Synthesis of 2,3-Diphosphono-DL-glyceric Acid, a Racemic Analogue of 2,3-Diphospho-D-glyceric Acid, the Cofactor of both Phosphoglyceric Acid Mutase and Hemoglobin

1971 ◽  
Vol 49 (3) ◽  
pp. 300-305 ◽  
Author(s):  
Erich Baer ◽  
Ranga Robinson
Keyword(s):  
Hydrobromic Acid ◽  
Methyl Esters ◽  
Acid Methyl Ester ◽  
Triethyl Phosphite ◽  
Glyceric Acid ◽  
Acid Methyl ◽  
Acid Analogue ◽  
Phosphoglyceric Acid ◽  
Major Reaction Product ◽  
Major Reaction

2,3-Diphosphono-DL-glyceric acid, a racemic phosphonic acid, analogue of 2,3-diphospho-D-glyceric acid, the cofactor of phosphoglyceric acid mutase and hemoglobin, has been synthesized. It was obtained by treating the methyl esters of either β-chlorolactic acid, β-bromolactic acid, or glyceric acid with triethyl phosphite at 140–145° for 48 h, hydrolyzing the major reaction product tetraethyl 2,3-diphosphono-DL-glyceric acid methyl ester with concentrated hydrobromic acid at 140° for 24 h, and isolating 2,3-diphosphono-DL-glyceric acid as pentabarium or tricyclohexylammonium salt. 2,3-Diphosphonoglyceric acid and 2,3-diphosphoglyceric acid are readily distinguished from each other by chromatographic and chemical as well as by spectroscopic methods.

Synthesis of Glycerol-1,3-diphosphonic Acid

1973 ◽  
Vol 51 (8) ◽  
pp. 1203-1205 ◽  
Author(s):  
Ranga Robinson ◽  
Erich Baer
Keyword(s):  
Acid Hydrolysis ◽  
Phosphonic Acid ◽  
Hydrobromic Acid ◽  
Condensation Product ◽  
Triethyl Phosphite ◽  
Phosphate Esters ◽  
Glyceric Acid ◽  
Diphosphonic Acid ◽  
Naturally Occurring ◽  
Acid Analogue

The synthesis of glycerol-1,3-diphosphonic acid, the phosphonic acid analogue of the naturally occurring glycerol-1,3-diphosphoric acid, is described. The phosphonic acid analogue was obtained in an overall yield of 29.7%, by heating a mixture of 1,3-dibromo-2-hexadecanoyloxypropane and triethyl phosphite to 140° for 48 h, distilling off in vacuo the excess of triethyl phosphite, hydrolyzing the condensation product, 1,3-bis(diethylphosphono)-2-hexadecanoyloxypropane, with 2 N hydrobromic acid at 100° for 5 h, and isolating the glycerol-1,3-diphosphonic acid in form of the dibarium salt. The glycerol-1,3-diphosphonate differs from glycerol-1,3-diphosphate and other phosphate esters of glycerol and glyceric acid by its greater stability towards acid hydrolysis. The glycerol-1,3-diphosphonic acid is readily distinguished from glycerol-1,3-diphosphoric acid and glycerol-1,2-diphosphoric acid by paper chromatography.

scholarly journals Evaluation of 3-Methylbutanoic Acid Methyl Ester as a Factor Influencing Flavor Cleanness in Arabica Specialty Coffee

2021 ◽  
Vol 11 (12) ◽  
pp. 5413
Author(s):  
Keiko Iwasa ◽  
Harumichi Seta ◽  
Yoshihide Matsuo ◽  
Koichi Nakahara
Keyword(s):  
Methyl Ester ◽  
Methyl Esters ◽  
Acid Methyl Ester ◽  
Chemical Compounds ◽  
Gas Chromatography Mass Spectrometry ◽  
Arabica Coffee ◽  
Acid Methyl ◽  
Coffee Brew ◽  
Coffee Beans ◽  
Specialty Coffee

