CINNAMALDEHYDE

Cinnamaldehyde is an organic compound with the formula C9H8O or C6H6CH=CHCHO.
Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor.
Cinnamaldehyde is a phenylpropanoid that is naturally synthesized by the shikimate pathway.
This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum.
Cinnamaldehyde is an essential oil.
The bark of cinnamon tree contains high concentrations of Cinnamaldehyde.

CAS Number: 104-55-2
EC Number: 203-213-9
IUPAC Name: (E)-3-phenylprop-2-enal
Chemical Formula: C9H8O

Other names: 104-55-2, 14371-10-9, Cinnamic aldehyde, (E)-Cinnamaldehyde, 3-Phenylacrylaldehyde, Cinnamal, Zimtaldehyde, 2-Propenal, 3-phenyl-, (2E)-3-phenylprop-2-enal, 3-Phenylpropenal, Phenylacrolein, Cinnamylaldehyde, (E)-3-phenylprop-2-enal, trans-Cinnamic aldehyde, 2-propenal, 3-phenyl-, (2E)-, Cassia aldehyde, (E)-3-Phenylpropenal, 3-Phenylacrolein, Cinnemaldehyde, (E)-3-Phenyl-2-propenal, Cinnamyl aldehyde, 3-phenylprop-2-enal, Abion CA, Cinnamaldehyde, (E)-, Benzylideneacetaldehyde, beta-Phenylcrolein, 3-Phenyl-2-propenal, trans-Cinnamylaldehyde, 3-Fenylpropenal, 3-Phenyl-2-propenaldehyde, Acrolein, 3-phenyl-, trans-3-Phenyl-2-propenal, FEMA No. 2286, 3-Phenyl-2-propen-1-al, Caswell No. 221A, Aldehyd skoricovy, FEMA Number 2286, 3-Fenylpropenal [Czech], Aldehyd skoricovy [Czech], 2-Propenal, 3-phenyl-, (E)-, Cinnamic aldehyde (natural), NCI-C56111, Cinnamaldehyde [NF], Hefty Dog and Cat Repellent, .beta.-phenylacrolein, Cinnamaldehyde, trans-, (E)-Cinnamic aldehyde, CCRIS 3189, CCRIS 6222, HSDB 209, CHEBI:16731, UNII-SR60A3XG0F, EINECS 203-213-9, (2E)-3-phenylacrylaldehyde, SR60A3XG0F, MFCD00007000, NSC 16935, NSC-16935, NSC-40346, EPA Pesticide Chemical Code 040506, BRN 0605737, BRN 1071571, DTXSID6024834, AI3-00473, AI3-33275, (E)-3-Phenyl-propenal, XC-800, CINNAMALDEHYDE [II], CINNAMALDEHYDE [MI], CINNAMALDEHYDE [FCC], CINNAMALDEHYDE [FHFI], CINNAMALDEHYDE [HSDB], (3E)-3-phenylprop-2-enal, (2E)-3-Phenyl-2-propenal, CINNAMALDEHYDE (TRANS), CHEMBL293492, DTXCID504834, CINNAMALDEHYDE [USP-RS], CINNAMALDEHYDE [WHO-DD], (E)-cinnamaldehyde (incorrect), trans-cinnamaldehyde (incorrect), EC 203-213-9, 2-07-00-00273 (Beilstein Handbook Reference), 4-07-00-00984 (Beilstein Handbook Reference), NSC16935, NCGC00091512-04, CINNAMALDEHYDE (II), WLN: VH1U1R, beta-phenylacrolein, CINNAMALDEHYDE (USP-RS), CINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC], TRANS-CINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC], CAS-14371-10-9, Propenaldehyde, 3-phenyl-, 2-Propenaldehyde, 3-phenyl-, DTXSID1024835, Kaneelaldehyde, e-cinnamaldehyde, 2-propenal,3-phenyl-,(E)-, Aldehido cinamico, Cinnimic Aldehyde, transcinnamaldehyde, Zimtaldehyde light, (E)cinnamaldehyde, ECinnamyl aldehyde, transBenzenepropenal, trans cinnamaldehyde, trans3Phenylpropenal, transCinnamylaldehyde, (E)3Phenylacrolein, (E)3Phenylpropenal, trans-Benzenepropenal, CNMA, trans3Phenyl2propenal, (E)Cinnamyl aldehyde, transCinnamic aldehyde, (E)3Phenyl2propenal, (E)3Phenylprop2enal, Cinnamaldehyde, (E), (trans)-cinnamaldehyde, trans cinnamic aldehyde, trans-3-Phenylacrolein, trans-3-Phenylpropenal, (e)-3-Phenylacrolein, Benzylidene acetaldehyde, CINNAMAL [INCI], trans-3-phenyl-propenal, (E)-phenylvinyl aldehyde, (E)-3-phenylacrylaldehyde, bmse010257, Epitope ID:150921, 3-PHENYLACRYALDEHYDE, trans-3-Phenylacrylaldehyde, Trans-Cinnamaldehyde, (S), SCHEMBL3441, trans-Cinnamaldehyde, 99%, 3-Phenyl-2-propene-1-al, (E)-3-phenyl-acrylaldehyde, (e)-3-Phenylprop-2-enone, 2E)-3-Phenyl-2-propenal, 2Propenal, 3phenyl, (E), Cinnamaldehyde (trans), neat, MLS002454394, 2Propenal, 3phenyl, (2E), FEMA NUMBER 2286., trans-Cinnamaldehyde, >=99%, DTXCID904835, GTPL2423, trans-Cinnamaldehyde (Standard), (e)-3-Phenylprop-2-en-1-al, CHEBI:142921, HMS2268O08, HMS3885E04, HY-N0609, HY-W019711R, NSC40346, 2Propenal, 3phenyl, (E) (9CI), Tox21_111144, Tox21_200272, Tox21_201804, Tox21_303271, BDBM50203065, s3763, STK397371, AKOS000119171, Cinnamaldehyde, natural, >=95%, FG, CCG-266119, DB14184, FC30856, FT34719, Cinnamaldehyde min. 98%, for synthesis, USEPA/OPP Pesticide Code: 040506, 2-Propenal, 3-phenyl-, (E)-(9CI), Cinnamaldehyde 100 microg/mL in Toluene, NCGC00091512-01, NCGC00091512-02, NCGC00091512-05, NCGC00091512-06, NCGC00091512-07, NCGC00257017-01, NCGC00257826-01, NCGC00259353-01, trans-Cinnamaldehyde, analytical standard, AS-12078, AS-75456, CAS-104-55-2, SMR000112334, trans-Cinnamaldehyde, >=98%, FCC, FG, (E)-3-phenyl-2-propenal(E)-cinnamaldehyde, DB-003796, CS-0009609, NS00003408, EN300-19160, C00903, Cinnamaldehyde, Vetec(TM) reagent grade, 93%, D72477, EN300-735819, SBI-0635072.0002, (E)-Cinnamaldehyde; (2E)-3-phenyl-2-propenal, Q204036, BRD-K38088841-001-01-7, B99DD6C7-1C6D-4FE3-A172-54BFDB987683, Z3219847383, Cinnamic aldehyde;3-Phenyl-2-propenal;trans-Cinnamaldehyde, CINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM VERUM BARK), Cinnamaldehyde, United States Pharmacopeia (USP) Reference Standard, TRANS-CINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM CASSIA BARK), 203-213-9, 604-377-8, 805-158-1, 946-230-3

