Neochlorogenic acid. Cinnamic Acid Structure. It is not intended as a substitute for professional advice of any kind. Significance and Impact of the Study [8] The reactants for this are benzaldehyde and malonic acid in the presence of a weak base, followed by acid-catalyzed decarboxylation. 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. It is found in Cinnamomum cassia. Another study which used mice models saw that cinnamic acid improved glucose tolerance by promoting insulin secretion. 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. It is mainly used to prepare ester derivatives that are used in perfume industry. In the pharmaceutical industry, it is used in the synthesis of important drugs for the treatment of coronary heart disease. Stars This entity has been manually annotated by the ChEBI Team. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. 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 . 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. Certain studies suggest that the acid may prove useful in diabetes management and cancer prevention. 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. Cinnamic acid for use in tea containing beverages Download PDF Info Publication number CA2307658C. Cinnamic acid is a derived compound that has been used as a flavor enhancer or as a crucial component in perfumes. 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, compoundâs 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. 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. trans-Cinnamic acid. It is a conjugate acid of a All trademarks, registered trademarks and servicemarks mentioned on this site are the property of their respective owners. It is used in the manufacture of methyl, ethyl, and benzyl esters for perfume industry. 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! These substances are all used as fragrance ingredients. 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 has not been known to have any medicinal benefit until recently. 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 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•. 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. trans-Cinnamic acid is an α,β-unsaturated aromatic acid that can be used as a flavoring agent. Cinnamic acid, a naturally occurring aromatic fatty acid of low toxicity, has a long history of human exposure. Cinnamic acid is an organic compound with the formula C6H5CH=CHCOOH. PubChem Substance ID 24848120 Your use of this website indicates your agreement to these terms and those published here. Nonetheless, this all came to naught when a more profitable use for the acid was found: as a flavor enhancer. It is synthesized by the Perkin reaction between Ac 2 O and PhCHO. Molecular Weight 148.16 . A more recent botanical review noted that cinnamic acid may help pre-diabetic and diabetic patients. Further research into this area is … The ‘Substance identity’ section is calculated from substance identification information from all ECHA databases. [4] Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. 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. Either variety is generally used for the manufacture of dyes, flavors, and certain pharmaceuticals. Accordingly, oral cinnamic acid also normalized striatal neurotransmitters and improved locomotor activities in MPTP-intoxicated mice. Despite aspartame’s negative health effects on the body, cinnamic acid is in itself quite healthy. Cinnamic acid used in flavorings, certain pharmaceuticals , and synthetic indigo. Tuesday, September 12, 2017 by Rhonda Johansson, http://www.naturalpedia.com/cinnamic-acid-sources-health-benefits-and-uses.html. 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. 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. 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. Cinnamic Acid Uses. Moreover, some currently investigated natural and synthetic derivatives of cinnamic acid have shown skin lightening and anti-ageing properties. Turmeric vs Curcumin: Whatâs the Difference and Which is Better? The information on this site is provided for educational and entertainment purposes only. Research into this area, though, is limited and nothing can be conclusively stated regarding this supposed effect. These esters are important components of perfumes. Cinnamic acid is a polyphenol and an antioxidant. 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 broad strokes, cinnamic acid helps the gastrointestinal system as it — allegedly — helps balance insulin levels. Cinnamic acid, also known as β-phenylacetic acid, 3-phenyl-2-propenoic acid. 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. Until recently, cinnamic acid was used in the, Cinnamic acid has not been known to have any medicinal benefit until recently. Résultats des tests de spécification. Cinnamic acid is preferably used according to the invention. Based on the available literature, this broad range of usage of cinnamic acid derivatives might be extended by skin lightening and anti‐ageing functions. Â. It can also be prepared by oxidation of cinnamaldehyde, condensation of benzal chloride and sodium acetate (followed by acid hydrolysis), and the Perkin reaction. [5] Cinnamic acid can dimerize in non-polar solvents resulting in different linear free energy relationships. 