This paper reports on the chemical compounds in arabica coffee beans with a high Specialty Coffee Association (SCA) cupping score, especially those in specialty coffee beans. We investigated the relationship between the chemical compounds and cupping scores by considering 16 types of Coffea arabica (arabica coffee) beans from Guatemala (SCA cupping score of 76.5–89.0 points). Non-targeted gas chromatography-mass spectrometry-based chemometric profiling indicated that specialty beans with a high cupping score contained considerable amounts of methyl-esterified compounds (MECs), including 3-methylbutanoic acid methyl ester (3-MBM), and other fatty acid methyl esters. The effect of MECs on flavor quality was verified by spiking the coffee brew with 3-MBM, which was the top-ranked component, as obtained through a regression model associated with cupping scores. Notably, 3-MBM was responsible for the fresh-fruity aroma and cleanness of the coffee brew. Although cleanness is a significant factor for specialty beans, the identification of compounds that contribute to cleanness has not been reported in previous research. The chemometric profiling approach coupled with spiking test validation will improve the identification and characterization of 3-MBM commonly found in arabica specialty beans. Therefore, 3-MBM, either alone or together with MECs, can be used as a marker in coffee production.

scholarly journals Identification of Three Strains of Mycobacterium Species Isolated from Clinical Samples Using Fatty Acid Methyl Ester Profiling

2003 ◽  
Vol 31 (2) ◽  
pp. 133-140 ◽  
Author(s):  
A Ozbek ◽  
O Aktas
Keyword(s):  
Fatty Acid ◽  
Methyl Esters ◽  
Acid Methyl Ester ◽  
Cellular Fatty Acid ◽  
Clinical Samples ◽  
Identification System ◽  
Cyclopropane Fatty Acid ◽  
Mycobacterium Species ◽  
Microbial Identification ◽  
Acid Methyl

The cellular fatty acid profiles of 67 strains belonging to three different species of the genus Mycobacterium were determined by gas chromatography of the fatty acid methyl esters, using the MIDI Sherlock® Microbial Identification System (MIS). The species M. tuberculosis, M. xenopi and M. avium complex were clearly distinguishable and could be identified based on the presence and concentrations of 12 fatty acids: 14:0, 15:0, 16:1ω7c, 16:1ω6c, 16:0, 17:0, 18:2ω6,9c, 18:1ω9c, 18:0, 10Me-18:0 tuberculostearic acid, alcohol and cyclopropane. Fatty acid analysis showed that there is great homogeneity within and heterogeneity between Mycobacterium species. Thus the MIS is an accurate, efficient and relatively rapid method for the identification of mycobacteria.

scholarly journals Electronic Structures and Optical Properties of Phenyl C71Butyric Acid Methyl Esters

2013 ◽  
Vol 2013 ◽  
pp. 1-8 ◽  
Author(s):  
Cai-Rong Zhang ◽  
Li-Heng Han ◽  
Jian-Wu Zhe ◽  
Neng-Zhi Jin ◽  
Yu-Lin Shen ◽  
...  
Keyword(s):  
Optical Properties ◽  
Electronic Structures ◽  
Density Functional ◽  
Bulk Heterojunction ◽  
Methyl Esters ◽  
Acid Methyl Ester ◽  
Heterojunction Solar Cells ◽  
Acid Methyl ◽  
B3lyp Functional ◽  
Ir And Raman

Phenyl C71butyric acid methyl ester (PC71BM) has been adopted as electron acceptor materials in bulk heterojunction solar cells with relatively higher power conversion efficiency. The understanding of the mechanism and performance for the devices based upon PC71BM requires the information of conformations, electronic structures, optical properties, and so forth. Here, the geometries, IR and Raman, electronic structures, polarizabilities, and hyperpolarizabilities of PC71BM isomers are studied by using density functional theory (DFT); the absorption and excitation properties are investigated via time-dependent DFT with B3LYP, PBE0, and CAM-B3LYP functionals. The calculated results show that [6,6]PC71BM is more stable than [5,6]PC71BM due to the lower total energy. The vibrational modes of the isomers at IR and Raman peaks are quite similar. As to absorption properties, CAM-B3LYP functional is the suitable functional for describing the excitations of PC71BM because the calculated results with CAM-B3LYP functional agree well with that of the experiment. The analysis of transition configurations and molecular orbitals demonstrated that the transitions at the absorption maxima in UV/Vis region are localizedπ-π*transitions in fullerenes cages. Furthermore, the larger isotropic polarizability of PC71BM indicates that the response of PC71BM to applied external electric field is stronger than that of PC61BM, and therefore resulting into better nonlinear optical properties.

