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CINNAMIC ACID

CAS NO.: 140-10-3
EC/LIST NO.: 205-398-1

Cinnamic acid is an organic compound with the formula C6H5CH=CHCOOH.
Cinnamic acid is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents.
Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants.
Cinnamic acid exists as both a cis and a trans isomer, although the latter is more common

Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position.
Cinnamic acid is found in Cinnamomum cassia. It has a role as a plant metabolite. It is a member of styrenes and a member of cinnamic acids.
Cinnamic acid is a conjugate acid of a cinnamate.

Cinnamic acid (C9H8O2) is an organic acid isolated from cinnamon bark and generally used as a common food additive being antimicrobial against common postharvest pathogen such.

Cinnamic acid, also known as (Z)-cinnamate or 3-phenyl-acrylate, belongs to the class of organic compounds known as cinnamic acids.
These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
Cinnamic acid can be obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is a weakly acidic compound (based on its pKa).
Cinnamic acid is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents.
Cinnamic acid exists in all living organisms, ranging from bacteria to plants to humans.
Outside of the human body, cinnamic acid has been detected, but not quantified in, chinese cinnamons.
In plants, cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids.

Cinnamic acid (CA) and its hydroxy-derivatives are aromatic building blocks whose structural peculiarities (unsaturation, hydroxylic and/or carboxylic groups) have driven them to a prominent position in polymer science

Cinnamic acid is an organic acid occurring naturally in plants that has low toxicity and a broad spectrum of biological activities.
In the search for novel pharmacologically active compounds, cinnamic acid derivatives are important and promising compounds with high potential for development into drugs.
Many cinnamic acid derivatives, especially those with the phenolic hydroxyl group, are well-known antioxidants and are supposed to have several health benefits due to their strong free radical scavenging properties.
Cinnamic acid is also well known that cinnamic acid has antimicrobial activity.
Cinnamic acid derivatives, both isolated from plant material and synthesized, have been reported to have antibacterial, antiviral and antifungal properties.
Acids, esters, amides, hydrazides and related derivatives of cinnamic acid with such activities are here reviewed.

Cinnamic acid exists in cis and trans forms. the more stable isomer is the trans isomer, which occurs naturally and is the usual commercial product.
Cinnamic acid appears as white monoclinic prisms with slight cinnamon aroma.
Cinnamic acid is soluble in ethanol, methanol, petroleum ether and chloroform;
Cinnamic acid is easily soluble in benzene, ether, acetone, acetic acid, carbon disulfide and oils but insoluble in water.

Cinnamic acid was first isolated as crystals from cinnamon oil by Trommsdorf in 1780.
He thought it was benzoic acid.
Dumas and Peligot ´ identified it in 1835, and in 1856 Bertagnini succeeded in synthesizing it from benzaldehyde and acetyl chloride.
Cinnamic acid undergoes reactions typical of a carboxyl group and an olefinic double bond.
The carboxyl group can be esterified to form cinnamates, some of which are important flavorings and fragrances.
When reacted with inorganic acid chlorides, such as thionyl chloride or phosphorus chlorides, cinnamic acid gives cinnamoyl chloride [102-92-1].
When heated, cinnamic acid forms styrene [100-42-5] and carbon dioxide.
With oxidizing agents or when heated with alkali, the olefinic double bond cleaves to give benzaldehyde

Cinnamic acid is a hydroxycinnamic acid, a type of polyphenol.
Cinnamic acid is part of the biosynthetic shikimate and phenylpropanoid pathways.
Cinnamic acids biosynthesis is performed by action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine.
Cinnamic acid has a honey-like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent.

Cinnamic acid or (E)-3-phenylprop-2-enoic acid is an aromatic organic compound which has crystalline structure and is freely soluble in various organic solvents.
Cinnamic acid has odor similar to that of honey which makes suitable as flavoring agent.
Cinnamic acid occurs naturally in several plants including cinnamon. The major applications for cinnamic acid include synthetic indigo, flavoring agent and preparation of various esters, amides and cinnamoyl acids which find range of pharmaceutical uses especially in diseases like malaria and tuberculosis.

