Esters sweet

Properties Colorless liquid sweet ester odor. Bp 198C, fp -50C, d 1.055 (25/25C), flash p 200F (93.3C). Insoluble in water soluble in alcohol, ether, chloroform, and benzene. Combustible. Derivation By passing hydrogen chloride into cya-noacetic acid dissolved in absolute alcohol with subsequent distillation. 

Properties Colorless liquid sweet ester odor. Bp 169.2C, d 0.890. Insoluble in water very soluble in alcohol and ether. 

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... 

Both esters have a sweet pungent odor and present a vapor inhalation ha2ard. They are rapidly absorbed through the skin and hydroly2ed to chloroacetic acid. The oral LD q for ethyl chloroacetate is between 50 and 100 mg/kg (52). 

Bois de Rose. Bois de rose oil is obtained by steam distillation of wood chips from South American rosewood trees, Aniba rosaeodora. The tree, a wild evergreen, grows mainly in the Amazon basin. The oil is used as obtained in perfumery for its sweet, woody-floral odor and as a source of linalool [78-70-6] (3), which it contains to the extent of 70%. Linalool distilled from bois de rose oil is also used directly in perfumery and for conversion to esters, eg, the acetate (1). 

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). 

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). 

Phenyl-2-propenoic acid [621 -82-9] commonly referred to as cinnamic acid, is a white crystalline soHd having a low intensity sweet, honeylike aroma. It has been identified as a principal constituent in the botanical exudates from Styrax IJquidamber orientalis) Benzoin Styrax ben in Pern Balsam [Myroxylon pereirae and Tolu Balsam (]Ayro>ylon balsamum) (4,5). In these, as well as numerous other natural products, it exists both as the free acid and in the form of one or more of its esters, as for example, methyl cinnamate, ben2yl cinnamate [103 1 -3] and cinnamyl cinnamate. 

Phenyl-2-propen-l-ol [104-54-1], commonly referred to as cinnamyl alcohol, is a colorless crystalline soHd with a sweet balsamic odor that is reminiscent of hyacinth. Its occurrence in nature is widespread as, for example, in Hyacinth absolute (Hyacinthus orientalis) (42), the leaf and bark oils of cinnamon Cinnamomum cassia, Cinnamomum lancium, etc), and Guava fmit [Psidiumguajava L.) (43). In many cases it is also encountered as the ester or in a bound form as the glucoside. 

Essential oils are obtained from fmits and flowers (61,62). Volatile esters of short- and medium-chain carboxyHc acids or aromatic carboxyHc acids with short- and medium-chain alcohols are primary constituents of essential oils, eg, ethyl acetate in wines, brandy, and in fmits such as pineapple ben2yl acetate in jasmine and gardenia methyl saHcylate in oils of wintergreen and sweet birch. Most of these naturally occurring esters in essential oils have pleasant odors, and either they or their synthetic counterparts are used in the confectionery, beverage, perfume, cosmetic, and soap industries (see Oils, essential). 

Esters — These are not very reactive. Only the lowest molecular weight esters have appreciable solubility in water (e.g., ethyl acetate, 8%). Methyl and ethyl esters are more volatile than the corresponding unesterified acids. Most common esters are flammable. Esters are often easily recognizable due to their sweet to pungent odors. 

Chemical Designations - Synonyms Acetic acid, methyl ester Chemical Formula CH3COOCH3. Observable Characteristics - Physical State (as shipped) Liquid Color Colorless Odor Slightly acrid, sweet fragrant. 

The add is obtained by the reduction of cinnamic acid by means of sodium amalgam. The acid is then esterified by the condensing action of a mineral acid in methyl alcohol solution. The ester is an oil of very sweet odour, and is very useful for flower bouquets. 

Methyl Salicylate.—This ester is practically identical with oil of winter-green or oil of sweet birch, both of which contain about 99 per cent, of the ester. It is also present in numerous other plants, and its artificial production is carried out on a very large scale. The artificial ester is quite suitable for replacing the natural oil, and is used to a very large extent for flavouring tooth powders, pastes, and washes, being exceedingly popular in America. The ester has the constitution... 

Ethyl Cinnamate.—The cinnamic ester of ethyl alcohol is a natural constituent of a few essential oils, including camphor oil and storax. It is formed synthetically by condensing cinnamic acid and ethyl alcohol by dry hydrochloric acid gas. It has a soft and sweet odour, and is particularly suitable for blending in soap perfumes. It is an oil at ordinary temperatures, melting at 12°, and boiling at 271°. Its specific gravity is 1 0546, and its refractive index 1 5590. 

Benzyl Ginnamate.—The cinnamic acid ester of benzyl alcohol is a natural constituent of storax, tolu, and Peru balsams. It is a crystalline Bubstance with a characteristic sweet balsamic odour. It may be prepared by heating sodium cinnamate, alcohol, and benzyl chloride together under a reflux condenser. It is a useful ester where a sweet balsamic odour is required to be introduced into a perfume, especially cf the heavy type. It forms white, glistening prisms, which melt at 39°, and.decompose when heated to 350°. The best commercial specimens have the following characters —... 

Terpinyl Ginnamate.—Cinnamic acid forms an ester with terpineol, which has an indescribable odour, but which is exceedingly sweet. It is a useful oil to blend with lilac and similar odours. It is a heavy oil of the constitution Cj j OOC. CH CH. CpHi . 

Aspartame, a nonnutritive sweetener marketed under the trade name Nutra-Sweet (among others), is the methyl ester of a simple dipeptide, Asp-Phe-OCH.3. 

Koenigs-Knorr reaction of, 990 molecular model of, 119, 126, 985 mutarotation of, 985-986 pentnacetyl ester of, 988 pentamethyl ether of, 988 pyranose form of, 984-985 pyruvate from. 1143-1150 reaction with acetic anhydride, 988 reaction with ATP, 1129 reaction with iodomethane, 988 sweetness of. 1005 Williamson ether synthesis with. 988... 

Oil of wintergreen salicylic acid methyl ester methyl sweet birch oil betula oil... 

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... 

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