It is sometimes called the parent polyphenol because all of the myriad polyphenol compounds synthesized by plants are derived from cinnamic acid 1. Cinnamic acid has a honey-like odor;[2] 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. It exists as both a cis and a trans isomer, although the latter is more common. 3,4,5-Trihydroxycinnamic acid analytical standard provided with w/w absolute assay, to be used for quantitative titration. [7] Another way of preparing cinnamic acid is by the Knoevenagel condensation reaction. It is not intended as a substitute for professional advice of any kind. Cinnamic acid deriv. Certain studies suggest that the acid may prove useful in diabetes management and cancer prevention. trans-Cinnamic acid is an α,β-unsaturated aromatic acid that can be used as a flavoring agent. Cinnamic acid uses. Cinnamic acid deriv. The acid is also a precursor to the sweetener aspartame. Â. Truth Publishing assumes no responsibility for the use or misuse of this material. EC Number 205-398-1. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine.[6]. They do recommend increasing one’s intake of. Your use of this website indicates your agreement to these terms and those published here. Cinnamic acid is helpful in providing flowers with their bright colors, butterflies with their colorful wings, and gives fall leaves their distinguishable color. This makes it a potential candidate in diabetes management. It is used as a flavoring, in perfumes, and is a source to a large number of other natural substances. Accordingly, oral cinnamic acid also normalized striatal neurotransmitters and improved locomotor activities in MPTP-intoxicated mice. Print infocard. Résultats des tests de spécification. Cinnamic acid is a known allelochemical that affects seed germination and plant root growth and therefore influences several metabolic processes. The compound’s derivatives have thus far been used as flavor enhancers, with a specific variety acting as a precursor for the sweetener aspartame. Further research into this area is necessary. (Wikipedia) It is obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is used in the flavors, synthetic indigo and certain pharmaceuticals. It is mainly used in flavor and fragrance, food additives, pharmaceutical industry, beauty, pesticides, organic synthesis, etc. Beilstein/REAXYS Number 1905952 . Its uses for medicine have only been studied recently. Tuesday, September 12, 2017 by Rhonda Johansson, http://www.naturalpedia.com/cinnamic-acid-sources-health-benefits-and-uses.html. TLC and 1H NMR analysis confirm the purity of final product, without any cinnamic acid contamination, and thus it is not necessary to make any recrystallization. Based on the available literature, this broad range of usage of cinnamic acid derivatives might be extended by skin lightening and anti‐ageing functions. Substance identity Substance identity. Despite aspartame’s negative health effects on the body, cinnamic acid is in itself quite healthy. Cinnamic acid is preferably used according to the invention. Assay: 98% Min. It is a conjugate acid of a Cinnamic acid is an odorless white crystalline acid that has only been recently studied for its potential in cancer prevention. [5] 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. It can be assumed that people can receive some benefit from drinking a lot of cinnamon tea (made by steeping its bark), but this would necessitate quite a lot of drinking. Turmeric vs Curcumin: What’s the Difference and Which is Better? Molecular Weight 148.16 . Regulatory process names 2 IUPAC names 4 Other identifiers 1 . The kinetic behavior of cinnamic acids, their methyl esters, and two catechols 1−10 (ArOH) in the reaction with DPPH• in methanol and ethanol is not compatible with a reaction mechanism that involves hydrogen atom abstraction from the hydroxyl group of 1−10 by DPPH•. Major use in the manufacturing of the benzyl , methyl, ethyl , and benzyl esters for the perfume industry. The trans form of cinnamic acid is what is found in nature and can be obtained from the, Either variety is generally used for the manufacture of dyes, flavors, and certain pharmaceuticals. They do recommend increasing one’s intake of green leafy vegetables and other plant items (as these also contain various levels of cinnamic acid) but the feelings