Standard Preparation. 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. 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 purpose of this study was to develop a sensitive method for quantifying cinnamic acid in human plasma using UPLC–ESI–MS/MS. 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 … x�b```"V� >�c`��0p4�)00. Cinnamic acid was prepared by oxidation of benzalacetone which was synthesized by condensing benzaldehyde and acetone. In support of the Krubsack mechanism, when an electron-releasing group, such as methoxy, was present on the benzene ring, … 0000001089 00000 n 133°C. 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. In this study, trans-cinnamic acid (CA) was used as a representative substance of goreisan constituents, and assayed by HPLC-UV. very low. 0000003521 00000 n 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. The commercially available standard of trans-cinnamaldehyde normally contains trans-cinnamic acid as an impurity. startxref The procedure of Example l was repeated except 2000 ml of aqueous sulfuric acid solution containing 0.085 mol of sulfuric acid were used in place of the aqueous acid solution in acidification. The resultant suspension was cooled to room temperature and filtered with suction. 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. © 2004-2021 FreePatentsOnline.com. The yield was 88.8% of the theoretical. Both methods gave products in similar yields. 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. The cinnamate esters mentioned above can be prepared by various methods. As a result the product is deteriorated in quality and the yield tends to decrease. In the operation of adding the mineral acid into the aqueous solution of alkali cinnamate, however, the reaction mixture often forms a slurried liquid having a high viscosity. 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]. CGWW, pp 703 Background: Those reactions that are called aldols derive their name from the early nineteenth-century organic literature. It is found in Cinnamomum cassia. 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. The term was first applied to a … 50611/'72, Japanese Patent Laid-Open No. It was then dissolved in a small amount of DMF and added into ice water with stirring. For example, quantity of the raw materials can be set so as to obtain the pH value of not more than 4 after the reaction. 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. Besides a step of acidifying the resultant alkaline solution with mineral acids after alkali hydrolysis is required in order to finally obtain the cinnamic acids. The partial purified cinnamic acid is obtained after column chromatography application. Stenotrophomonas sp. 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. After charging about 20 grams of sulfuric acid in the flask in advance, the aqueous alkaline solution of sodium cinnamate was added dropwise with stirring until pH of 2 was indicated. 6 to < 2 log cfu g −1 for 21 d at 4°C; however, undesirable colour and odour changes were also observed. 0000002417 00000 n Application: CN20051061075 on 2005-10-12. Vigorous stirring is effective for the process of this invention because the hydrolysis reaction of the alkyl cinnamate with the alkali starts in the heterogeneous binary-phase liquid system except when special cinnamate esters are used as raw materials. Herein, we report a simple, dependable, and scalable preparation method for CBDA-4 (Scheme 1). The mixture was reacted at 80°C for 15 minutes with vigorous stirring. The cinnamic acids can be separated from the mixture by suitable means, for example, filtration, and decantation. The reaction pressure is normally atmospheric and yet in some cases slightly decreased or increased pressure is effective. 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. The cinnamic acid is soluble in dichloromethane at room temperature and thus before the bromine addition the reaction vessel holds a colourless solution. 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. Preparation curve calibration of trans-cinnamic acid Cinnamic acid were weighed and transferred to 50 mL stoppered volu-metric flasks and volume adjusted with ethanol. 2. CGWW, pp 703 Background: Those reactions that are called aldols derive their name from the early nineteenth-century organic literature. 4-M..: thoxy cinnamic acid was filtered and washed with water until free of acid and then it was dried in an oven (Table 2). 31 0 obj<> endobj Cinnamic acid was prepared by oxidation of benzalacetone which was synthesized by condensing benzaldehyde and acetone. 0000018252 00000 n J Chromatogr Sci. The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58∼90% de). The main advantage of the method we present is the Preferably the whole binary-phase system is substantially free of organic solvents. 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. The reaction time depends upon reaction temperature and pressure and is preferably in the range of 1 to 120 minutes, and more preferably 3 to 30 minutes. 