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 has a role as a plant metabolite. Certain studies suggest that the acid may prove useful in diabetes management and cancer prevention. It exists as both a cis and a trans isomer, although the latter is more common. Its uses for medicine have only been studied recently. It is a member of styrenes and a member of cinnamic acids. Cinnamic acid. It is sometimes called the parent polyphenol because all of the myriad polyphenol compounds synthesized by plants are derived from cinnamic acid 1. eCl@ss 39023931 . Cinnamic acid is helpful in providing flowers with their bright colors, butterflies with their colorful wings, and gives fall leaves their distinguishable color. Linear Formula C 6 H 5 CH=CHCOOH . The process in which this type of cinnamic acid is synthesized ensures that the compound is removed from all its impurities. MDL number MFCD00004369. Truth Publishing International, LTD. is not responsible for content written by contributing authors. (Wikipedia) It is obtained from oil of cinnamon, or from balsams such as storax. A major use is as a precursor to produce methyl cinnamate, ethyl cinnamate, and benzyl cinnamate for the perfume industry. This continued until 2014 when scientists began re-exploring the possibility that cinnamic acid may slow down and lessen tumor growth. It is created by the deamination of phenylalanine and it is then itself converted to any of the various polyphenols synthesized by plants. 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. It is mainly used in flavor and fragrance, food additives, pharmaceutical industry, beauty, pesticides, organic synthesis, etc. Cinnamic acid can modulate apples and cherries. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. 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 … See more. [4] It is also found in shea butter. 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 … Cinnamic acid was first synthesized by the base-catalysed condensation of acetyl chloride and benzaldehyde, followed by hydrolysis of the acid chloride product. The compoundâs derivatives have thus far been used as flavor enhancers, with a specific variety acting as a precursor for the sweetener aspartame. Needless to say, it is possible according to the invention to use cinnamic acid or its derivatives alone or as a mixture. Major use in the manufacturing of the benzyl , methyl, ethyl , and benzyl esters for the perfume industry. Substance identity Substance identity. risk assessment of related esters and alcohols of cinnamic acid and cinnamyl alcohol (see Table 1). Truth Publishing assumes no responsibility for the use or misuse of this material. We now show that cinnamic acid induces cytostasis and a reversal of malignant properties of human tumor cells in vitro. As B. cinerea , P. expansum , and A. niger ( Sadeghi et al., 2013 ). Its uses for medicine have only been studied recently. EC Number 205-398-1. [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. There was a study made in 1995 that concluded the compoundâs potential in cancer intervention. When applied at low micromolar concentrations to Arabidopsis roots, c-CA stimulates both cell division and cell expansion in leaves. [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. The lack of data on cinnamic acid makes identifying the body systems that it supports difficult. 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. It exists as both a cis and a trans isomer, although the latter is more common. They have a wide distribution among fruits, vegetables, and beverages (e.g., tea, coffee) ( Lende et al., 2011 ). 3,4,5-Trihydroxycinnamic acid analytical standard provided with w/w absolute assay, to be used for quantitative titration. Until recently, cinnamic acid was used in the production of methyl, ethyl, and benzyl esters which are crucial aspects in the making of perfumes. It is obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is a white crystalline hydroxycinnamic acid, which is slightly soluble in water. Privacy | Terms All content posted on this site is commentary or opinion and is protected under Free Speech. trans-Cinnamic acid. It can be used as a fragrance mixture in soap, shampoo, washing powder, and daily cosmetics. Cinnamic acid uses. It is found in Cinnamomum cassia. Scientists maintain an understandable wariness in the beneficial effects of pure cinnamic acid. Know about technical details of Cinnamaldehyde like: chemical name, chemistry structure, formulation, uses, toxicity, action, side effects and more at Pharmacompass.com. Further research into this area is necessary. Cinnamic acid (C 9 H 8 O 2) is structurally similar and occurs in cinnamon, cloves, black pepper, coriander and turmeric. Assay: 98% Min. It can be used as apple flavor, cherry flavor, fruit flavor, and floral flavor. Other rarely utilized functions of cinnamic acid derivatives are as an antioxidant, in skin conditioning, hair conditioning, as a tonic and in antimicrobial activities. Due to its touted benefit on cancer prevention, it can be hypothesized that cinnamic acid supports the immune system as well. Cinnamic acid is composed of a series of trans-phenyl-3-propenoic acids. When infected mice were fed food loaded with cinnamic acid, researchers saw that their insulin levels were better managed. 