172376-82-8Relevant articles and documents
Synthesis, characterization and transfection activity of new saturated and unsaturated cationic lipids
Arpicco, Silvia,Canevari, Silvana,Ceruti, Maurizio,Galmozzi, Enrico,Rocco, Flavio,Cattel, Luigi
, p. 869 - 878 (2004)
We synthesized new cationic lipids, analogue to N-[1-(2,3-dioleoyloxy) propyl]-N,N,N-trimethylammonium chloride (DOTMA) and 1,2-dimyristyloxypropyl-3- dimethyl-hydroxyethylammonium bromide (DMRIE), in order to compare those containing a dodecyl chain with those having a relatively long chain with two or five double bonds, such as squalenyl and dihydrofarnesyl derivatives, or complex saturated structures, such as squalane derivatives. The fusogenic helper lipid dioleoylphosphatidylethanolamine (DOPE) was added to cationic lipids to form a stable complex. Liposomes composed of 50:50 w/w cationic lipid/DOPE were prepared and incubated with plasmidic DNA at various charge ratios and the diameter and zeta potential of the complexes were measured. The surface charge of the DNA/lipid complexes can be controlled by adjusting the cationic lipid/DNA ratio. Finally, we tested the in vitro transfection efficiency of the cationic lipid/DNA complexes using different cell lines. The transfection efficiency was highest for the dodecyloxy derivative containing a single hydroxyethyl group in the head, followed by the dodecyloxy and the farnesyloxy trimethylammonium derivatives. Instead the C27 squalenyl and C27 squalanyl derivatives resulted inactive.
Total Synthesis of (±)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation
Tao, Eriko,Inoue, Masaki,Jeong, Taejoo,Kim, In Su,Yoshimitsu, Takehiko
, p. 9064 - 9070 (2020)
A synthetic route to liphagal, a natural PI3Kα inhibitor isolated from Aka coralliphaga, was established. The present route features an organic redox process where an alkynylquinone undergoes reductive cyclization in the presence of a hydroquinone derivative such as hydroxyquinol (1,2,4-benzenetriol) and catalytic PdCl2 to provide a substituted benzofuran suitable for accessing the natural product. The benzofuran formation takes place via the redox transformation between the alkynylquinone and the electron-rich hydroquinones followed by the concomitant Pd(II)-catalyzed oxycyclization of the resultant alkynylhydroquinone.
Sex pheromone of Ascogaster quadridentata, a parasitoid of Cydia pomonella
DeLury, Naomi C.,Gries, Gerhard,Gries, Regine,Judd, Gary J. R.,Brown, John J.
, p. 2229 - 2245 (1999)
Porapak Q volatile extracts of female Ascogaster quadridentata, an egg- larval endoparasitoid of codling moth, Cydia pomonella, bioassayed in Y-tube olfactometers attracted male, but not female, A. quadridentata. Coupled gas chromatographic-electroantennographic detection (GC-EAD) analysis of bioactive extracts revealed three compounds that elicited responses by male A. quadridentata antennae. GC-mass spectra (MS) indicated, and comparative analyses of authentic standards confirmed, that these compounds were (Z,Z)9.12-octadecadienal, (Z)-9-hexadecenal, and 3,7,11-trimethyl-6E, 10- dodecadienal. (Z,Z)-9,12-Octadecadienal alone attracted laboratory-reared male A. quadridentata in Y-tube olfactometer and field-cage bioassays, and attracted feral A. quadridentata in a field experiment. This sex pheromone could be used to help detect populations of A. quadridentata, delineate their distributions, and determine potential sources of parasitoids for capture and release in integrated programs for control of C. pomonella.
Identification and Composition of Clasper Scent Gland Components of the Butterfly Heliconius erato and Its Relation to Mimicry
Darragh, Kathy,Ehlers, Stephanie,H?tling, Susan,Harig, Tim,Jiggins, Chris D.,Schulz, Stefan,Stell, Matthew,Szczerbowski, Daiane
, p. 3300 - 3313 (2021/10/12)
The butterfly Heliconius erato occurs in various mimetic morphs. The male clasper scent gland releases an anti-aphrodisiac pheromone and additionally contains a complex mixture of up to 350 components, varying between individuals. In 114 samples of five different mimicry groups and their hybrids 750 different compounds were detected by gas chromatography/mass spectrometry (GC/MS). Many unknown components occurred, which were identified using their mass spectra, gas chromatography/infrared spectroscopy (GC/IR)-analyses, derivatization, and synthesis. Key compounds proved to be various esters of 3-oxohexan-1-ol and (Z)-3-hexen-1-ol with (S)-2,3-dihydrofarnesoic acid, accompanied by a large variety of other esters with longer terpene acids, fatty acids, and various alcohols. In addition, linear terpenes with up to seven uniformly connected isoprene units occur, e. g. farnesylfarnesol. A large number of the compounds have not been reported before from nature. Discriminant analyses of principal components of the gland contents showed that the iridescent mimicry group differs strongly from the other, mostly also separated, mimicry groups. Comparison with data from other species indicated that Heliconius recruits different biosynthetic pathways in a species-specific manner for semiochemical formation.