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. The procedure of Example 10 was repeated except the dropwise addition rate of aqueous sulfuric acid solution was reduced and pH of the reaction mixture was kept at 5 in acidification. Therefore the method of this invention is technically very advantageous for preparing the cinnamic acid. A high-performance liquid chromatographic method for the determination of cinnamic acid in Cinnamomi ramulus and paeoniflorin in Paeoniae radix was established. %PDF-1.4 %���� Consequently, cinnamic acid obtained was 14.5 grams (97.9% yield) and had purity of above 99.9%. OBJECTIVE: To prepare cinnamic acid derivatives-g-CTS and to study its antioxidation activity. All the stock solutions were stored in a refrigerator at 4°C. Commercially available trans-cinnamic acid (m.p. Blacklight irradiation the The mineral acid includes, for example, hydrochloric acid, sulfuric acid and phosphoric acid. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. The temperature in the acidification reaction is suitably 10 to 80°C. The charge or discharge operation may not always be continuous. A high-performance liquid chromatographic method for the determination of cinnamic acid in Cinnamomi ramulus and paeoniflorin in Paeoniae radix was established. Cinnamic acid, benzoic acid and p-hydroxybenzoic acid were determined spectrophoto­ metrically after separation on paper chromatogram. 1b), cinnamyl alcohol (Fig. The benzalacetone was further oxidized with sodium hypochlorite to give 88.2% of cinnamic acid, m.p. conditions, through a new direct synthesis. 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. 0000003232 00000 n 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 aim of this study to purified the cinnamic acid from the cinnamon bark. For producing benzalacetone, benzaldehyde was reacted with acetone in 1% NaOH solution. The quantity of alkali in use is at least one equivalent to the cinnamate ester. 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. … TRMK2 cells grown on cinnamic acid were harvested at mid-logarithmic growth phase by centrifugation at 8000 rpm (10 min at 4 °C). 1. The procedure of Example l was repeated except 6.9 grams of 85% potassium hydroxide was used in place of sodium hydroxide in hydrolysis. : 133 oC) was first melted and heated in an oven at 180 oC for 30 minutes. The stock solution of IS (300 µg/ml) was prepared with water. 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. Naturally occurring compounds from this group include, among others: cinnamic acid, cinnamaldehyde (Fig. The operation may be intermittent with a suitable interval so long as the operation does not make this invention invalid. 0000007639 00000 n The solution was distilled at about 100°C, a fraction of 98 to 99°C was collected, and 17.8 grams of methanol were recovered as an aqueous solution. 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. The yield was 88.8% of the theoretical. It was validated to be specific, precise, and accurate for the detection and quantitative assessment of these four constituents in encapsulated cinnamon flavoring powder. The benzalacetone was further oxidized with sodium hypochlorite to give 88.2% of cinnamic acid, m.p. 12736/'85). The procedure of Example l was repeated except 64 grams of water were used in the hydrolysis. Hence the cinnamic acid having good quality can be obtained efficiently and in good yield. The reaction was always carried out at the pH of not more than 2 and terminated after one hour. As a result, the separated cinnamic acid was 85.5 grams and the yield was reduced to 93.5%. Regarding the processes for the synthesis of cinnamic acid and its derivatives, a variety of methods has been known up to the present time. α-Cyano-4-hydroxycinnamic acid; Caffeic acid – burdock, hawthorn, artichoke, pear, basil, thyme, oregano, apple Commercially available trans-cinnamic acid (m.p. Ref. Herein, we report a simple, dependable, and scalable preparation method for CBDA-4 (Scheme 1). Consequently, cinnamic acid obtained was 13.8 grams and the yield was reduced to 93.2%. Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. The total reaction mixture was discharged and filtered with suction. 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. A high-performance liquid chromatographic method for the determination and pharmacokinetic study of cinnamic acid in the plasma of rats after having We use cookies to enhance your experience on our website.By continuing to use our website, you are agreeing to our use of cookies. Consequently, cinnamic acid obtained was 13.9 grams and the yield was reduced to 93.8%. 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. 0000018061 00000 n 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. A silane type cinnamic acid derivative represented by the formula (I'): wherein R 1 represents an alkyl group having 1 to 4 carbon atoms, a phenyl group, or a trimethylsiloxy group, R² is a divalent hydrocarbon group having at least two carbon atoms, which may include a heteroatom O, X is an alkoxy group, and a is an integer of 2 or 3. & Terms of Use. 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. 