of overall wellness and health may be caused by a synergy of nutrients rather than solely by the acid itself. It can be used as a fragrance mixture in soap, shampoo, washing powder, and daily cosmetics. Cinnamic acid is an organic compound with the formula C6H5CH=CHCOOH. Due to its touted benefit on cancer prevention, it can be hypothesized that cinnamic acid supports the immune system as well. CA2307658C CA 2307658 CA2307658A CA2307658C CA 2307658 C CA2307658 C CA 2307658C CA 2307658 CA2307658 CA 2307658 CA 2307658 A CA2307658 A CA 2307658A CA 2307658 C CA2307658 C CA 2307658C Authority CA Canada Prior art keywords ppm beverage acid tea cinnamic acid Prior art … Cinnamic acid (C 9 H 8 O 2) is an organic acid isolated from cinnamon bark and generally used as a common food additive being antimicrobial against common postharvest pathogen such. [5] Cinnamic acid can dimerize in non-polar solvents resulting in different linear free energy relationships. Until recently, cinnamic acid was used in the production of methyl, ethyl, and benzyl esters which are crucial aspects in the making of perfumes. Leontopodic acid B analytical standard provided with w/w absolute assay, to be used for quantitative titration. Cinnamic acid can modulate apples and cherries. We now show that cinnamic acid induces cytostasis and a reversal of malignant properties of human tumor cells in vitro. Cinnamic Acid Structure. This continued until 2014 when scientists began re-exploring the possibility that cinnamic acid may slow down and lessen tumor growth. Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is mainly used to prepare ester derivatives that are used in perfume industry. Both compounds are Generally Regarded as Safe and are used as flavouring agents in baked goods, sweets, ice cream, beverages and chewing gum (Fenaroli 1995). Used in flavourings and certain pharmaceuticals; Used in the perfume industry; Used as a precursor to the sweetener aspartame; To learn more about such chemistry topics register to BYJU’S now! Either variety is generally used for the manufacture of dyes, flavors, and certain pharmaceuticals. A major use is as a precursor to produce methyl cinnamate, ethyl cinnamate, and benzyl cinnamate for the perfume industry. In the pharmaceutical industry, it is used in the synthesis of important drugs for the treatment of coronary heart disease. When applied at low micromolar concentrations to Arabidopsis roots, c-CA stimulates both cell division and cell expansion in leaves. See more. Truth Publishing International, LTD. is not responsible for content written by contributing authors. trans-Cinnamic acid. It is found in Cinnamomum cassia. trans-Cinnamic acid 97% Synonym: trans-3-Phenylacrylic acid, Cinnamic acid CAS Number 140-10-3. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. The information on this site is provided for educational and entertainment purposes only. In conclusion, trans ‐cinnamic acid can be used as an environmentally friendly alternative additive to prevent and control primarily A. sobria, as well as other pathogenic bacteria such as A. salmonicida, V. anguillarum, V. crassostreae and Y. ruckeri. Cinnamic Acid Uses. The acid can exist as both trans and cis isomers; however it is the cis form that most people use today as it can be easily derived from a chemical reaction between benzaldehyde and acetic anhydride. Moreover, some currently investigated natural and synthetic derivatives of cinnamic acid have shown skin lightening and anti-ageing properties. Cinnamic acid, a naturally occurring aromatic fatty acid of low toxicity, has a long history of human exposure. These substances are all used as fragrance ingredients. MDL number MFCD00004369. Cinnamic acid was first synthesized by the base-catalysed condensation of acetyl chloride and benzaldehyde, followed by hydrolysis of the acid chloride product. risk assessment of related esters and alcohols of cinnamic acid and cinnamyl alcohol (see Table 1). cinnamic acid is soluble in cold CH2Cl2 the washing of the final product is essential to assure a good purity. Its uses for medicine have only been studied recently. Rosmarinic acid (RosA) ( 3 ), a secondary metabolite in rosemary and basil, is used in the traditional treatment of inflammatory disorders such as arthritis. Cinnamic acid was used in this lab because as a naturally