Caraway seed

Enantiomers can have striking differences however m properties that depend on the arrangement of atoms m space Take for example the enantiomeric forms of carvone (R) (—) Carvone is the principal component of spearmint oil Its enantiomer (5) (+) carvone is the principal component of caraway seed oil The two enantiomers do not smell the same each has its own characteristic odor... 

Caraway Seed. This spice is the dried ripe fmit of Carum carvi L. (UmbeUiferae). It is a biennial plant cultivated extensively in the Netherlands and Hungary, Denmark, Egypt, and North Africa. The seed is brown and hard, about 0.48 cm long, and is curved and tapered at the ends. It is perhaps the oldest condiment cultivated in Europe. The odor is pleasant and the flavor is aromatic, warm, and somewhat sharp (carvone). Caraway is used in dark bread, potatoes, sauerkraut, kuemmel Hqueurs, cheese, applesauce, and cookies. 

Chin-chin is crisp, slightly sweet, golden brown knots of pastry. These deep fat fried cakes are made in different shapes and styles. Chin-chin is often flavored with vanilla extract, nutmeg, caraway seed, orange or lemon rind. The African panel preferred the chin-chin with no substitution for all characteristics except appearance. The non-African panel preferred chin-chin without any substitutions for all characteristics. The soybean flour was the most desirable substitution at 30% of the all purpose flour. 

Caraway oil is obtained by steam distillation of crushed caraway seeds from Carvum carvi L. (Apiaceae). It is a colorless to yellow liquid with a characteristic caraway odor and a mild-spicy taste. 

AUasch Caraway seeds, bitter almonds, aniseed... 

FIGURE 1-23 Stereoisomers distinguishable by smell and taste in humans, (a) Two stereoisomers of carvone R) carvone (isolated from spearmint oil) has the characteristic fragrance of spearmint (S)-carvone (from caraway seed oil) smells like caraway, (b) Aspartame, the artificial sweetener sold under the trade name NutraSweet, is easily distinguishable by taste receptors from its bitter-tasting stereoisomer, although the two differ only in the configuration at one of the two chiral carbon atoms. 

Caraway seed is the fruit of a herb within the parsley family. Each seed is a half of the fruit and is about Vi cm long, tan to brown, and curved with five lighter coloured ridges along the length of the seed. Caraway is mostly cultivated in Europe and Western Asia. 

As another example of the effects of shape and molecular handedness, look at the substance called carvone. Left-handed carvone occurs in mint plants and has the characteristic odor of spearmint, while right-handed carvone occurs in several herbs and has the odor of caraway seeds. Again, the two structures are the same except for their shapes, yet they have entirely different odors. 

Two plants both produce carvone, but the mint leaves yield the "left-handed" form, while the caraway seeds yield the "right-handed" form. 

Chemat, A., A. Lagha, H. AitAmar, P.V. Bartels and F. Chemcat, Comparison of Conventional and Ultrasound-Assisted Extraction of Carvone and Limonene from Caraway Seeds, Flavour and Fragrance Journal, 19, 188-195 (2004). 

The preparation of the polarographic sample becomes more complicated in the analysis of drugs [211], e.g., of seeds or barks. A typical procedure can be exemplified with the determination of cinnamaldehyde in cinnamon bark. A quantity of about 2-5 g of this bark is pulverised and extracted with chloroform for 10 hr in a Soxhlet apparatus. The solvent is then distilled off and the residue dissolved in ethanol. An aliquot of this is mixed with an aqueous solution of the supporting electrolyte and polaro-graphed. A similar procedure proved successful in the determination of carvone in Semen carvi it differs only in the application of ethanol for the extraction. This extraction in the determination of cuminaldehyde in the Roman caraway seeds was a failure because electroactive impurities were extracted simultaneously. For this reason, it was necessary to make use of steam distillation. 

Menthol (mint) Carvone (caraway seeds) Camphor ... 

Baysal, T. and Starmans, D.A.J. (1999). Supercritical carbon dioxide extraction of carvone and limonene from caraway seed. Journal of Supercritical Fluids, 14 225-234. 

Odstrcilova, L. (2007b). Changes in the occurence of mycoflora on caraway seeds after fungicide application. Plant Protection Science, 43 (4) 146-150. 

Q8. (-)-Carvone (73) occurs in spearmint and its enantiomer (+)-carvone (74) is found in caraway seed. To the human sense of smell, these two enantiomers have different odours. Where is the stereogenic centre in 73 and in 74 What conclusions can be drawn about the human olfactory receptor site ... 

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