CINNAMAL

CAS Number: 14371-10-9; 104-55-2
ChemSpider: 553117 
EC Number: 203-213-9
PubChem CID: 637511
CAS Number: 104-55-2
EINECS/ELINCS No: 203-213-9
COSING REF No: 32846
IUPAC Name: (E)-3-phenylprop-2-enal
Common name: 3-phenyl-2-propenal
Chemical category: aldehyde

APPLICATIONS

Cinnamal exhibits excellent anti-inflammatory activities and antidepressant-like effects in stressed mid-aged rats as a COX-2 inhibitor. 
Cinnamal 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.  
Cinnamal 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: Cinnamal Makes cosmetics unpleasant. Mainly added to cosmetics containing ethyl alcohol
-Fragrance Agent: Cinnamal is Used for perfume and aromatic raw materials
-Flavoring agent: Cinnamal Gives an aroma to the cosmetic product.
Cinnamal is Aromatic aldehyde. 
Cinnamal is Used to give the smell of chamomile. 
Cinnamal is used for UV protection.
Cinnamal is a fragrance material that lends a sweet and warm cinnamon note to a formula.
Cinnamal acts as an antibacterial agent against Escherichia Coli and Salmonella in vitro. 
Cinnamal Causes cell structural damage resulting in leakage of cellular content.
Cinnamal is used in flavor and perfumes.
Cinnamal occurs in cinnamon oils.
Cinnamal is used In the flavor and perfume industry.
Cinnamal 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 Cinnamal 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%). 
Cinnamal 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.
Cinnamal can be used as a food adulterant; powdered beechnut husk aromatized with cinnamaldehyde can be marketed as powdered cinnamon. 
Some breakfast cereals contain as much as 187 ppm cinnamal.

As an agrichemical

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

Miscellaneous uses

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

DESCRIPTION

Cinnamal is an organic compound with the formula C6H5CH=CHCHO. 
Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. 
Cinnamal is a phenylpropanoid that is naturally synthesized by the shikimate pathway. 
This pale yellow, viscous liquid, Cinnamal occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. 
Cinnamal is a yellow oily liquid with a cinnamon odor and sweet taste.
The essential oil of cinnamon bark is about 90% cinnamal.
Cinnamal is a clear yellow liquid with an odor of cinnamon and a sweet taste.
(E)-cinnamaldehyde is the E (trans) stereoisomer of Cinnamal, the parent of the class of cinnamaldehydes. 
Cinnamal 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. 
Cinnamal is a 3-phenylprop-2-enal and a member of cinnamaldehydes.
Cinnamal is a common ingredient in perfumes for household products like deodorizers, detergents and soap. 
Cinnamal is also used for flavor in toothpaste, sweets, ice cream, soft drinks, chewing gums and cakes. 
Cinnamal 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 Cinnamal.
Cinnamal is an α,β-unsaturated aromatic aldehyde that can be used as a flavoring agent. 
Cinnamal is the principal flavor component of cinnamon oil.
Cinnamal is a fragrance material that lends a sweet and warm cinnamon note to a formula.
Sometimes Cinnamal occurs naturally in the essential oil we use, and sometimes we add Cinnamal in its synthetic form to enrich the fragrance of products.
Cinnamal, also known as (E)-3-phenyl-2-propenal or 3-phenylacrylaldehyde, is a member of the class of compounds known as cinnamaldehydes. 
Cinnamal are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. 
Cinnamal is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 
Cinnamal 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 cinnamaldehyde a potential biomarker for the consumption of these food products. 
Cinnamal can be found primarily in feces, as well as in human neuron and skin tissues. 
Cinnamal exists in all eukaryotes, ranging from yeast to humans. Cinnamal is a non-carcinogenic (not listed by IARC) potentially toxic compound. 
Cinnamal is an organic compound with the formula C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, Cinnamal gives cinnamon its flavor and odor. It is a flavonoid that is naturally synthesized by the shikimate pathway. 
Cinnamal, 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% cinnamal. 
The specific symptoms that can result from Cinnamal allergy can vary considerably amongst patients from a severe anaphylactic reaction to asthma, abdominal symptoms, eczema or headaches.
Cinnamal Belongs to the class of organic compounds known as cinnamaldehydes. 
These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.
Cinnamal is the bivalent radical C6H5CH:CHCH< derived from cinnamaldehyde by removal of the oxygen atom.
Cinnamal is a yellow oily liquid with a sweetly warm, spicy scent. 
Cinnamal is soluble in oils and ethanol. 
Cinnamal occurs naturally, for example, in cinnamon essential oil (it contains up to 90% cinnamal) or in chamomile essential oil. 
Cinnamal can also be found in the bark of the Camphor tree (Cinnamomum camphora) or the Chinese cassia / cinnamon (Cinnamomum cassia). 
Synthetic cinnamal is also produced, but only purely natural is used in natural certified cosmetics. 
The presence of Cinnamal 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.
Cinnamal is  an aromatic oily aldehyde C9H8O occurring as the chief constituent of cinnamon-bark oil and cinnamon oil and used as a flavor.
Cinnamal (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 cinnamal in non-alcoholic beverages, ice cream, candy, baked goods,
chewing gum, condiments and meats at levels ranging from 9 ppm to 4900 ppm.
Cinnamal 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% cinnamal, is also classified as GRAS, and, like cinnamal, is used in the food and flavoring industry.
Cinnamal is Multi-action pesticide used to control downy mildew, powdery mildew, aphids and mites. 
Cinnamal is  Also used as a mammal repellant.
Cinnamal is a naturally occurring flavonoid that gives the spice cinnamon its flavour and odour. 
Cinnamal occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum such as camphor and cassia.
Cinnamal is used as a flavoring agent, ingredient of fragrance in soft drinks, ice creams, dentifrices, pastries, chewing-gum, etc. 
Cinnamal can induce both contact urticaria and delayed-type reactions. 
Cinnamal can be implicated in contact dermatitis in those who work in the perfume industry or food handlers. 
Cinnamal is contained in the "fragrance mix".
Cinnamal exists as yellowish to greenish-yellow oily liquid with a Strong pungent, spicy, cinnamon odor. 
Cinnamal 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.
Cinnamal (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. 
Cinnamal is used as a flavoring and aromatic agent in a variety of food products, perfumes, and household products. 
Cinnamal 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 Cinnamal. 
Cinnamal 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, Cinnamal 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. 
Cinnamal, 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. 
Cinnamal 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. 
Cinnamal is mainly used as a flavouring agent or as a scent for candles. 
Cinnamal is non-toxic but can irritate skin if in contact for too long. 
As with many components of essential oils cinnamal displays antiviral, antibacterial and antifungal properties. 
Cinnamal 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. 
Cinnamal 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