Cinnamic Acid is a white crystalline organic compound with the chemical formula C6H5CHCHCO2H.
Cinnamic Acid is slightly soluble in water and is soluble in many organic solvents.
Cinnamic Acid is classified as an unsaturated carboxylic acid, which is an organic compound that contains a carboxyl group (C(O)OH).
There are cis and a trans isomer exist naturally in a number of plants and the trans isomer is more common.

Scientists at Creative Proteomics utilize a highly quantitative method with high-performance liquid chromatography (HPLC) for the determination of Cinnamic Acid levels in various samples, including Plant and more.
High-Performance Liquid Chromatography (HPLC) with UV detection is used for the determination of Cinnamic Acid (270 nm) levels in a lot of biological samples.
This Methodology provides accurate, reliable, and reproducible results of Cinnamic Acid measurement, which enables us to analyze of Cinnamic Acid levels in vitro and in vivo.

Cinnamic Acid is is a key intermediate of the biosynthetic shikimate and phenylpropanoid pathways.
Shikimic acid is a cyclohexene and is an important biochemical metabolite in plants and microorganisms.
For example, shikimic acid is a precursor for synthesis many alkaloids, aromatic amino acids, and indole derivatives.
Phenylpropanoid are a class of plant metabolites based on phenylalanine and they are widely distributed in plants fulfilling many functions including plant defense mechanism, pigmentation and external signaling system.
Cinnamic Acid is also the precursor of cinnamates, coumarines, caffeic acids, ferulic acids, and sinapic acids.
Cinnamic Acid and Its derivatives, for instance, esters and carboxylic functional derivatives are also can be used as important components for producing flavours, perfumes, synthetic indigo and pharmaceuticals.
Cinnamic Acid is also a kind of self-inhibitor produced by fungal spores to prevent plants germination, which is is the process by which a plant grows from a seed.

Cinnamic acid is a white crystalline acid with a molecular formula C9H8O2.
Cinnamic acid is a crystalline compound that is white in colour and is slightly soluble in water.
Cinnamic acid is collected from the oil of cinnamon and is also found in shea butter.
Cinnamic acid has a honey-like odour.
In this short piece of article, we shall be discussing more about the cinnamic acid formula along with its chemical structure and properties.

CINNAMIC ACID, or Phenylacrylic Acid, C9H80 2 or C 6 H 5 CH: CHCOOH, an acid found in the form of its benzyl ester in Peru and Tolu balsams, in storax and in some gumbenzoins.
Cinnamic acid can be prepared by the reduction of phenyl propiolic acid with zinc and acetic acid, by heating benzal malonic acid, by the condensation of ethyl acetate with benzaldehyde in the presence of sodium ethylate or by the so-called "Perkin reaction"; the latter being the method commonly employed.
In making the acid by this process benzaldehyde, acetic anhydride and anhydrous sodium acetate are heated for some hours to about 180 C., the resulting product is made alkaline with sodium carbonate, and any excess of benzaldehyde removed by a current of steam.
The residual liquor is filtered and acidified with hydrochloric acid, when cinnamic acid is precipitated, C 6 H 5 CH0+CH 3 000Na= C 6 H 5 CH :CH 000Na-}-H 2 O.
Cinnamic acid may be purified by recrystallization from hot water. Considerable controversy has taken place as to the course pursued by this reaction, but the matter has been definitely settled by the work of R. Fittig and his pupils (Annalen, 1883, 216, pp. loo, 115; 1885, 227, pp. 55, 119), in which it was shown that the aldehyde forms an addition compound with the sodium salt of the fatty acid, and that the acetic anhydride plays the part of a dehydrating agent.

Cinnamic acid crystallizes in needles or prisms, melting at 133° C.; on reduction it gives phenyl propionic acid, C 6 H 5 CH 2 CH 2 000H. Nitric acid oxidizes it to benzoic acid and acetic acid. Potash fusion decomposes it into benzoic and acetic acids.
Being an unsaturated acid it combines directly with hydrochloric acid, hydrobromic acid, bromine, &c.
On nitration it gives a mixture of ortho and para nitrocinnamic acids, the former of which is of historical importance, as by converting it into orthonitrophenyl propiolic acid A. Baeyer was enabled to carry out the complete synthesis of indigo.
Reduction of orthonitrocinnamic acid gives orthoaminocinnamic acid, C 6 H 4 (NH 2)CH:CH000H, which is of theoretical importance, as it readily gives a quinoline derivative.
An isomer of cinnamic acid known as allo-cinnamic acid is also known

Cinnamic acid is an α,β-unsaturated aromatic acid that can be used as a flavoring agent.
Cinnamic acid is mainly used to prepare ester derivatives that are used in perfume industry.
Cinnamic acid is the key volatile components of cinnamon essential oil.

