Calcium butyrate

Calcium butyrate [5743-36-2] M 248.2. Crystd from water (5mL/g) by partial evapn in a desiccator. 

Butyric acid is obtained from the animal charcoal wluch has been used in the purification of glycerin, in which it exists as calcium butyrate. It is also formed by subjecting to fermentation a mixture composed of glucose, water, chalk, and cheese or gluten. The calcium butyrate is decomposed by H,SO, and the butyric acid separated by distillation. 

Butyric acid is a thick, sour liquid, which boils at 162°, and is miscible with water in all proportions. Addition of calcium chloride to an aqueous solution of the acid causes the latter to separate as an oil. The other soluble fatty acids, with the exception of formic and acetic acids, act in this way. The salts of butyric acid are soluble in water. Calcium butyrate, (C4H702)2Ca.H20, is more soluble in cold than in hot water. It is precipitated, in part, when a cold saturated solution of the salt is heated to boiling. The calcium salt of isobutyric acid (C4H702)2Ca.5H20, is more soluble in hot than in cold water. 

Calcium butyrate [5743-36-2] M 248.2, d 4 1.271. Reciystallise the butyrate from water (5ml/g) by partial evaporation in a desiccator and dry it in a vacuum to constant weight. [Pathak Bhide J Indian Chem Soc 30 47, 48 1953.] Its dissociation constant at 25° is 0.29 [Colman-Porter Monk J Chem Soc 4363 1952, Beilstein 2IV 785]. 

Erlenmeyer found that the butyl alcohol present in fusel oil yields iso-butyric acid (see below) on oxidation, and is therefore isobutyl alcohol, and he also showed that from isobutyl iodide the same valeric acid is obtained as from the amyl alcohol of fusel oil, which is therefore isoamyl alcohol, derived from dimethylethylmethane. Secondary butyl alcohol was first obtained as hydrate de butylene from erythritol by de Luynes. A. Lieben obtained it from zinc ethyl and dichloroethyl ether, and since he found that on oxidation it gives a ketone he recognised it as secondary butyl alcohol. Lieben and A. Rossi obtained normal butyl alcohol from butyric acid, which was converted into butyraldehyde by distilling calcium butyrate and calcium formate, and a solution of this reduced with a large amount of sodium amalgam. They give structural formulae for the four butyl alcohols, with the boiling-points. 

A major use of butyric acid is in the manufacture of cellulose acetate butyrate plastics. They are used as textile fibers and in situations where resistance to heat and sunlight is essential. Calcium butyrate has been used in some leather tanning processes. Butyric acid esters are added as flavors in some soft drinks and chewing gums. Various derivatives of butyric acid are used as vasoconstrictor drugs, in anesthetics, and as antioxidants (Playne 1985). 

Many substances are known to act as accelerators for concrete. These include soluble inorganic chlorides, bromides, fluorides, carbonates, thiocyanates, nitrites, nitrates, thiosulfates, silicates, aliuninates, alkali hydroxides, and soluble organic compounds such as triethanolamine, calcium formate, calcium acetate, calcium propionate, and calcium butyrate. Some of them are used in combination with water reducers. Quick setting admixture s used in shotcrete applications and which promote setting in a few minutes may contain sodium silicate, sodium aluminate, aluminum chloride, sodium fluoride, strong alkalis, and calcium chloride. Others are solid admixtures such as calcium aluminate, seeds of finely divided Portland cement, silicate minerals, finely divided magnesium carbonate, and calcium carbonate. Of these, calcium chloride has been the most widely used because of its ready availability, low cost, predictable performance characteristics, and successful application over several decades.In some countries the use of calcium chloride is prohibited, in some others, such as Canada and the USA, the use of calcium chloride is permitted provided certain precautions are taken. Attempts have continued to find an effective alternative to calcium chloride because of some of the problems associated with its use. 

Salts of neodecanoic acid have been used in the preparation of supported catalysts, such as silver neodecanoate for the preparation of ethylene oxide catalysts (119), and the nickel soap in the preparation of a hydrogenation catalyst (120). Metal neodecanoates, such as magnesium, lead, calcium, and zinc, are used to improve the adherence of plasticized poly(vinyl butyral) sheet to safety glass in car windshields (121). Platinum complexes using neodecanoic acid have been studied for antitumor activity (122). Neodecanoic acid and its esters are used in cosmetics as emoUients, emulsifiers, and solubilizers (77,123,124). Zinc or copper salts of neoacids are used as preservatives for wood (125). 