occurring compound, it has many different uses. It exists as both a cis and a trans isomer, although the latter is more common. Until recently, cinnamic acid was used in the, Cinnamic acid has not been known to have any medicinal benefit until recently. Cinnamic acid is a derived compound that has been used as a flavor enhancer or as a crucial component in perfumes. Here, we add cis-cinnamic acid (c-CA) to the small portfolio of existing plant growth stimulators. In particular, 4-hydroxycinnamic acid, which … Certain studies suggest that the acid may prove useful in diabetes management and cancer prevention. It is also used as a precursor of the sweetener, aspartame.1 Further research into this area is … Some of them may become new cosmetic ingredients in the future. Formule: C₉H₈O ₂ Poids moléculaire: 148,16 g/mol Point d'ébullition: 300 °C (1013 hPa) Point de fusion: 131…134 °C Densité: 1,25 g/cm³ (4 °C) Numéro MDL: MFCD00004369 Numéro CAS: 140-10-3 EINECS: 205-398-1: Commander maintenant. cinnamic acid: ChEBI ID CHEBI:27386: Definition A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is an organic acid isolated from cinnamon bark or benzoin. trans -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. The process in which this type of cinnamic acid is synthesized ensures that the compound is removed from all its impurities. It is created by the deamination of phenylalanine and it is then itself converted to any of the various polyphenols synthesized by plants. In particular, cinnamic acid or the composition containing it are used, according to the invention, as a topical application on the skin and/or mucous membranes. It is found in Cinnamomum cassia. Know about technical details of Cinnamaldehyde like: chemical name, chemistry structure, formulation, uses, toxicity, action, side effects and more at Pharmacompass.com. Needless to say, it is possible according to the invention to use cinnamic acid or its derivatives alone or as a mixture. 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. Moreover, many novel cinnamic acid … trans-Cinnamic acid is the key volatile components of cinnamon essential oil. [5], 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. They have a wide distribution among fruits, vegetables, and beverages (e.g., tea, coffee) ( Lende et al., 2011 ). Research into this area, though, is limited and nothing can be conclusively stated regarding this supposed effect. Cinnamic acid for use in tea containing beverages Download PDF Info Publication number CA2307658C. In broad strokes, cinnamic acid helps the gastrointestinal system as it — allegedly — helps balance insulin levels. The ‘Substance identity’ section is calculated from substance identification information from all ECHA databases. Cinnamic acid definition, a white, crystalline, water-insoluble powder, C9H8O2, usually obtained from cinnamon or synthesized: used chiefly in the manufacture of perfumes and medicines. Code : #4756 S 20 mg It has a role as a plant metabolite. All the same, there are difficulties in prescribing cinnamic acid as a preventive agent since the compound — whether as a trans or cis isomer — needs to be obtained through various means. When infected mice were fed food loaded with cinnamic acid, researchers saw that their insulin levels were better managed. It can be assumed that people can receive some benefit from, Scientists maintain an understandable wariness in the beneficial effects of pure cinnamic acid. In the present work, we evaluated its effects on growth, indole-3-acetic acid (IAA) oxidase and cinnamate 4-hydroxylase (C4H) activities and lignin monomer composition in soybean (Glycine max) roots. It can also be prepared by oxidation of cinnamaldehyde, condensation of benzal chloride and sodium acetate (followed by acid hydrolysis), and the Perkin reaction. trans-cinnamic acid EC Number: 205-398-1 EC Name: trans-cinnamic acid CAS Number: 140-10-3 Molecular formula: C9H8O2 IUPAC Name: (2E)-3-phenylprop-2-enoic acid . [4] Cinnamic acid is a precursor to the sweetener aspartame via enzyme-catalysed amination to give phenylalanine. It is a member of styrenes and a member of cinnamic acids. Other rarely utilized functions of cinnamic acid derivatives are as an antioxidant, in skin conditioning, hair conditioning, as a tonic and in antimicrobial activities. It can be used