Benzaldehyde cinnamon

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

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. 

Cinnamomum zeglanicum Blume Ceylon Rou Gui (Ceylon cinnamon) (bark) Cinnamic aldehyde, p-cymene, hydrocinnamic aldehyde, pinene, benzaldehyde, cuminic aldehyde, nonylic aldehyde, eugenol, caryophyllene, 1-phellandrine, methyl-n-amyl ketone, 1-linalool.60 Stimulant to digestion, respiration, circulation. 

Many aldehydes are particularly fragrant. A number of flowers, for example, owe their pleasant odor to the presence of simple aldehydes. The smells of lemons, cinnamon, and almonds are due to the aldehydes citral, cinnamalde-hyde, and benzaldehyde, respectively. The structures of these three aldehydes are shown in Figure 12.21. The aldehyde vanillin, introduced at the beginning of this chapter, is the key flavoring molecule derived from the vanilla orchid. You may have noticed that vanilla seed pods and vanilla extract are fairly expensive. Imitation vanilla flavoring is less expensive because it is merely a solution of the compound vanillin, which is economically synthesized from the waste chemicals of the wood pulp industry. Imitation vanilla does not taste the same as natural vanilla extract, however, because in addition to vanillin many other flavorful molecules contribute to the complex taste of natural vanilla. Many books made in the days before acid-free paper smell of vanilla because of the vanillin formed and released as the paper ages, a process that is accelerated by the acids the paper contains. 

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. 

Table II lists 13 of the most commonly-used chemicals in the flavor industry. For example, cinnamic aldehyde is used for the generation of cassia or cinnamon flavors, carvone for spearmint flavors, citral for citrus flavors, and benzaldehyde for cherry flavors. As can be seen, the known s values for these compounds are...

Cinnamic Aldehyde.—The other aromatic aldehyde which we shall mention is cinnamic aldehyde. It contains the aldehyde group in the side chain and not in the benzene ring, and is thus an aliphatic aldehyde substitution product of benzene. The aliphatic side chain is also an unsaturated chain. Its formula is CeHs—CH=CH—CHO, and it may be considered as beta-phenyl acrylic aldehyde. As an aldehyde it yields by oxidation an acid, viz., beta-phenyl acrylic acid or, as it is commonly known, cinnamic acid. The aldehyde is found in oil of cinnamon obtained from cinnamon bark, hence its name and the name of the acid. The most important synthesis is by the condensation of benzaldehyde and acetaldehyde, as follows ... 

Aldehydes.—Some essential oils contain aldehydes e.g.y oil of hitter almondsy which is benzaldehyde (p. 654). Oil of cinnamon and oil of cassia contain mostly cinnamic aldehyde (p. 656). 

Benzaldehyde and salicy-laldehyde are two components of the flavor of almonds. o The aroma and flavor of cinnamon are produced largely by cin-namaldehyde. Cinnamon is the ground bark of a tropical tree. 

Composition 65-80% (E)-ciimamaldehyde, up to app. 10% eugenol, methyl eugenol, linalool, which, has been reported not to occur in cassia oil [56], (E)-cirmamyl acetate, geranylacetate, benzyl benzoate, caryophyllene, hydrocirmamic aldehyde, benzaldehyde, a-terpineol, pinene, phellandrene, p-cymene and others [57, 58, 59], Note that Cinnamon bark and leaf oil are also specified in the European Pharmacopoeia. 

G. Remaud, A.A. Debon, Y.-L. Martin, G.G. Martin, G.J. Martin (1997) Authentication of bitter almond oil and cinnamon oil application of the SNIF-NMR method to benzaldehyde. J. Agric. Food Chem. 45, 4042-4048... 

Derivation (1) From Ceylon and Chinese cinnamon oils (2) by condensation of benzaldehyde and acetaldehyde. 

Cinnamaldehyde. 3-Phenyl-2-propenat cinnamic aldehyde phenylacrolein cinnamal. C HsO mol wt 132.15. C 81.79%, H 6.10%, O 12.11%. C H CH—CHCHO- Found in Caylon and Chinese cinnamon oils. Prepn by condensation of benzaldehyde and acetaldehyde Peine, Ber. 17, 2117 (1884) Japan, pat. 163,097 (1944 to Ogawa Chem. Ind.) from 2-chloroallylbenzene Bert, Dorier. Compi. Rend. 191, 332 (1930) Bert, Annequin, ibid. 192, 1315 (1931) by condensation of styrene with foimylmethylaniline Brit. pat. 

With a characteristic aroma of bitter almond oil and a typical sweet cherry taste, benzaldehyde is widely used as an important ingredient for creating cherry, peach, vanilla, chocolate, and many other flavors. Benzaldehyde can be produced from botanical sources such as cinnamon, cassia, bitter almonds, pits of apricot, peaches, plums, and cherries, or from petroleum products such as toluene. 