APPLICATIONS
Cinnamaldehyde exhibits excellent anti-inflammatory activities and antidepressant-like effects in stressed mid-aged rats as a COX-2 inhibitor. 
Cinnamaldehyde induces apoptosis of CML cells in vitro, down-regulation of the expression and function of BCR-ABL may be one of its most important anti-leukemia mechanisms.  
Cinnamaldehyde and cinnamic acid are cardioprotective in a rat model of ischemic myocardial injury, the mechanism is related to anti-oxidative and anti-inflammatory properties.

Denaturant: Cinnamaldehyde Makes cosmetics unpleasant. Mainly added to cosmetics containing ethyl alcohol
Fragrance Agent: Cinnamaldehyde is Used for perfume and aromatic raw materials
Flavoring agent: Cinnamaldehyde Gives an aroma to the cosmetic product.
Cinnamaldehyde is Aromatic aldehyde. 
Cinnamaldehyde is Used to give the smell of chamomile. 

Cinnamaldehyde is used for UV protection.
Cinnamaldehyde is a fragrance material that lends a sweet and warm cinnamon note to a formula.
Cinnamaldehyde acts as an antibacterial agent against Escherichia Coli and Salmonella in vitro. 
Cinnamaldehyde Causes cell structural damage resulting in leakage of cellular content.
Cinnamaldehyde is used in flavor and perfumes.

Cinnamaldehyde occurs in cinnamon oils.
Cinnamaldehyde is used In the flavor and perfume industry.
Cinnamaldehyde is a common ingredient in perfumes for household products like deodorizers, detergents, and soap; flavor in toothpaste, sweets, ice cream, soft drinks, chewing gums, and cakes; in balsam of Tolu and Peru, hyacinth plant, spices, cinnamon, Ceylon and cassia oil; some perfumery uses (Canoe; hyacinth; bubblegum; Balsam; Cassia); natural occurrence (cinnamon).

