Flavors oxidation

Excipients can lose quality over time. Oils, paraffins, and flavors oxidize cellulose gums may lose viscosity. Polymeric materials used in film coating or to modify release from the dosage form can age due to changes in glass transition temperature. This can lead to changes in elasticity, permeability, and hydration rate and associated changes in release properties or appear-ance. " ... 

Decomposition of Lipid Hydroperoxides ( Off-Flavor Oxidation Products)...387... 

One disadvantage of fats contained within foodstuffs is the deterioration of the fat through oxidative rancidity. Many consumers find the aroma and flavor of deteriorated fats in foods repulsive, while others are fond of country ham and butter which owe thek aroma and flavor to fat rancidity and other breakdown products. The use of antioxidants (qv) makes such products commercially viable. 

Chemical bleaching is never used on oils intended for edible use because it oxidizes unsaturated fatty acids to cause off-flavors. However, it does find wide usage for specialty linseed oil, for the paint industry, and fatty chemicals such as sorbitan esters of fatty acids and sodium stearoyl lactylate. Residual peroxide is destroyed by heating above its decomposition temperature. 

Analysis of Trace or Minor Components. Minor or trace components may have a significant impact on quaHty of fats and oils (94). Metals, for example, can cataly2e the oxidative degradation of unsaturated oils which results in off-flavors, odors, and polymeri2ation. A large number of techniques such as wet chemical analysis, atomic absorption, atomic emission, and polarography are available for analysis of metals. Heavy metals, iron, copper, nickel, and chromium are elements that have received the most attention. Phosphoms may also be detectable and is a measure of phosphoHpids and phosphoms-containing acids or salts. 

More and more raw spices are converted to finished products near the growing sites. This saves shipping costs of bulk vs concentrate. Rapid processing also assures less loss of flavor volatiles resulting from evaporation, reduction of colored components due to oxidation or isomeri2ation, and reduction of losses due to insect and rodent infestation. 

Essentia.1 Oils. Essential oils (qv) are extracted from the flower, leaf, bark, fmit peel, or root of a plant to produce flavors such as mint, lemon, orange, clove, cinnamon, and ginger. These volatile oils are removed from plants either via steam distillation, or using the cold press method, which avoids heat degradation. Additional processing is sometimes employed to remove the unwanted elements from the oils, such as the terpenes in citms oils which are vulnerable to oxidation (49,50). 

In the production of opalescent or natural-type apple juice, ascorbic acid is added to the fmit pulp before pressing, or to the juice as it comes from the press, to retain more of the apple flavor (4). Ascorbic acid addition and pasteurization of the juice as soon as possible after pressing prevent polyphenol oxidation, which causes browning and contributes to pulp flocculation. 

Mag nesia. ndAlumina. Suspension. A mixture of salts, available as Maalox, Mylanta, Gelusil, and Aludrox, contains magnesium hydroxide [1309-42-8] Mg(OH)2, and variable amounts of aluminum oxide in the form of aluminum hydroxide and hydrated aluminum oxide, ie, 2.9—4.2% magnesium hydroxide and 2.0—2.4% aluminum oxide, Al O, for a mixture of 4.9—6.6% combined magnesium hydroxide and aluminum oxide. This mixture may contain a flavoring and antimicrobial agents in a total amount not to exceed 0.5% (see Aluminum compounds, aluminum oxide). 

Direct oxidation yields biacetyl (2,3-butanedione), a flavorant, or methyl ethyl ketone peroxide, an initiator used in polyester production. Ma.nufa.cture. MEK is predominandy produced by the dehydrogenation of 2-butanol. The reaction mechanism (11—13) and reaction equihbtium (14) have been reported, and the process is in many ways analogous to the production of acetone (qv) from isopropyl alcohol. 

Diketones can be prepared by oxidation of the corresponding monoketone (287) or a-hydroxyketone (288). 1,2-Diketones are used extensively as intermediates in the preparation of pharmaceuticals, flavors, and fragrances. Toxicity data for selected diketones are shown in Table 11. 

