Cinnamaldehyde cinnamon

Camphene, a- Rosemary plant, P-Pinene, Cineole, and spruce needles Camphor, Bomeol, Bomyl Acetate, Humulene Cinnamaldehyde, Cinnamon Coumarin, C15H24 Isomers Limonene, a- Orange peel P-Pinene, C15H24 Limonene, Menthol, Chewing gum Isomenthone, Carvone, Menthone, C15H24 45 0.90 300... 

Carvacrol, carvone, cinnamaldehyde, cinnamon oil, clove bud oil, eugenol, and oregano oil have resulted in a 30%-50% reduction in ammonia N concentration in diluted ruminal uid with a 50 50 forage concentrate diet during the 24 h incubation (Busquet et al., 2006). 

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). 

The original identifications of character aroma compounds were from isolates of spice oils and herbs. Many of these early discoveries paralleled developments in synthetic organic chemistry (9). The first identifications and syntheses of character flavor molecules include benzaldehyde (cherry), vanillin (vanilla), methyl-salicylate (wintergreen), and cinnamaldehyde (cinnamon). A listing of character impact compounds found in herb and spice flavors is presented in Table 1. 

Phenyl-2-propenal [104-55-2], also referred to as cinnamaldehyde, is a pale yeUowHquid with a warm, sweet, spicy odor and pungent taste reminiscent of cinnamon. It is found naturally in the essential oils of Chinese cinnamon Cinnamomum cassia, Blume) (75—90%) and Ceylon cinnamon Cinnamomum lanicum, Nees) (60—75%) as the primary component in the steam distilled oils (27). It also occurs in many other essential oils at lower levels. 

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. 

Zimt, m. cinnamon. — weisser —, canella bark, canella. — chinesischer cassia bark. Zimt-. cinnamic cinnamon. -aldehyd, n. cinnamaldehyde, cinnamic aldehyde, -alko-hol, m. cinnamic alcohol, -blute,/. cinnamon flower, cassia bud. -bliltendl, n. cassia oil. zimtbraun, a. cinnamon-brown. Zimtcarbonsaure, /. carboxycinnamic acid, zimt-farbig, -farben, a. cinnamon-colored. Zimt-kaneel, m. canella bark, canella. -kassia, /. cassia bark, cassia, -kassienbl, n. oil of cassia. 

Yet another complication in 1H NMR spectroscopy arises when a signal is split by two or more nonequivalent kinds of protons, as is the case with trans-cinnamaldehyde, isolated from oil of cinnamon (Figure 13.19). Although the n + l rule predicts splitting caused by equivalent protons, splittings caused by nonequivalent protons are more complex. 

Cinnamaldehyde, the aromatic constituent of cinnamon oil, can be synthesized by a mixed aldol condensation. Show the starling materials you would use, and write the reaction. 

Aromatic aldehydes. Benzaldehyde, vanillin, and cinnamaldehyde are aldehydes with pleasant aromas that are found in almonds, vanilla beans, and cinnamon, respectively. 

Aldehydes, ketones and carboxylic acids are widespread in plants and animal kingdom. They play an important role in biochemical processes of life. They add fragrance and flavour to nature, for example, vanillin (from vanilla beans), salicylaldehyde (from meadow sweet) and cinnamaldehyde (from cinnamon) have veiy pleasant fragrances. 

Cinnamaldehyde is used in many compositions for creating spicy and oriental notes (e.g., soap perfumes). It is the main component of artificial cinnamon oil. In addition, it is an important intermediate in the synthesis of cinnamic alcohol and dihydrocinnamic alcohol. 

Raw materials are isolated from various parts of plants, e.g., blossoms, buds, fruit, peel, seeds, leaves, bark, wood, roots, or from resinous exudates. Different parts of the same plant may yield products with different compositions. For instance, steam distillation of the bark of the cinnamon tree gives cinnamon bark oil, which contains mainly cinnamaldehyde, whereas cinnamon leaf oil obtained from the leaves of the tree contains eugenol as its major constituent. 

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],... 

Cinnamon bark, Ceylon Cinnamomum zey-lanicum Nees Cinnamaldehyde (55-75)... 

Phenylpropanoids are widespread in higher plants, especially in the plants that produce essential oils, e.g. plants of the families, Apiaceae, Lamiaceae, Lauraceae, Myrtaceae and Rutaceae. For example, Tolu balsam (Myroxylon balsamum, family Fabaceae) yields a high concentration of cinnamic acid esters, cinnamon (Cinnamomum verum, family Lauraceae) produces cinnamaldehyde, fennel (Foeniculum vulgare, family Apiaceae) is a good... 

When the groups on either end of a double bond are the same or are structurally similar to each other, it is a simple matter to describe the configuration of the double bond as cis or trans. Oleic acid, for example, a compound that can be obtained from olive oil, has a cis double bond. Cinnamaldehyde, responsible for the characteristic odor of cinnamon, has a trans double bond. 

The odor of cinnamon oil is due to cinnamaldehyde, CgHgO. What is the hybridization of each carbon atom in cinnamaldehyde How many a bonds and how many it bonds does cinnamaldehyde have ... 

The determination of aldehydes and ketones is of importance in the analysis of those essential oils characterised especially by aldehydic or ketoruc principles, e g.,the citral contained in lemon and lemongrass oils, citronellal in citronella Oil and some eucalyptus oils, benzaldehyde in bitter almond oil, salicylaldehyde in meadow-sweet oil, anisaldehyde in aniseed and fennel oils, cuminaldehyde m cumin oil, cinnamaldehyde in cinnamon oil, carvone in caraway oil, pulegone in pennyroyal oil and methyl nonyl ketone in rue oil The determination of the aldehydes and ketones presents, however, difficulties and the above methods are moderately exact in only a few cases, especially when the content of aldehydes or ketones is considerable The bisulphite method is applicable particularly to the determination of cinnamaldehyde and benzaldehyde in cinnamon oil and bitter almond oil, and, up to a certain pomt, to that of citral in lemongrass Oil. The sulphite method gives good results in the same cases and for the determination of carvone and pulegone... 

The carbonyl number method gives moderately exact results for the determinations of benzaldehyde in bitter almond oil, of cuminaldehyde in cumin oil and of methyl nonyl ketone in rue oil. The method devised by Hanus gives, according to this author, good results for the amount of cinnamaldehyde in cinnamon oil. 

Cassia Cinnamomum cassia (Lauraceae) dried bark, or leaves and twigs 1-2 cinnamaldehyde (70-90) 2-methoxycinnamal-dehyde (12) flavour, carminative known as cinnamon oil in USA... 

Cinnamon bark Cinnamomum zeylanicum (Lauraceae) dried bark 1-2 cinnamaldehyde (70-80) eugenol (1-13) cinnamyl acetate (3-4) flavour, carminative, aromatherapy... 

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. 

---