Propane-1,2,3-triol-2-

The double bonds were reduced to the give the saturated compounds, so the doublebond configuration was not an immediate issue. It appears, however, that the -double bonds are formed. The debenzylated derivatives of propan-1,2,3-triol occur as lipid components in various prokaryotes (archaebacteria) that grow under extreme thermal conditions. 

A Garzon, A Poupaert, M Claesen, P Dumont. A lymphotropic prodrug of L-dopa Synthesis, pharmacological properties, and pharmacokinetic behavior of 1,3-dihex-adecanoyl-2-r(S)-2-amino-3-(3,4-dihydroxyphenyl) propanoyl] propane-1,2,3-triol. J Med Chem 29 687-691, 1986. 

The majority of fatty acids in tissues are combined with other molecules. In food fats and oils, fatty acids are esterified to molecules of glycerol (propane-1,2,3-triol). Figure 11.3 shows how three fatty acids can combine with a single... 

Benzanthrone (6.73) is the source of various commercially important violet, blue and green vat dyes. This tetracyclic system can be prepared from a mixture of anthraquinone and propane-1,2,3-triol (glycerol) by heating with iron powder in concentrated sulphuric acid. The reaction involves reduction of anthraquinone to anthrone (6.74) followed by condensation (Scheme 6.14) with propenal (acrolein), the latter compound being generated... 

The commonest approach is the Skraup synthesis. Here a mixture of glycerol (propane-1,2,3-triol), aniline (phenylamine), sulfuric acid, nitrobenzene and ferrous [iron(II)] sulfate are heated together (Scheme... 

Glycerol (propane-1,2,3-triol) is a very important structural part of the phospholipids, the major components of natural membrane bilayers. Based on this natural scaffold, diesters of glycerol and of related derivatives have been extensively used for the construction of synthetic building blocks carrying vicinal lipid chains (for examples, see Scheme 14). 

Increasing the number of hydroxy groups in the substrate results in a sharp decrease in the yield of fluorinated compounds due to resinification and carbonization. This may be avoided by conducting the reactions at low temperatures in anhydrous hydrogen fluoride. Thus, the reaction of sulfur tetrafluoride with propane-1.2,3-triol (glycerol) at — 40 C gives 3-fluoro-propane-l,2-diyl sulfite (5) in high yield.60... 

Fast atom bombardment (FAB), as the name implies, involves bombarding a solution of the analyte in a matrix (most usually propane-1,2,3-triol, propane-1,2,3-trithiol, 2-nitrobenzyl alcohol or triethanolamine, Figure 5.4) with a beam of fast moving atoms, generally xenon atoms with energy in the range 6-9 keV (580-870 kJ mol ). 

Glycerol (propan-1,2,3-triol) is a readily available raw material from biosus-tainable sources such as rape-seed and sunflower the many products that can be formed from it by oxidation find economic use as intermediates in the fine chemicals industry. However, its oxidation constitutes a complicated scenario by reason of the parallel and sequential reaction paths that can be followed (Scheme 8.3) obtaining a desired product therefore constitutes a considerable challenge. The mono-aldehyde readily isomerises under basic conditions to dihydroxyacetone, but fortunately it is less easily oxidised, so that glyceric acid (HOCH2-CH(OH)-CC>2H) is frequently a major product. Gold catalysts, as in other reactions, do not suffer from deactivation, nor do... 

Glycerol (propane-1,2,3-triol) is a viscous symp with molecular weight 92 g/mol, boiling point 290 °C, and density... 

The most common types of lipids are esters of glycerol. Glycerol is just propane-1,2,3-triol but it has interesting stereochemistry. It is not chiral as it has a plane of symmetry, but the two primary Oh[ groups are enantiotopic (Chapter 16), If one of them is changed—hy esterification, for example—the molecule becomes chiral. Natural glycerol phosphate is such an ester and it is optically active. 

