- Products of the determination of the iodine value with iodine monobromide
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The iodine value (iodine number) is an important analytical characteristic of fats and oils. Leading pharmacopeias determine it using iodine monobromide (Hanus method). We used methyl oleate as a simple analog of unsaturated triacylglycerols to identify the products. After performing the reaction in deuterated solvents under pharmacopeial conditions, NMR spectroscopy revealed the presence of the 9, 10-diiodo, 9, 10-dibromo, and 9, 10-bromoiodo adducts, leaving no educt olefin. The prescribed subsequent addition of potassium iodide led to the formation of methyl 9, 10diiodo and bromoiodo stearate in equal amounts.
- Imming, Peter,Germershaus, Oliver
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- Designing, synthesis, and antimicrobial action of oxazoline and thiazoline derivatives of fatty acid esters
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In this study, a novel series of oxazoline and thiazoline were designed as inhibitors of cytochrome P450 14 alpha-sterol demethylase (CYP51) from Candida albicans and peptide deformylase (PDF) of Escherichia coli. The long chain dibromo derivative of fatty acid esters on reaction with urea and thiourea gave their corresponding oxazolines and thiazolines, respectively. All the compounds were characterized by their spectral data (IR, 1H NMR, 13C NMR and MS) and tested for antibacterial and antifungal activity by disk diffusion assay and minimum inhibitory concentration by the broth microdilution method against gram-positive and gram-negative strains of bacteria as well as fungus strains. The investigation into antimicrobial screening revealed that all the compounds were found to be potent antimicrobial agents. After calculating likeness drug properties of the compounds by Prediction of Activity Spectra for Substances software, ADMET-related descriptors were computed to predict the pharmacokinetic properties for the active and bioavailable compounds by discovery studio 2.5. Molecular docking studies have been performed on PDF of E. coli and CYP 450-14DM of C. albicans to understand the mode of binding of the molecules in the active site of the receptor. Compounds (2-amino-5-(carbomethoxyoctyl)-1,3-oxazoline, 2-amino-5-(carbomethoxyoctyl)-1,3-thiazoline and 2-amino-4-pentyl-5-[(8’R)-8’ hydroxy (carbomethoxydecyl)-1,3-oxazoline) showed excellent antimicrobial activity nearly equivalent to the control compounds and compounds, 2-amino-4-octyl-5-(carbomethoxyheptyl)-1,3-oxazolin, 2-amino-4-(2’R)(2’-hydroxy octyl)-5-(carbomethoxyheptyl)-1,3-oxazoline and 2-amino-4-pentyl-5-[(8’R)-8’-hydroxy(carbomethoxy decyl)-1,3-oxazolineshowed vasodilation and antihypertensive properties. Furthermore, a computational analysis of physicochemical parameters revealed that the most of the compounds possessed drug-like attributes. Using Bioinformatics approach, we found a correlation between the observed and predicted antimicrobial activities.
- Ahmad, Anis,Ahmad, Aiman,Sudhakar, Raja,Varshney, Himani,Subbarao, Naidu,Ansari, Saba,Rauf, Abdul,Khan, Asad U.
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p. 3412 - 3431
(2017/11/16)
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- Ultrasound in fatty acid chemistry: facile dehydrobromination of dibromo fatty esters to acetylenic ester derivatives
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Dehydrobromination of dibromo derivatives of olefinic fatty acids was accomplished using KOH in 20percent aqueous ethanol under cocomitant ultrasonic irradiation (20 kHz) for 30 min at ambient temperature to give the corresponding acetylenic fatty acid derivatives (52-72percent yield).Ten different dibromo fatty acid substrates were used.Products include: fatty acids with a terminal or internal acetylenic bond; acetylenic fatty acids containing an additional functional group, such as hydroxy, chloro or azide group.The structures of the products were characterized by infrared and NMR spectroscopy. - Keywords: acetylenic fatty esters; dehydrobromination; dibromo fatty esters; ultrasond
- Jie, Marcel S. F. Lie Ken,Kalluri, P.
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- Quantitative Treatment of the Rotational Dynamics of Flexible-Chain Molecules. 13C NMR Relaxation Study of Hydrocarbon Chains Attached to the Fluorene Anchor
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13C spin-lattice relaxation times (T1) and nuclear Overhauser enhancements (NOEs) were measured for individual carbons in flexible-chain molecules consisting of a hydrocarbon chain attached to fluorene moiety at position 3 through an ester bond.Quantitative treatment of the relaxation data of the ring carbons revealed an anisotropic motion for all the molecules studied.The relaxation times of the chain carbons were analysed in terms of a correlation function describing multiple internal rotations about successive C-C bonds.The results (rotational diffusion constants) were used to discuss features of the chain mobility as a function of chain length and chain unsaturation.The assumptions involved in the quantitative treatment were examined and the values were compared with those of n-alkanes and lipid bilayers. - Keywords: 13C NMR spin-lattice relaxation times Rotational diffusion constants Rotational dynamics Overall and internal motions Hydrocarbon-chain esters of fluorene-3-carboxylic acid
- Pissas, D.,Dais, Photis,Mikros, E.
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p. 263 - 275
(2007/10/02)
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- Fatty Tetrazoles from Long Chain Olefinic Substrates
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Methyl undec-10-enoate (I), oct-1-ene (II) and methyl octadec-9(Z)-enoate (VII) have been converted into α-bromoalkyltetrazole derivatives (V, IX) using bromine, nitriles and sodium azide as reagents.Dehydrobromination of the α-bromoalkyltetrazoles with sodium ethoxide furnishes the alkenyltetrazoles (VI, X).
- Agarwal, Rajiv,Rauf, Abdul,Ahmad, M.,Osman, S. M.
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p. 175 - 177
(2007/10/02)
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- Synthesis of fatty phosphono esters from vicinal dibromofatty esters
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Reaction of methyl vicinal dibromofatty esters (I and II) with triethyl phosphite under refluxing condition results in the formation of vinyl phosphonates (IV and V) whereas a similar treatment of the dibromofatty ester III with triethyl phosphite affords the bis-phosphonate (VI).
- Afaque, Shahla,Ansari, M. H.,Siddiqui, M. S.
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p. 308 - 310
(2007/10/02)
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- Synthesis and Evaluation of Radioiodinated (E)-18-Iodo-17-octadecenoic Acid as a Model Iodoalkenyl Fatty Acid for Myocardial Imaging
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125I-labeled (E)-18-iodo-17-octadecenoic acid (13) has been prepared and evaluated in rats to determine the myocardial uptake and retention and degree of in vivo deiodination of this model iodovinyl-substituted fatty acid, which contains no structural perturbation to inhibit metabolism.This new agent was prepared by NaI-chloramine-T treatment of (17-carbomethoxyheptadec-1-en-1-yl)boronic acid (11) prepared by catecholborane treatment of methyl 17-octadecynoate (10), followed by basic hydrolysis to the free acid (13).The pivotal substrate, 17-octadecynoic acid (9), was prepared by two new routes .The 125I-labeled acid 13 showed high myocardial uptake (1 h, 1.90-2.28percent dose/g) with 45percent washout after 2 h but lower heart/blood ratios in comparison to analogues containing the tellurium heteroatom.Deiodination was low for the first 2 h after injection (2 h, 61percent dose/g).Excellent myocardial images were obtained in a dog with the 123I-labeled agent.
- Knapp, F. F.,Goodman, M. M.,Kabalka, G. W.,Sastry, K. A. R.
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