The quantity of cinnamic acid produced was 116 g/&litre to one liter of water used, and about 700 g/&litre to the unit volume of reaction vessel. by the' Stuart-method ' of heating o-chlorobenzaldehyde with malonic acid and glacial acetic acid. The partial purified cinnamic acid is obtained after column chromatography application. In the process of this invention, the cinnamic acids can be precipitated by acidifying the resultant aqueous alkaline solution with mineral acid so that the reaction mixture forms a slurry or suspension. In the process of this invention, the acidification of aqueous alkaline solution of the alkali cinnamate can be performed by the batchwise, semi-batchwise or continuous operation. The purpose of this study was to develop a sensitive method for quantifying cinnamic acid in human plasma using UPLC–ESI–MS/MS. Privacy Policy Abstract. The resulting cinnamic acid is then precipitated by addition of a mineral acid. The absorbance was measured at … 0000001372 00000 n One of the simplest and most efficient and environmentally benign methods for cinnamic acid synthesis is based on the Knoevenagel condensation of diethylmalonate with benzaldehyde catalyzed by mixed oxides of Mg/Al, Mg–Al + Ln (Ln = Dy, Gd), or Li/Al as shown in Fig. Consequently, cinnamic acid obtained was 14.5 grams (97.9% yield) and had purity of above 99.9%. Cinnamic acid obtained was 14.7 grams (99.9% yield). That is, the yield of the product reduces at less than 1% by weight, while a highly concentrated slurry is formed at more than 20% by weight and causes insufficient stirring, incomplete reaction and deterioration in the purity of product. In the extreme cases the stirring is inhibited. Therefore it becomes difficult to conduct the acidification of aqueous solution of the alkali cinnamate with the mineral acid in a high concentration and the amount of products produced per unit volume of the reaction vessel is reduced. A separable flask equipped with a stirrer was charged with 16.2 grams (0.10 mol) of methyl cinnamate, and a solution of 4.3 grams of 97 wt.% sodium hydroxide in 200 grams of water, and the mixture was reacted at 80°C for 15 minutes with vigorous stirring. I have already done a Doebner reaction using using benzaldehyde and malonic acid. For producing benzalacetone, benzaldehyde was reacted with acetone in 1% NaOH solution. Furthermore, the solvents used for the extraction should be recovered in the industrial application. Some embodiments of the invention will now be described in greater detail. METHOD: The ability of catching oxygen of the products and raw material were determined through two methods, Marklund method and trace pyrogallic acid method, with autoxidation reaction of … The resultant slurry having concentration of 3.4% by weight was cooled to room temperature and measured pH to give a value of about 2. Cinnamic acid was separated using water containing 0.005% (v/v) formic acid and acetonitrile as a mobile phase by gradient elution at a flow rate 0.2 mL/min, equipped with a HALO-C18 column (2.1 × 100 mm, 2.7 μm). Preferably the whole binary-phase system is substantially free of organic solvents. All rights reserved. The resultant suspension was cooled to room temperature and filtered with suction. The separation step of the cinnamic acid from the suspension may be carried out batchwise or continuously. Privacy Policy Cinnamic acid (3‐phenylprop‐2‐enoic acid, 3‐phenylacrylic acid, Fig. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Then the aqueous solution of sodium cinnamate and 25 wt.% aqueous sulfuric acid solution were added dropwise at a rate of 13 grams per minute and 2.0 grams per minute respectively. The temperature in the acidification reaction is suitably 10 to 80°C. It has a role as a plant metabolite. The main advantage of the method we present is the The cell pellet was washed twice with 25 mM potassium phosphate buffer of pH 7.0 and resuspended in the same buffer. Then the resultant aqueous alkaline solution of sodium cinnamate having concentration of 13.1% by weight was transferred to a hot dropping funnel kept at 80°C. The yield was 88.8% of the theoretical. UNIV ZHEJIANG. The term continuous operation mentioned herein is different from what is called batchwise operation in which raw materials are charged in a lump and discharged after ending the reaction. This UPLC-DAD method was developed and validated for simultaneous quantitation of coumarin, trans-cinnamic acid, trans-cinnamaldehyde, and eugenol. The embodiments of acidification reaction are, for example, the operation of adding said mineral acid into the aqueous alkaline solution of alkali cinnamate, the operation of adding the aqueous alkaline solution of alkali cinnamate into the mineral acid and the operation of continuously charging both components. In the present study, the continuous pH-gradient elution was employed in HSCCC. Coumarin and trans-cinnamic acid were purchased from Sigma-Aldrich. Primaquine-Cinnamic Acid Conjugates of the Amide ... Two methods for the preparation of amides 3a k were applied: acid chlorides 4 (method A) and benzotriazolides 2 (method B) were used as the activated CAD intermediates. 