The cinnamic acids [(2E)-3-phenylprop-2-enoic acid] and its four homologous derivatives such as p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, and dihydroxy are well known for their antioxidant, antitumor, antimicrobial, and antimycobacterial properties.
The cinnamic acids have higher levels of reactive oxygen scavenging activity.
Reactive oxygen species can modify essentially biological molecules, such as lipids, proteins, and DNA and it is consistent that rates of reactive oxygen species production are increased in most diseases.
Under oxidative stress conditions, superoxide anion, hydroxyl radical, and hydrogen peroxide react with various biological macromolecules (proteins, enzymes, DNA, etc.) in the presence of reactive oxygen species or indirectly may inhibit the mechanisms of DNA repair (Pontiki et al., 2014).
Thereby consumption of cinnamic acids can prevent the multiple diseases in human body.

Cinnamic acid is an organic compound with the formula C6H5CHCHCO2H.
Cinnamic acid is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents.
Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants.
Cinnamic acid exists as both a cis and a trans isomer, although the latter is more common.

Cinnamic acid is a white crystalline organic acid, which is slightly soluble in water.
Cinnamic acid is obtained from oil of cinnamon, or from balsams such as storax.
Cinnamic acid is also found in shea butter and is the best indication of its environmental history and post-extraction conditions.
Cinnamic acid can also be made synthetically.
Cinnamic acid is used in flavors, synthetic indigo, and certain pharmaceuticals, though its primary use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry.
Cinnamic acid has a honey- like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent.
Cinnamic acid is also part of the biosynthetic shikimate and phenyl propanoid pathways.
Cinnamic acids biosynthesis is performed by action of the enzyme phenylalanine ammonia - lyase (PAL) on phenylalanine.
Cinnamic acid is freely soluble in benzene, diethyl ether, acetone, and it is insoluble in hexane.
Cinnamic acid is also a kind of self-inhibitor produced by fungal spore to prevent germination

Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids.
Cinnamic acids biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine
Cinnamic acid is obtained from oil of cinnamon, or from balsams such as storax.
Cinnamic acid is also found in shea butter.
Cinnamic acid has a honey-like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent.

Cinnamic acid was first synthesized by the base-catalysed condensation of acetyl chloride and benzaldehyde, followed by hydrolysis of the acid chloride product.
In 1890, Rainer Ludwig Claisen described the synthesis of ethyl cinnamate via the reaction of ethyl acetate with benzaldehyde in the presence of sodium as base.
Another way of preparing cinnamic acid is by the Knoevenagel condensation reaction.
The reactants for this are benzaldehyde and malonic acid in the presence of a weak base, followed by acid-catalyzed decarboxylation.
Cinnamic acid can also be prepared by oxidation of cinnamaldehyde, condensation of benzal chloride and sodium acetate (followed by acid hydrolysis), and the Perkin reaction.
The oldest commercially used route to cinnamic acid involves the Perkin reaction, which is given in the following scheme

Cinnamic acid is a white crystalline hydroxycinnamic acid, which is slightly soluble in water.
Cinnamic acid is obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is found in many foods, some of which are green bell pepper, olive, pepper (spice), and pear.

Cinnamic acid exists as trans and cis isomers, but the trans form is the one most often found in nature and is the article of commerce.
Cinnamic acid is obtained from cinnamon bark and balsam resins such as storax.
Cinnamic acid was first isolated in 1872 by F. Beilstein (of Handbook of Organic Chemistry fame) and A. Kuhlberg.
Cinnamic acid is synthesized by the Perkin reaction between Ac2O and PhCHO.

Cinnamic acid is used in the manufacture of flavors, dyes, and pharmaceuticals; but its major use is for the production of its methyl, ethyl, and benzyl esters.
These esters are important components of perfumes.
The acid is also a precursor to the sweetener aspartame.

