- Pheromone synthesis. Part 258. Synthesis of the enantiomers of the beetle pheromones ethyl 4-methylheptanoate, 4-methyloctanoic acid and 4-methyl-1-nonanol, and HPLC analysis of their derivatives to determine their enantiomeric purities
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The enantiomers of citronellal have been converted into the enantiomers of the following beetle pheromones: ethyl 4-methylheptanoate (produced by male Nicrophorus vespilloides), 4-methyloctanoic acid (produced by male Oryctes elegans), and 4-methyl-1-nonanol (produced by female Tenebrio molitor). The enantiomeric purities of the synthetic pheromones were determined by HPLC analysis of the corresponding acids after derivatization with Ohrui's reagent [(S)-1-(anthracene-2,3-dicarboximido)-2-propanol]. The enantiomers of 4-methyl-1-nonanol could also be analyzed employing another Ohrui's reagent [(1S,2S)-2-(naphthalene-2,3-dicarboximido)cyclohexane-1-carboxylic acid].
- Mori, Kenji,Akasaka, Kazuaki
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p. 182 - 187
(2018/10/16)
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- Method for Producing Isononanoic Acid Esters, Starting from 2-Ethyl Hexanol
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A Process for preparing carboxylic esters of a mixture of structurally branched C9 monocarboxylic acids proceeding from 2-ethylhexanol is characterized in that (a) 2-ethylhexanol is dehydrated to an octene mixture in the presence of a catalyst; (b) the octene mixture obtained in step a) is reacted in the presence of a transition metal compound of group VIII of the periodic table of the elements with carbon monoxide and hydrogen to give a mixture of isomeric isononanals; (c) the mixture of isomeric isononanals obtained in step b) is oxidized to a mixture of structurally branched C9 monocarboxylic acids; and (d) the mixture of structurally branched C9 monocarboxylic acids obtained in step c) is reacted with alcohols to give carboxylic esters.
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Paragraph 0081-0087
(2015/06/17)
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- Method for Producing Isononanoic Acids from 2-Ethyl Hexanol
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Process for preparing isononanoic acid proceeding from 2-ethylhexanol, characterized in that (a) 2-ethylhexanol is dehydrated to octene in the presence of a catalyst; (b) the octene obtained in step a) is reacted in the presence of a transition metal compound of group VIII of the periodic table of the elements with carbon monoxide and hydrogen to give isononanal; and (c) the isononanal obtained in step b) is oxidized to isononanoic acid.
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Paragraph 0062-0071
(2015/07/15)
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- New synthesis of vanillin by degradation of lignin in presence of functional basic ionic liquid
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The degradation of lignin catalyzed by functional basic ionic liquid was investigated. Higher conversion of lignin and simpler degradation product composition were obtained in the presence of basic ionic liquid, comparing with that under traditional NaOH
- Yi, Fengping,Jiang, Xiaoyan,Niu, Jihua,Zhang, Lirong,Wang, Zhen
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p. 885 - 888
(2015/02/05)
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- Carboxy-directed asymmetric hydrogenation of 1,1-diarylethenes and 1,1-dialkylethenes
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Carboxy marks the spot: A carboxy-directed asymmetric hydrogenation of 1,1-diarylethenes and 1,1-dialkylethenes with chiral iridium/spiro phosphine-oxazoline catalysts has been developed. A wide range of chiral diarylethanes and chiral γ-methyl fatty acids were synthesized with excellent enantioselectivity (see scheme). Copyright
- Song, Song,Zhu, Shou-Fei,Yu, Yan-Bo,Zhou, Qi-Lin
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supporting information
p. 1556 - 1559
(2013/04/24)
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- Diastereoselective, large-scale synthesis of β-amino acids via asymmetric aza-Michael addition as α2δ ligands for the treatment of generalized anxiety disorder and insomnia
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Scalable synthetic routes to β-amino acids 1 and 2 are presented. These two compounds, which bind to the α2δ subunit of calcium channels and have important medical applications, have been prepared on kilogram scale in our pilot plant through an improved synthesis that avoids the use of highly toxic reagents and hazardous chemistry present in the original Medicinal Chemistry route. The two chiral centers are introduced through asymmetric Michael and aza-Michael reactions with excellent diastereoselectivity.
- Magano, Javier,Bowles, Daniel,Conway, Brian,Nanninga, Thomas N.,Winkle, Derick D.
