Tastes, bitter

Me2NCH2) C2H5)(Me)C-OOC Ph-HCI. Colourless crystalline powder with a bitter taste, m.p. 177-179"C. Prepared by the action of ethyl magnesium bromide on dimethyl-aminoaceione. It is a local anaesthetic, mainly used to produce spinal anaesthesia. 

C8H10N4O2. An alkaloid occurring in tea, coffee and guarana, from which it may be prepared by extraction, It is also manufactured by the methylation of theobromine and by the condensation of cyanoacetic acid with urea. Crystallizes with H2O or anhydrous from organic solvents. M.p. (anhydrous) 235"C, sublimes at 176 C. Odourless, and with a very bitter taste. Caffeine acts as a stimulant and diuretic, and is a constituent of cola drinks, tea and coffee. 

Acetamide [60-35-5] C2H NO, mol wt 59.07, is a white, odorless, hygroscopic soHd derived from acetic acid and ammonia. The stable crystalline habit is trigonal the metastable is orthorhombic. The melt is a solvent for organic substances it is used ia electrochemistry and organic synthesis. Pure acetamide has a bitter taste. Unknown impurities, possibly derived from acetonitrile, cause its mousy odor (1). It is found ia coal mine waste dumps (2). 

Human perception creates difficulty ia the characterization of flavor people often, if not always, perceive flavors differently due to both psychological and physiological factors. For example, certain aryl thiocarbamates, eg, phenylthiocarbamide, taste exceedingly bitter to some people and are almost tasteless to others (5). This difference is genetically determined, and the frequency of its occurrence differs from one population to another 40% of U.S. Caucasians are nontasters, whereas only 3% of the Korean population caimot perceive the strong bitter taste of the aryl thiocarbamates (6). Similar differences were found ia the sense of smell for compounds such as menthol, carvone, and ethyl butyrate (7). 

Several aspects affect the extent and character of taste and smell. People differ considerably in sensitivity and appreciation of smell and taste, and there is lack of a common language to describe smell and taste experiences. A hereditary or genetic factor may cause a variation between individual reactions, eg, phenylthiourea causes a bitter taste sensation which may not be perceptible to certain people whose general abiUty to distinguish other tastes is not noticeably impaired (17). The variation of pH in saUva, which acts as a buffer and the charge carrier for the depolarization of the taste cell, may influence the perception of acidity differently in people (15,18). Enzymes in saUva can cause rapid chemical changes in basic food ingredients, such as proteins and carbohydrates, with variable effects on the individual. 

When food contains both sweet and bitter substances, the temporal pattern of reception, ie, the order in which sweet and bitter tastes are perceived, affects the total quaUtative evaluation. This temporal effect is caused by the physical location of taste buds. The buds responding to sweet are located on the surface and the tip of the tongue, the bitter in grooves toward the rear. Therefore, the two types of taste buds can be activated sequentially. 

Organic aromatic molecules are usually sweet, bitter, a combination of these, or tasteless, probably owing to lack of water solubiUty. Most characteristic taste substances, especially salty and sweet, are nonvolatile compounds. Many different types of molecules produce the bitter taste, eg, divalent cations, alkaloids, some amino acids, and denatoirium (14,15). 

Ranitidine. Ranitidine hydrochloride [66357-59-3] (Zantac) is a white to pale yellow granular substance. It is freely soluble in water and acetic acid, soluble in methanol, sparingly soluble in ethanol, and practically insoluble in chloroform. It has a slightly bitter taste and a sulfur-fike odor. It may be made by the method described in Reference 5. 

Ca.sca.ra. Sagrada. Cascara sagrada, also known as sacred bark, chitten, dogwood, coffeeberry, bearberry, bitter bark, and bearwood, is the dried bark of Jdamnus Purshiana DeCandoUe. It is ia the form of browa, purpHsh browa, or brownish red flattened or transversely curved pieces, 1- to 5-mm thick, and has a characteristic odor and bitter taste. It should be collected at least one year prior to use. The active constituents are aloe-emodin... 