Melting point:133 °C(lit.)
Boiling point:300 °C(lit.)
Density 1.2475
FEMA 2288 | CINNAMIC ACID
refractive index 1.5049 (estimate)
Flash point:>230 °F
storage temp. Sealed in dry,Room Temperature
pkapK (25°) 4.46
Water Solubility 511.2mg/L(25 ºC)
JECFA Number657
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
Substances Added to Food (formerly EAFUS)CINNAMIC ACID

Cinnamic acid, also known benzal acetate, 3-phenyl-2-propenoic acid, belongs to a kind of unsaturated aromatic acid with a slight smell of cinnamon.
Cinnamic acid is presented in balsam, cinnamon oil and coca leaf in the form of free or ester form.
Owing to the presence of a double bond, cinnamic acid has trans-/ cis-two isomers with the cis form containing an extra three kinds of homogeneous polycrystalline.
Both trans-form and cis-form are in the presence of nature.
The trans-form exists in the presence of essential oils including storax, cinnamon oil, Peruvian balsam, basil oil and cocoa leaves.
The cis-form exists in Malacca galangal oil with the trans-form being more stable than the cis-form.
The commercially available products are mostly in the form of trans.
Cinnamic acid has a relative molecular mass of 148.17.
The first crystalline form of the cis form is called allocinnamic acid with the compound precipitated from water being monoclinic.
Cinnamic acid is colorless to white prismatic crystals with the relative density being 1.284 (4 ℃), the melting point being 42 ℃, the boiling point 265 ℃ (decomposition ) and 125 ℃ (2.533 × 103Pa); it is slightly soluble in water (25 ℃ when 0.937) but easily soluble in alcohol, ether and ethyl acetate.
The second polymorph is called alpha-iso-cinnamic acid with the compound precipitated from ligroin being the monoclinic crystal.
Cinnamic acid is colorless to white prismatic crystals with the mp being 58 ℃ and the boiling point being 265 ℃.
Cinnamic acid is soluble in ethanol, acetic acid, chloroform and acetone and easily soluble in ether.
The third polymorph is called beta-iso-cinnamic acid; it appears as monoclinic colorless to white prismatic crystals with the mp being 68 ℃.
Cinnamic acid is soluble in alcohol, ether, acetic acid, chloroform and acetone.
Trans-isomer precipitated from dilute ethanol belongs to the monoclinic crystal and appears as white to pale yellow prismatic crystals with the relative density being 1.2475 (4 ℃), melting point being 133 ℃ and the boiling point being 300 ℃.
Cinnamic acid is very slightly soluble in water (25 ℃: 0.1; 98 ℃: 0.588), soluble in ethanol (25 ℃: 23), chloroform (15 ℃: 5.9), easily soluble in benzene, ether, acetone, acetic acid and carbon disulfide.
When being distilled at 140 ℃, it undergoes decarboxylation to become styrene (Styrax BP).
Upon oxidation, it generates benzoic acid. Both the cis-and trans-isomers have flower honey aroma with sweet and spicy flavor.
Rat-Oral LD50: 2500 mg/kg.

Cinnamic acid is also produced by Knoevenagel condensation of benzaldehyde with malonic acid in the presence of weakly basic catalysts, such as ammonia and amines.
Reflux together 10ml of benzaldehyde with 10gm of malonic acid and 40ml of 8% ethanolic ammonia solution placed in a 100ml round bottom flask fitted with a reflux condensor on water bath till a clear solution is obtained (about 8-10hours).
Set the assembly for downward distillation and distill off the excess alcohol.
Continue heating the residual oily portion until the evolution of carbon dioxide ceases. Dissolve the residue in 20ml water, cool and add dilute hydrochloric acid till acidic.
Collect the precipitated unsaturated acid on buchner funnel，wash with cold water.
Recrystallise from hot water and collect crystals of cinnamic acid, m.p 132°C.