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). The procedure of Example l was repeated except 2100 grams of water in the hydrolysis and 200 grams of aqueous sulfuric acid solution containing 0.08 mol of sulfuric acid were used in acidification. is acid possessesantibacterial,elevatedwhitebloodcell,cholagogue, and anticancer e ects [] . 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. 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 purity was above 99.9% according to analysis. 1c), 4‐hydroxycinnamic acid (p‐coumaric acid, Fig. 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]. <<5220accd0bdd5d40b272c22775533a02>]>> 0000010308 00000 n Curve calibration pre-pared from standar solution of trans-cinnamic acid containing 0.5-2.5 µg/mL. The mixture generally forms a homogeneous solution after ending the reaction. 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. Determination of mangiferin, jateorrhizine, palmatine, berberine, cinnamic acid, and cinnamaldehyde in the traditional Chinese medicinal preparation Zi-Shen pill by high-performance liquid chromatography. The formed suspension had pH of approximately 1.5 after cooling to room temperature. Preparation of cell free extract and enzyme assays. Preparation of cell free extract and enzyme assays. In the extreme cases the stirring is inhibited. The hydrolysis, however, is generally performed by use of alkali such as sodium hydroxide in a homogeneous system which contains aqueous mixture of alcohol, dioxane or acetone (as described in Japanese Patent Laid-Open No. A round bottomed flask having an overflow port of about 20 mm in diameter in the middle of the vessel (the volume below the port was about 130 ml) was respectively equipped with a stirrer, an electrode of pH meter, a discharge orifice of tube pump capable of delivering 25 wt.% aqueous sulfuric acid solution at a constant flow rate, and an orifice of hot dropping funnel containing aqueous alkaline solution of sodium cinnamate. Patent: Unexamined APPLIC. 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. As a concrete method, for example, from a flooding port equipped on the reaction vessel, the suspension may be discharged by an overflow mode, or may also be discharged by use of a pump. 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. open to Public inspection - China. mixtufe was acidified with dilute hydrochloric acid. 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. 0 5570/'84 and 23661/'85). 102614/'74). by the' Stuart-method ' of heating o-chlorobenzaldehyde with malonic acid and glacial acetic acid. Cinnamic acid, benzoic acid and p-hydroxybenzoic acid were determined spectrophoto­ metrically after separation on paper chromatogram. Besides, the following facts have also been found. The separated precipitates were 87.8 grams (96.0% yield) and had purity of above 99.9%. 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. Cinnamic acid preparation method (PAT - CN1762962) LI HAORAN WENG. 1a) and its simple derivatives are widely represented in plants. The procedure of Example l0 was repeated except 19 wt.% hydrochloric acid was used in place of 25 wt.% sulfuric acid and pH was kept at not more than 3 in the reaction vessel in acidification. 31 22 A process of preparing a cinnamic acid by hydrolyzing a cinnamate ester represented by the following formula: Click for automatic bibliography It was then dissolved in a small amount of DMF and added into ice water with stirring. 0000004005 00000 n It is found in Cinnamomum cassia. The yield was low though. Some embodiments of the invention will now be described in greater detail. And the materials may be fed continuously or intermittently at a certain rate. 0000017832 00000 n Preparation of calibration solution Stock solutions (500 µg/ml) of cinnamic acid and harpagoside were prepared by dissolving cinnamic acid and harpagoside into methanol. Besides in embodiments of this invention, the aqueous alkaline solution of the alkali cinnamate obtained by the alkali hydrolysis of the cinnamic acid ester can be acidified at a high concentration, the quantity of products per unit volume of the reaction vessel can be increased, the quantity of water in use can be reduced, the environmental problems of drainage can be mitigated and the loss by dissolving the products into the drainage can be decreased. Cinnamic acid (3‐phenylprop‐2‐enoic acid, 3‐phenylacrylic acid, Fig. The developed HPLC methods are summarized in table (1) Cinnamic acid and Cinnamic acid derivatives 8.6 [140]. The reaction temperature is preferably in the range of 40 to 120°C and more preferably 60 to 100°C. The alkali can also be applied as a mixture of two or more. When the acidification of aforementioned aqeuous alkaline solution is conducted either by adding the aqueous alkaline solution into mineral acid or by continuously charging the aqueous alkaline solution and said mineral acid into the reaction vessel so as to keep the pH value at not more than the specific value in the mixture obtained by acidifying and continuously discharging the product, this method can decrease the quantity of water in use, and thus the amount of product produced per unit volume of the reaction vessel can be increased, the environmental problems on drainage is mitigated, the loss of the product by dissolving in the drainage is reduced and the cinnamic acids having an excellent qualify can be obtained in good efficiency. 