Taste esters

HOCHj CHjOH. Colourless, odourless, rather viscous hygroscopic liquid having a sweet taste, b.p. 197 C. Manufactured from ethylene chlorohydrin and NaHC03 solution, or by the hydration of ethylene oxide with dilute sulphuric acid or water under pressure at 195°C. Used in anti-freezes and coolants for engines (50 %) and in manufacture of polyester fibres (e.g. Terylene) and in the manufacture of various esters used as plasticizers. U.S. production 1979 1 900 000 tonnes. 

CH3 CH0H CH20H, a colourless, almost odourless liquid. It has a sweet taste, but is more acrid than ethylene glycol b.p. 187. Manufactured by heating propylene chlorohydrin with a solution of NaHCO under pressure. It closely resembles dihydroxyethane in its properties, but is less toxic. Forms mono-and di-esters and ethers. Used as an anti-freeze and in the preparation of perfumes and flavouring extracts, as a solvent and in... 

The predominant cellulose ester fiber is cellulose acetate, a partially acetylated cellulose, also called acetate or secondary acetate. It is widely used in textiles because of its attractive economics, bright color, styling versatiUty, and other favorable aesthetic properties. However, its largest commercial appHcation is as the fibrous material in cigarette filters, where its smoke removal properties and contribution to taste make it the standard for the cigarette industry. Cellulose triacetate fiber, also known as primary cellulose acetate, is an almost completely acetylated cellulose. Although it has fiber properties that are different, and in many ways better than cellulose acetate, it is of lower commercial significance primarily because of environmental considerations in fiber preparation. 

Pish protein concentrate and soy protein concentrate have been used to prepare a low phenylalanine, high tyrosine peptide for use with phenylketonuria patients (150). The process includes pepsin hydrolysis at pH 1.5 ptonase hydrolysis at pH 6.5 to Hberate aromatic amino acids gel filtration on Sephadex G-15 to remove aromatic amino acids incubation with papain and ethyl esters of L-tyrosine and L-tryptophan, ie, plastein synthesis and ultrafiltration (qv). The plastein has a bland taste and odor and does not contain free amino acids. Yields of 69.3 and 60.9% from PPG and soy protein concentrate, respectively, have been attained. 

Some peptides have special tastes. L-Aspartyl phenylalanine methyl ester is very sweet and is used as an artificial sweetener (see Sweeteners). In contrast, some oligopeptides (such as L-ornithinyltaurine HQ. and L-oriuthinyl-jB-alariine HQ), and glycine methyl or ethyl ester HQ have been found to have a very salty taste (27). 

Aspartame (L-aspartyl-L-phenylalanine methyl ester [22839-47-0]) is about 200 times sweeter than sucrose. The Acceptable Daily Intake (ADI) has been estabUshed by JECFA as 40 mg/kg/day. Stmcture-taste relationship of peptides has been reviewed (223). Demand for L-phenylalanine and L-aspartic acid as the raw materials for the synthesis of aspartame has been increasing, d-Alanine is one component of a sweetener "Ahtame" (224). 

Physical properties of isopropyl alcohol are characteristic of polar compounds because of the presence of the polar hydroxyl, —OH, group. Isopropyl alcohol is completely miscible ia water and readily soluble ia a number of common organic solvents such as acids, esters, and ketones. It has solubiUty properties similar to those of ethyl alcohol (qv). There is a competition between these two products for many solvent appHcations. Isopropyl alcohol has a slight, pleasant odor resembling a mixture of ethyl alcohol and acetone, but unlike ethyl alcohol, isopropyl alcohol has a bitter, unpotable taste. 

A commercially interesting low calorie fat has been produced from sucrose. Proctor Gamble has patented a mixture of penta- to octafatty acid ester derivatives of sucrose under the brand name Olestra. It was approved by the FDA in January 1996 for use as up to 100% replacement for the oil used in preparing savory snacks and biscuits. Olestra, a viscous, bland-tasting Hquid insoluble in water, has an appearance and color similar to refined edible vegetable oils. It is basically inert from a toxicity point of view as it is not metabolized or absorbed. It absorbs cholesterol (low density Hpoprotein) and removes certain fat-soluble vitamins (A, D, E, and K). Hence, Olestra has to be supplemented with these vitamins. No standard LD q tests have been performed on Olestra however, several chronic and subchronic studies were performed at levels of 15% in the diet, and no evidence of toxicity was found. No threshold limit value (TLV), expressed as a maximum exposure per m of air, has been estabhshed, but it is estimated to be similar to that of an inert hpid material at 5 mg/m. ... 