Cinnamal 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-cinnamaldehyde. 
Cinnamal consists of a benzene ring attached to an unsaturated aldehyde. 
As such, Cinnamal molecule can be viewed as a derivative of acrolein. 
Cinnamal'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-cinnamaldehyde.
Cinnamal occurs widely, and closely related compounds give rise to lignin. 
All such compounds are biosynthesized starting from phenylalanine, which undergoes conversion.

The biosynthesis of cinnamal 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 cinnamal.

Preparation

Several methods of laboratory synthesis exist, but cinnamal is most economically obtained from the steam distillation of the oil of cinnamon bark. 
Cinnamal  can be prepared from related compounds such as cinnamyl alcohol, (the alcohol form of cinnamaldehyde), 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 cinnamal are commercially useful. 
Dihydrocinnamyl alcohol occurs naturally but is produced by double hydrogenation of cinnamal. 
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 cinnamal. 
Dihydrocinnamaldehyde is produced by the selective hydrogenation of the alkene subunit. 
α-Amylcinnamaldehyde and α-hexylcinnamaldehyde are important commercial fragrances, but they are not prepared from cinnamal. 
Hydrogenation of cinnamal, if directed to the alkene, gives hydrocinnamaldehyde.

Toxicology

Cinnamal is used in agriculture because of its low toxicity, but Cinnamal is a skin irritant. 
Allergy to cinnamal is not common.
Cinnamal can cause moderate to severeskin irritation. Exposure to 40 mg in48 hours produced a severe irritation effecton human skin. 
The toxicity of Cinnamal 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.
Cinnamal is a mutagen. 
Cinnamal's carcinogeniceffect is not established.

SYNONYMS

-Cinnamaldehyde, 
-trans-Cinnamaldehyde, 
-Cinnamal, 
-Phenylacrolein
-3-PHENYL-2-PROPENAL
-CINNAMALDEHYDE, 
-CINNAMIC ALDEHYDE
-CINNAMYL ALDEHYDE
-Cinnamic aldehyde
-3-Phenyl-2-propenal
-trans-Cinnamaldehyde