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. 0000004081 00000 n 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. When n is not less than 2, each R1 is the same or different. 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. & Terms of Use. 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 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. The present inventors have made an intensive effort on the study of alkali hydrolysis of cinnamate esters to render the above objects achievable. 0000001824 00000 n Sodium hydroxide or potassium hydroxide is preferably employed among these compounds. While excessive quantity of water leads to the reduction of yield. Cinnamic acid thus obtained was 14.6 grams (98.5% yield) and had purity of more than 99.9% according to analysis. 133°C. 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 [, ]. 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 … : 133 oC) was first melted and heated in an oven at 180 oC for 30 minutes. It has a role as a plant metabolite. 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. As a result, it has been found that a cinnamic acid of excellent quality can be favorably obtained by a process embodying the invention employing alkali hydrolysis in a heterogeneous binary-phase liquid system; the aqueous solvent being free of organic solvents; followed by acidifying the resultant aqueous alkaline solution so that the pH value of the solution obtained by the reaction was not more than a specific value. I have already done a Doebner reaction using using benzaldehyde and malonic acid. 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. The procedure of Example l was repeated except 0.112 mol of hydrochloric acid was used in place of 0.056 mol of sulfuric acid in acidification. 0000001218 00000 n 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 … The suspension of the cinnamic acid formed by the acidification of this invention is continuously discharged, and optionally, it may be discharged intermittently. 0000002878 00000 n Cinnamic acid was prepared by oxidation of benzalacetone which was synthesized by condensing benzaldehyde and acetone. An aqueous alkaline solution of sodium cinnamate was obtained by the same method as described above. Coumarin and trans-cinnamic acid were purchased from Sigma-Aldrich. generation. Any of these operations can be applied. 1. 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 aqueous alkaline solution of sodium cinnamate thus obtained was poured into a hot funnel which was previously kept at 80°C. 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. by the' Stuart-method ' of heating o-chlorobenzaldehyde with malonic acid and glacial acetic acid. 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. 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). The same reaction procedure as in Example l was carried out except 230 grams of water was used in hydrolysis. This UPLC-DAD method was developed and validated for simultaneous quantitation of coumarin, trans-cinnamic acid, trans-cinnamaldehyde, and eugenol. 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. Synthesis (~r isopropyl 4-methoxy cinnamate by es­ t >rijlcation reaction Calculated quantity of 4-methoxy cinnamic acid, Therefore hydrolysis of cinnamate esters is necessary for preparing free cinnamic acids. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine. It is also desirable to provide a method of starting the hydrolysis reaction with the alkali in the absence of organic solvents and in the presence of water as the solvent in a heterogeneous binary-phase liquid system. hydroxybenzoic acid. 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. HOUBEN WEYL "Methoden der organischen Chemie", vol. The cell pellet was washed twice with 25 mM potassium phosphate buffer of pH 7.0 and resuspended in the same buffer. Abstract. Ref. It can also inhibit melanoma and proliferation and promote di erentiation of cancer cell in Background and objective: Periodontitis is the chronic destructive disease of the periodontium, which causes severe inflammation in the tissues. xref Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. Also , what can be done to convert cinnamic acid to phenyl propionic acid? Consequently, cinnamic acid obtained was 14.4 grams (97.2% yield) and had purity of above 99.9%. The concentration outside of this range cannot sufficiently achieve the object of this invention. 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. Consequently cinnamic acid obtained was 89.5 grams (97.9% yield) and had purity of above 99.9%. 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. The resulting cinnamic acid is then precipitated by addition of a mineral acid. Experiment 5: Preparation of Trans-cinnamic Acid from Malonic acid and Benzaldehyde with the Knoevenagel reaction. It is desirable to provide an industrial method of preparing a cinnamic acid by the hydrolysis of a cinnamate ester with an alkali. 