Phosphonolipids. XXVII. Synthesis of phosphonic acid analogs of saturated and unsaturated L-α-lecithins

1977 ◽  
Vol 55 (8) ◽  
pp. 907-910
Author(s):  
Ranga Robinson ◽  
Erich Baer
Keyword(s):  
Fatty Acid ◽  
Low Temperature ◽  
Acid Chloride ◽  
Phosphonic Acid ◽  
Cadmium Chloride ◽  
Chloride Complex ◽  
Fatty Acid Chloride

A procedure for the synthesis of saturated and unsaturated phosphonolecithin from the cadmium chloride complex of sn-glycerol-3-(2-trimethylammoniumethyl)-phosphonate is reported. The phosphonolecithins are obtained by acylating sn-glycerol-3(2-trimethylammoniumethyl)-phosphonate – cadmium chloride complex with fatty acid chloride and pyridine at low temperature. The preparation of the distearoyl, dipalmitoyl, dimyristoyl, and dioleoyl phosphonolecithins by this procedure is described.

SYNTHESIS OF SATURATED AND UNSATURATEDL-α-LECITHINS ACYLATION OF THE CADMIUM CHLORIDE COMPOUND OFL-α-GLYCERYLPHOSPHORYLCHOLINE

1959 ◽  
Vol 37 (8) ◽  
pp. 953-959 ◽  
Author(s):  
Erich Baer ◽  
Dmytro Buchnea
Keyword(s):  
Fatty Acid ◽  
Low Temperature ◽  
Sodium Hydroxide ◽  
Optical Activity ◽  
Mercuric Chloride ◽  
Acid Chloride ◽  
Cadmium Chloride ◽  
Addition Compound ◽  
Fatty Acid Chloride

A facile procedure for the preparation of saturated and unsaturated L-α-lecithins from L-α-glycerylphosphorylcholine (GPC) is reported. The lecithins are obtained by acylating L-α-GPC, in the form of its cadmium chloride addition compound, with fatty acid chloride and pyridine at low temperature (0°–25°). The acylation proceeds rapidly and yields optically pureL-α-lecithins. The preparation of the distearoyl-, dimyristoyl-, and dioleoyl L-α-lecithins by this procedure is described.The deacylation of lecithins with mercuric chloride or sodium hydroxide was investigated. Both procedures give a partially racemized L-α-GPC. This was established by the finding that the optical activity of the lecithins resulting from reacylating the L-α-GPC preparations in the form of their cadmium chloride compounds was considerably lower than that of the corresponding authentic lecithins.

SYNTHESIS OF SATURATED AND UNSATURATEDL-α-LECITHINS ACYLATION OF THE CADMIUM CHLORIDE COMPOUND OFL-α-GLYCERYLPHOSPHORYLCHOLINE

1959 ◽  
Vol 37 (1) ◽  
pp. 953-959 ◽  
Author(s):  
Erich Baer ◽  
Dmytro Buchnea
Keyword(s):  
Fatty Acid ◽  
Low Temperature ◽  
Sodium Hydroxide ◽  
Optical Activity ◽  
Mercuric Chloride ◽  
Acid Chloride ◽  
Cadmium Chloride ◽  
Addition Compound ◽  
Fatty Acid Chloride

A facile procedure for the preparation of saturated and unsaturated L-α-lecithins from L-α-glycerylphosphorylcholine (GPC) is reported. The lecithins are obtained by acylating L-α-GPC, in the form of its cadmium chloride addition compound, with fatty acid chloride and pyridine at low temperature (0°–25°). The acylation proceeds rapidly and yields optically pureL-α-lecithins. The preparation of the distearoyl-, dimyristoyl-, and dioleoyl L-α-lecithins by this procedure is described.The deacylation of lecithins with mercuric chloride or sodium hydroxide was investigated. Both procedures give a partially racemized L-α-GPC. This was established by the finding that the optical activity of the lecithins resulting from reacylating the L-α-GPC preparations in the form of their cadmium chloride compounds was considerably lower than that of the corresponding authentic lecithins.

scholarly journals Esterification of Lignin Isolated by Deep Eutectic Solvent Using Fatty Acid Chloride, and Its Composite Film with Poly(lactic acid)

Polymers ◽  
2021 ◽  
Vol 13 (13) ◽  
pp. 2149
Author(s):  
Chan-Woo Park ◽  
Song-Yi Han ◽  
Rajkumar Bandi ◽  
Ramakrishna Dadigala ◽  
Eun-Ah Lee ◽  
...  
Keyword(s):  
Lactic Acid ◽  
Fatty Acid ◽  
Composite Film ◽  
Acid Chloride ◽  
Pinus Densiflora ◽  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Morphological Characteristics ◽  
Poly Lactic Acid ◽  
Fatty Acid Chloride