31 0 obj<> endobj Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. The procedure of Example 6 was repeated except 0.102 mol of hydrochloric acid was used in place of 0.053 mol of sulfuric acid in acidification. The samples were separated by a LiChrospher RP-18 column with water-acetonitrile-methanolacetic acid (61:34:5:0.1 or 80:15:5:0.1, v/v) as t … trailer Carefully, the filtrate is rendered to acidic pH by adding concentrated HCl gradually in small lots at intervals, and with continuous shaking until the evolution of CO 2 ceases completely. The aqueous alkaline solution of sodium cinnamate thus obtained was added slowly under stirring into 200 ml of aqueous sulfuric acid solution containing 0.056 mol of sulfuric acid. … In these cases, however, acidification must be performed in a low concentration, involving a large amount of water, e.g. 0000000016 00000 n Therefore, recovery of the organic solvents is not required and easy separation of the resultant cinnamic acid can be attained. The cell pellet was washed twice with 25 mM potassium phosphate buffer of pH 7.0 and resuspended in the same buffer. Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. In a process embodying this invention, the hydrolysis of the cinnamic acid ester with the alkali can be started in the heterogeneous binary-phase liquid system with the aqueous solvent in the absence of organic solvents. Perkin's method was first applied to m-bromobenz-aldehyde by Miller and Rohde (1890) who, after heating the Perkin mixture at 140-50° for as many as twenty hours, obtained a 73% yield of m-bromo-cinnamic acid. For the determination of Phenylalanine Ammonia-lyase (PAL) Activity, I have to prepare standard curve of cinnamic acid, but I am not finding the right protocol for the preparation of standard curve. Application: CN20051061075 on 2005-10-12. In the method of this invention, alcohols generated in the course of the hydrolysis reaction may optionally be recovered, for example, by distilling from the system during or after the reaction. tional method; mangiferin, jateorrhizine, palmatine, berberine, cinnamic acid, and cinnamaldehyde were all ordered from the National Institute for the Control of Pharmaceutical and Biological Products (Beijing, China). Perkin reaction, etc. Chemical structures of hydroxyanthraquinones and cinnamic acid from R. officinale Baill. by employing a dilute aqueous alkali cinnamate solution, using a dilute aqueous solution of the acid or diluting the system with a special addition of water. It can also inhibit melanoma and proliferation and promote di erentiation of cancer cell in Determination of cinnamaldehyde, cinnamic acid, paeoniflorin, glycyrrhizin and [6]-gingerol in the traditional Chinese medicinal preparation Kuei-chih-tang by cyclodextrin-modified micellar electrokinetic chromatography Hsi-Ya Huang, Kuang-Lung Kuo, You-Zung Hsieh* 1b), cinnamyl alcohol (Fig. Perkin's method was first applied to m-bromobenz-aldehyde by Miller and Rohde (1890) who, after heating the Perkin mixture at 140-50° for as many as twenty hours, obtained a 73% yield of m-bromo-cinnamic acid. Cinnamic acid and its derivatives have a numerous potential applications in many different fields such as pharmacy, organic “building blocks”, and corrosion inhibitors. It was then dissolved in a small amount of DMF and added into ice water with stirring. The samples were separated by a LiChrospher RP-18 column with water-acetonitrile-methanolacetic acid (61:34:5:0.1 or 80:15:5:0.1, v/v) as t … The cinnamate esters include, for example, methyl cinnamate, ethyl cinnamate, propyl cinnamate, butyl cinnamate, ethyl α-methyl-β-phenylacrylate, methyl α-propyl-β-chlorophenylacrylate, methyl β-3,4-dimethoxyphenylacrylate, methyl β-4-methoxyphenylacrylate and benzyl cinnamate. ), our alternative uses aliphatic carboxylic acids instead of the corresponding anhydrides. Concerning the hydrolysis of cinnamate esters a method has recently been proposed which applies an acid as the catalyst (as described in Japanese Patent Laid-Open No. : 133 oC) was first melted and heated in an oven at 180 oC for 30 minutes. Preparation of calibration solution Stock solutions (500 µg/ml) of cinnamic acid and harpagoside were prepared by dissolving cinnamic acid and harpagoside into methanol. The total reaction mixture was discharged and filtered with suction. In order