The purity of the zinc is unimportant, within wide limits, in determining its life, which is roughly proportional to thickness under any given set of exposure conditions. In the more heavily polluted industrial areas the best results are obtained if zinc is protected by painting, and nowadays there are many suitable primers and painting schemes which can be used to give an extremely useful and long service life under atmospheric corrosion conditions. Primers in common use are calcium plumbate, metallic lead, zinc phosphate and etch primers based on polyvinyl butyral. The latter have proved particularly useful in marine environments, especially under zinc chromate primers . 

Etch primers are widely used. They are mostly based on polyvinyl butyral and contain chromates and phosphoric acid. They are said to act both as primers and as etching solutions because it is believed that the chromates and phosphoric acid form an inorganic him, which provides adhesion, while oxidised polyvinyl butyral provides an organic him. For direct application to new galvanised steel, the best known primers are based on calcium orthoplumbate pigment and metallic lead, but these are now less used for environmental reasons. Zinc-dust paints and zinc-phosphate pigmented paints are also used, but the trend is to use pretreatments to assure good adhesion. 

The ability to disperse the calcium soap formed from a given amount of sodium oleate has been studied for a number of a-sulfo fatty acid esters with 14-22 carbon atoms [28,30]. In principle, the lime soap dispersion property increases with the number of C atoms and the dissymmetry of the molecule. Esters with 14 C atoms have no dispersion power and in the case of esters with 15-17 carbon atoms the least symmetrical are the better lime soap-dispersing agents. However this property does not only depend on the symmetry but on the chain length of the fatty acid group. For example, methyl and ethyl a-sulfomyristate have better dispersing power than dodecyl propionate and butyrate. The esters with 18 and more carbon atoms are about equal in lime soap dispersion power. Isobutyl a-sulfopalmitate is the most effective agent under the test conditions. 

Biocatalysis has emerged as an important tool for the enantioselective synthesis of chiral pharmaceutical intermediates and several review articles have been published in recent years [133-137]. For example, quinuclidinol is a common pharmacophore of neuromodulators acting on muscarinic receptors (Figure 6.50). (JJ)-Quinudidin-3-ol was prepared via Aspergillus melleus protease-mediated enantioselective hydrolysis of the racemic butyrate [54,138]. Calcium hydroxide served as a scavenger of butyric acid to prevent enzyme inhibition and the unwanted (R) enantiomer was racemized over Raney Co under hydrogen for recycling. 

Invertebrate prey species contain analogous, but not identical, sites to those considered above. In many phylla, calcium channels play the role normally ascribed to sodium channels in vertebrates. In addition, the peripheral locomotor neurotransmitter is not acetylcholine but amino acids such as gamma amino butyric acid (GABA). In other phylla, the channels which underly locomotion remain poorly understood. 

Aluminum phosphide Amyl trichlorosilane Benzoyl chloride Boron tribromide Boron trifluoride Boron trifluoride etherate Bromine pentafluoride Bromine trifluoride n-Butyl isocyanate Butyllithium Butyric anhydride Calcium Calcium carbide Chlorine trifluoride Chloro silanes Chlorosulfonic acid Chromium oxychloride Cyanamide Decaborane Diborane... 

Bromine (dry gas) Bromine (liquid) Bromobenzene Butanol Butyl acetate Butylamine Butylchloride Butyric acid Calcium chloride Carbon tetrachloride Castor oil Cellosolve Cellosolve acetate Chlorine (dry gas) Chlorine water Chloroacetic acid Chlorobenzene Chloroform Chlorosulfonic acid Chromic acid Citric acid Colza oil Copper sulfate Cyclohexane Cyclohexanol Cyclohexanone... 

Clladopa, 20,22 Cilastatin, 181 Cilazapril, 170 Cimaterol, 23 Cimetidine, 89,95, 112 Cinflumide, 35 Ciprofloxacin, 141 Clprostene calcium, 14 Qsapride, 42 Cisplatin, 15,16, 17 Qavulanic acid, 180 Clebopride, 42 Clobetasol propionate, 72 Clobetasone butyrate, 72 Clonidine, 5, 38, 88 Clorsulon, 50 Closantel, 36... 