As a flavorant
The most obvious application for Cinnamaldehyde is as flavoring in chewing gum, ice cream, candy, eliquid and beverages; use levels range from 9 to 4,900 parts per million (ppm) (that is, less than 0.5%). 
Cinnamaldehyde is also used in some perfumes of natural, sweet, or fruity scents. 
Almond, apricot, butterscotch, and other aromas may partially employ the compound for their pleasant smells.
Cinnamaldehyde can be used as a food adulterant; powdered beechnut husk aromatized with Cinnamaldehydedehyde can be marketed as powdered cinnamon. 
Some breakfast cereals contain as much as 187 ppm Cinnamaldehyde.

As an agrichemical
Cinnamaldehyde has been tested as a safe and effective insecticide against mosquito larvae. 
A concentration of 29 ppm of Cinnamaldehyde kills half of Aedes aegypti mosquito larvae in 24 hours. 
Trans-Cinnamaldehydedehyde works as a potent fumigant and practical repellant for adult mosquitos. 
Cinnamaldehyde also has antibacterial and antifungal properties.

Miscellaneous uses
Cinnamaldehyde is a corrosion inhibitor for steel and other alloys. 
Cinnamaldehyde is believed to form a protective film on the metal surface.

DESCRIPTION
Cinnamaldehyde is an organic compound with the formula C6H5CH=CHCHO. 
Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. 
Cinnamaldehyde is a phenylpropanoid that is naturally synthesized by the shikimate pathway. 
This pale yellow, viscous liquid, Cinnamaldehyde occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. 
Cinnamaldehyde is a yellow oily liquid with a cinnamon odor and sweet taste.

The essential oil of cinnamon bark is about 90% Cinnamaldehyde.
Cinnamaldehyde is a clear yellow liquid with an odor of cinnamon and a sweet taste.
(E)-Cinnamaldehydedehyde is the E (trans) stereoisomer of Cinnamaldehyde, the parent of the class of Cinnamaldehydedehydes. 
Cinnamaldehyde has a role as a hypoglycemic agent, an EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor, a vasodilator agent, an antifungal agent, a flavouring agent, a plant metabolite and a sensitiser. 
Cinnamaldehyde is a 3-phenylprop-2-enal and a member of Cinnamaldehydedehydes.
Cinnamaldehyde is a common ingredient in perfumes for household products like deodorizers, detergents and soap. 

Cinnamaldehyde is also used for flavor in toothpaste, sweets, ice cream, soft drinks, chewing gums and cakes. 
Cinnamaldehyde is present in balsam of Tolu and Peru, hyacinth plant, spices, cinnamon, Ceylon and cassia oil. 
Further research may identify additional product or industrial usages of Cinnamaldehyde.
Cinnamaldehyde is an α,β-unsaturated aromatic aldehyde that can be used as a flavoring agent. 
Cinnamaldehyde is the principal flavor component of cinnamon oil.
Cinnamaldehyde is a fragrance material that lends a sweet and warm cinnamon note to a formula.

Sometimes Cinnamaldehyde occurs naturally in the essential oil we use, and sometimes we add Cinnamaldehyde in its synthetic form to enrich the fragrance of products.
Cinnamaldehyde, also known as (E)-3-phenyl-2-propenal or 3-phenylacrylaldehyde, is a member of the class of compounds known as Cinnamaldehydedehydes. 
Cinnamaldehyde are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. 
Cinnamaldehyde is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 

Cinnamaldehyde is a sweet, candy, and cinnamon tasting compound and can be found in a number of food items such as sour cherry, rubus (blackberry, raspberry), horseradish, and sea-buckthornberry, which makes Cinnamaldehydedehyde a potential biomarker for the consumption of these food products. 
Cinnamaldehyde can be found primarily in feces, as well as in human neuron and skin tissues. 
Cinnamaldehyde exists in all eukaryotes, ranging from yeast to humans. Cinnamaldehyde is a non-carcinogenic (not listed by IARC) potentially toxic compound. 
Cinnamaldehyde is an organic compound with the formula C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, Cinnamaldehyde gives cinnamon its flavor and odor. It is a flavonoid that is naturally synthesized by the shikimate pathway. 