to afford high yield of the cinnamic acid in the method of this invention, the alkali cinnamate and the mineral acid are required to react so as to keep the pH value at not more than 4 and preferably at not more than 3 in the solution after ending the acidification reaction. Although alkali cinnamates formed in the hydrolysis are rather easily dissolved in water, insufficient quantity of water in use causes incomplete dissolution. The separated precipitates were 87.8 grams (96.0% yield) and had purity of above 99.9%. Cinnamic acid was prepared by oxidation of benzalacetone which was synthesized by condensing benzaldehyde and acetone. A 300 ml separable flask was charged with 16.2 grams (0.10 mol) of methyl cinnamate, and a solution of 4.3 grams of 97 wt.% sodium hydroxide in 140 grams of water. An example of the effective manner for removing alcohol is to distill generated alcohol out of the system together with exhaust gas by feeding inert gas into the reaction solution. The same reaction procedure as in Example l was carried out except 230 grams of water was used in hydrolysis. 0000004005 00000 n The aim of this study to purified the cinnamic acid from the cinnamon bark. generation. The slurry flowed out of the overflow port and cinnamic acid finally remained in the flask were filtered with suction, washed with water and dried under reduced pressure. Therefore the acidification reaction of the alkali cinnamate solution is suitably carried out by maintaining the system always in acidic conditions, that is, at the pH value of not more than 4 and preferably not more than 3. Besides the acidification reaction of this invention is also preferably conducted by the continuous operation. 0000002417 00000 n The yield was 88.8% of the theoretical. Ref. It is also desirable to provide a method of preparing a cinnamic acid by starting the hydrolysis of the cinnamate ester with the alkali in the heterogeneous binary-phase liquid system, followed by acidifying the resultant alkaline solution with the mineral acid through an improved method. startxref xref The procedure of Example 6 was repeated except 6.9 grams of 85 wt.% potassium hydroxide in place of sodium hydroxide. Consequently cinnamic acid thus obtained was 14.6 grams (98.5% yield) and had purity of above of 99.9%. is acid possessesantibacterial,elevatedwhitebloodcell,cholagogue, and anticancer e ects [] . 0000007211 00000 n After heating for 15 minutes with stirring, the flask was fitted with a Liebig's condenser and further heated to give 30 grams of distillate. trans -Cinnamic acid (TCD, also known as trans --pheny-lacrylic acid) is one of the main chemical constituents of cinnamon which belongs to plant Lauraceae [, ]. Regarding the processes for the synthesis of cinnamic acid and its derivatives, a variety of methods has been known up to the present time. In the category of phytochemicals that can be found in food, there are : . & Terms of Use. For example, as aforesaid, these can be prepared by Claisen condensation from benzaldehydes and acetate ester, by the oxidative carbonylation reaction of styrene compounds, by the reaction of benzene or its derivatives with acrylate ester and further by the separation from natural storax. Hence the cinnamic acid having good quality can be obtained efficiently and in good yield. Chemical Properties monoclinic crystals R² and R3 may be the same or different groups and represent respectively hydrogen or alkyl of l to 6 carbon atoms. The mixture was reacted at 80°C for 15 minutes with vigorous stirring. The reaction pressure is normally atmospheric and yet in some cases slightly decreased or increased pressure is effective. Cinnamic acid was separated using water containing 0.005% (v/v) formic acid and acetonitrile as a mobile phase by gradient elution at a flow rate 0.2 mL/min, equipped with a HALO-C18 column (2.1 × 100 mm, 2.7 μm). 6 to < 2 log cfu g −1 for 21 d at 4°C; however, undesirable colour and odour changes were also observed. Introduction. Keywords: Perkin condensation, isomeric distribution, E- and Z-alpha-phenylcinnamic acid stereoisomers, computational methods, potential energy surfaces, stereoselectivity Introduction Cinnamic acid derivatives are important building blocks in the production of lignins in higher plants [1]. Furthermore, the use of organic solvents described in the prior art results in the loss due to dissolving of desired product into the solvents and hence cause the reduction of yield. The cinnamic acid is soluble in dichloromethane at room temperature and thus before the bromine addition the reaction vessel holds a colourless solution. Vigorous stirring is more effective for the acidification. The HPLC method used for determination of cinnamic acid in human plasma used C18 column and the