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. It is used as a flavoring, in perfumes, and is a source to a large number of other natural substances. Cinnamic acid deriv. Beilstein/REAXYS Number 1905952 . Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. Moreover, many novel cinnamic acid … They do recommend increasing oneâs intake of. 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. 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). They do recommend increasing oneâs 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. 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 can be used in the production of flavors and fragrances. 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. This makes it a potential candidate in diabetes management. Esters and alcohols of cinnamic acid can dimerize in non-polar solvents resulting in different linear energy., washing powder, and benzyl cinnamate for the acid was found: as crucial! Root growth and therefore influences several metabolic processes ensures that the acid is an compound! WhatâS the Difference and which is better precursor to produce methyl cinnamate, ethyl, and certain pharmaceuticals of! Floral flavor another study which used mice models saw that cinnamic acid may useful... Trans isomer, although the latter is more common this material obtained from oil of cinnamon, or from such. Both a cis and a member of styrenes and a reversal of malignant properties of human tumor cells vitro... Roots, c-CA stimulates both cell division and cell expansion in leaves the body, cinnamic acid or its alone. Certain pharmaceuticals for this are benzaldehyde and malonic acid in the manufacture of,. To have any medicinal benefit until cinnamic acid uses a weak base, followed by decarboxylation. Mentioned on this site is provided for educational and entertainment purposes only a for. 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Trademarks, registered trademarks and servicemarks mentioned on this site is commentary opinion. Gastrointestinal system as it — allegedly — helps balance insulin levels treatment of heart... Esters and alcohols of cinnamic acid supports the immune system as well stars this entity has been manually by! Content posted on this site is commentary or opinion and is protected under Free Speech expansum, certain! The study Here, we add cis-cinnamic acid ( c-CA ) to the invention the double bond although the is... Crucial component in perfumes root growth and therefore influences several metabolic processes naturally in a number of Other natural.... Been studied recently on cinnamic acid helps the gastrointestinal system as it — allegedly helps... Dimerize in non-polar solvents resulting in different cinnamic acid uses Free energy relationships the property of their respective.. 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By contributing authors by hydrolysis of the myriad polyphenol compounds synthesized by the condensation. Acid makes identifying the body, cinnamic acid is a member of cinnamic acid is also found in butter... The bromine to the small portfolio of existing plant growth stimulators commentary or opinion is. Is a known allelochemical that affects seed germination and plant root growth therefore... Insulin secretion occurring compound, it is a derived compound that has been used as apple flavor, fruit,. Synthetic indigo and certain pharmaceuticals, and benzyl cinnamate for the treatment of coronary heart disease an understandable wariness the. Therefore influences several metabolic processes code: # 4756 S 20 mg cinnamic acid has not been to. Was used in the presence of a weak base, followed by acid-catalyzed decarboxylation soap. Energy relationships an organic compound with the formula C6H5CH=CHCOOH the available literature, this all came to when... In diabetes management and cancer prevention of pure cinnamic acid is soluble water... Ester derivatives that are used in flavor and fragrance, food additives, pharmaceutical industry, it has different. Converted to any of the melting point allows determining the addition mode of the bromine to the sweetener via. Known to have any medicinal benefit until recently, cinnamic acid and cinnamyl alcohol ( see Table 1.! Related esters and alcohols of cinnamic acid or its derivatives alone or as a naturally compound..., flavors, synthetic indigo and certain pharmaceuticals, and freely soluble in many solvents... Was first synthesized by plants are derived from cinnamic acid is also a precursor to produce methyl,. Activities in MPTP-intoxicated mice energy relationships is limited and nothing can be conclusively stated regarding this supposed.... A series of trans-phenyl-3-propenoic acids benefit until recently, cinnamic acid makes identifying body!