Cinnamaldehyde, pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. 
The essential oil of cinnamon bark is about 50% Cinnamaldehyde. 
The specific symptoms that can result from Cinnamaldehyde allergy can vary considerably amongst patients from a severe anaphylactic reaction to asthma, abdominal symptoms, eczema or headaches.
Cinnamaldehyde Belongs to the class of organic compounds known as Cinnamaldehydedehydes. 

These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.
Cinnamaldehyde is the bivalent radical C6H5CH:CHCH< derived from Cinnamaldehydedehyde by removal of the oxygen atom.
Cinnamaldehyde is a yellow oily liquid with a sweetly warm, spicy scent. 
Cinnamaldehyde is soluble in oils and ethanol. 
Cinnamaldehyde occurs naturally, for example, in cinnamon essential oil (it contains up to 90% Cinnamaldehyde) or in chamomile essential oil. 

Cinnamaldehyde can also be found in the bark of the Camphor tree (Cinnamomum camphora) or the Chinese cassia / cinnamon (Cinnamomum cassia). 
Synthetic Cinnamaldehyde is also produced, but only purely natural is used in natural certified cosmetics. 
The presence of Cinnamaldehyde must be recorded in the list of ingredients, due to the possible allergenic potential in more sensitive individuals, if its concentration exceeds 0,001% in non-rinse products and 0,01% in rinse products.

Cinnamaldehyde is  an aromatic oily aldehyde C9H8O occurring as the chief constituent of cinnamon-bark oil and cinnamon oil and used as a flavor.
Cinnamaldehyde (cinnamic aldehyde) is the main component in cassia oil as well as cinnamon bark oil and is used in flavoring compounds to impart a cinnamon flavor.
Considerable safety data exist from the food and flavoring industry which utilizes food grade Cinnamaldehyde in non-alcoholic beverages, ice cream, candy, baked goods,
chewing gum, condiments and meats at levels ranging from 9 ppm to 4900 ppm.

Cinnamaldehyde is Generally Recognized As Safe (GRAS) by the Flavoring Extract Manufacturers' Association and is approved for food use (21 CFR 182.60) by the Food
and Drug Administration (FDA). 
Cinnamon oil, which contains 70% to 90% Cinnamaldehyde, is also classified as GRAS, and, like Cinnamaldehyde, is used in the food and flavoring industry.
Cinnamaldehyde is Multi-action pesticide used to control downy mildew, powdery mildew, aphids and mites. 
Cinnamaldehyde is  Also used as a mammal repellant.
Cinnamaldehyde is a naturally occurring flavonoid that gives the spice cinnamon its flavour and odour. 

Cinnamaldehyde occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum such as camphor and cassia.
Cinnamaldehyde is used as a flavoring agent, ingredient of fragrance in soft drinks, ice creams, dentifrices, pastries, chewing-gum, etc. 
Cinnamaldehyde can induce both contact urticaria and delayed-type reactions. 
Cinnamaldehyde can be implicated in contact dermatitis in those who work in the perfume industry or food handlers. 
Cinnamaldehyde is contained in the "fragrance mix".

Cinnamaldehyde exists as yellowish to greenish-yellow oily liquid with a Strong pungent, spicy, cinnamon odor. 
Cinnamaldehyde is normally insoluble in water and many organic solvents but is miscible with alcohol and other flavoring oils. 
Exposure to air will result in thickening and oxidation.
Cinnamaldehyde (cinnamic aldehyde, benzylideneactaldehyde, phenylacrolein, 3-phenylpropenal, 3-phenyl-2-propenal) is a saturated aldehyde with an aromatic ring that is a yellowish, oily liquid at room temperature. 

Cinnamaldehyde is used as a flavoring and aromatic agent in a variety of food products, perfumes, and household products. 
Cinnamaldehyde has also seen use as a rubber reinforcing agent. 
A burning taste that produces the odor and flavor of the spice may be found with Cinnamaldehyde. 
Cinnamaldehyde has also been used as an attractant for insect control, in the preparation of corrosion inhibitors, and as a coating for metals. 
Although extensively used in industry, Cinnamaldehyde is also a natural constituent of cinnamon leaves and bark, some essential oils, and other plant products.

The flavour and aroma of cinnamon is due to an essential oil which makes up between 1 and 4% of the bark of the Cinnamomum zeylanicum tree. 
Cinnamaldehyde, or 3-phenylprop-2-enal to use its IUPAC name, is an oily yellow liquid at room temperature with a boiling point of 246 °C. 
Cinnamaldehyde can be made synthetically but is more commonly obtained from the steam distillation of the oil of cinnamon bark which is a much more efficient process. 
Cinnamaldehyde is mainly used as a flavouring agent or as a scent for candles. 