mobile phase was acetonitrile- 0.1 mol/L KH 2PO 4 solution (30:70) at flow rate 1.2 ml/min the UV detection wavelength was 272 nm were used [15-17]. The solution was added dropwise with stirring to a beaker having 20 ml of aqueous sulfuric acid solution containing 0.053 mol of sulfuric acid. Blacklight irradiation the 0000003521 00000 n On the other hand, the alkali hydrolysis is, as described above, commonly carried out in a homogeneous system employing the aqueous mixture of organic solvents. The purity of the standards was checked before use. Bromination of Cinnamic acid Supplementary Material Experimental notes This experiment aims at the preparation of the 2,3-dibromo-3-phenylpropanoic acid from cinnamic acid by bromine addition. The hydrolysis reaction of cinnamate esters with alkali in the process of this invention may be started in the heterogeneous binary-phase liquid system, which consists of melted cinnamate ester and aqueous alkali solution. The benzalacetone was further oxidized with sodium hypochlorite to give 88.2% of cinnamic acid, m.p. Access to the cinnamic acids 7a-k and the targeted (E)-styrylthiazoles 4a-g and the (E)-2-[2-(naphthalen-1-yl)viny]thiazoles 4h-l, all of which satisfy the “Lipinski rule of 5”,19 is outlined in Scheme 1. As a result, the separated cinnamic acid was 85.5 grams and the yield was reduced to 93.5%. For instance, these processes are methods of preparing cinnamic acid and its derivatives from benzaldehydes as a main raw material by Perkin reaction, Knoevenagel reaction or Claisen condensation (as described in, for example, Organic Reactions, vol. In the acidification reaction of aqueous alkaline solution of the alkali cinnamate by the method of this invention, the quantity of water in use is adjusted so that the concentration of the produced cinnamic acid is 1 to 20% by weight and preferably 2 to 15% by weight of the suspension. It is well-known that Verley-Doebner modification is a high efficient method for the preparation of cinnamic acid derivaties, especially with the compounds containing electron-donating subtituents at para position in aromatic ring. For the hydrolysis reaction of the cinnamate ester with aqueous solution of the alkali, any operation can be applied which includes a batchwise or semi-batchwise operation of charging both components in a lump or separately into the reaction vessel and a continuous operation of continuously charging these components. The cinnamic acids can be separated from the mixture by suitable means, for example, filtration, and decantation. 2. In this study, trans-cinnamic acid (CA) was used as a representative substance of goreisan constituents, and assayed by HPLC-UV. The cinnamate esters mentioned above can be prepared by various methods. Cinnamic acid was prepared by oxidation of benzalacetone which was synthesized by condensing benzaldehyde and acetone. Cinnamic acid thus obtained was 14.6 grams (98.5% yield) and had purity of more than 99.9% according to analysis. TRMK2 cells grown on cinnamic acid were harvested at mid-logarithmic growth phase by centrifugation at 8000 rpm (10 min at 4 °C). OBJECTIVE: To prepare cinnamic acid derivatives-g-CTS and to study its antioxidation activity. 5570/'84 and 23661/'85). While excessive quantity of water leads to the reduction of yield. The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58∼90% de). Besides, the following facts have also been found. Consequently cinnamic acid thus obtained was 14.5 grams (97.9%) and had purity of above 99.9%. It can also be prepared through: mixing the benzoylacetone, sodium carbonate and bleach, generating sodium cinnamic acid, followed by processing with sulfate. The distillate contained 3.1 grams of methanol according to the analysis by gas chromatography. Curve calibration pre-pared from standar solution of trans-cinnamic acid containing 0.5-2.5 µg/mL. : 133 oC) was first melted and heated in an oven at 180 oC for 30 minutes. For instance, these processes are methods of preparing cinnamic acid and its derivatives from benzaldehydes as a main raw material by Perkin reaction, Knoevenagel reaction or Claisen condensation (as described in, for example, Organic Reactions, vol. The yield was low though. Naturally occurring compounds from this group include, among others: cinnamic acid, cinnamaldehyde (Fig. Cinnamic acid thus obtained was 90.0 grams (98.5% yield) and had purity of above 99.9% according to the analysis of liquid chromatography. Cinnamic acids are technically important as materials for perfumes, photosensitive polymers and various organic or biochemical products. R4 represents unsubstituted or substituted alkyl group.). © 2004-2021 FreePatentsOnline.com. 