In this study, the effect of lignin esterification with fatty acid chloride on the properties of lignin and lignin/poly(lactic acid) (PLA) composites was investigated. Lignocellulose (Pinus densiflora S. et Z.) was treated using a deep eutectic solvent (DES) with choline chloride (ChCl)/lactic acid (LA). From the DES-soluble fraction, DES-lignin (DL) was isolated by a regeneration process. Lignin esterification was conducted with palmitoyl chloride (PC). As the PC loading increased for DL esterification, the Mw of esterified DL (EDL) was increased, and the glass transition temperature (Tg) was decreased. In DL or EDL/PLA composite films, it was observed that EDL/PLA had cleaner and smoother morphological characteristics than DL/PLA. The addition of DL or EDL in a PLA matrix resulted in a deterioration of tensile properties as compared with neat PLA. The EDL/PLA composite film had a higher tensile strength and elastic modulus than the DL/PLA composite film. DL esterification decreased water absorption with lower water diffusion coefficients. The effect of lignin esterification on improving the compatibility of lignin and PLA was demonstrated. These results are expected to contribute to the development of high-strength lignin composites.

scholarly journals Esterified Coconut Coir by Fatty Acid Chloride as Biosorbent in Oil Spill Removal

BioResources ◽  
2015 ◽  
Vol 10 (4) ◽  
Author(s):  
Nor Azah Yusof ◽  
Hayati Mukhair ◽  
Emilia Abdul Malek ◽  
Faruq Mohammad
Keyword(s):  
Fatty Acid ◽  
Oil Spill ◽  
Acid Chloride ◽  
Fatty Acid Chloride ◽  
Coconut Coir

Effect of Fluff Pulp Characteristics on the Efficiency of Gas Grafting by Fatty Acid Chloride

2016 ◽  
Vol 48 (5) ◽  
pp. 5
Author(s):  
Jin Ho Seo ◽  
Tai Ju Lee ◽  
Kwang Seob Lee ◽  
Dong Jin Lee ◽  
Myoung Ku Lee ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Acid Chloride ◽  
Fatty Acid Chloride

Gas Grafting of Fatty Acid Chloride and Recycled Fibers

2016 ◽  
Vol 48 (4) ◽  
pp. 54 ◽  
Author(s):  
Tai Ju Lee ◽  
Jin Ho Seo ◽  
Myung Ku Lee ◽  
Jeong Yong Ryu
Keyword(s):  
Fatty Acid ◽  
Acid Chloride ◽  
Fatty Acid Chloride ◽  
Recycled Fibers

Study on the Gas Grafting Efficiency of Paper According to Carbon Number of Fatty Acid Chloride

2020 ◽  
Vol 52 (4) ◽  
pp. 5-11
Author(s):  
Kyoung-Hwa Choi ◽  
Ji-Seon Choi ◽  
Cheol-Woo Lee ◽  
Kwang-Seob Lee ◽  
Jeong-Yong Ryu
Keyword(s):  
Fatty Acid ◽  
Acid Chloride ◽  
Carbon Number ◽  
Fatty Acid Chloride ◽  
Grafting Efficiency

PHOSPHONOLIPIDS: XI. SYNTHESIS OF PHOSPHONOLIPID METABOLITES. L-α-GLYCERYL-(2-TRIMETHYLAMMONIUMETHYL)PHOSPHONATE

1967 ◽  
Vol 45 (11) ◽  
pp. 1747-1754 ◽  
Author(s):  
Erich Baer ◽  
Ranga Robinson
Keyword(s):  
Acid Hydrolysis ◽  
Phosphonic Acid ◽  
Cadmium Chloride ◽  
Condensation Product ◽  
Hydrolysis Product ◽  
Chloride Complex ◽  
Acid Analogue ◽  
Benzene Removal

The synthesis of a possible intermediate in phosphonolipid metabolism, viz. L-α-glyceryl-(2-trimethylammoniumethyl)phosphonate, a phosphonic acid analogue of L-α-glycerylphosphorylcholine, is described. The compound was obtained by condensation of D-acetone glycerol with (2-bromoethyl)metaphosphonate in boiling benzene, removal of the acetone group of the condensation product by acid hydrolysis, treatment of the hydrolysis product in dimethylformamide with trimethylamine at 60–62° for 3 days, isolation of L-α-glyceryl-(2-trimethylammoniumethyl)phosphate as cadmium chloride complex. Removal of the cadmium chloride was effected with a mixture of Amberlites IR-45 and IRC-50. A procedure for the preparation of (2-bromoethyl)metaphosphonate is reported.

