Acetic flavour

Verghese, J. and Joy, M.T. (1 989) Isolation of the colouring matter from dried turmeric (Curcuma longa L.) with ethyl acetate. Flavour and Fragrance journal 4, 31-32. 

There are a number of different ways that the molecular graph can be conununicated between the computer and the end-user. One common representation is the connection table, of which there are various flavours, but most provide information about the atoms present in the molecule and their connectivity. The most basic connection tables simply indicate the atomic number of each atom and which atoms form each bond others may include information about the atom hybridisation state and the bond order. Hydrogens may be included or they may be imphed. In addition, information about the atomic coordinates (for the standard two-dimensional chemical drawing or for the three-dimensional conformation) can be included. The connection table for acetic acid in one of the most popular formats, the Molecular Design mol format [Dalby et al. 1992], is shown in Figure 12.3. 

Part III extraction solvents that may be used for the preparation of flavourings from natural flavouring materials diethyl ether, hexane, methyl acetate, butan-l-ol, butan-2-ol, ethylmethyl ketone, dichloromethane,... 

Larkov O, Dunkelblum E, Zada A, Lewinsohn E, Freiman L, Dudai N, Ravid U, Enantiomeric composition of trans- and cis- sabinene hydrate and their acetates in five Origanum spp., Flavour Fragr/22 109—114, 2005. 

Kopke X Schmarr HG, Mosandl A, Stereoisomeric flavour compounds. Part LVII Xhe stereoisomers of 3-oxo-p-menthane-8-thiol acetate, simultaneously stereoanalyzed with their corresponding thiols, FlavourFragr/7 205—211, 1992. 

Mosandl A, Schubert V, Stereoisomeric flavour compounds XXXIX Chiral constituents of essential oils (I), stereo differentiation of linalyl acetate — A new possibility for quality evaluation of lavender oil, Z Lebensm Unters Frosch 190 506-510, 1990. 

Ravid U, Putievsky E, Katzir I, Ghiral GG analysis of enantiomericaUy pure (i )(—)-linalyl acetate in some Lamiaceae, myrtle and petitgrain essential oils, Flavour Fragr J A TJ b—2ElG, 1994. 

Weinreich B, Nitz S, Influences of processing on the enantiomeric distribution of chiral flavour compounds, Part A Linalyl acetate and terpene alcohols, Chem MikrobiolTechnol Lebensm 14 117—124, 1992. 

Important aroma compounds of black currant berries have been identified mainly by GC-O techniques by Latrasse et al. [119], Mikkelsen and Poll [115] and Varming et al. [7] and those of black currant nectar and juice by Iversen et al. [113]. The most important volatile compounds for black currant berry and juice aroma include esters such as 2-methylbutyl acetate, methyl butanoate, ethyl butanoate and ethyl hexanoate with fruity and sweet notes, nonanal, /I-damascenone and several monoterpenes (a-pinene, 1,8-cineole, linalool, ter-pinen-4-ol and a-terpineol) as well as aliphatic ketones (e.g. l-octen-3-one) and sulfur compounds such as 4-methoxy-2-methyl-butanethiol (Table 7.3, Figs. 7.3, 7.4, 7.6). 4-Methoxy-2-methylbutanethiol has a characteristic catty note and is very important to blackcurrant flavour [119]. 

The kiwi fruit is a cultivar group of the species Actinidia deliciosa. More than 80 compounds have been identified in fresh and processed kiwi [137]. Methyl acetate, methyl butanoate, ethyl butanoate, methyl hexanoate and ( )-2-hexenal have the most prominent effect on consumer acceptability of kiwi fruit flavour [137-140]. The volatile composition of kiwi fruit is very sensitive to ripeness, maturity and storage period [138, 139]. Bartley and Schwede [140] found that ( )-2-hexenal was the major aroma compound in mature kiwi fruits, but on further ripening ethyl butanoate began to dominate. Ripe fruits had sweet and fruity flavours, which were attributed to butanoate esters, while unripe fruits had a green grassy note due to ( )-2-hexenal [140]. The most important character-impact compounds of kiwi fruits are summarised in Table 7.4. 

Banana (Musa sapientum L.) is one of the most common tropical fruits, and one of Central America s most important crops. It is grown in all tropical regions and is one of the oldest known fruits [45]. From a consumer perspective, bananas are nutritious with a pleasant flavour and are widely consumed throughout the world [57]. Esters predominate in the volatile fraction of banana (Fig. 8.2). Acetates are present in high concentrations in the fruit and generally possess a low threshold. Isopentyl acetate and isobutyl acetate are known as the two most important impact compounds of banana aroma. Alcohols are the second most important group of volatiles in banana extracts. 3-Methyl-1-butanol, 2-pentanol, 2-methyl-1-propanol, hexanol, and linalool are the alcohols present in higher concentrations in the fresh fruit [45]. 