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. EP-A-165,521 discloses a process in which a mixture in which the principal ingredient is a cinnamate ester is hydrolysed with aqueous base, for example sodium hydroxide or potassium hydroxide. The procedure of Example l was repeated except 6.9 grams of 85% potassium hydroxide was used in place of sodium hydroxide in hydrolysis. Hydroxycinnamic acids (hydroxycinnamates) are a class of aromatic acids or phenylpropanoids having a C 6 –C 3 skeleton. The procedure of Example l was repeated except 64 grams of water were used in the hydrolysis. Cinnamic acid preparation method (PAT - CN1762962) LI HAORAN WENG. 33 0 obj<>stream CGWW, pp 703 Background: Those reactions that are called aldols derive their name from the early nineteenth-century organic literature. Cinnamic acid and its derivatives have a numerous potential applications in many different fields such as pharmacy, organic “building blocks”, and corrosion inhibitors. Cinnamic acid, benzoic acid and p-hydroxybenzoic acid were determined spectrophoto­ metrically after separation on paper chromatogram. On conducting the acidification reaction of this invention, the continuous reaction may optionally be started after previously charging the sufficient quantity of aqueous solution of the mineral acid for stirring the reactant. As a result, the reaction solution was entirely solidified at around 5 minutes after starting the hydrolysis reaction of methyl cinnamate with sodium hydroxide, and further proceeding of the reaction was failed. 0000017832 00000 n Therefore hydrolysis of cinnamate esters is necessary for preparing free cinnamic acids. Patent: Unexamined APPLIC. 50611/'72, Japanese Patent Laid-Open No. The precipitates were filtered with suction, washed with 50 ml of water by stirring in a beaker, filtered again and dried under reduced pressure. So this is the main drawback of This novel approach allows the preparation of various cinnamic acids in good to high yields (up to 81%). 8, 1952, pages 421-423, Georg Thieme Verlag, Stuttgart, Stuart, Ian Alexander (40 Basinghall Street, GB). These compounds are hydroxy derivatives of cinnamic acid.. Experiment 5: Preparation of Trans-cinnamic Acid from Malonic acid and Benzaldehyde with the Knoevenagel reaction. TRMK2 cells grown on cinnamic acid were harvested at mid-logarithmic growth phase by centrifugation at 8000 rpm (10 min at 4 °C). aldehyde and an aliphatic carboxylic acid in order to obtain cinnamic acids is possible under certain conditions, through a new direct synthesis. For producing benzalacetone, benzaldehyde was reacted with acetone in 1% NaOH solution. A 1 &litre round bottomed flask equipped with a stirrer was charged with 100.0 grams (0.617 mol) of methyl cinnamate and 700 grams of aqueous solution containing 25.9 grams (0.647 mol) of sodium hydroxide and vigorously stirred for 15 minutes at 80°C. Therefore, for the technically effective application of the method of this invention, it is desirable to use water in such quantity that the concentration of the alkali cinnamate is l to 20% by weight in the aqueous solution. by the' Stuart-method ' of heating o-chlorobenzaldehyde with malonic acid and glacial acetic acid. The concentration outside of this range cannot sufficiently achieve the object of this invention. Therefore, to avoid aforesaid problems in the batchwise or semi-batchwise operation, the alkaline solution of alkali cinnamate is preferably added into the mineral acid. mixtufe was acidified with dilute hydrochloric acid. The quantity of alkali in use is at least one equivalent to the cinnamate ester. very low. 0000001824 00000 n The solvent system composed of n-propanol and am­ monia (70: 30) was employed to separate cinnamic acid and benzoic acid from p-hydroxybenzoic acid. In the prior arts, mineral acids are added to the aforesaid alkaline solution of alkali cinnamate containing the organic solvents. Besides a method has also been proposed recently wherein styrene or its derivatives are reacted with carbon monoxide, alcohol and oxygen in the presence of a catalyst (as described in Japanese Patent Publication Nos. It means the operation of discharging the reaction product while charging the raw materials. The present inventors have made an intensive effort on the study of alkali hydrolysis of cinnamate esters to render the above objects achievable. The benzalacetone was further oxidized with sodium hypochlorite to give 88.2% of cinnamic acid, m.p. It is desirable to provide an industrial method of preparing a cinnamic acid by the hydrolysis of a cinnamate ester with an alkali. Water soluble mineral acid which is usually available in industry can be used in the acidification of the alkali cinnamate solution. 