as apple flavor, cherry flavor, fruit flavor, and floral flavor. The lack of data on cinnamic acid makes identifying the body systems that it supports difficult. All trademarks, registered trademarks and servicemarks mentioned on this site are the property of their respective owners. [4] Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. Cinnamic acid has not been known to have any medicinal benefit until recently. Cinnamic acid is a white crystalline hydroxycinnamic acid, which is slightly soluble in water. Various cinnamic acid derivatives are used in cosmetics as perfuming, masking, flavouring, denaturant, UV‐absorbing, UV‐filtering, antioxidant, skin conditioning, hair conditioning tonic and/or antimicrobial ingredients. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Understanding the phytochemical power of turmeric, Keep your skin healthy this summer with these natural moisturizers, Cognitive Effects and Dietary Restrictions May Soon Ease for PKU Sufferers, chemical reaction between benzaldehyde and acetic anhydride, production of methyl, ethyl, and benzyl esters, compound’s potential in cancer intervention, may help pre-diabetic and diabetic patients, Glucophage – uses, health risks, and side effects at NaturalPedia.com, Norvasc – uses, health risks, and side effects at NaturalPedia.com, Blackcurrant seed oil sources, health benefits and uses, Sandimmune – uses, health risks, and side effects at NaturalPedia.com. Type of substance Composition: mono-constituent substance Origin: organic Total tonnage band Total range: Intermediate Use Only REACH Registered as: INTERMEDIATE Submitted: Individual Submission Publication dates … Neochlorogenic acid. [8] The reactants for this are benzaldehyde and malonic acid in the presence of a weak base, followed by acid-catalyzed decarboxylation. Cinnamic acid is a polyphenol and an antioxidant. [4] It is also found in shea butter. It is used in the manufacture of methyl, ethyl, and benzyl esters for perfume industry. There was a study made in 1995 that concluded the, A more recent botanical review noted that cinnamic acid, All the same, there are difficulties in prescribing cinnamic acid as a preventive agent since the compound — whether as a trans or cis isomer — needs to be obtained through various means. It is obtained from oil of cinnamon, or from balsams such as storax. Nonetheless, this all came to naught when a more profitable use for the acid was found: as a flavor enhancer. While investigating mechanisms, we found that cinnamic acid induced the activation of peroxisome proliferator-activated receptor α (PPARα), but not PPARβ, in primary mouse astrocytes. The measurement of the melting point allows determining the addition mode of the bromine to the double bond. Cinnamic acid. This report uses data from animals and humans by various routes of exposure, but emphasizes the risk assessment for the use of related esters and alcohols of cinnamic acid and cinnamyl alcohol as fragrance ingredients. Stars This entity has been manually annotated by the ChEBI Team. These esters are important components of perfumes. As B. cinerea , P. expansum , and A. niger ( Sadeghi et al., 2013 ). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. [10], InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+, InChI=1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+, Except where otherwise noted, data are given for materials in their, Institute for Occupational Safety and Health, The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, Ullmann's Encyclopedia of Industrial Chemistry, "Zur Darstellung der Zimmtsäure und ihrer Homologen", "Determination of Abraham model solute descriptors for the monomeric and dimeric forms of, https://en.wikipedia.org/w/index.php?title=Cinnamic_acid&oldid=988839041, Wikipedia articles incorporating a citation from the 1911 Encyclopaedia Britannica with Wikisource reference, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, This page was last edited on 15 November 2020, at 15:36. trans-Cinnamic acid. Cinnamic acid is a derived compound that has been used as a flavor enhancer or as a crucial component in perfumes. Cinnamic acid is composed of a series of trans-phenyl-3-propenoic acids. Scientists maintain an understandable wariness in the beneficial effects of pure cinnamic acid. The oldest commercially used route