Cascara sagrada is used as a cathartic. It is most useful when prepared as a fluid extract, and tends to be a mild laxative causing Htfle discomfort. However, on prolonged use it may result in characteristic melanotic pigmentation of the rectal mucosa. The bitter taste can be lessened, owing to neutralization of the acid constituents, if the ground substance is moistened and mixed with magnesium or calcium hydroxide. This treatment may lessen the potency of the preparation. 

Cyclizine Hydrochloride. l-(Diphenylmethyl)-4-methylpipera2ine monohydrochloride [303-25-3] (Mare2ine) (17) is a white crystalline powder, or small colorless crystals, that is odorless or nearly so and has a bitter taste. It melts indistinctly and with decomposition at ca 285°C. One gram of cycli2ine hydrochloride [303-25-3] is soluble in 115 mL water, 115 mL ethanol, and 5 mL chloroform it is insoluble in diethyl ether. It may be made by the synthesis shown in Reference 15. 

Tolbutamide. Tolbutamide (l-but5l-3-(p-tolylsulfonyl)urea), with mol wt 270.35, is known as Orinase. It is a white to off-white practically ododess crystalline powder having a slightly bitter taste, mp 126—132°C. It is practically insoluble in water, and soluble in alcohol and chloroform. The toxicity of tolbutamide appears to be low, and reactions are similar to those observed with other sulfonylureas. 

Phenformin. Phenformin hydrochloride [834-28-6] (1-phenethylbiguanide, A/-(2-phenylethyl)imidodicarbonimidic diamide), is a white to off-white odorless crystalline power having a bitter taste. The melting point is 175—178°C. It is freely soluble in water and alcohol, and practically insoluble in chloroform, ether, and hexane. Its pH in solution is 6.0—7.0. 

The enzymatic hydrolysates of milk casein and soy protein sometimes have a strong bitter taste. The bitter taste is frequently developed by pepsin [9001 -75-6] chymotrypsin [9004-07-3] and some neutral proteases and accounted for by the existence of peptides that have a hydrophobic amino acid in the carboxyhc terminal (226). The relation between bitter taste and amino acid constitution has been discussed (227). 

Hydroxyacetanilide. This derivative (21), also known as 4-acetamidophenol, acetaminophen, or paracetamol, forms large white monoclinic prisms from water. The compound is odorless and has a bitter taste. 4-Hydroxyacetani1 ide is insoluble in petroleum ether, pentane, and ben2ene slightly soluble in diethyl ether and cold water and soluble in hot water, alcohols, dimethylformamide, 1,2-dichloroethane, acetone, and ethyl acetate. The dissociation constant, pfC, is 9.5 (25°C). 

Ethoxyacetanilide. This compound (22), also known as phenacetin, is a white crystalline powder. The compound is odorless and has a slightly bitter taste. It is sparingly soluble in cold water and more soluble in hot water, ethanol, diethyl ether, and chloroform. At relative humidities between 15 and 90% the equiUbtium moisture content is about 2% (25°C). 

Sodium iodide [7681-82-5] Nal, occurs as colorless crystals or as a white crystalline solid. It has a salty and slightly bitter taste. In moist air, it gradually absorbs as much as 5% water, which causes caking or even Hquefaction (dehquescence). The soHd slowly becomes brown when exposed to air because some iodide is oxidized to iodine. Water solutions are neutral or slightly alkaline and gradually become brown for the same reason. Aqueous solutions are stabilized with respect to oxidation by raisiag the pH to 8—9.5 (see Iodine and iodine compounds). 

Propylthiouracil. This compound is a white, powdery, crystalline substance of starch-like appearance with a bitter taste. It is slightly soluble in water, chloroform, and ethyl ether, sparingly soluble in ethanol, and soluble in aqueous alkaline solutions (53). An extensive compilation of its chemical, spectral, and chromatographic properties is available (43). It is assayed titrimetrically with NaOH (53). 