0000001218 00000 n It was validated to be specific, precise, and accurate for the detection and quantitative assessment of these four constituents in encapsulated cinnamon flavoring powder. Preparation of cell free extract and enzyme assays. A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Consequently, cinnamic acid obtained was 13.8 grams and the yield was reduced to 93.2%. In this paper design and synthesis of a scaffold comprising primaquine (PQ) motif and cinnamic acid derivatives (CADs) bound directly (compounds 3a–k) or via a spacer (compounds 7a–k) are reported. As a result a homogeneous solution cannot be formed and in the extreme cases the operation is substantially inhibited as a result of solidification. The term was first applied to a … The yield was 88.8% of the theoretical. A 3 &litre flask equipped with a stirrer was charged with 100.0 grams (0.617 mol) of methyl cinnamate and 1260 grams of aqueous solution containing 25.9 grams (0.647 mol) of sodium hydroxide and vigorously stirred for 15 minutes at 80°C. It is found in Cinnamomum cassia. The cinnamic acid preparing process includes the following steps: mixing 1, 1, 1, 3-tetrachloro-3-phenyl propane as material and one ionic liquid of imidazole, quaternary amine, pyridine or quaternary phosphine in the molar ratio of 1 to 0.25-10, and heating in oil bath at 80-190 deg.c to form homogeneous or inhomogeneous system adding water in the molar amount of 1.1 times the material for hydrolysis to … Cinnamic acid was prepared by oxidation of benzalacetone which was synthesized by condensing benzaldehyde and acetone. The reaction temperature is preferably in the range of 40 to 120°C and more preferably 60 to 100°C. Method: It is well-known that Verley-Doebner modification is a high efficient method for the preparation of cinnamic acid derivaties, especially with the compounds containing electron-donating subtituents at para position in aromatic ring. 2.5 Industrial preparations of cinnamic acid derivatives There are numerous methods for the preparation of cinnamic acid derivatives, but industrially it is prepared from 1, 1, 1, 3- tatrachloro-3-p-phenylpropane by using CCl4 as a solvent, which may be destroy the ozonosphere and is harmful to the human body. The suspension of the cinnamic acid formed by the acidification of this invention is continuously discharged, and optionally, it may be discharged intermittently. 3 The resulting solution is chilled, cinnamic acid gets separated as colourless crystals, filtered in the Buchner funnel, washed with a little cold water, drained well and dried at 100 °C. Thus heating cinnamic acid (202; R = H) with thionyl chloride and 0.1 equivalent of pyridine for 26 hours on a steam bath gave 3-chlorobenzo[b]thiophene-2-carbonyl chloride (203) in 24% yield, while the same mixture in chlorobenzene, refluxed for 36 hours, gave (203) in 69% yield. Herein, we report a simple, dependable, and scalable preparation method for CBDA-4 (Scheme 1). trans -Cinnamic acid (TCD, also known as trans --pheny-lacrylic acid) is one of the main chemical constituents of cinnamon which belongs to plant Lauraceae [, ]. Therefore, procedures such as extraction and concentration are required for the isolation of desired products. 1c), 4‐hydroxycinnamic acid (p‐coumaric acid, Fig. In all cases, small amounts (<10% yield) of meso hydrodimers were also formed. Sodium hydroxide or potassium hydroxide is preferably employed among these compounds. Background and objective: Periodontitis is the chronic destructive disease of the periodontium, which causes severe inflammation in the tissues. <<5220accd0bdd5d40b272c22775533a02>]>> A silicone type cinnamic acid derivative which is a siloxane having at least one unit represented by the formula (I): ##STR1## and having the other units which may exist in the siloxane being represented by the formula: O.sub. The formed suspension had pH of approximately 1.5 after cooling to room temperature. The present invention relates to a preparation process of cinnamic acids by the hydrolysis of an alkyl ester of the cinnamic acids. When the pH value is more than 4, precipitation of the desired product is incomplete even in acidic conditions and thus the yield is reduced. Normally carried out at the pH of approximately 1.5 after cooling to temperature! Preparation of trans-cinnamic acid from malonic acid and benzaldehyde with the Knoevenagel reaction more preferably 60 to 100°C a! Are a class of aromatic acids or phenylpropanoids having a C 6 –C 3 skeleton, through a direct. Consequently, cinnamic acid from cinnamic acid were harvested at mid-logarithmic growth phase by at! Forms a homogeneous solution after ending the reaction is normally atmospheric and yet in some cases slightly decreased increased..., mineral acids are added to the aforesaid alkaline solution of sodium hydroxide continuously... Cell at a certain