Retro-aldol hydrolysis of cinnamic aldehyde forms benzaldehyde and acetaldehyde. Interestingly, the reverse reaction, i.e., aldol condensation of benzaldehyde and acetaldehyde lias also been used to produce cinnamic aldehyde. In the food industry, many users prefer benzaldehyde produced using cinnamic aldehyde isolated from cinnamon because it is a material with a natural origin and a reasonable price. 

Benzaldehyde obtained from bitter almond oil and from the retro-aldol reaction of ciimamic aldehyde from cinnamon originate from different biosynthetic pathways. Therefore, benzaldehyde from bitter almond oil can be easily differentiated from benzaldehyde ex-cassia by comparing tlieir site-specific deuterium distributions. 

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. 

There are naturally occurring food preservatives. One has recently been identified. It is a substance in cinnamon named benzaldehyde. It is also found in black pepper, vanilla, and peaches. We may be seeing it in the future as a preservative in canned foods that now require heating for lengthy times before they are safe. 

Ludera-Zimoch, G. 1981. Case of urticaria with immediate local and generalized reaction to cinnamon oil and benzaldehyde.] Przegl. Dermatol. 68(l) 67-70. 

C10H10O2, Mr 162.19) (12%), by the occurrence of which C. differs from cinnamon oil. Important minor components of C. are benzaldehyde, salicylaldehyde, (C7H6O2, Mr 122.12), and coumarin. 

Anise oil Basil oil Laurel leaf oil Benzaldehyde Caraway oil Carrot oil Celery oil Cinnamon oil Coriander oil Dill oil Smoke oil Garlic oil Lemon oil Marjoram oil Mustard oil Onion oil Orange oil Mint oil Raspberry oil Sage oil... 

Artichoke leaves. See Artichoke (Cyanara scolymus) leaves Artie Mist . See Talc Artificial almond oil. See Benzaldehyde Artificial ant oil. See Furfural Artificial barite. See Barium sulfate Artificial cinnabar. See Mercury sulfide (ic), red Artificial cinnamon oil. See Cinnamon (Cinnamomum cassia) oil Artificial gum. See Dextrin Artificial heavy spar. See Barium sulfate Artificial musk ambrette. See Musk ambrette... 

Cinnamic aldehyde is found in cinnamon and cassia barks— Cinnamomum spp. (Lauraceae). Benzaldehyde is the main constituent of bitter almond essential oil. 

Benzaldehyde is found in the kernels of bitter almonds. Cinnamaldehyde is found in Ceylon and Chinese cinnamon oils. 

The most familiar aldehyde is probably formaldehyde, shown earlier in this section. Formaldehyde is a gas with a pungent odor. It is often mixed with water to make formalin, a preservative and disinfectant. Formaldehyde is also found in wood smoke, which is one reason that smoking foods preserves them—the formaldehyde kills the bacteria. Aromatic aldehydes, those that also contain an aromatic ring, have pleasant aromas. For example, cirmamaldehyde is the sweetsmelling component of cinnamon, benzaldehyde accoxmts for the smell of almonds, and vanillin is responsible for the smell of vanilla. 

Cinnamaldehyde is one of the primary constituents of cinnamon oil and contributes significantly to the odor of cinnamon. Starting with benzaldehyde and using any other necessary reagents, show how you might prepare cinnamaldehyde. 

Acrolein forms when molecules in some foods decompose during heating. Its acrid smell is enjoyed when barbecuing meats, and its flavor is found in caramelized sugar. Other aldehydes of interest include cinnamaldehyde, which gives cinnamon its distinctive smell and flavor, and benzaldehyde, also called oil of almond. 

Benzaldehyde is found in oil of almond, and cinnamaldehyde is found in cinnamon. 

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). 

Everyone has at least some first-hand sensory knowledge of aldehydes and ketones. Some aldehydes are responsible for very pleasant tastes and odors, such as vanillin from vanilla beans, benzaldehyde from almonds, and cinnamaldehyde from cinnamon (shown above). On the other hand, acetaldehyde (ethanal) causes the unpleasant "hangover" feeling that can result from consuming alcoholic beverages, and formaldehyde (methanal) is highly toxic and has a very pungent odor, as do many other aldehydes. 

A common aldehyde is formaldehyde. Formaldehyde has a sharp, somewhat unpleasant odor. The aromatic aldehydes in the figure below, on the other hand, have a very pleasant "flavor." Benzaldehyde has the characteristic odor of almonds, vanillin is responsible for the flavor of vanilla, and cinnamaldehyde makes an important contribution to the flavor of cinnamon. 

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