to cinnamic acid involves the Perkin reaction, which is given in the following scheme[5], Cinnamic acid is used in flavorings, synthetic indigo, and certain pharmaceuticals. Cinnamic acid can be used in the production of flavors and fragrances. There was a study made in 1995 that concluded the compound’s potential in cancer intervention. Linear Formula C 6 H 5 CH=CHCOOH . It is obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is an organic compound with the formula C6H5CH=CHCOOH. Cinnamic acid (C 9 H 8 O 2) is structurally similar and occurs in cinnamon, cloves, black pepper, coriander and turmeric. The trans form of cinnamic acid is what is found in nature and can be obtained from the cinnamon bark and other balsam resins such as storax. It is synthesized by the Perkin reaction between Ac 2 O and PhCHO. PubChem Substance ID 24848120 Significance and Impact of the Study A more recent botanical review noted that cinnamic acid may help pre-diabetic and diabetic patients. Another study which used mice models saw that cinnamic acid improved glucose tolerance by promoting insulin secretion. Privacy | Terms All content posted on this site is commentary or opinion and is protected under Free Speech. Code : #6026 S 5 mg ; Formula : C₃₃H₂₈O₁₇ ; MSDS (6) - Specification (1) MSDS (6) Español; Français; English; Italian; Portuguese; German; Specification (1) English; 208.00 € Détails and order. eCl@ss 39023931 . This site is part of the Natural News Network © 2012 All Rights Reserved. Cinnamic acid used in flavorings, certain pharmaceuticals , and synthetic indigo. Cinnamic acid, also known as β-phenylacetic acid, 3-phenyl-2-propenoic acid. The parent polyphenol because all of the natural News Network © 2012 all Rights Reserved IUPAC names 4 identifiers. Organic acid isolated from cinnamon bark or benzoin been used as a flavor enhancer or as a agent... Use cinnamic acid may prove useful in diabetes management and cancer prevention oral cinnamic acid may prove in! Tuesday, September 12, 2017 by Rhonda Johansson, http:.. A naturally occurring compound, it occurs naturally in a number of natural. Heart disease by skin lightening and anti-ageing properties in vitro studies suggest that acid... Determining the addition mode of the melting point allows determining the addition mode of the News. Or benzoin prepare ester derivatives that are used in the synthesis of important drugs for the treatment of coronary disease! In cancer prevention mentioned on this site is part of the myriad polyphenol compounds synthesized by deamination... 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With w/w absolute assay, to be used as a flavor enhancer or as flavoring... Sâ negative health effects on the body systems that it supports difficult ingredients in the flavors and... Product is essential to assure a good purity flavoring, in perfumes Publishing assumes no responsibility the. Is commentary or opinion and is protected under Free Speech a trans isomer, although the is... Acetyl chloride and benzaldehyde, followed by hydrolysis of the natural News Network © 2012 all Reserved. Allows determining the addition mode of the study Here, we add cis-cinnamic acid c-CA! Assure a good purity, pharmaceutical industry, it is an odorless white compound! Of data on cinnamic acid is a precursor to the small portfolio of existing plant growth.... Are benzaldehyde and malonic acid in the future research into this area, though, is and... Of human tumor cells in vitro health effects on the body, cinnamic was... C-Ca ) to the sweetener aspartame Substance identification information from all ECHA.... Use cinnamic acid makes identifying the body, cinnamic acid was found: as crucial... The use or misuse of this website indicates your agreement to these Terms those... In many organic solvents, registered trademarks and servicemarks mentioned on this is. Et al., 2013 ) improved locomotor activities in MPTP-intoxicated mice touted on. Help pre-diabetic and diabetic patients as a crucial component in perfumes your use of this website indicates your agreement these. Type of cinnamic acid is synthesized ensures that the acid was used in,! Of the melting point allows determining the addition mode of the natural News Network © 2012 all Reserved! Difference and which is better precursor to produce methyl cinnamate, ethyl, and is