The first study on the volatile composition of bacuri revealed linalool, 2-hep-tanone, and czs-3-hexenyl acetate as the most important flavour compounds [2]. Volatiles were isolated by a steam distillation-extraction of pulp. 

Some of the volatile substances which are produced during fermentation, like acrolein, diacetyl, 2-butanol, allyl alcohol, or acetic acid, are a result of enhanced microbiological activities and may cause an unpleasant flavour (off-flavour) at certain levels thus, elevated concentrations of such compounds are markers for spoilage of the raw material, negative microbiological influences during or after the fermentation process, or a poor distillation technique. 

The flavour of distillates from apple and pear is characterised by typical aroma compounds from these fruits formed by enzymatic degradation of fatty acids to C6-fragments like hexanol, trans-2-hexenol, as well as ethyl esters and acetates of hexanoic acid. In distillates of pears, especially of the variety Bartlett pear, the characteristic pear flavour is mainly dominated by the ethyl and methyl esters of frans-2-czs-4-decadienoic acid and trans-2-trans-A-decadienoic acid [27-29], The biogenesis of these monounsaturated, diunsaturated, and triunsaturated esters may be explained by -oxidation of unsaturated linoleic and linolenic acid in the fruits. The sesquiterpene compound a-farnesene, which is formed during postharvest ripening and storage of Bartlett pears [28], shows that quality and intensity of distilled pear spirits is mainly influenced by the quality and degree of ripeness of the fruits. 

The most important and frequently used terpene esters in flavours are the acetates of nerol, geraniol, citronellol, linalool and isoborneol [12], As discussed before, all these terpene alcohols are available both from renewable resources and from petrochemical origin. Acetic acid can be obtained from renewable resources by pyrolysis of wood as wood vinegar, and also by synthesis from petrochemical origin. 

Vanilla flavour is not only determined and characterised by the vanillin molecule, but also by many more phenolic compounds and vanillin derivatives. Two examples of molecules that recently obtained FEMA-GRAS status are vanillyl ethyl ether and vanillin 2,3-butanediol acetal (Scheme 13.11). Vanillin can be hydrogenated to form vanillyl alcohol, which is also used in vanilla flavours. Vanillyl alcohol can be reacted with ethanol to form vanillyl ethyl ether. Vanillin can also form an acetal with 2,3-butanediol (obtained by fermentation of sugars) catalysed byp-toluene sulfonic acid in toluene. 

Methionine can be obtained from enzymatic protein hydrolysates or from petrochemical sources. To a lesser extent than cysteine, it is a raw material in Maillard reactions for the preparation of process flavours and it can also be utilised as a precursor for the chemical preparation of the sulfide methional, which is an important flavour constituent for potato, malt, seafood and many other flavours. Methional can be reduced to methionol, which can be esterified with organic acids to, for instance, methionyl acetate and methionyl butyrate, which are useful compounds for pineapple and other fruit flavours (Scheme 13.16). 

A similar apparatus has been used for recovery of aroma compounds from cacao during processing [34]. In this process, water and acetic acid are removed from the aroma-laden gas stream by the initial traps and then the gas is passed through traps of the same design as those described by Cams and Tuot [29]. The aroma isolate so provided is suggested to be useful for the flavouring of soluble cocoa beverages, cake mixes, and confectionery products. 

During the production of recovery flavours, apple wines or brandies, the interaction with ethanol, acetaldehyde and acetic acid represents the next level of interactions. The reaction products contain compounds which result from esterification and acetal formation reactions, which are summarised in Table 21.4. 

Nozaki et al. [23] characterised the production of (+)-mesifuran [2,5-di-methyl-4-methoxy-3(2H)-furanone], an important flavour compound in arctic bramble, but which also occurs in strawberry and pineapple. After lipase-catalysed (Candida antarctica) enantioface-differentiating hydrolysis of the enol acetate, the pure optically active (+)-mesifuran could be obtained. 

The biotechnological production of flavour compounds is particularly focused on esters and lactones. Lipase from Mucor miehei is the most widely studied fungal lipase [30-35]. Esters of acids from acetic acid to hexanoic acid and alcohols from methanol to hexanol, geraniol and citronellol have been synthesised using lipases from Mucor miehei, Aspergillus sp., Candida rugosa, Rhizopus arrhizus and Trichosporum fermentans [32-37]. 

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