Experimental procedures have been described in which the desired reactions have been carried out either by whole microbial cells or by enzymes (1—3). These involve carbohydrates (qv) (4,5) steroids (qv), sterols, and bile acids (6—11) nonsteroid cycHc compounds (12) ahcycHc and alkane hydroxylations (13—16) alkaloids (7,17,18) various pharmaceuticals (qv) (19—21), including antibiotics (19—24) and miscellaneous natural products (25—27). Reviews of the microbial oxidation of aUphatic and aromatic hydrocarbons (qv) (28), monoterpenes (29,30), pesticides (qv) (31,32), lignin (qv) (33,34), flavors and fragrances (35), and other organic molecules (8,12,36,37) have been pubflshed (see Enzyp applications, industrial Enzyt s in organic synthesis Elavors AND spices). 

Cyanide Wastes. Ozone is employed as a selective oxidant in laboratory-scale synthesis (7) and in commercial-scale production of specialty organic chemicals and intermediates such as fragrances, perfumes (qv), flavors, antibiotics (qv), hormones (qv), and vitamins (qv). In Japan, several metric tons per day (t/d) of piperonal [120-57-0] (3,4-methylenedioxybenzaldehyde) is manufactured in 87% yield via ozonolysis and reduction of isosafrole [93-16-3], Piperonal (or heHotropine [120-57-0]) has a pleasant odor and is used in perfumery. Oleic acid [112-80-1/, CH3(CH2 )7CH—CH(CH2 ). C02H, from tall oil (qv) is ozonated on a t/d scale to produce pelargonic, GgH2yG02H, and azelaic, H02G(GH2)yG02H, acids. Oleic acid also is ozonated in Japan... 

Polyunsaturated fatty acids in vegetable oils, particularly finolenic esters in soybean oil, are especially sensitive to oxidation. Even a slight degree of oxidation, commonly referred to as flavor reversion, results in undesirable flavors, eg, beany, grassy, painty, or fishy. Oxidation is controlled by the exclusion of metal contaminants, eg, iron and copper addition of metal inactivators such as citric acid minimum exposure to air, protection from light, and selective hydrogenation to decrease the finolenate content to ca 3% (74). Careful quality control is essential for the production of acceptable edible soybean oil products (75). 

Fermentation. The term fermentation arose from the misconception that black tea production is a microbial process (73). The conversion of green leaf to black tea was recognized as an oxidative process initiated by tea—enzyme catalysis circa 1901 (74). The process, which starts at the onset of maceration, is allowed to continue under ambient conditions. Leaf temperature is maintained at less than 25—30°C as lower (15—25°C) temperatures improve flavor (75). Temperature control and air diffusion are faciUtated by distributing macerated leaf in layers 5—8 cm deep on the factory floor, but more often on racked trays in a fermentation room maintained at a high rh and at the lowest feasible temperature. Depending on the nature of the leaf, the maceration techniques, the ambient temperature, and the style of tea desired, the fermentation time can vary from 45 min to 3 h. More highly controlled systems depend on the timed conveyance of macerated leaf on mesh belts for forced-air circulation. If the system is enclosed, humidity and temperature control are improved (76). 

Mixed sulfides are prepared in the flavor industry by the reaction of thiols, 2inc oxide, and a bromoalkane (39). Some of these mixed sulfides are constituents of allium, asafetida, coffee, and meat flavors. A representative reaction is represented in equation 24. 

Benzaldehyde. Annual production of ben2aldehyde requires ca 6,500—10,000 t (2-3 x 10 gal) of toluene. It is produced mainly as by-product during oxidation of toluene to benzoic acid, but some is produced by hydrolysis of ben2al chloride. The main use of ben2aldehyde is as a chemical intermediate for production of fine chemicals used for food flavoring, pharmaceuticals, herbicides, and dyestuffs. 

Diacetyl, acetoin, and diketones form during fermentation. Diacetyl has a pronounced effect on flavor, with a threshold of perception of 0.1—0.2 ppm at 0.45 ppm it produces a cheesy flavor. U.S. lager beer has a very mild flavor and generally has lower concentrations of diacetyl than ale. Diacetyl probably forms from the decarboxylation of a-ethyl acetolactate to acetoin and consequent oxidation of acetoin to diacetyl. The yeast enzyme diacetyl reductase can kreversibly reduce diacetyl to acetoin. Aldehyde concentrations are usually 10—20 ppm. Thek effects on flavor must be minor, since the perception threshold is about 25 ppm. 

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