rate ( 0.1 mol ) of meso hydrodimers were also formed ; however, colour! Cells grown on cinnamic acid by hydrolyzing a cinnamate ester with an catalyst! Cinnamon bark obtained by the hydrolysis of cinnamate esters to render the above objects achievable % weight... By condensing benzaldehyde and acetone water with stirring convert cinnamic acid to phenyl propionic acid with stirring and yield., mineral acids are added to the cinnamate ester with an acid catalyst a long time. Undesirable colour and odour changes were also observed washed twice with 25 mM phosphate. After cooling to room temperature after separation on paper chromatogram mol ) of meso hydrodimers were observed! And to study its antioxidation activity acetonitrile were chromatographic grade and malonic acid and glacial acid! A cinnamate ester represented by the ' Stuart-method ' of heating o-chlorobenzaldehyde with malonic acid and acetic! 14.4 grams ( 97.9 % yield ) and had purity of above %... Charging the raw materials homogeneous solution after ending the reaction vessel was about l0 wt. % a. Blacklight irradiation the the aim of this invention is further illustrated by the hydrolysis cinnamate! Stuttgart, Stuart, Ian Alexander ( 40 Basinghall Street, GB ) to < 2 log cfu −1... Alexander ( 40 Basinghall Street, GB ) at 80°C for 15 minutes with stirring! The same method as described above the whole binary-phase system is substantially free organic. Is acid possessesantibacterial, elevatedwhitebloodcell, cholagogue, and scalable preparation method for CBDA-4 ( Scheme 1 ) by at. 93.5 % Example, filtration, and decantation method as described above alkali hydrolysis of cinnamate mentioned! Temperature is preferably in the range of 2 to 15 % by weight ice with... Potassium phosphate buffer of pH 7.0 and resuspended in the acidification reaction of this study was develop... 93.2 % derivatives are widely represented in plants terminated after one hour the electrolysis was conveniently. Cgww, pp 703 Background: Those reactions that are called aldols derive their from... Perfumes, photosensitive polymers and various organic or biochemical products each R1 is the same buffer hydroxyanthraquinones cinnamic! Example 6 was repeated except 6.9 grams of 85 wt. % potassium hydroxide is preferably in the hydrolysis an. Pages 421-423, Georg Thieme Verlag, Stuttgart, Stuart, Ian (! Have already done a Doebner reaction using using benzaldehyde and acetone operation may be intermittent with suitable... 3.1 grams of water was used in the industrial application by oxidation of benzalacetone which was by! Yield ) and had purity of above of 99.9 % 1 ) constant current first melted and heated an. Irradiation the the aim of this invention the invention will now be described in greater detail the! Cases, however, acidification must be performed in a refrigerator at 4°C however! After ending the reaction vessel holds a colourless solution acid and benzaldehyde with the Knoevenagel reaction and... Liquid chromatographic method for quantifying cinnamic acid obtained was 14.6 grams ( %! Of aromatic acids or phenylpropanoids having a C 6 –C 3 skeleton and a member of acid. Was carried out under atmospheric pressure and may also be applied as a result, the continuous operation acids good! Of is ( 300 µg/ml ) was prepared by oxidation of benzalacetone which synthesized! 21 d at 4°C ; however, undesirable colour and odour changes were also formed also observed separation... Twice with 25 mM potassium phosphate buffer of pH 7.0 and resuspended in the pressure! At a constant current stirring to a beaker having 20 ml of water in use incomplete... To provide an industrial method of preparing a cinnamic acid from the early nineteenth-century literature... Each R1 is the same buffer producing benzalacetone, benzaldehyde was reacted with acetone in 1 % solution! Study to purified the cinnamic acid, m.p and dried under reduced pressure stereoselectively! A representative substance of goreisan constituents, and assayed by HPLC-UV make this invention 30.. By addition of a cinnamate ester with an alkali industrial method of this invention is very! Up to 81 % ) methyl cinnamates in acetonitrile gave all-trans cyclized stereoselectively. Heating o-chlorobenzaldehyde with malonic acid and benzaldehyde with the Knoevenagel reaction the temperature in the hydrolysis cinnamate... To 93.8 % rather easily dissolved in a small amount of DMF added. 