to inhibit sea urchin egg cleavage. Pd0- or CoII-mediated cross coupling of 5-iodo-penta-2,4-dienal with organo-zincates allows the fast and flexible synthesis of numerous aldehydes from this universal precursor. The stereochemistry of the double bond system of the precursor was preserved during the coupling. Bioassays showed that the polarity of the side chain is important for antiproliferative activity with 2,4-decadienal as the most active compound tested compared to the shorter-chain aliphatic homologues and to ω-oxo acids with conjugated double systems. In contrast, the double bond geometry has no influence on biological activity. The α,β-unsaturated 2E-decenal was also highly active, while activity diminished in the case of saturated aldehydes of similar chain length. 1-Decanol, 2-decanone and decanoic acid were not active.
- Adolph, Sven,Poulet, Serge A.,Pohnert, Georg
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p. 3003 - 3008
(2007/10/03)
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- 2,4-Decadienals are produced via (R)-11-HPITE from arachidonic acid in marine green alga Ulva conglobata
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Marine green alga Ulva conglobata was investigated for the biogeneration of oxygenated products from exogenously added arachidonic acid (ARA). A crude enzyme from the alga afforded the detectable amount of a hydroperoxyicosatetraenoic acid (HPITE), which was identified as (R)-11-HPITE by HPLC and GC-MS. Headspace-SPME method indicated that ARA was selectively used to form 2,4-decadienals. These results showed that 2,4-decadienals are produced via (R)-11-HPITE from ARA exclusively.
- Akakabe, Yoshihiko,Matsui, Kenji,Kajiwara, Tadahiko
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p. 3607 - 3609
(2007/10/03)
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- Palladium catalyzed cross-coupling reaction of functional organozinc reagents with (2E,4E)- and (2E,4Z)-5-bromopenta-2,4-dienals: Easy access to functional conjugated dienic aldehydes
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Functional zinc reagents can be applied to palladium catalyzed cross-coupling reaction with (2E,4E)- and (2E,4Z)-5-bromopenta-2,4-dienal. The corresponding functional dienic aldehydes were obtained in goods yields. From the (2E,4E) isomer, the (2E,4E) dienals were isolated as single isomer according to a total stereoselective reaction. But, from the (2E,4Z) isomer the coupling reaction has lead to a mixture of (2E,4E) and (2E,4Z) isomers. A mechanism for the loss of stereoselectivity in the last case is proposed.
- Vicart, Nicolas,Saboukoulou, Gerard-Simplice,Ramondenc, Yvan,Ple, Gerard
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p. 1509 - 1521
(2007/10/03)
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- (2E)-4,4-dimethoxy-2-butenal in the synthesis of conjugated dienes and dienals
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Using (2E)-4,4-dimethoxy-2-butenal as starting compound, methods were developed for synthesis of (2E,4E)-and (2E,4Z)-dimethoxyalkadienes. Deacetalization of the latter gives with high yield the corresponding dienals which are naturally occurring compounds
- Badanyan,Makaryan,Ovanesyan,Panosyan
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p. 633 - 639
(2007/10/03)
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- Stereoselective synthesis of methyl and ethyl (2E,4Z)-2,4-decadienoates from (E)-4,4-dimethoxy-2-butenal
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Methyl and ethyl (2E,4Z)-2,4-decadienoates were synthesized starting from (E)-4,4-dimethoxy-2-butenal.
- Ovanesyan,Garibyan,Badanyan
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p. 951 - 954
(2007/10/03)
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- Application of (2E,4E)-5-bromo-2,4-pentadienal in palladium catalyzed cross-coupling: Easy access to (2E,4E)-2,4-dienals
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Palladium catalyzed cross-coupling reactions of (2E,4E)-5-bromo-2,4-pentadienal 1 with organozinc reagents gives an easy access to the corresponding (2E,4E)-2,4-dienals. The improved preparation of all trans 1 by isomerization of its (2E,4Z) isomer is reported.
- Vicart, Nicolas,Castet-Caillabet, Dominique,Ramondenc, Yvan,Plé, Gérard,Duhamel, Lucette
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p. 411 - 412
(2007/10/03)
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- Synthesis of (2E,4E)-dienals by double formyl-olefination with an arsonium salt and its application in the syntheses of lipoxygenase metabolites of arachidonic acid
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A new facile route to (2E,4E)-dienals by a double formyl-olefination with arsonium salts has been developed. By this method and with other arsonium reagents in the key step some lipoxygenase metabolites of arachidonic acid, lipoxin A4 and B4 and leukotriene B4, have been synthesized.
- Peng, Zhi-Hui,Li, Yun-Long,Wu, Wen-Lian,Liu, Cui-Xian,Wu, Yu-Lin
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p. 1057 - 1066
(2007/10/03)
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- The preparation and electrocyclic ring-opening of cyclobutenes: Stereocontrolled approaches to substituted conjugated dienes and trienes
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Thermal electrocyclic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alkadienals exclusively, and the process is exploited in transforming cis-3-cyclobutene-1,2-dimethanol 1 into a variety of naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates. Desymmetrisation of 1 with Pseudomonas fluorescens lipase gives access to both enantiomers of 3-oxabicyclo[3.2.0]hept-6-en-2-one 4, for use in stereocontrolled routes to 6-oxygenated (2Z,4E)-alkadienals.
