Reaktionen und Synthesen im organisch‐chemischen Praktikum und Forschungslaboratorium

The territorial marking fluid of the male Bengal tiger, Panthera tigris, consists of a mixture of urine and a small quantity of lipid material that may act as a controlled-release carrier for the volatile constituents of the fluid. Using gas chromatography and gas chromatography-mass spectrometry, 98 volatile compounds and elemental sulfur were identified in the marking fluid. Another 16 volatiles were tentatively identified. The majority of these compounds were alkanols, alkanals, 2-alkanones, branched and unbranched alkanoic acids, dimethyl esters of dicarboxylic acids, γ-and δ-lactones, and compounds containing nitrogen or sulfur. Several samples of the marking fluid contained pure (R)-3-methyl-2-octanone, (R)-3-methyl-2-nonanone, and (R)-3-methyl-2-decanone, but these ketones were partly or completely racemized in other samples. The γ-lactone (S)-(+)-(Z)-6-dodecen-4-olide and the C8 to C16 saturated (R)-γ-lactones and (S)-δ-lactones were present in high enantiomeric purities.The chiral carboxylic acids, 2-methylnonanoic acid, 2-methyldecanoic acid, 2-methylundecanoic acid, and 2-ethylhexanoic acid were racemates. Cadaverine, putrescine, and 2-acetylpyrroline, previously reported as constituents of tiger urine, were not detected. The dominant contribution of some ketones, fatty acids, and lactones to the composition of the headspace of the marking fluid suggests that these compounds may be important constituents of the pheromone. Although it constitutes only a small proportion, the lipid fraction of the fluid contained larger quantities of the volatile organic compounds than the aqueous fraction (urine). The lipid derives its role as controlled-release carrier of the chemical message left by the tiger, from its affinity for the volatiles of the marking fluid. Six proteins with masses ranging from 16 to 69 kDa, inter alia, the carboxylesteraselike urinary protein known as cauxin, previously identified in the urine of the domestic cat and other felid species, were identified in the urine fraction of the marking fluid.

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“…Condensation of benzaldehyde (11.11 g, 0.1 mol) with 2-phenylethylamine (14 g, 0.12 mol) according to Tietze and Eicher (1981) …”

Section: N-benzylidene-2-phenylethylamine (117)mentioning

confidence: 99%

Chemical Characterization of Territorial Marking Fluid of Male Bengal Tiger, Panthera tigris

Burger

Viviers

Bekker³

et al. 2008

J Chem Ecol

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“…All solvents and reagents were purified and prepared according to the literature data. 52 Compounds 6-8 were synthesized according to the procedures described in the literature. C HSQC and HMBC experiments.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, X-ray crystal structure and antimycobacterial activity of enantiomerically pure 1-ethyl-2,3-dicyano-5-(het)aryl-6-hetaryl-1,6-dihydropyrazines

Verbitskiy¹,

Toporova²,

Кодесс³

et al. 2014

Arkivoc

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The Petasis reaction of 6-alkoxy adducts of 1-alkyl-2,3-dicyano-5-arylpyrazinium salts with aromatic boronic acids, such as 2-thienylboronic, 2-furanylboronic and 3-thienylboronic acids, or their benzo analogs in dichloromethane proceeds smoothly at room temperature with the formation of the corresponding 5-aryl-6-hetaryl substituted 1,6-dihydropyrazine derivatives. All dihydropyrazines were separated as pure enantiomers by chiral HPLC, and their absolute configurations for each pair of enantiomers have been determined by X-ray analysis. Individual enantiomers were screened in vitro for their antimycobacterial activities against Mycobacterium tuberculosis H 37 Rv, avium, terrae and extensively drug-resistant and multi-drug-resistant strains isolated from tuberculosis patients in Ural region (Russia). It has been shown that several compounds exhibit a good level of antituberculosis activity compared to the reference drugs.

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“…A synthesis of 9a-fluoro-17,17-dimethyl-18-norandrostane-4,13-dien-11b-ol-3-one from FOM was carried out by a general method. 11 It was very simple, as shown in Fig. 3.…”

Section: Structure Characterization Of F1mentioning

confidence: 99%

Characterization and Quantification of Fluoxymesterone Metabolite in Horse Urine by Gas Chromatography/Mass Spectrometry

et al. 2008

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Reaktionen und Synthesen im organisch‐chemischen Praktikum und Forschungslaboratorium

Cited by 271 publications

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Chemical Characterization of Territorial Marking Fluid of Male Bengal Tiger, Panthera tigris

Chemical Characterization of Territorial Marking Fluid of Male Bengal Tiger, Panthera tigris

Synthesis, X-ray crystal structure and antimycobacterial activity of enantiomerically pure 1-ethyl-2,3-dicyano-5-(het)aryl-6-hetaryl-1,6-dihydropyrazines

Characterization and Quantification of Fluoxymesterone Metabolite in Horse Urine by Gas Chromatography/Mass Spectrometry

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