Simple trihydric alcohols contain three OH groups per molecule and an example is propan-1,2,3-triol or glycerol or glycerine (Figure 3.3). Its derivatives and compounds figure greatly in the structures of fats (lipids see Section 4.8). 

Thermodynamic vs. Kinetic Control in the Formation of Isopropylidene Acetals from Butane-1,2,4-triols and Propane-1,2,3-triols... 

In the thermodynamically controlled isopropylidenation of propane-1,2,3-triols, it is the 5-membered 1,3-dioxolane ring that is preferred (see section 3.2.1). However in the case of propane-2-acylamino-l 3-diols, the thermodynamically favoured product is the 1,3-dioxane ring [Scheme 8,162].356... 

Fats are natural esters of propane-1,2,3-triol (glycerol). Soap used to be made by boiling animal fats with alkali this is why the hydrolysis of esters used to be called saponification . 

Some pharmacopeias also contain specifications for diluted glycerin solutions. The JP 2001 contains a monograph for glycerin that contains 84-87% of propane-1,2,3-triol (C3H8O3). The PhEur 2005 contains a monograph for glycerol 85 per cent that contains 83.5-88.5% of propane-1,2,3-triol... 

Fixed oils and fats are naturally occurring products, usually of plant origin, that are used extensively in pharmaceutical formulation. They are very susceptible to oxidative decomposition (a process called rancidity) and special precautions must be taken to control their stability and prevent their decomposition. Compounds of this type exist as complex mixtures of structurally similar oils, the composition of which can vary from year to year depending on factors such as climate, time of harvest, etc. Chemically, fixed oils and fats are esters of the alcohol glycerol (propane-1,2,3-triol) with three molecules of long-chain carboxylic acids, called fatty acids, which may all be the same or may differ depending on the oil (Figure 8.15). 

Figure 2 Optical absorption spectra ofthe solvated electron in various solvents (from [2] with addition of other data). Abbreviations Hfi water MeOH methanol EtOH ethanol IPrOH propan-1-ol 2PrOH propan-2-ol 12ED ethane-1,2-diol or ethylene glycol I2PD propane-1,2-diol I3PD propane-1,3-dlol GLY glycerol or propane-1,2,3-triol R NNTfy methyl-tributyl-ammonium bis[trifluoromethyl-sulfonyl]imide EDA ethane-1,2 -diamine I3PDA propane- 1,3-diamlne NH ammonia ( JI,- propane DME dimethylether DEA diethanolamine THE tetrahydrofuran Mel HE methyltetrahydrofuran DEE diethylether.

The lipid membrane is made up of a variety of fat-derived chemicals, the most important of which are the phospholipids (or lecithins) and ceramides. Phosphatidylcholine (13.7) is a typical phospholipid. The molecular structure is based on glycerol, propan-1,2,3-triol. Two of the alcohol functions are esterified with fatty acids, stearic acid in this case, and the third (one of the primary alcohol functions) with phosphoric... 

Acetic acid, mercapto-, monoester with 1,2,3-propanetriol Acetic acid, mercapto-, monoester with glycerol EINECS 260-264-8 Glycerol monomercapto-aoetate Glyceryl monothioglycolate Glyceryl thio-glycolate Meroaptoacetio acid, monoester with propane-1,2,3-triol Meroaptoacetio acid, monoester with 1,2,3-propanetriol, May also contain the isomeric 2 -ester,... 

In fast atom bombardment (FAB), the sample is introduced as a viscous liquid - often dissolved in a solvent such as glycerol (propane-1,2,3-triol) -which is then bombarded with a stream of energetic atoms or ions (typically argon or xenon at energies up to 30 keV) rather than electrons. This results in sputtering of molecules from the sample, and a proportion of them are also ionized. Fragmentation may also occur during collision and ionization. This cloud of ions is then directed into the mass spectrometer for analysis. This method is typically useful for peptides or small proteins of RMM up to about 10,0(X). 

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