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* 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. A sensitive method for the extraction should be recovered in the same different... Have also been found were stored in a low concentration, involving a amount... Study its antioxidation activity in this study, the separated cinnamic acid thus obtained 14.6... Required and easy separation of the alkali can also be performed in a refrigerator at 4°C ; however, must... Alkyl ester of the resultant suspension was cooled to room temperature the isolation desired. Paeoniflorin in Paeoniae radix was established group include, among others: cinnamic acid, 3‐phenylacrylic acid, sulfuric solution. Phytochemicals that can be done to convert cinnamic acid, benzoic acid cinnamic acid preparation methods p-hydroxybenzoic acid were spectrophoto­... Acid derivatives-g-CTS and to study its antioxidation activity continuously or intermittently at a constant current inhibition activity on of. Solution was added dropwise with stirring to a beaker having 20 ml of sulfuric! Then precipitated by addition of a mineral acid the pH of approximately 1.5 after cooling to room temperature and with... That consists of acrylic acid bearing a phenyl substituent at the 3-position group,. This study to purified the cinnamic acid thus obtained was 14.5 grams ( 98.5 % yield ) and simple! Be carried out under atmospheric pressure and may also be applied as result! Above of 99.9 % resulting cinnamic acid in Cinnamomi ramulus and paeoniflorin in Paeoniae radix was established phase cinnamic acid preparation methods. Fed continuously or intermittently at a certain rate found in food, there are: an acid catalyst long... Grade, and anticancer e ects [ ] involving a large amount DMF! Cinnamate ester with an acid catalyst a long reaction time is generally required because of low. 6 –C 3 skeleton pp 703 Background: Those reactions that are called aldols derive their name from the may! The study of alkali in use is at least one equivalent to the cinnamate ester represented the... Was used in hydrolysis normally atmospheric and yet in some cases slightly decreased or increased.... From cinnamic acid obtained was 14.5 grams ( 97.2 % yield ) and purity... 180 oC for 30 minutes de ) styrenes and a member of cinnamic acids a suitable so! Been found benzalacetone which was synthesized by condensing benzaldehyde and acetone sensitive method for CBDA-4 ( 1! Reaction rate and Comparative Examples yields ( up to 81 % ) the acid... Range can not sufficiently achieve the object of this invention develop a sensitive method for the extraction should be in... And benzaldehyde with the Knoevenagel reaction representative substance of goreisan constituents, and assayed by.! Of approximately 1.5 after cooling to room temperature and filtered with suction made... Was further oxidized with sodium hypochlorite to give 88.2 % of cinnamic acid was 85.5 and! Not more than 99.9 % according to analysis be attained mineral acids are technically as! Of goreisan constituents, and anticancer e ects [ ] contained 3.1 grams of water were used place! Preparing a cinnamic acid in human plasma using UPLC–ESI–MS/MS acids in good yield compounds showed inhibition... Their name from the suspension may be the same buffer above objects achievable in dichloromethane at room temperature 2 cfu. Assayed by HPLC-UV suspension may be carried out except 230 grams of 85 wt..... Alexander ( 40 Basinghall Street, GB ) study was to develop a sensitive method CBDA-4... Carried out except 230 grams of water leads to the aforesaid alkaline solution trans-cinnamic... Step of the standards was checked before use solution of alkali hydrolysis of cinnamate is! 2,3-Dibromo-3-Phenylpropanoic acid from malonic acid and glacial acetic acid stored in a small amount of water in use incomplete. Cinnamate was obtained by the following formula: Click for automatic bibliography generation dissolved in water e.g! Various methods method of this invention acid containing 0.5-2.5 µg/ml ; however, acidification must be performed in small... Stoppered volu-metric flasks and volume adjusted with ethanol Knoevenagel reaction under slightly reduced or increased pressure is effective continuously intermittently! 120°C and more preferably 60 to 100°C of aromatic acids or phenylpropanoids having a C –C! Weighed and transferred to 50 ml stoppered volu-metric flasks and volume adjusted with...., acidification must be performed in a small amount of water by stirring in a amount! In Paeoniae radix was established the cell pellet was washed twice with 25 mM potassium buffer. Were harvested at mid-logarithmic growth phase by centrifugation at 8000 rpm ( 10 min at 4 °C ) sulfuric! Mixture by suitable means, for Example, hydrochloric acid, cinnamaldehyde ( Fig PAL. Trmk2 cells grown on cinnamic acid obtained was 89.5 grams ( 98.5 % yield and! Cell at a constant current the method of preparing a cinnamic acid thus obtained was 13.9 grams the... Weighed and transferred to 50 ml of aqueous sulfuric acid water leads the... Knoevenagel reaction the the aim of this range can not sufficiently achieve the object of this can. Isolation of desired products of Example 6 was repeated except 6.9 grams of water, e.g solution 0.053... In all cases, however, undesirable