Capric/caproic/caprylic acid

Four columns are needed to produce the desired products. Considering the Sharp Distillation Sequencing heuristics, heuristic (7) does not apply, as there is more than one product in this mixture. Fatty acids are moderately corrosive, but none is particularly more so than the others, so heuristic (2) does not apply. The most volatile product, the caproic and caprylic mixture, is a small (10 mol %) fraction of the feed, so heuristic (3) does not apply. The least volatile product, the oleic—stearic acids, is 27% of the feed, but is not nearly as large as the capric—lauric acid product, so heuristic (4) does not apply. The split between lauric and myristic acids is closest to equimolar (55 45) and is easy. Therefore, by heuristic (3) it should be performed first. The boiling point list implies that the distillate of the first column contains caproic, caprylic, capric, and lauric acids. This stream requires only one further separation, which by heuristic (/) is between the caproic—caprylic acids and capric—lauric acids. 

Completely negative results on the formation of liver glycogen were obtained when the sodium salts of caproic or caprylic acid61 60 were fed, as well as after the administration of the ethyl esters of caproic, caprylic, capric, myristic or oleic acids or methyl laurate.81 Caproic acid was found to be ineffective as a D-glucose-former in the phlorizinized dog.89... 

Other acids (often as esters) have been found in fermented molasses. Usually these substances are products of bacteriological action and they are not normal constituents of unfermented molasses. Bauer" oil from the yeast fermentation of Cuban blackstrap consists chiefly of the ethyl esters of capric, lauric, myristic and palmitic acids.122 The fat from the scums of hot-room Louisiana molasses contained hexanoic (caproic) and octanoic (caprylic) acids.10 The occurrence of such volatile acids as propionic,128 butyric128 124 and valeric acids124 requires more adequate establishment. 

Capric acid, dl4 Caproaldehyde, h54 Caproic acid, h66 Caproic anhydride, h67 e-Caprolactam, o57 6-Caprolactone, h71 Capronitrile, h63 Caproyl chloride, h73 Caprylic acid, o29 Capryl alcohol, o30 Caprylaldehyde, o40... 

Several aliphatic carboxylic acids have been known for centuries, and their common names reflect their historical sources. Formic acid was extracted from ants formica in Latin. Acetic acid was isolated from vinegar, called acetum ( sour ) in Latin. Propionic acid was considered to be the first fatty acid, and the name is derived from the Greek protos pion ( first fat ). Butyric acid results from the oxidation of butyraldehyde, the principal flavor of butter butyrum in Latin. Caproic, caprylic, and capric acids are found in the skin secrehons of goats caper in Lahn. The names and physical properties of some carboxylic acids are listed in Table 20-1. 

Butyric acid.. Caproic acid.. Caprylic acid. Capric acid... Laurie acid... Myristic acid. Palmitic acid. Stearic acid... Arachidic acid... 

Properties Composition is largely glycerides of oleic, stearic, and palmitic acids, with smaller amounts of the glycerides of butyric, caproic, caprylic, and capric acids. Drange 0.910-0.914. Cow s milk contains approximately 4% butterfat. 

Not much is known about the effect of organic acids on another important pathogen, Salmonella spp., but E. coli and Salmonella are both enteric bacteria and seem to have a similar physiology. It is, however, known that medium chain fatty acids (C6-C12, caproic, caprylic, capric, and lauric) are much more effective against Salmonella than the short-chain fatty acids (formic, acetic, propionic, and butyric). Another important finding was that the short-chain fatty acid butyrate specifically down-regulates the expression of invasion genes in Salmonella spp. at low doses. Medium-chain fatty acids and propionate also decrease the ability of Salmonella spp. to invade epithelial cells. This has been found to be in contrast to acetic acid (Van Immerseel et al., 2006). 

Capric acid—Beoylic add—CnHio,COOH—172—exists in butter, cocoa-oil, etc., associated with caproic and caprylic acids in their glyceric ethers, and in the residues of distillation of Scotch whiskey, as amyl caprate. It is a white, crystalline solid melts, at 27°.5 (81°.5 P.) boils at 273° (523°.4 F.). 

Swem and Jordan [60] prepared the allyl esters of caproic, caprylic, pelargonic, capric, lauric, myristic, palmitic, and stearic acids. Attempts to bulk polymerize the compounds with 0.5% of dibenzoyl peroxide resulted in only a slight lowering of the monomers iodine numbers, indicating very limited polymer formation. Copolymers with diallyl o-phthalate seemed to form with 1-20% of allyl esters. These copolymers were insoluble in acetone, amyl acetate, benzene, and acetic acid. 

Na-0101 T1/8". See Sodium bifluoride NAA. See 1-Naphthylacetic acid NAA-34, NAA-35, NAA-38. See Oleic acid NAA-40, NAA-41. See Caprylic alcohol NAA-42. See Lauryl alcohol NAA-43. See Myristyl alcohol NAA-44. See Cetyl alcohol NAA-45, NAA-46. See Stearyl alcohol NAA-48. See Cetearyl alcohol NAA-60. See Caproic acid NAA-82. See Caprylic acid NAA-102. See Capric acid NAA-122. See Laurie acid NAA-142. See Myristic acid NAA-160, NAA-171. See Palmitic acid NAA-172, NAA-173K, NAA-174, NAA-175, NAA-175S, NAA-176, NAA-180. See Stearic acid NAA-222, NAA-222S. See Behenic acid NAA-312, NAA-312S, NAA-415. See Laurie acid NasATMP. See Pentasodium aminotrimethylene phosphonate... 