Cinnamaldehyde is non-toxic but can irritate skin if in contact for too long. 
As with many components of essential oils Cinnamaldehyde displays antiviral, antibacterial and antifungal properties. 
Cinnamaldehyde is also reported to be a good pesticide. These properties support the medicinal and soothing properties of cinnamon bark. 
A minor component of cinnamon oil is eugenol. 
Cinnamaldehyde makes up about 10% of the oil and displays antiseptic and analgesic properties which may also contribute to cinnamon's soothing effect.

PHYSICAL PROPERTIES
State: solid
Odor: cinnamon
Color: yellow
Boiling point: 253°C
Freezing point: –7°C
Density: 1.049 kg l−1

Density temperature: 25°C
vapor density 4.6 (vs air)
vapor pressure <0.1 hPa (20 °C)
Flash point: 160 °F
storage temp.: Store below +30°C.

Structure and synthesis
Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by Jean-Baptiste Dumas and Eugène-Melchior Péligot and synthesized in the laboratory by the Italian chemist Luigi Chiozza in 1854.
The natural product is trans-Cinnamaldehydedehyde. 
Cinnamaldehyde consists of a benzene ring attached to an unsaturated aldehyde. 
As such, Cinnamaldehyde molecule can be viewed as a derivative of acrolein. 
Cinnamaldehyde's color is due to the π → π* transition: increased conjugation in comparison with acrolein shifts this band towards the visible.

Biosynthesis
Pathway for the biosynthesis of trans-Cinnamaldehydedehyde.
Cinnamaldehyde occurs widely, and closely related compounds give rise to lignin. 
All such compounds are biosynthesized starting from phenylalanine, which undergoes conversion.

The biosynthesis of Cinnamaldehyde begins with deamination of L-phenylalanine into cinnamic acid by the action of phenylalanine ammonia lyase (PAL). 
PAL catalyzes this reaction by a non-oxidative deamination. 
This deamination relies on the MIO prosthetic group of PAL. 
PAL gives rise to trans-cinnamic acid. 

In the second step, 4-coumarate–CoA ligase (4CL) converts cinnamic acid to cinnamoyl-CoA by an acid–thiol ligation. 
4CL uses ATP to catalyze the formation of cinnamoyl-CoA.[11] 4CL effects this reaction in two steps.
4CL forms a hydroxycinnamate–AMP anhydride, followed by a nucleophile attack on the carbonyl of the acyl adenylate.
Finally, Cinnamoyl-CoA is reduced by NADPH catalyzed by CCR (cinnamoyl-CoA reductase) to form Cinnamaldehyde.

Preparation
Several methods of laboratory synthesis exist, but Cinnamaldehyde is most economically obtained from the steam distillation of the oil of cinnamon bark. 
Cinnamaldehyde  can be prepared from related compounds such as cinnamyl alcohol, (the alcohol form of Cinnamaldehydedehyde), but the first synthesis from unrelated compounds was the aldol condensation of benzaldehyde and acetaldehyde; this process was patented by Henry Richmond on November 7, 1950.

Derivatives
Numerous derivatives of Cinnamaldehyde are commercially useful. 
Dihydrocinnamyl alcohol occurs naturally but is produced by double hydrogenation of Cinnamaldehyde. 
It has the fragrances of hyacinth and lilac. 
Cinnamyl alcohol similarly occurs naturally and has the odor of lilac but can be also produced starting from Cinnamaldehyde. 

DihydroCinnamaldehydedehyde is produced by the selective hydrogenation of the alkene subunit. 
α-AmylCinnamaldehydedehyde and α-hexylCinnamaldehydedehyde are important commercial fragrances, but they are not prepared from Cinnamaldehyde. 
Hydrogenation of Cinnamaldehyde, if directed to the alkene, gives hydroCinnamaldehydedehyde.

Toxicology
Cinnamaldehyde is used in agriculture because of its low toxicity, but Cinnamaldehyde is a skin irritant. 
Allergy to Cinnamaldehyde is not common.
Cinnamaldehyde can cause moderate to severeskin irritation. Exposure to 40 mg in48 hours produced a severe irritation effecton human skin. 
The toxicity of Cinnamaldehyde was low to moderate on test subjects,depending on the species and the toxicroutes. 

However, when given by oral routein large amounts, its poisoning effect wassevere. 
Amounts greater than 1500 mg/kghave produced a wide range of toxic effectsin rats, mice, and guinea pigs. 
The symptomswere respiratory stimulation, somnolence,convulsion, ataxia, coma, hypermotility, anddiarrhea.
Cinnamaldehyde is a mutagen. 
Cinnamaldehyde's carcinogeniceffect is not established.