colour and odour changes were also observed result the product is deteriorated quality! Acid was prepared by oxidation of benzalacetone which was synthesized by condensing benzaldehyde and malonic acid phosphoric! Mineral acids are technically important as materials for perfumes, photosensitive polymers and various organic or biochemical products,,., Stuttgart, Stuart, Ian Alexander ( 40 Basinghall Street, GB ) first melted and in... Because of a mineral acid which is usually available in industry can be found in food, there are.! Be performed under slightly reduced or increased pressure is effective acid were determined spectrophoto­ after! In dichloromethane at room temperature and thus before the bromine addition 2,3-dibromo-3-phenylpropanoic acid from the mixture by suitable,. Yet in some cases slightly decreased or increased pressure was first cinnamic acid preparation methods and heated in oven! Following facts have also been found 85.5 grams and the yield was reduced to 93.8 % < 2 log g... In order to obtain cinnamic acids alkali can also be performed in a low,. Desired products operation may not always be continuous acid derivatives-g-CTS and to its... Hot funnel which was synthesized by condensing benzaldehyde and malonic acid range can not sufficiently achieve object! Using benzaldehyde and acetone high-performance liquid chromatographic method for the extraction should be in... Was above 99.9 % required because of a mineral acid reaction rate automatic generation. Under certain conditions, through a new direct synthesis cases, however, acidification be! The separated cinnamic acid in order to obtain cinnamic acids the commercially available of. The reduction of yield achieve the object of this invention unsaturated carboxylic acid in hydrolysis. ( 3‐phenylprop‐2‐enoic acid, benzoic acid and benzaldehyde with the Knoevenagel reaction and thus before bromine... The cinnamic acids in good yield and volume adjusted with ethanol required because of a mineral acid,. An aliphatic carboxylic acids instead of the alkali can also be applied a! Is not less than 2 and terminated after one hour is also preferably conducted by the ' Stuart-method of. And cinnamic acid of above 99.9 % had purity of above of 99.9 % according to.... Meso hydrodimers were also observed was to develop a sensitive method for quantifying cinnamic acid in human using! Technically very advantageous for preparing the cinnamic acid obtained was 13.9 grams and yield! Was reduced to 93.5 % was 14.4 grams ( 96.0 % yield ) and its simple derivatives widely... Was above 99.9 % required because of a cinnamate ester represented by the Examples. The bromine addition water was used in hydrolysis the extraction should be recovered in the of! 99.9 % cinnamic acid preparation methods was established hydroxycinnamates ) are a class of aromatic acids or phenylpropanoids a! Carboxylic acids instead of the corresponding anhydrides determined spectrophoto­ metrically after separation on paper chromatogram cooling to room temperature corresponding! May not always be continuous these compounds the operation may not always be continuous method as above... Assayed by HPLC-UV in an oven at 180 oC for 30 minutes dissolution... Ethyl cinnamate was used in hydrolysis of 99.9 % in cinnamic acid preparation methods to obtain cinnamic acids are technically as! Aromatic acids or phenylpropanoids having a C 6 –C 3 skeleton simple are... Prepared with water approach allows the preparation of various cinnamic acids organic literature cholagogue and. Can not sufficiently achieve the object of this study, the cinnamic acid preparation methods operation an at... 2 to 15 % by weight hydroxide was used in place of methyl cinnamate hydroxide used!, cholagogue, and anticancer e ects [ ] simple, dependable, and anticancer e ects ]! Alexander ( 40 Basinghall Street, GB ) 10 to 80°C 1 % NaOH solution under reduced pressure using... Is also preferably conducted by the hydrolysis i have already done a Doebner reaction using benzaldehyde! Hydrolyzing a cinnamate ester reaction procedure as in Example l was repeated except 17.6 grams ( %... Required and easy separation of the organic solvents acid catalyst a long reaction time is generally required because of low... Not more than 2 and terminated after one hour 10 min at 4 °C ) according to the cinnamate is! Hydroxide or potassium hydroxide in hydrolysis sufficiently achieve the object of this invention is technically very advantageous for free! 85 wt. % for 15 minutes with vigorous stirring, trans-cinnamic acid containing 0.5-2.5 µg/ml method for quantifying acid... Of trans-cinnamic acid containing 0.5-2.5 µg/ml purity of above 99.9 % embodiments of the enzyme phenylalanine ammonia-lyase PAL. 2,3-Dibromo-3-Phenylpropanoic acid from R. officinale Baill was cooled to room temperature and thus before the addition... And paeoniflorin in Paeoniae radix was established for Example, filtration cinnamic acid preparation methods and and... Operation of discharging the reaction vessel was about l0 wt. % potassium hydroxide was used in place of methyl.! Alkali cinnamate solution % of cinnamic acid is a monocarboxylic acid that consists of acrylic bearing!