- Binns, Falmai,Hayes, Roy,Hodgetts, Kevin J.,Saengchantara, Suthiweth T.,Wallace, Timothy W.,Wallis, Christopher J.
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p. 3631 - 3658
(2007/10/03)
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- Reduction of 1,1-difluoro-1-alken-3-ols with lithium tetrahydroaluminate. Application to the synthesis of 1,1-difluoro-2-alkenes and 2-alkenals
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The reduction of 1,1-difluoro-1-alken-3-ols with lithium tetrahydroaluminate is described. The 1-fluoro-1-alken-3-ols obtained can be transformed to enals or difluoromethylated allylic derivatives.
- Telliera, Frederique,Sauvetre, Raymond
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p. 181 - 185
(2007/10/03)
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- Stereoselective synthesis of conjugated dienals: A new approach for the synthesis of Pellitorine and Trichonine
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An alternate synthesis of 2E, 4E conjugated dienals (8a, 8b) of high stereoisomeric purity is described. γ-Haloallylic alcohols prepared from alkenes of appropriate chain length have been selected to serve as synthons for the preparation of diene aldehydes, the key intermediates leading to the synthesis of natural dienamides Pellitorine and Trichonine.
- Bhalerao,Raju, B. China,Neelakantan, Parvathi
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p. 530 - 533
(2007/10/03)
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- Two- and Four-Carbon Homologation of Aldehyde by AgClO4-Catalyzed Addition of Alkoxyalkenylzirconocene Chloride
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Two-and four-carbon homologation of aldehyde is described, which is based on the AgClO4-catalyzed addition of zirconocene complexes, derived from hydrozirconation of 1-ethoxyethyne (1) and (Z)-1-methoxy-1-buten-3-yne (2) with Cp2Zr(H)Cl, followed by acidic hydrolysis.
- Maeta, Hideki,Suzuki, Keisuke
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p. 341 - 344
(2007/10/02)
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- Use of cis-3-cyclobutene-1,2-dimethanol in stereoselective routes to some naturally occurring conjugated dienes and trienes
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Thermal electronic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alka-2,4-dienals exclusively, and this process is exploited en route to various isomeric naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates from a single precursor, cis-3-cyclobutene-1,2-dimethanol 4.
- Hodgetts, Kevin J.,Saengchantara, Suthiweth T.,Wallis, Christopher J.,Wallace, Timothy W.
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p. 6321 - 6324
(2007/10/02)
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- Stereoselective synthesis of (3E,5E)-dien-2-ones and (2E,4E)-dienals via 2-phenylsulfonyl 1,3-dienes
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Michael addition of nitroalkanes to 2-phenylsulfonyl 1,3 dienes proceeded smoothly in the presence of DBU to give nitrosulfones (e.g. 2) in high yield. Transformation of the nitro group of the adduct to a keto function (Nef type reaction) and subsequent elimination of benzenesulfinic acid afforded conjugated dienones and dienals with high stereoselectivity.
- Baeckvall, Jan-E.,Ericsson, Anna M.,Plobeck, Niklas A.,Juntunen, Seppo K.
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p. 131 - 134
(2007/10/02)
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- PALLADIUM-CATALYZED DIASTEREOSELECTIVE SYNTHESES OF (E)-1-TRIMETHYLSILYL-2-ALKENES, (E)-1-TRIMETHYLSILYL-1-ALKEN-3-YNES, (1E,5E)-1-TRIMETHYLSILYL-1,5-ALKADIEN-3-YNES, (1E,3Z)- AND (1E,3E)-1-TRIMETHYLSILYL-1,3-ALKADIENES
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On the basis of our observation that (E)-1-bromo-1-alkenes undergo preferentially stereospecific Pd-catalyzed cross-couplings with a variety of organometallics, in the presence of the corresponding (Z)-stereoisomers, efficient and convenient diastereoselective procedures have been developed to prepare nearly stereoisomerically pure (E)-1-trimethylsilyl-2-alkenes (4), (E)-1-trimethylsilyl-1-alken-3-ynes (5), (1E,5E)-1-trimethylsilyl-1,5-alkadien-3-ynes (6), and (1E,3E)-1-trimethylsilyl-1,3-alkadienes (8) from stereoisomeric mixtures of alkenyl bromides.Compounds 5 have been stereoselectively converted into (1E,3Z)-1-trimethylsilyl-1,3-dienes (7) by selective hydrometallations, followed by hydrolysis.Some synthetic applications of compounds 5-8 have been also examined.
- Andreini, Bianca Patrizia,Carpita, Adriano,Rossi, Renzo,Scamuzzi, Barbara
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p. 5621 - 5640
(2007/10/02)
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- HIGHLY STEREOCONTOROLLED SYNTHESIS OF (2E,4Z)-DIENIC ESTERS BY ALUMINA CATALYST
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Thermal treatment of β-allenic esters (2) with alumina catalyst in aprotic solvents yielded (2E,4Z)-dienoic esters (3) in 57-87percent yields with 91-100percent stereoselectivity.
- Tsuboi, Sadao,Masuda, Toshihide,Makino, Hiroshi,Takeda, Akira
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p. 209 - 212
(2007/10/02)
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