scholarly journals ANALYSIS OF THE ECOLOGICAL PARAMETERS OF THE DIESEL ENGINE POWERED WITH BIODIESEL FUEL CONTAINING METHYL ESTERS FROM CAMELINA SATIVA OIL

Transport ◽  
2010 ◽  
Vol 25 (1) ◽  
pp. 22-28 ◽  
Author(s):  
Sergejus Lebedevas ◽  
Galina Lebedeva ◽  
Violeta Makarevičienė ◽  
Irina Kazanceva ◽  
Kiril Kazancev
Keyword(s):  
Diesel Engine ◽  
Diesel Fuel ◽  
Methyl Esters ◽  
Chemical Properties ◽  
Acid Methyl Ester ◽  
Fuel Mixture ◽  
Camelina Sativa ◽  
Biodiesel Fuel ◽  
Load Range ◽  
Acid Methyl

The article explores the possibilities of using fatty acid methyl esters derived from the oil of a new species of oily plant Camelina sativa not demanding on soil. The performed research on the physical and chemical properties of pure methyl esters from Camelina sativa show that biofuels do not meet requirements for the biodiesel fuel standard (LST EN 14214:2009) of a high iodine value and high content of linoleic acid methyl ester, so they must be mixed with methyl esters produced from pork lard the content of which in the mixture must be not less than 32%. This article presents the results of tests on combustion emission obtained when three‐cylinder diesel engine VALMET 320 DMG was fuelled with a mixture containing 30% of this new kind of fuel with fossil diesel fuel comparing with emissions obtained when the engine was fuelled with a fuel mixture containing 30% of conventional biodiesel fuel (rapeseed oil methyl esters) with fossil diesel fuel. The obtained results show that using both types of fuel, no significant differences in CO and NOx concentrations were observed throughout the tested load range. When operating on fuels containing methyl esters from Camelina sativa, HC emissions decreased by 10 to 12% and the smokeness of exhaust gas by 12 to 25%.

Effect of Saturation and Unsaturation of Fatty Methyl Esters on Biodiesel NOx Emission Characteristics

2015 ◽  
Vol 787 ◽  
pp. 766-770 ◽  
Author(s):  
J. Thangaraja ◽  
S. Rajkumar
Keyword(s):  
Fatty Acid ◽  
Methyl Ester ◽  
Fatty Acid Methyl Ester ◽  
Fatty Acid Methyl Esters ◽  
Methyl Esters ◽  
Acid Methyl Ester ◽  
Degree Of Saturation ◽  
Oxides Of Nitrogen ◽  
Nox Formation ◽  
Acid Methyl

Biodiesel is a renewable fuel and an attractive alternative to replace fossil diesel without major engine modifications. However, the emissions of oxides of nitrogen (NOx) from biodiesel fuelled engines are reported to be higher compared to diesel engine. The characteristics of biodiesel are known to depend on their fatty acid methyl ester (FAME) contents which vary with the feedstock. Thus the contribution of saturation and unsaturation of pure components of fatty acid methyl esters on NOx formation warrants a systematic investigation. This paper attempts to relate the composition of biodiesel with NOx formation. For this purpose, the NO formation from pure fatty acid methyl esters are predicted using extended Zeldovich reaction scheme. Also, the experiments are conducted for measuring oxides of nitrogen from a compression ignition engine operated using neat palm and karanja methyl esters and their blends providing biodiesel combinations of varying degree of saturation for investigation. The measured NOx concentrations are compared with the corresponding predictions to affirm the influence of fatty acid methyl ester on engine NOx characteristics. The results clearly indicate that the change in degree of saturation influences the NOx formation and an increase in the degree of saturation of biodiesel decreases the engine NOx emission.