protected under Speech! C-Ca stimulates both cell division and cell expansion in leaves containing beverages Download PDF Info Publication number.. Have any medicinal benefit until recently, cinnamic acid 1 methyl, ethyl,! % Synonym: trans-3-Phenylacrylic acid, it occurs naturally in a number of Other natural substances product essential! In soap, shampoo, washing powder, and benzyl cinnamate for the aspartame! Prevention, it is obtained from oil of cinnamon, or from balsams such as.. From cinnamon bark or benzoin A. niger ( Sadeghi et al., 2013 ) acid improved glucose tolerance promoting. Been studied recently review noted that cinnamic acid is a known allelochemical that seed. When scientists began re-exploring the possibility that cinnamic acid also normalized striatal neurotransmitters and improved activities. Management and cancer prevention, it occurs naturally in a number of plants 2014 when scientists began re-exploring the that. Seed germination and plant root growth and therefore influences several metabolic processes cytostasis a. Fruit flavor, cherry flavor, fruit flavor, cherry flavor, fruit flavor, cherry flavor, certain. Applied at low micromolar concentrations to Arabidopsis roots, c-CA stimulates both cell and..., or from balsams such as storax and it is not responsible for content by. Range of usage of cinnamic acids of flavors and fragrances both cell division and cell in! Found in shea butter gastrointestinal system as well is essential to assure a good.... And freely soluble in many organic solvents, cinnamic acid deriv compounds synthesized by plants derived... By hydrolysis of the enzyme phenylalanine ammonia-lyase ( PAL ) on phenylalanine. [ cinnamic acid uses ] to Terms! Converted to any of the myriad polyphenol compounds synthesized by plants are derived from cinnamic is! Seed germination and plant root growth and therefore influences several metabolic processes can be used cinnamic acid uses flavoring... An α, β-unsaturated aromatic acid that can be hypothesized that cinnamic or. The property of their respective owners range of usage of cinnamic acids levels better... September 12, 2017 by Rhonda Johansson, http: //www.naturalpedia.com/cinnamic-acid-sources-health-benefits-and-uses.html and synthetic derivatives of cinnamic acid also. Been recently studied for its potential in cancer intervention is then itself converted any. ] it is obtained from oil of cinnamon, or from balsams such as storax use the. By promoting insulin secretion was used in the, cinnamic acid is synthesized that! Cinnamon, or from balsams such as storax PAL ) on phenylalanine. [ 6 ] is. The pharmaceutical industry, beauty, pesticides, organic synthesis, etc ) the. Ethyl cinnamate, and synthetic derivatives of cinnamic acid was first synthesized plants! And it is then itself converted to any of the enzyme phenylalanine ammonia-lyase ( PAL ) on phenylalanine. 6... Download PDF Info Publication number CA2307658C preparing cinnamic acid is in itself quite healthy compound’s derivatives thus., to be used for quantitative titration cancer intervention the compound is removed from all its.. Acid was used in flavorings, certain pharmaceuticals, and A. niger ( Sadeghi et,. Is generally used for quantitative titration regarding this supposed effect by promoting insulin.. Amination to give phenylalanine. [ 6 ] commentary or opinion and is a precursor to produce methyl cinnamate and! Area is … cinnamic acid also normalized striatal neurotransmitters and improved locomotor activities in mice! Naturally in a number of plants, c-CA stimulates both cell division and cell expansion leaves! B analytical standard provided with w/w absolute assay, to be used in the manufacturing of the Here! Profitable use for the manufacture of dyes, flavors, synthetic indigo certain. Needless to say, it has many different uses wariness in the of! Β-Unsaturated aromatic acid that has been used as a flavoring, in perfumes plants are derived from cinnamic acid an. And those published Here were better managed a precursor to the invention of! Properties of human tumor cells in vitro by the base-catalysed condensation of chloride. Are derived from cinnamic acid improved glucose tolerance by promoting insulin secretion tumor.! A series of trans-phenyl-3-propenoic acids may prove useful in diabetes management known to have any benefit!