Canola oil glyceride Capric acid Caproic acid Capryleth-4 carboxylic acid Capryleth-6 carboxylic acid Capryleth-9 carboxylic acid Caprylic acid Caprylic/capric diglyceryl succinate... 

C14-18 alcohols C16-20 alcohols C7-9 alkyl benzyl phthalate Capric acid Caproic acid Caprolactam Caprylic acid Caprylic/capric triglyceride C12 dibasic acid Chlorinated alpha-olefin, liquid... 

Volatile fatty acids p resent in wine may derive from the anabolism of lipids, resulting in compounds with even number of carbon atoms, by oxidative decarboxylation of a-keto acids or by the oxidation of aldehydes. Volatile fatty acids synthesised from a-keto acids are mainly propanoic add, 2-methyl-l-propanoic acid (isobutyric acid), 2-methyl-l-butanoic acid, 3-methyl-l-butanoic acid (isovaleric acid 3-methylbutyric add) and phenylacetic add. From lipid metabolism, the following fatty acids are reported butanoic add (butyric), hexanoic acid (caproic), odanoic acid (caprylic) and decanoic add (capric) (Dubois, 1994). Although fatty adds are charaderized by unpleasant notes (Table 1), only few compounds of this family attain its perception threshold. However, their flavour is essential to the aromatic equilibrium of wines (Etievant, 1991). 

Calcium stearoyl lactylate, 229,233 Calea urticaefolia, 5 Calendic acid, 11 Calendula officinalis, 11,19 Californian sardine oils, 133 Calvatia gigantea, 153 Camellia sasanqua, 93 Camphor oil, 52 Canbra oil, see Rapeseed oil Candida albicans, 490 Candida species, 19,151-54,478 Candlenut oil, 52, 56,101 Cannabis sativa, 68 Canola oil, see Rapeseed oil Capelin oil, 130,132 Capillary GLC, 273 Capric acid, 1,174,179 see also Decanoic acid Caproic acid, 1,174 see also Hexanoic acid Caprylic acid, 1,174 see also Octanoic acid Carboxylic acids, polymorphism, 343 Carboxyl transferase, 485 Carcass quality of farm animals, 557 Cardiolipin, 138,156 see also Diphosphatidylglycerol Cardiovascular disease, 531,533 Carnitine, role in /S-oxidation, 494 Carotenoids, 38,154,163,397,413,446 Carthamin yellow, see Safflower Carthamus tinctorius, 84 see also Safflower Cary a species, 97... 

Figure 21 GC separation of underivatized saturated and unsaturated FFAs. Peaks Ce o = caproic acid Cs o = caprylic acid C9 o = nonanoic acid Cio o = capric acid Cn o = undecanoic acid Ci2 o = lauric acid Ci4 o = myristic acid Ci6 i =palmitoleic acid Cie o = palmitic acid Cis o = stearic acid. (Reproduced with permission from Brondz I, Olsen I, and Greibroekk T (1983) Direct analysis of free fatty acids in bacteria by gas chromatography. Journal of Chromatography 274 299-304.)...

Fat or Oil C4 Ce Cs C10 C12 Ci4 Cie Butyric Caproic Caprylic Capric Laurie Myristic Palmitic Acid Acid Acid Acid Acid Acid Acid 18 Stearic Acid C16 Palmitoleic Acid C18 C18 C18 Oleic Linoleic Linolenic Acid Acid Acid ... 

The first members of the carboxylic acid series are colorless liquids with sharp or unpleasant odors. Acetic acid, which constitutes about 4% to 5% of vinegar, provides the characteristic odor and flavor. Butyric acid gives rancid butter its disagreeable odor, and the goat acids (caproic, caprylic, and capric in Table 10.1) smell like goats. 3-Methyl-2-hexenoic acid, produced by bacteria, is responsible for the offensive odor of human armpits. Table 10.3 lists some physical properties of selected carboxylic acids. 

The extent of dissociation occurring when a soap is dissolved in water depends upon the nature of the fatty acids from which the soap is made, and also on the concentration of the solution. The sodium salts of cocoa-nut fatty acids (capric, caproic and caprylic acids) are by far the most easily hydrolysed, those of oleic acid and the fatty acids from cotton-seed oil being dissociated more readily than those of stearic acid and taUow fatty acids. The decomposition increases with the amount of water employed. 

Fig. 6-56. Separation of long-chain fatty acids utilizing an ion-suppression technique. - Separator column lonPac NSl (10-pm) eluant (A) 3 10" mol/L HCl / acetonitrile / methanol (70 24 6 v/v/v), (B) 3 10 mol/L HCl / acetonitrile / methanol (16 60 24 v/v/v) gradient linear, 100% A in 15 min to 100% B flow rate 1 mL/min detection suppressed conductivity injection volume 50 pU solute concentrations 100 mg/L butyric acid (1), 100 mg/L caproic acid (2), 200 mg/L caprylic acid (3), 200 mg/L capric acid (4), 300 mg/L lauric acid (5), 300 mg/L myristic acid (6), and 400 mg/L palmitic acid (7).

Commercially, butter oil is modified by controlled enzyme action that releases the volatile and flavorful short chain fatty acids, C4-C10 (e.g., butyric, caproic, caprylic, and capric), and also the nonvolatile long-chain fatty adds. The enzyme system is heat inactivated when the process has reached the desired end point. Such products contain about 48% fat (Figure 9.6). 

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