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scheme or table
p. 6325 - 6328
(2010/02/27)
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- Asymmetric synthesis of (R)- and (S)-4-methyloctanoic acids. A new route to chiral fatty acids with remote stereocenters
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The enantioselective synthesis of both enantiomers of 4-methyloctanoic acid, one major aggregation pheromone component of the rhinoceros beetles of the genus Oryctes and an important aroma compound, is described. The key step of the synthesis is based on
- Munoz, Lourdes,Bosch, Ma Pilar,Rosell, Gloria,Guerrero, Angel
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experimental part
p. 420 - 424
(2009/09/06)
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- Efficient synthesis of (±)-4-methyloctanoic acid, aggregation pheromone of rhinoceros beetles of the genus oryctes (Coleoptera: Dynastidae, Scarabaeidae)
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(±)-4-Methyloctanoic acid and its ethyl ester are aggregation pheromones of many rhinoceros beetles of the genus Oryctes and are investigated for the control of these pests by olfactory trapping. A simple, economical, and high-yield (>50%) synthesis of (±)-4-methyloctanoic acid and its ethyl ester is presented starting from n-hexanal. The key step in this sequence is an orthoester Claisen rearrangement for the elongation of the carbon chain by two.
- Ragoussis, Valentine,Giannikopoulos, Alexandros,Skoka, Efthymia,Grivas, Panagiotis
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p. 5050 - 5052
(2008/02/12)
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- Combinations comprising alpha-2-delta ligands
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The instant invention relates to a combination, particularly a synergistic combination, of an alpha-2-delta ligand and a dual serotonin-noradrenaline re-uptake inhibitor (DSNRI) or one or both of a selective serotonin re-uptake inhibitor (SSRI) and a selective noradrenaline re-uptake inhibitor (SNRI), and pharmaceutically acceptable salths thereof, pharmaceutical compositions thereof and their use in the treatment of pain, particularly neuropathic pain.
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Page/Page column 18
(2008/06/13)
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- Combinations
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The instant invention relates to a combination of an alpha-2-delta ligand and an AChE inhibitor for use in therapy, particularly in the treatment of pain, particularly neuropathic pain. Particularly preferred alpha-2-delta ligands are gabapentin and pregabalin. Particularly preferred ACHE inhibitors are donepezil (Aricept?), tacrine (cognex?), rivastigmine (Exelon?), physostgmine (Synapton?), galantamine (Reminyl), metrifonate (Promem), neostigmine (Prostigmin) and icopezil.
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Page/Page column 15
(2008/06/13)
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- METHODS FOR USING AMINO ACIDS WITH AFFINITY FOR THE ALPHA-2-DELTA PROTEIN
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This invention relates to certain ?-amino acids that bind to the alpha-2-delta ((x2S) subunit of a calcium channel. These compounds and their pharmaceutically acceptable salts are useful in the treatment of a variety of psychiatric, pain and other disorders.
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Page/Page column 58-59
(2008/06/13)
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- Synergistic combinations
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The instant invention relates to a combination of an alpha-2-delta ligand and a PDEV inhibitor for use in therapy, particularly in the curative, prophylactic or palliative treatment of pain, particularly neuropathic pain. Particularly preferred alpha-2-delta ligands are gabapentin and pregabalin. Particularly preferred PDEV inhibitors are sildenafil, vardenafil and tadalafil.
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- Alpha2delta ligands for fibromyalgia and other disorders
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This invention relates to a method of treating a disorder selected from OCD, agoraphobia, agoraphobia without history of panic disorder, specific phobia, social phobia, PTSD, restless legs syndrome, premenstrual dysphoric disorder, hot flashes, and fibromyalgia by administering a compound of the formula 1 or a pharmaceutically acceptable salt thereof, wherein: R1 is hydrogen, straight or branched alkyl of from 1 to 6 carbon atoms or phenyl; and R2 is straight or branched alkyl of from 4 to 8 carbon atoms, straight or branched alkenyl of from 2 to 8 carbon atoms, cycloalkyl of from 3 to 7 carbon atoms, alkoxy of from 1 to 6 carbon atoms, -alkylcycloalkyl, -alkylalkoxy, -alkyl OH, -alkylphenyl, -alkylphenoxy, or -substituted phenyl. The invention also relates to a method of treating the above disorders by administering the compound (3S, 5R)-3-Aminomethyl-5-methyl-octanoic acid
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- Substrate sorption into the polymer matrix of Novozym 435 and its effect on the enantiomeric ratio determination
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In the enantioselective esterification of 4-methyloctanoic acid with ethanol by immobilised Candida antarctica lipase B (Novozym 435), the enantiomeric excesses determined during the course of the reaction deviated strongly from the theoretical values, le
- Heinsman, Nicole W. J. T.,Schroen, Carin G. P. H.,Van Der Padt, Albert,Franssen, Maurice C. R.,Boom, Remko M.,Van'T Riet, Klaas
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p. 2699 - 2704
(2007/10/03)
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- Amino acids with affinity for the alpha-2-delta-protein
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This invention relates to certain β-amino acids that bind to the alpha-2-delta (α2δ) subunit of a calcium channel. These compounds and their pharmaceutically acceptable salts are useful in the treatment of a variety of psychiatric, pain and other disorders.