Cinnamic acid is found in most green plants, and it has low toxicity.
Cinnamic acid is used in flavors and in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry.
Cinnamic acid is also a precursor to the sweetener aspartame. Cinnamic acid has been reported to exhibit antioxidant and antibacterial activities .
This acid and its hydroxylated derivatives have also been reported to have antifungal activity , preventing fungal spore germination and antityrosinase enzyme activity with potential skin-whitening activity .
Like other phenolic acids, such as gallic acid, cinnamic acid has reported anticancer activity.
Cinnamic acid induces cytostasis and reverses malignant properties of human tumor cells in vitro; it is a differentiation inducer for melanoma cells disrupts cytoskeleton and induces apoptosis and proliferation of nasopharyngeal carcinoma cells and leukemic cells in vitro .
the hydroxylated cinnamic acid derivative p-coumaric acid has antioxidant properties and is believed to reduce the risk of stomach cancer by reducing the formation of carcinogenic nitrosamines.
Also, para-coumaric acid found in honey has in vitro antiinflammatory activity.
Ellagic acid, phenolic acids, and flavonoids in Malaysian honey extracts demonstrate in vitro antiinflammatory activity.
Several dihydroxycinnamic acids, including ferulic acid, chlorogenic acid, caffeic acid, and curcumin, were found to inhibit tumor promotion in mouse skin induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate.
In addition, ferulic acid exhibited antitumor activity against breast cancer cells.

Cinnamic acid (Benzenepropenoic acid, Isocinnamic acid, trans-Cinnamic acid, Phenylacrylic acid), a naturally occurring aromatic fatty acid of low toxicity, induces cytostasis and a reversal of malignant properties of human tumor cells in vitro.

Cinnamic acid and its phenolic analogues are natural substances.
Chemically, cinnamic acids or the 3-phenyl acrylic acids, offer three main reactive sites:
substitution on the phenyl ring, addition on the α,β-unsaturation and reactions of the carboxylic acid.
Owing to these chemical aspects, cinnamic acid derivatives received much attention in medicinal research as traditional as well as valuable scaffolds in recent synthetic bioactive agents.
In the last two decades, there has been huge attention towards various cinnamoyl derivatives and their biological efficacy.
This review provides a comprehensive literature compilation concerning the synthesis of various cinnamoyl acids, esters, amides, hydrazides and related derivatives and their biological activity evaluations against diseases such as tuberculosis and malaria, which are frequent in developing countries and cardiovascular diseases, which cause a high mortality rate worldwide.
We envisage that our effort in this review contributes a much needed and timely addition to the literature of medicinal research

Cinnamic acid is used in flavorings, synthetic indigo, and certain pharmaceuticals.
A major use is as a precursor to produce methyl cinnamate, ethyl cinnamate, and benzyl cinnamate for the perfume industry.
Cinnamic acid is a precursor to the sweetener aspartame via enzyme-catalysed amination to give phenylalanine.
Cinnamic acid can dimerize in non-polar solvents resulting in different linear free energy relationships

Cinnamic acid is an important intermediate in the preparation of its esters, which are used as fragrances, for pharmaceuticals, and for the enzymatic production of l-phenylalanine, the starting material for peptide sweeteners.
Sodium cinnamate is a known corrosion inhibitor.
Cinnamic acid is also used as a brightener in cyanide-free zinc electroplating baths, a corrosion inhibitor during removal of scale from zinc and in aerosol cans, a low-toxicity heat stabilizer for poly(vinyl chloride) , a cross-linking agent for dimethyl terephthalate – ethylene glycol copolymer and polyurethanes, a fireproofing agent for polycaprolactam, in laundry-resistant polyurethane adhesives for polyester fibers, and for improvement of the storage stability of drying-oil-modified alkyd resin coatings.

The derivatives of cinnamic acid are used as main components in anti-oxidants, anti-diabetic and anti-cholesterolemic medicines.
The market for cinnamic acid is governed by its major application in perfume industry and as a flavoring agent which are in greater demand across Asia-pacific region.

The other drivers for cinnamic acid include its derivative preparations which are mostly used in various medicinal preparations including that of tuberculosis and malaria which are predominant in developing countries like India and Brazil.
Cinnamic acid’s application in skin care products (usually sun screen products) makes it grow across developed countries like the U.S and Western Europe as these countries are major consumers of cosmetic industry across globe.

Cinnamic acid occurs naturally through oils of cinnamon;
however Cinnamic acid can be industrially synthesized through interaction of benzyl dichloride and sodium acetate.
The chemical arrangement of cinnamic acid offers reactive sites mainly in substitution on phenyl ring or reactions in carboxyl acids making them suitable in preparation of several derivatives having pharmaceutical applications.