In a SOO-ml. round-bottomed flask fitted with a calcium chloride drying tube are placed 226 g. (1.35 moles) of a-bromo- -butyric acid (Note 1) and 284 g. (175 ml., 2.39 moles) of thionyl chloride (Note 2). A small piece of porous plate is added, and the reaction mixture is allowed to stand at room temperature for 48 hours (Note 3). The excess thionyl chloride is removed by distillation, and the acid chloride is collected at 147-153° (Note 4). The yield of colorless product is 168-197 g. (67-78%). 

Euphorbia coraroides Thunb. E. lasiocaula Boiss. E. lunulata Bunge. E. pallasii Turcz. E. pekinensis Rupr. E. sampsoni Hance E. sieboldiana Moore et Decne. Da Ji (Peking spurge) (root) Euphorbon, euphorbias, butyric acid, calcium malate, calcium oxalate, vitamin C.48-50 Diuretic, emetic, emmenagogue, purgative. 

Some Effects of Lipolysis. The most serious effect of lipolysis is the appearance of the so-called rancid flavor which becomes detectable in milk when the ADV exceeds 1.2-1.5 mEq/liter (Brathen 1980). The fatty acids and their soaps, which are thought to be implicated in the rancid flavor, have been studied in an effort to assess the role of the individual acids in the overall rancid flavor picture. Scanlan et al (1965) reported that only the even-numbered fatty acids from C4 to Cl2 account for the contribution of fatty acids to the flavor, but that no single acid exerts a predominating influence. Another study has implicated the sodium and/or calcium salts of capric and lauric acids as major contributors to the rancid flavor (Al-Shabibi, et al. 1964). Butyric acid, assumed to be the compound most intimately associated with the flavor, was not singled out in either study as being especially involved. 

The basis of phenotypic discrimination of closely related species via Raman spectroscopy lies in its sensitivity to the intracellular molecular components including extrachromosomally encoded phenotypes, such as the Bacillus anthracis or B. thuringiensis toxins or polyglutamic acid capsules. Other prominent examples are cell storage materials like the polyhydroxy butyric acid (PHB), carotenoid-based pigments like sarcinaxanthin, hemoproteins like cytochrome or calcium dipicolinate (CaDPA). Raman spectra of single bacteria, in which the latter four intracellular substances occur, are shown in... 

Fig. 19.2. Micro-Raman spectra of different single bacterial cells normal bacterial Raman spectrum of Staph, wameri compared to Raman spectra with enhanced amounts of subcellular components calcium dipicolinate for a spore of B. pumilus polyhydroxy butyric acid (PHB) in B. megaterium cytochrome in Staph, cohnii and sarcina xanthin in M. luteus...

The formation of the neurite-like processes appears to be dependent on assembly of microtubules as colchicine and Colcemid, antimicrotubule drugs, prevented shape changes in the presence of butyrate (2,8). The amount of tubulin per cell did not change when HeLa were treated with butyrate (R.C.Henneberry, unpublished observations). The role of microtubule assembly was further explored with a calcium ionophore which alters intracellular calcium levels and thus promotes microtubule depolymerization. 

Morphological changes were prevented in butyrate-treated HeLa cells by actinomycin D and cycloheximide (2,8,13). After removal of butyrate, the cells reverted to a normal morphology over a 24 h time course (2,8,12,13). When butyrate-treated cells were detached from the cuTture dishes with trypsin, they assumed a spherical shape and, when replated in the absence of butyrate, their neurite-like processes transiently re-extended (13). This re-extension was blocked when cycloheximide but not the calcium ionophore was included during the initial exposure of the cells to butyrate (13). Process formation, however, did resume in the presence of cycloheximide (1 3). These results were interpreted as indicating that the fatty acid induces a protein(s) required for process formation which can accumulate in the absence of processing and promote processing in the absence of inducer (13). 

HI - BUTYRIC ACID, 9-(2,9-DIHYDROXY-3,3-OIM6THYLBUTYRAMIDO)-, CALCIUM SALT, HYORATE (9 2 1)... 

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