Alitame (trade name Adame) is a water-soluble, crystalline powder of high sweetness potency (2000X, 10% sucrose solution sweetness equivalence). The sweet taste is clean, and the time—intensity profile is similar to that of aspartame. Because it is a stericaHy hindered amide rather than an ester, ahtame is expected to be more stable than aspartame. At pH 2 to 4, the half-life of aUtame in solution is reported to be twice that of aspartame. The main decomposition pathways (Fig. 6) include conversion to the unsweet P-aspartic isomer (17) and hydrolysis to aspartic acid and alanine amide (96). No cyclization to diketopiperazine or hydrolysis of the alanine amide bond has been reported. AUtame-sweetened beverages, particularly colas, that have a pH below 4.0 can develop an off-flavor which can be avoided or minimized by the addition of edetic acid (EDTA) [60-00-4] (97). 

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. 

Ester derivatives of oleandomycia (17, R = CH ) were also pursued leading to commercial development of (31) also known as troleandomycin (TOA), which improved oral bioavadabihty and taste as compared to the parent (135). 

Ben /ben ate [120-51-4] CgH COOCH2CgH, mp, 21°C, cff , 1.118 bp, 323—324°C at 101.3 kPa , 1.5681. This is a colorless, oily liquid with a faiat, pleasant aromatic odor and a sharp, burning taste. It occurs naturally iu Pern and Tolu balsams, is spariugly volatile with steam, and is iusoluble iu water. Benzyl benzoate is prepared commercially by the direct esterification of benzoic acid and benzyl alcohol or by reaction of benzyl chloride and sodium benzoate. The pleasant odor of benzyl benzoate, like other benzoic esters, has long been utilized iu the perfume iadustry, where it is employed as a solvent for synthetic musks and as a fixative. It has also been used iu confectionery and chewing gum flavors. 

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. 

Denatonium benzoate is the bitterest-tasting substance known. It gets its name from denatured alcohol—alcohol that has been rendered unfit for drinking—and is often used in the denaturing process. Specially denatured alcohol 40, or SD-40, is ethanol that has been denatured by a tiny amount of denatonium benzoate. Denatonium benzoate is an ester of PABA, and is related to lidocaine, benzocaine, novocaine, and cocaine. 

Acetaldehyde is formed during the degradation of PET. Vinyl ester endgroups formed during thermal degradation of PET liberate vinyl alcohol on transesterification with hydroxyethylterephthalate polymeric endgroups (Fig. 10.6). The vinyl alcohol tautomerizes to form acetaldehyde, which can affect the taste of foods in PET food contact applications.1... 

Problems Pear ester (43) is an important industrial flavouring compound with a pear-like taste and smell. Consider all possible Wittig disconnections and choose a reaction which should give the right geometrical isomer. 

The AH unit was assigned to the carboxyl group, as the sweet taste of compounds 2 and 3 in Table XXIVa is lost when the carboxyl group is absent or when it is converted into the methyl ester (compound 4 in Table XXIVa). It was suggested " that this group mainly interacts with its counterpart on the receptor by ionic interaction. The absence of sweet taste... 

The organoleptic properties of black tea depend to a considerable extent on the astringency resulting from the interaction of caffeine with the oxidized galloyl ester of the flavanols. The aroma components of black tea also constitute a unique flavor profile that blends well with the taste of the nonvolatile materials. The caffeine provides a moderate level of stimulation, which adds further to the appeal of the beverage, although tea has been shown to provide relaxation as well as revival of character.119... 

Esters are the product of reaction between an alcohol and a carboxylic acid. Although the reaction can be slow - particularly at lower temperatures - the equilibrium constant is sufficiently high for the eventual yield of ester to be significant. We see how even a small amount of carboxylic acid and alcohol can generate a sufficient amount of ester to be detected by smell or taste. 

This helps explain why a wine should be left to stand some of the natural alcohols in the wine are oxidized by oxygen dissolved from the air to form carboxylic acids. These acids then react with the natural alcohols to generate a wide range of esters, which connoisseurs of wines will recognize as a superior taste and bouquet . 

Esters often have pleasant odours and tastes, so they are used to produce perfumes and artificial flavours. In fact, the characteristic tastes and smells of many fruits come from esters. (See Figure 1.28.)... 

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