The applications of cinnamic acid largely include in perfume or fragrance industry, followed by flavoring agent (as a precursor of sweetener aspartame), preparation of synthetic indigo and also in the form of derivatives in medicinal drug preparations for diseases like tuberculosis and malaria.
These applications make the market for cinnamic acid more lucrative.

The skin care products forms another major driver for cinnamic acid as these are widely used in cosmetic industry.
As the cosmetic industry flourishes globally the requirement for cinnamic acid continues to grow.
Cinnamic acid is also used in form of derivatives as a diabetic drug (insulin releasing agent) which makes it extremely important globally as the number of diabetic patients soar high owing to changed lifestyle and improper food eating habits.

The medicinal applications in form of derivatives make cinnamic acid highly important.
The developing countries like India and Brazil form the major market for cinnamic acid owing to the increase in number of patients suffering from tuberculosis and malaria especially in rural areas.
Thus the demand for cinnamic acid would boost up in these countries. Cinnamic acid market is also driven by its application in cosmetic industry.
There is a huge demand for skin care products across developed countries like the U.S., Russia and other European market.

This requirement will act as a catalyst for the market of cinnamic acid to thrive in these countries.
The application of cinnamic acid in perfume industry is largely in demand across Middle East and other Asia-pacific countries like India.
The growth in fragrance industry will further propel the need of cinnamic acid.
Synthetic indigo, another major application of cinnamic acid mainly goes in dyeing industry find huge potential in several applications causing additional growth in cinnamic acid market.

Cinnamic acid is used in flavors, synthetic indigo and pharmaceuticals.
Cinnamic acid is involved in the production of methyl, ethyl and benzyl esters, which is used in the perfume industry.
Cinnamic acid serves as a precursor to the sweetener aspartame through enzyme-catalyzed amination to phenylalanine.
Cinnamic acid is a self-inhibitor produced by fungal spores to prevent germination.
In addition, it is used to establish phenolic compounds by liquid chromatography, ultraviolet and mass spectrometry.
Cinnamic acid is utilized as a potential agent, thereby preventing lung tumor cells from metastasizing.
Further, Cinnamic acid induces intracellular release of calcium ions from the vacuole to the cytoplasm in order to trigger phytotoxicity in cucumber.

Cinnamic acid and its simple derivatives are widely represented in plants.
Naturally occurring compounds from this group include, among others: cinnamic acid, cinnamaldehyde , cinnamyl alcohol , 4-hydroxycinnamic acid , 3,4-dihydroxycinnamic acid and 4-hydroxy-3-methoxycinnamic acid .
The biosynthetic pathways of cinnamic acid derivatives are shared with other secondary metabolites such as coumarins, lignins, isoflavonoids, flavonoids, stilbens, anthocyanins and tannins.
These compounds play a key role in plant physiology including growth, development, reproduction and disease resistance 1, 2.
Since ancient times, naturally occurring cinnamic acid derivatives have been known to be beneficial for human skin and hair and have been used in plant extracts for skin- and hair-conditioning purposes.

Cinnamic acid is used in flavors, synthetic indigo, and certain pharmaceuticals.
A major use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry.
Cinnamic acid is a precursor to the sweetener aspartame via enzyme-catalysed amination to phenylalanine.
Cinnamic acid can dimerize in non-polar solvents resulting in different linear free energy relationships

IUPAC NAME :

(2E)-3-phenylprop-2-enoic acid

(E)-3-phenylprop-2-enoic acid

2-Propenoic acid, 3-phenyl-, (E)-

3-phenylacrylic acid

3-phenylprop-2-enoic acid

cinnamic acid

SYNONYMS:

(2Z)-3-Phenyl-2-propenoic acid
(2Z)-3-Phenylacrylic acid
(2Z)-3-Phenylacrylsäure
(Z)-3-Phenyl-2-propenoic acid
(Z)-3-Phenylacrylic acid
(Z)-3-Phenylprop-2-enoic acid
102-94-3
2-Propenoic acid, 3-phenyl-, (2Z)-
Acide (2Z)-3-phénylacrylique
cis-cinnamic acid