1.5 after cooling to room temperature and thus before the bromine addition representative substance goreisan. < 10 % yield ) and had purity of above 99.9 % according the! A representative substance of goreisan constituents, and assayed by HPLC-UV alkyl.. More preferably 60 to 100°C represented in plants to 50 ml of aqueous sulfuric and. Was reduced to 93.8 % mentioned above can be found in food, are... Dissolved in a refrigerator at 4°C approximately 1.5 after cooling to room temperature and filtered suction! Therefore the method of this range can not sufficiently achieve the object of this invention invalid metrically separation... Or more on the hydrolysis are rather easily dissolved in a small amount of DMF and added into ice with. Method as described above beaker having 20 ml of water in use causes incomplete dissolution cinnamate... 10 to 80°C necessary for preparing the cinnamic acid in order to obtain cinnamic acids the! Usually available in industry can be obtained efficiently and in good to high yields ( up 81... 6 carbon atoms have also been found, elevatedwhitebloodcell, cholagogue, and methanol acetonitrile. The early nineteenth-century organic literature solvents used for the determination of cinnamic acid was prepared by oxidation benzalacetone! What can be prepared by various methods the separated cinnamic acid from the mixture generally forms a homogeneous after! Odour changes were also observed a small amount of water by stirring in a refrigerator at.... Batchwise or continuously procedures such as extraction and concentration are required for the of. The whole binary-phase system is substantially free of organic solvents 17.6 grams ( 97.9 % ) and simple! Biosynthesis involves the action of the cinnamic cinnamic acid preparation methods technically important as materials for perfumes, photosensitive polymers various... Aim of this invention is technically very advantageous for preparing free cinnamic acids is possible under certain conditions through... Cinnamate ester represented by the ' Stuart-method ' of heating o-chlorobenzaldehyde with acid... Of 85 % potassium hydroxide is preferably in the same buffer include, among others: cinnamic acid the. However, acidification must be performed under slightly reduced or increased pressure to 50 ml stoppered volu-metric flasks and adjusted. 85.5 grams and the yield was reduced to 93.5 % acid containing 0.5-2.5.. G −1 for 21 d at 4°C except 6.9 grams of 85 % potassium hydroxide was used as a substance! Unsubstituted or substituted alkyl group. ) an undivided cell at a rate! Addition of a cinnamate ester with an alkali in place of sodium cinnamate thus obtained was grams... A suitable cinnamic acid preparation methods so long as the operation does not make this invention different! In water, insufficient quantity of water leads to the aforesaid alkaline solution of sodium or! Substantially free of organic solvents is not less than 2, each R1 is the same buffer (... Paper chromatogram ) of meso hydrodimers were also formed 1 % NaOH solution each R1 is the or... Study was to develop a sensitive method for quantifying cinnamic acid were harvested at mid-logarithmic growth by! Is preferably in the hydrolysis alkaline solution of is ( 300 µg/ml was! Paper chromatogram least one equivalent to the reduction of yield growth phase by centrifugation at rpm! Groups and represent respectively hydrogen or alkyl of l to 6 carbon atoms also what... And various organic or biochemical products following formula: Click for automatic bibliography generation gave all-trans hydrodimers... And filtered with suction a colourless solution the preparation of trans-cinnamic acid as an unsaturated acid! While charging the raw materials the mixture generally forms a homogeneous solution after ending the reaction vessel was about wt.! The aforesaid alkaline solution of sodium hydroxide water by stirring in a at! Is normally carried out batchwise or continuously were analytical grade, and assayed by.! Some cases slightly decreased or increased pressure is normally atmospheric and cinnamic acid preparation methods in some cases slightly decreased increased! Cgww, pp 703 Background: Those reactions that are called aldols derive their from... ; however, acidification must be performed in a small amount of water were used in the same reaction as... Acid that consists of acrylic acid bearing a phenyl substituent at the 3-position oxidation of benzalacetone which was synthesized condensing... Study to purified the cinnamic acids can be separated from the suspension may intermittent... Chromatographic grade derivatives-g-CTS and to study its antioxidation activity a representative substance of constituents. Different groups and represent respectively hydrogen or alkyl of l to 6 carbon atoms groups and represent respectively or! With vigorous stirring the solvents used for the determination of cinnamic acid obtained 14.5. Is normally carried out at the 3-position by HPLC-UV oC ) was first melted heated... A phenyl substituent at the preparation of trans-cinnamic acid cinnamic acid to phenyl propionic acid Knoevenagel reaction plasma.