Spearmint

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... 

There are interesting examples of enantiomers that not only are found separately but also have different chemical properties when reacting with some reagent which is itself an enantiomer. For example (+ )-glucose is metabolized by animals and can be fermented by yeasts, but (—)-glucose has neither of these properties. The enantiomer ( + )-carvone smells of caraway whereas (—)-carvone smells of spearmint. 

The FCC is to food-additive chemicals what the USP—NF is to dmgs. In fact, many chemicals that are used in dmgs also are food additives (qv) and thus may have monographs in both the USP—NF and in the FCC. Examples of food-additive chemicals are ascorbic acid [50-81-7] (see Vitamins), butylated hydroxytoluene [128-37-0] (BHT) (see Antioxidants), calcium chloride [10043-52-4] (see Calcium compounds), ethyl vanillin [121-32-4] (see Vanillin), ferrous fumarate [7705-12-6] and ferrous sulfate [7720-78-7] (see Iron compounds), niacin [59-67-6] sodium chloride [7647-14-5] sodium hydroxide [1310-73-2] (see lkaliand cm ORiNE products), sodium phosphate dibasic [7558-79-4] (see Phosphoric acids and phosphates), spearmint oil [8008-79-5] (see Oils, essential), tartaric acid [133-37-9] (see Hydroxy dicarboxylic acids), tragacanth [9000-65-1] (see Gums), and vitamin A [11103-57-4]. 

United States Exports of Spices and Oleoresins. The United States (ca 1993) is the foremost grower of peppermint, spearmint, orange, lemon, lime, and grapefmit products. The mints are processed to essential oils, and the citms fmit are sold as fresh fmit or processed to fro2en... 

Other synthetics with cost advantages and large volume productions are L-carvone [6485-40-17, the primary component in natural spearmint essence D-carvone [2244-16-8], the primary component in natural diU and caraway anethol [4180-23-8], in place of anise and fennel spices and smaller amounts of thymol [89-83-8] replacing thyme and disulfide synthetics for onion and gadic. AH of these synthetics must be labeled as artificial which may limit their use among consumers. 

In 1993, the United States imported nearly 22 x 10 kg of essential oils at a total value of almost 190 x 10 , an increase over 1992 of ca 2.3 X 10 kg and 935,000. Table 1 fists the quantities and values of 35 imported essential oils. The United States exports seven principal essential oils orange, lemon, peppermint, spearmint, cedarwood, clove, and nutmeg. The latter two are not grown in the United States but are imported as dried spice, processed for oil, and then exported. 

Table 56. Comparison of Headspace Volatiles of Living vs Picked Spearmint and Commercial Oil ...

Sensitization results are based on a human maximization test (103) usiag a petrolatum vehicle. The effect is expressed as the number of paneHsts responding over the total number of paneHsts tested and was 0/25 except for spearmint (0/32). That is, at the dose iadicated, the oils werenot irritating when tested ia a 48-h closed patch test ia humans. 

Dimethyl sulfoxide occurs widely at levels of <3 ppm. It has been isolated from spearmint oil, com, barley, malt, alfalfa, beets, cabbage, cucumbers, oats, onion, Swiss chard, tomatoes, raspberries, beer, coffee, milk, and tea (5). It is a common constituent of natural waters, and it occurs in seawater in the 2one of light penetration where it may represent a product of algal metaboHsm (6). Its occurrence in rainwater may result from oxidation of atmospheric dimethyl sulfide, which occurs as part of the natural transfer of sulfur of biological origin (7,8). 

Limonene (+15) is an important raw material for producing (-)-carvone [6485-40-1]. The process uses nitrosyl chloride and proceeds via nitrosochloride and oxime (78,79). The (-)-carvone (40) is found as the main component of spearmint oil and the (+)-carvone produced from (—)-limonene has the characteristic odor of diU. 

Flavor. Dentifrices are used to refresh the oral cavity. Flavor oils and other flavoring materials are key to that function (see Flavors and spices). Generally recognized as safe (GRAS) flavors or flavors from approved lists are used. The most popular flavors are peppermint [8006-90-4], spearmint [8008-79-5], cinnamon [8006-79-9], and mixtures of these. Menthol is a principal constituent of the mint flavors and a source of refreshment and coolness. 

Examine actual three-dimensional structures for the twc enantiomers of carvone. One occurs naturally in carawa> while the other is found in spearmint oil, and are responsible for the characteristic odors of these materials. Determine which form, R or S, is responsible for which odor. 

Linalol is found very widely distributed in essential oils. It forms the principal constituent, in the free state, of oil of linaloe, and the chief odorous constituent, in the form of esters, in bergamot and lavender oils. It is also found in ylang-ylang, rose, champaca leaf, cinnamon, petit-grain, spike, geranium, lemon, spearmint, and numerous. other essential oils. 

As regards the use of hydroxylamine for the estimation of ketones, it was recommended by Kremers in 1901 for the estimation of oarvone in spearmint oil, the ketoxime being formed by treating the oil with hydroxylamine, and the remainder of the oil removed by steam distillation, the crystalline ketoxime which is left being separated, dried, and weighed. 

Erauseminze, /. curled mint (Mentha criapa) spearmint (Mentha apicata). 

Carvone, a substance responsible for the odor of spearmint, has the following structure. Tell how many hydrogens are bonded to each carbon, and give the molecular formula of carvone. 

Carvone is an unsaturated ketone responsible for the odor of spearmint. If car-vone has M+ = 150 in its mass spectrum and contains three double bonds and one ring, what is its molecular formula ... 

Carvone is the major constituent of spearmint oil. What products would you expect from reaction of carvone with the following reagents ... 

Numerous examples of the different biological effects of enantiomers are available. One of the enantiomers of limonene smells of lemons, the other of oranges one of carvone smells of caraway, the other of spearmint These differences obviously have important... 

Yerba buena, or Cuban mint, specified in recipes as the mojito s native mint, is peppermint, though die classification is also loosely applied hi Cuba to bergamot and die rugose form of spearmint, according to Dr. Art Tucker from die Department of Agriculture and Natural Resources at Delaware State University. Dr. Tucker is an expert on mint. 

Aldehydes occur naturally in essential oils and contribute to the flavors of fruits and the odors of plants. Benzaldehyde, C6H5CHO (8), contributes to the characteristic aroma of cherries and almonds. Cinnamaldehvde (9) is found in cinnamon, and vanilla extract contains vanillin (10), which is present in oil of vanilla. Ketones can also be fragrant. For example, carvone (Section 18.1) is the essential oil of spearmint. 

Carminatives (peppermint, spearmint) Chocolate Coffee, cola, tea Medications Anticholinergics Barbiturates... 

Finally, another unique formulation is a chewable tablet available to women who have difficulty swallowing medications. Ovcon 35 (norethindrone/ethinyl estradiol) has all 28 tablets in chewable form and has added spearmint flavoring.30 Along with each of these unique oral contraceptives, there are preparations currently being studied that contain 24 active pills and 4 placebo pills per pack, shortening the hormone-free period.1... 

The main constituents of spearmint oil are /-carvone (Fig. 13.12.7) and /-limonene (Fig. 13.12.8). Oil of spearmint contains from 45 to 60% l-carvone, 6 to 20% of alcohols, and 4 to 20% of esters and terpenes, mainly /-limonene and cineole (see Fig. 13.12.4)J2J The optically isomeric form of carvone, d-carvone, is found in oil of caraway and oil of dill. Carvone appears to co-occur with limonene when present in a plant. 

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