Riboflavin forms fine yellow to orange-yeUow needles with a bitter taste from 2 N acetic acid, alcohol, water, or pyridine. It melts with decomposition at 278—279°C (darkens at ca 240°C). The solubihty of riboflavin in water is 10—13 mg/100 mL at 25—27.5°C, and in absolute ethanol 4.5 mg/100 mL at 27.5°C it is slightly soluble in amyl alcohol, cyclohexanol, benzyl alcohol, amyl acetate, and phenol, but insoluble in ether, chloroform, acetone, and benzene. It is very soluble in dilute alkah, but these solutions are unstable. Various polymorphic crystalline forms of riboflavin exhibit variations in physical properties. In aqueous nicotinamide solution at pH 5, solubihty increases from 0.1 to 2.5% as the nicotinamide concentration increases from 5 to 50% (9). 

The acid-instabihty of erythromycin makes it susceptible to degradation in the stomach to intramolecular cyclization products lacking antimicrobial activity. Relatively water-insoluble, acid-stable salts, esters, and/or formulations have therefore been employed to protect erythromycin during passage through the stomach, to increase oral bioavakabihty, and to decrease the variabiUty of oral absorption. These various derivatives and formulations also mask the very bitter taste of macroHdes. 

Caffeine. Caffeiae [58-08-2] CgH QN402, is usually added to cola beverages for its pleasantly bitter taste. Cola beverages not containing caffeiae are designated as caffeiae-free. 

Seawater. Salt extraction from seawater is done by most countries having coastlines and weather conducive to evaporation. Seawater is evaporated in a series of concentration ponds until it is saturated with sodium chloride. At this point over 90% of the water has been removed, and some impurities, CaSO and CaCO, have been crystallized. This brine, now saturated in NaCl, is transferred to crystallizer ponds where salt precipitates on the floor of the pond as more water evaporates. Brine left over from the salt crystallizers is called bitterns because of its bitter taste. Bitterns is high in MgCl2, MgSO, and KCl. In some isolated cases, eg, India and China, magnesium and potassium compounds have been commercially extracted, but these represent only a small fraction of total world production. 

Benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammoniumbenzoate (denatonium benzoate [3734-33-6] Bitrex) is an extremely bitter tasting, nonirritating, and nonmutagenic compound that has been widely used in many household products such as detergents, nail poHsh removers, and cleaning agents, to prevent childhood poisoning. It is also used as an alcohol denaturant. 

In recent years, many parent dmgs have been converted to esters to generate so-called prodmgs ia order to overcome some undesirable property such as bitter taste, poor absorption, poor solubiUty, and irritation at site of iajection. For example, antibiotics such as chloramphenicol [56-75-7] and clindamycin [18323-44-9] have been derivatized as their palmitate esters ia order to minimise their bitter taste. 

Because of its bitter taste and water iasolubiUty, guaiacol has been chemically modified to improve its properties. Sulfonation provides a mixture of guaiacol-4- and 5-sulfonic acids which, as the potassium salts, is water-soluble, comparatively tasteless, but less active than guaiacol. Treatment of the sodium salt of guaiacol with phosgene provides guaiacol carbonate [553-17-1] (3) which also lacks the bitter taste of guaiacol, but is less water-soluble. 

V-Allylthiourea (thiosinamine) [109-57-9] M 116.2, m 70-73 , 78 . Recrystd from H2O. Soluble in 30 parts of cold H2O, soluble in EtOH but insoluble in "CeHg. Also recrystd from acetone, EtOH or ethyl acetate, after decolorising with charcoal. The white crystals have a bitter taste with a slight garlic odour and are TOXIC. [Anal Chem 21 421 7949.]... 

Cocaine. This lias a bitter taste, is mydriatic, produces local anaesthesia and is toxic. After absorption, or when taken internally, it acts chiefly by stimulation of the central nervous system, succeeded by depression. Since the two phases may be present in different areas simultaneously, a mixed result may ensue. With large doses the chief symptoms are those of medullary depression. Death is due to paralysis of the respiratory centre. The main use of cocaine in medicine is as a local anaesthetic. 

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