Flavorings cinnamaldehyde

Formaldehyde is probably the best-known carbonyl compound. Large quantities are made into polymers such as Bakelite, Formica, and Melmac. Since formaldehyde has been cited as a probable carcinogen, its use in preserving biological specimens has virtually vanished. Acetaldehyde (ethanal) is used in manufacturing organic compounds such as acetic acid and ethyl acetate. Other aldehydes you have probably encountered are benzaldehyde (almond flavor), cinnamaldehyde (cinnamon flavor), and vanillin (vanilla flavor) (Fig. 21.26). 

Cinnamaldehyde, [14371-10-9] CgH CH=CHCHO (bp, 253°C at 101.3 kPa), produced by the alkaline condensation of benzaldehyde and acetaldehyde is the main ingredient in cassia oil. It is used in soap perfumes and as an intermediate in the production of other flavor and fragrance compounds. 

Pyrolytic Decomposition. The pyrolytic decomposition at 350—460°C of castor oil or the methyl ester of ricinoleic acid spHts the ricinoleate molecule at the hydroxyl group forming heptaldehyde and undecylenic acids. Heptaldehyde, used in the manufacture of synthetic flavors and fragrances (see Elavors and spices Perfumes) may also be converted to heptanoic acid by various oxidation techniques and to heptyl alcohol by catalytic hydrogenation. When heptaldehyde reacts with benzaldehyde, amyl cinnamic aldehyde is produced (see Cinnamic acid, cinnamaldehyde, and cinnamyl... 

Cinnamaldehyde has been efficiently isolated in high purity by fractional distillation from cassia and cinnamon bark essential oils. This material has been utili2ed in several manufacturing protocols (39—41) for the preparation of natural ben2aldehyde through a retro-aldol process. Since the late 1970s the demand for natural flavors has increased dramatically. This demand has led to a corresponding requirement for a more extensive line of readily available natural aroma chemicals for flavor creation. 

Several araliphatic aldehydes are of special commercial importance as fragrance and flavor materials. These include cinnamaldehyde and its homologues in which the side-chain carries an alkyl substituent a-amyl- and o-hexylcinnamaldehyde... 

In contrast to cinnamon bark oil, cassia oil contains a considerable amount of 2-methoxycinnamaldehyde (3—15%) in addition to its main constituent, cinnamaldehyde (70-88%) [346-350a]. Cassia oil is used predominantly in flavoring soft drinks (cola-type). Aimually a few hundred tons are are produced. FCT 1975 (13) p. 109 [8007-80-5], [91844-89-2],... 

The molecular encapsulation of flavors with cyclo-dextrins was found to improve the resistence of light sensitive flavor constituents against daylight and ultraviolet irradiation. The photodecomposition of adsorbed and complexed flavors was tested both in the solid state and in aqueous solutions. The results of the light stability tests are demonstrated in the example of complexed and adsorbed citral,beta-ionone and cinnamaldehyde formulations /Table III./. 

Aldehydes aid ketones often have pleasant odors. They are found as components of many perfumes and flavorings, both natural and artificial. For example, citral has a strong lemon odor and is found in lemon and orange oils, cinnamaldehyde has a strong cinnamon odor and is found in cinnamon oil, and vanillin is a major component of vanilla flavoring. Camphor, isolated from the camphor tree, is used in liniments and inhalants, and muscone, which has a musky aroma, is used in many perfumes. 

Cinnamaldehyde is used as a flavoring agent in cinnamon candies. Show how cinnamalde-hyde is synthesized by a crossed aldol condensation followed by dehydration. 

The phenylpropanoids rrans-anethole (61) and rran -cinnamaldehyde (62) are used as flavoring agents in foods in the United States and some other countries [20]. tranj-Cinnamaldehyde (62) Avas isolated from Cinnamomum osmophloeum Kanehira (Lauraceae) as a sweet principle, while tra/w-anethole (61) was isolated as the volatile oil constituent responsible for the sweet taste of several plant species, as listed in Table 1 [92]. These two compounds occur widely in the plant kingdom. Therefore, it is necessary to rule out their presence in any candidate sweet plant by a dereplication procedure in a natural product sweetener discovery program using gas chromatography-mass spectrometry (GC/MS) [46,47]. 

Challenge Problem. Cinnamaldehyde is the component responsible for cinnamon flavor. It is also a potent antimicrobial compound present in essential oils (see M. Friedman, N. Kozukue, and L. A. Harden, J. Agric. Food Chem., 2000, 48, 5702). The GC response of an artificial mixture containing six essential oil components and methyl benzoate as an internal standard is shown in the figure. 