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- Method of treating tinnitus
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The invention relates to a method of treating tinnitus by administering an alpha2delta ligand such as, for example, a compound of Formula and pharmaceutically acceptable salts thereof, wherein R1 is hydrogen or straight or branched lower alkyl, and n is an integer of from 4 to 6.
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- Mono-and disubstituted 3-propyl gamma-aminobutyric acids
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The instant invention is a series of novel mono- and disubstituted 3-propyl gamma aminobutyric acids of Formula I 1The compounds are useful as therapeutic agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, arthritis, sleep disorders, IBS, and gastric damage. Methods of preparing the compounds and useful intermediates are also part of the invention.
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- Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids
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Several racemic methyl decanoic acids have been synthesised and successfully resolved in esterification with 1-hexadecanol at aw=0.8 in cyclohexane using immobilised Candida rugosa lipase (CRL) as the catalyst. The enantiomeric ratios (E=2.8-68) obtained were surprisingly high even when the methyl group was as remotely located as in 8-methyldecanoic acid (E=25). Interestingly, the lipase shows enantiopreference for the S-enantiomer when the methyl group is located on even numbered carbons i.e. for the 2-,4-,6- and 8-methyldecanoic acids and to the R-enantiomer when the methyl group is located on uneven numbered carbons i.e. for the 3-,5- and 7-methyldecanoic acids.
- Hedenstroem, Erik,Nguyen, Ba-Vu,Silks III, Louis A.
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p. 835 - 844
(2007/10/03)
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- Method of treating cartilage damage
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The invention relates to a method of preventing or treating cartilage damage by administering a GABA analog such as, for example, a compound of Formula 1and pharmaceutically acceptable salts thereof, wherein R1 is hydrogen or straight or branched lower alkyl, and n is an integer of from 4 to 6.
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- Exploration of lipase-catalyzed direct amidation of free carboxylic acids with ammonia in organic solvents
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Lipase-catalyzed direct amidation of free carboxylic acids is possible with ammonia in organic solvents. For butyric acid as a model compound the reaction proceeds well despite precipitation of ammonium butyrate, provided that the added molar amounts of butyric acid and ammonia are in the same range. The addition of ammonium salts is a convenient way to ensure suitable ammonia concentrations. Using Candida antarctica lipase B as the biocatalyst, the amidation proceeds well for various carboxylic acids and is very enantioselective in the amidation of 4-methyloctanoic acid.
- Litjens, Mike J. J.,Straathof, Adrie J. J.,Jongejan, Jaap A.,Heijnen, Joseph J.
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p. 12411 - 12418
(2007/10/03)
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- Exo- and endohormones. XVII: Synthesis of racemic 5,9-dimethyl-heptadecane, the sex pheromone for the leafminer moth Leucoptera scitella
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The paper describes two practical syntheses of 5,9-dimethyl-heptadecane, the sex pheromone of the leafminer moth Leucoptera scitella (Lepidoptera, Lyonetidae). The first route (Scheme 1) involves as key reaction the coupling of 2-methyl-hexyl magnesium bromide with 3-methyl-undecanal. The second route (Scheme 3) is based on the Schlosser-Fouquet coupling reaction of 2-decyl-magnesium bromide with 4-methyl-octyl bromide.
- Ciocan-Tarta, Ilie,Oprean, Ioan,Ghizdavu, Iustin,Pojar-Fenesan, Maria
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p. 215 - 219
(2007/10/03)
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- Unusual Fatty Acids with Specific Odor from Mature Male Goat
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Unusual five 4-ethyl-fatty acids were estimated as main constituents of sebaceous gland secretion of male goat which showed the releaser pheromone activity against the estrous female.These acids exist in both free state and ester form.The structures were confirmed by synthesis.Among the five acids, 4-ethyloctanoic acid showed the strong goaty odor at low concentration.
- Sugiyama, Takeyoshi,Sasada, Hiroshi,Masaki, Junji,Yamashita, Kyohei
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p. 2655 - 2658
(2007/10/02)
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