The antifungal activity of the cuticular and internal fatty acid methyl esters and alcohols in Calliphora vomitoria

Parasitology ◽  
2013 ◽  
Vol 140 (8) ◽  
pp. 972-985 ◽  
Author(s):  
MAREK GOŁĘBIOWSKI ◽  
MAGDALENA CERKOWNIAK ◽  
MAŁGORZATA DAWGUL ◽  
WOJCIECH KAMYSZ ◽  
MIECZYSŁAWA I. BOGUŚ ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Fatty Acid ◽  
Fatty Acid Methyl Esters ◽  
Methyl Esters ◽  
Acid Methyl Ester ◽  
Cuticular Lipids ◽  
Carbon Chains ◽  
Acid Methyl ◽  
Males And Females ◽  
The Individual

SUMMARYThe composition of the fatty acid methyl ester (FAME) and alcohol fractions of the cuticular and internal lipids of Calliphora vomitoria larvae, pupae and male/female adults was obtained by separating these two fractions by HPLC–LLSD and analysing them quantitatively using GC–MS. Analysis of the cuticular lipids of the worldwide, medically important ectoparasite C. vomitoria revealed 6 FAMEs with odd-numbered carbon chains from C15:0 to C19:0 in the larvae, while internal lipids contained 9 FAMEs ranging from C15:1 to C19:0. Seven FAMEs from C15:0 to C19:0 were identified in the cuticular lipids of the pupae, whereas the internal lipids of the pupae contained 10 FAMEs from C13:0 to C19:0. The cuticular lipids of males and females and also the internal lipids of males contained 5, 7 and 6 FAMEs from C15:0 to C19:0 respectively. Seven FAMEs from C13:0 to C19:0 were identified in the internal lipids of females, and 7, 6, 5 and 3 alcohols were found in the cuticular lipids of larvae, pupae, males and females respectively. Only saturated alcohols with even-numbered carbon chains were present in these lipids. Only 1 alcohol (C22:0) was detected in the internal lipids of C. vomitoria larvae, while just 4 alcohols from – C18:0 to C24:0 – were identified in the internal lipids of pupae, and males and females. We also identified glycerol and cholesterol in the larvae, pupae, males and females of C. vomitoria. The individual alcohols and FAMEs, as well as their mixtures isolated from the cuticular and internal lipids of larvae, pupae, males and females of C. vomitoria, demonstrated antimicrobial activity against entomopathogenic fungi.

Fatty Acid Composition of Seeds of Satureja thymbra and S. cuneifolia

2003 ◽  
Vol 58 (7-8) ◽  
pp. 502-504 ◽  
Author(s):  
Ahmet C. Gören ◽  
Gökhan Bilsel ◽  
Mehmet Altun ◽  
Fatih Satıl
Keyword(s):  
Fatty Acid ◽  
Methyl Ester ◽  
Methyl Esters ◽  
Octadecenoic Acid ◽  
Acid Methyl Ester ◽  
Octadecatrienoic Acid ◽  
Octadecanoic Acid ◽  
Hexadecanoic Acid ◽  
Acid Methyl ◽  
Main Components

Abstract The chemical composition of fatty acid methyl esters (FAMEs) from seeds of S. thymbra and S. cuneifolia were analyzed by GC/MS. 7 FAMEs were identified from the seeds of S. thymbra mainly as 9-octadecenoic acid methyl ester (43.9%), hexadecanoic acid methyl ester (11.4%), 9,12,15-octadecatrienoic acid methyl ester (Z,Z,Z) (30.2%), and octadecanoic acid methyl ester (14.1%), while from the seed of S. cuneifolia 10 FAMEs were obtained with the main components, similar to S. thymbra. These were identified as 9-octadecenoic acid methyl ester (10.1%), hexadecanoic acid methyl ester (methyl palmitate, 34.6%), 9,12,15-octadecatrienoic acid methyl ester (Z,Z,Z) (6.3%) and octadecanoic acid methyl ester (1.8%).

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