Frogolide – An Unprecedented Sesquiterpene Macrolactone from Scent Glands of African Frogs
Menke, Markus,Melnik, Kristina,Peram, Pardha S.,Starnberger, Iris,H?dl, Walter,Vences, Miguel,Schulz, Stefan
, p. 2651 - 2656 (2018/03/29)
Some amphibians use chemical signals in addition to optical and acoustical signals to transmit information. Males of mantellid frogs from Madagascar and hyperoliid frogs from Africa emit complex, species- and sex-specific bouquets of volatiles from their femoral or gular glands. We report here on the identification, synthesis, and determination of the absolute configuration of a macrocyclic lactone occurring in several species of both families, (S)-3,7,11-dodec-6,10-dien-12-olide (S-14, frogolide). Macrolides are a preferred compound class of frog volatiles. Nevertheless, frogolide is the first macrocyclic lactone obviously derived from the terpene pathway, in contrast to known frog macrolides that are usually formed via the fatty acid biosynthetic pathway.
METHOD FOR PRODUCING OPTICALLY ACTIVE 2,3-DIHYDROFARNESAL
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, (2017/07/08)
PROBLEM TO BE SOLVED: To provide a synthetic intermediate useful for obtaining optically active 2,3-dihydrofarnesal high in chemical purity and optical purity, and a satisfactorily efficient method for producing the intermediate. SOLUTION: Provided is optically active farnesyl enamine represented by formula (4) (*denotes an asymmetric carbon atom; R1 and R2 respectively independently denote H, a substituted/unsubstituted 1-20C alkyl group, a substituted/unsubstituted 3-8 membered-ring alicyclic group, a substituted/unsubstituted 6-15C aryl group; a substituted/unsubstituted 2-15C heterocyclic group or a substituted/unsubstituted 7-12C aralkyl group; and R1 and R2 are not simultaneously H or R1 and R2 may be coupled to form a ring). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
METHOD FOR PRODUCING OPTICALLY ACTIVE 2,3-DIHYDROFARNESAL
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, (2015/09/22)
A method for producing an optically active 2,3-dihydrofarnesal of formula (1) is disclosed. The method includes subjecting β-farnesene f formula (2) to amination in the presence of a lithium salt of an amine to obtain (2E)-farnesyl allylamine of general formula (3); subjecting the (2E)-farnesyl allylamine to asymmetric isomerization to obtain an optically active farnesyl enamine of general formula (4); and subjecting the optically active farnesyl enamine to solvolysis:
FRAGRANCE COMPOSITION
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Paragraph 0073, (2015/09/22)
The present invention relates to: a fragrance composition containing (3S)-(6E)-2,3-dihydrofarnesal having a chemical purity of 90 mass% or more and an optical purity of 50% e.e. or more; a cosmetic product containing the fragrance composition; and a method for improving an aroma using the fragrance composition.
METHOD FOR PRODUCING OPTICALLY ACTIVE 2,3-DIHYDROFARNESAL
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, (2015/07/22)
A method for producing an optically active 2,3-dihydrofarnesal represented by formula (1): the method comprising: subjecting β-farnesene represented by formula (2) to amination in the presence of a lithium salt of an amine: to obtain (2E)-farnesyl allylamine represented by general formula (3): subsequently subjecting to asymmetric isomerization to obtain an optically active farnesyl enamine represented by general formula (4): and subjecting the optically active farnesyl enamine to solvolysis, wherein R1, R2, and * are as defined in claims of the present application.
Enantioselective access to (-)-Ambrox starting from β-farnesene
Chapuis, Christian
, p. 197 - 214 (2014/03/21)
Starting from inexpensive (E)-β-farnesene (1), an eight-step enantioselective synthesis of the olfactively precious Ambrox ((-)-2a) has been performed. The crucial step is the catalytic asymmetric isomerization of (2E,6E)-N,N-diethylfarnesylamine (3) to t