Synthesis of Biodegradable Plastic Films from Oil Palm Empty Fruit Bunch Cellulose

2015 ◽  
Vol 1123 ◽  
pp. 173-176 ◽  
Author(s):  
Tjahjono Herawan ◽  
Meta Rivani
Keyword(s):  
Fatty Acid ◽  
Acid Chloride ◽  
Oil Palm ◽  
Homogeneous System ◽  
Biodegradable Plastic ◽  
Molar Ratio ◽  
Cellulose Ester ◽  
Empty Fruit Bunch ◽  
Fatty Acid Chloride ◽  
Molar Ratios

Cellulose from Oil Palm Empty Fruit Bunch (OPEFB) has a possibility to be converted into biodegradable plastic cellulose ester due to its huge availability. Cellulose ester has thermoplastic properties and is widely used in many polymer applications. This paper describes about esterification OPEFB cellulose with long chain fatty acid chloride in homogeneous system. Some different molar ratios of anhydroglucose unit (AGU) to fatty acid chloride were applied to observe cellulose ester with regards to weight increase percentage (%WIP), recovery yield (%RY) and degree of substitution (DS). Others characteristics were also determined, such as solubility and tensile strength of film casting (MPa). Cellulose palmitate, cellulose laurate and cellulose oleate were successfully produced from OPEFB cellulose. The study found that there is a correlation between type and molar ratio of fatty acid chloride. In an identical reaction condition, a longer fatty acid chlorides and a higher ratio molar AGU to fatty acid chloride produce cellulose ester with high WPI except cellulose oleate ester.

scholarly journals Sustainable Large-Scale Aquaculture of the Northern Hemisphere Sea Lettuce, Ulva fenestrata, in an Off-Shore Seafarm

2021 ◽  
Vol 9 (6) ◽  
pp. 615
Author(s):  
Sophie Steinhagen ◽  
Swantje Enge ◽  
Karin Larsson ◽  
Joakim Olsson ◽  
Göran M. Nylund ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Low Temperature ◽  
Northern Hemisphere ◽  
Biochemical Composition ◽  
Large Scale ◽  
Biomass Yield ◽  
Phenolic Content ◽  
Seedling Density ◽  
Ulva Fenestrata ◽  
High Nutrient

The growing world population demands an increase in sustainable resources for biorefining. The opening of new farm grounds and the cultivation of extractive species, such as marine seaweeds, increases worldwide, aiming to provide renewable biomass for food and non-food applications. The potential for European large-scale open ocean farming of the commercial green seaweed crop Ulva is not yet fully realized. Here we conducted manipulative cultivation experiments in order to investigate the effects of hatchery temperature (10 and 15 °C), nutrient addition (PES and 3xPES) and swarmer density (500 and 10,000 swarmers ml−1) on the biomass yield and biochemical composition (fatty acid, protein, carbohydrate, pigment and phenolic content) of off-shore cultivated Ulva fenestrata in a Swedish seafarm. High seedling densities were optimal for the growth of this northern hemisphere crop strain and significantly increased the mean biomass yield by ~84% compared to low seedling densities. Variations of nutrients or changes in temperature levels during the hatchery phase were not necessary to increase the subsequent growth in an open-water seafarm, however effects of the factors on the thallus habitus (thallus length/width) were observed. We found no significant effect of the environmental factors applied in the hatchery on the total fatty acid or crude protein content in the off-shore cultivated Ulva. However, low seedling density and low temperature increased the total carbohydrate content and furthermore, high temperature in combination with high nutrient levels decreased the pigment content (chlorophyll a, b, carotenoids). Low temperature in combination with high nutrient levels increased the phenolic content. Our study confirms the successful and sustainable potential for large-scale off-shore cultivation of the Scandinavian crop U. fenestrata. We conclude that high seedling density in the hatchery is most important for increasing the total biomass yield of sea-farmed U. fenestrata, and that changing temperature or addition of nutrients overall does not have a large effect on the biochemical composition. To summarize, our study contributes novel insights into the large-scale off-shore cultivation potential of northern hemisphere U. fenestrata and underpins suitable pre-treatments during the hatchery phase of seedlings to facilitate a successful and cost-efficient large-scale rope cultivation.

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