Primary uses for Cinnamaldehyde are as a food flavoring and a medical herb. It has been used for many centuries to... 

In addition to its uses as a herhal remedy, the primary use of cinnamaldehyde is as a food additive to enhance the flavor and/or odor of food products. It is used most commonly in cake mixes, chewing gums, chocolate products, synthetic cinnamon oils, cola drinks, ice creams, soft drinks, and vermouth. The compound is also added to a number of cosmetics and home care products to improve their odor. Such products include deodorants, detergents, mouthwashes, perfumes, sanitary napkins, soaps, and toothpastes. Finally, cinnamaldehyde is used to some extent in agriculture as an insecticide and fungicide. 

Cinnamaldehyde is the component responsible for cinnamon flavor. It is also a potent antimicrobial compound present in essential oils (see M. Friedman. 

Formaldehyde has been used for preservation for many years, as shown in Figure 22.9. Industrially, large quantities of formaldehyde are reacted with urea to manufacture a type of grease-resistant, hard plastic used to make buttons, appliance and automotive parts, and electrical outlets, as well as the glue that holds the layers of plywood together. Benzaldehyde and salicylaldehyde, shown in Table 22.7, are two components that give almonds their natural flavor. The aroma and flavor of cinnamon, a spice that comes from the bark of a tropical tree, are produced largely by cinnamaldehyde, also shown in Table 22.7. 

Many flavors involve sugar glycosides. Two familiar ones are cinnamon and vanilla, in which the sugars bond to cinnamaldehyde (3-phenyl-2-propenal) and vanillin, respectively. Both of these compounds are aromatic aldehydes. The distinctive taste of the kernel in a peach or apricot pit (a bitter-almond flavor) is due to laetrile, a controversial substance suggested as a cancer treatment by some. 

Benzaldehyde is nsed as an intermediate in the prodnction of flavoring chemicals, such as cinnamaldehyde, cinnamalalcohol, and amyl- and hexylcinnamaldehyde for perfume, soap, and food flavor synthetic penicillin, ampicillin, and ephedrine and as a raw material for the herbicide Avenge. It occurs in nature in the seeds of almonds, apricots, cherries, and peaches. It occurs in trace amounts in com oil. 

Cinnamaldehyde is nsed in flavor and perfumes. It occurs in cinnamon oils. 

The compound cinnamaldehyde, which comprises approximately 55 to 75% of cinnamon essential oil, can cause skin sensitization and irritation in sensitive persons. Reactions to cinnamaldehyde occur most commonly with prolonged oral exposure to products such as toothpaste, gum, or hard candies. Such cinnamon-flavored products have been found to be responsible for a number of cases of oral inflammation or lesions (Allen and Blozis 1988 Endo and Rees 2006 Lamey et al. 1990 Miller et al. 1992 ... 

Use As flavor and aroma substance, as intermediate for aroma chemicals, e. g., cinnamaldehyde, dyes, and pharmaceuticals. 

Identify the functional groups in cinnamaldehyde, present in cinnamon flavoring. 

The oxidative dehydrogenation of alcohols represents key steps in the synthesis of aldehyde, ketone, ester, and acid intermediates employed within the fine chemical, pharmaceutical, and agrochemical sectors, with allylic aldehydes in particular high-value components used in the perfume and fiavoring industries [1]. For example, crotonaldehyde is an important agrochemical and a valuable precursor for the food preservative sorbic acid, while citronellyl acetate and cinnamaldehyde confer rose/fruity and cinnamon flavors and aromas, respectively. There is also considerable interest in the exploitation of biomass-derived feedstocks such as glycerol (a by-product of biodiesel synthesis from plant or... 

Among those from spices are eugenol (18), the major component (85%) of oil of cloves (Fig. 8.8), and cinnamalde-hyde (19), the principal flavor constituent of oil of cinnamon. However, the latter compound occurs in a bound form as cinnamyl acetate in the plant and fresh bark. During the fermentative processing of the bark, this ester almost completely disappears and is not found in any quantity in commercial cinnamon. Studies with radioactively labeled materials confirm that the ester is converted into cinnamaldehyde. 

In this particular example, the resulting mixed aldol eliminates water on heating to give cinnamaldehyde (the flavor constituent of cinnamon). 

Purpose. In this exercise you will extract oil of cinnamon from a native plant source, such as Cinnamomum zeylanicum, and then purify the principal flavor and odor component of the oil, cinnamaldehyde. The experiment demonstrates the importance of steam distillation techniques (at the semimicro level) [Pg.239]

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