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| | 3,4,5-Trimethoxycinnamic acid Basic information |
| Product Name: | 3,4,5-Trimethoxycinnamic acid | | Synonyms: | RARECHEM BK HC T328;OTAVA-BB BB7119152925;3-(3,4,5-trimethoxyphenyl)-2-propenoicaci;3-(3,4,5-trimethoxyphenyl)-2-propenoicacid;3,4,5-trimethoxy-cinnamicaci;3,4,5-TriMethoxycinnaMic acid, predoMinantly trans, 99% 5GR;3, 4, 5 - triMethoxy CinnaMate;3,4,5-TrimethoxyClnnamic aCld | | CAS: | 90-50-6 | | MF: | C12H14O5 | | MW: | 238.24 | | EINECS: | 201-999-8 | | Product Categories: | Aromatic Cinnamic Acids, Esters and Derivatives;Cinnamic acid;Organic acids;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Inhibitors;90-50-6;11 | | Mol File: | 90-50-6.mol |  |
| | 3,4,5-Trimethoxycinnamic acid Chemical Properties |
| Melting point | 125-127 °C (lit.) | | Boiling point | 300.83°C (rough estimate) | | density | 1.1416 (rough estimate) | | vapor pressure | 0-0Pa at 20-25℃ | | refractive index | 1.4571 (estimate) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | | pka | 4.48±0.10(Predicted) | | form | Solid:crystalline | | color | White | | BRN | 1537834 | | Major Application | food and beverages | | InChI | InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14) | | InChIKey | YTFVRYKNXDADBI-UHFFFAOYSA-N | | SMILES | C(O)(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1 | | LogP | 0.3-1.1 at 35℃ and pH2-7 | | CAS DataBase Reference | 90-50-6(CAS DataBase Reference) | | EPA Substance Registry System | 2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)- (90-50-6) |
| Hazard Codes | Xi | | Safety Statements | 24/25 | | WGK Germany | 2 | | RTECS | GE0722000 | | TSCA | TSCA listed | | HazardClass | IRRITANT | | HS Code | 29189900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Sens. 1 |
| | 3,4,5-Trimethoxycinnamic acid Usage And Synthesis |
| Chemical Properties | white to cream fine crystalline powder | | Uses | 3-(3,4,5-Trimethoxyphenyl)acrylic acid demonstrates antioxidant activity as it was detected to inhibit lipid peroxidation in rat brain homogenates. | | Definition | ChEBI: A methoxycinnamic acid with three methoxy substituents at the 3-, 4- and 5-positions. | | Synthesis | Example IV Synthesis of 3,4,5-trimethoxycinnamic acid (by microwave radiation method): in a 100 mL Erlenmeyer flask, a mixture of 3,4,5-trimethoxybenzaldehyde (5.0 g, 0.025 mol) and malonic acid (5.30 g, 0.050 mol) was added, followed by piperidine (4-8 mL) and acetic acid (25-35 mL). The flask was fitted with a loose funnel at the top and the mixture was shaken well and placed in a microwave oven and microwaved in batches for 4-8 min. Upon completion of the reaction, the cooled mixture was poured into ice-cold water and acidified with 5% HCl solution. The precipitated yellow solid was collected by filtration and recrystallized by aqueous ethanol to give 3,4,5-trimethoxycinnamic acid in 88% yield; the melting point was 127 °C (literature value 126-128 °C). The spectral data of the product were consistent with those reported in the literature: 1H NMR (CDCl3) δ 7.73 (1H, d, J = 16.0 Hz, -CH=CH-COOH), 6.78 (2H, s, H-2 and H-6), 6.38 (1H, d, J = 16.0 Hz, CH=CH-COOH), 3.91 (9H, s, 3-OCH3, 4- OCH3, 5-OCH3); 13C NMR: δ 172.6 (COOH), 153.8 (C-3 and C-5), 147.4 (C-4), 140.8 (CH=CH-COOH), 129.8 (C-1), 116.8 (CH=CH-COOH), 105.8 (C-2 and C-6), 61.4 (4- OCH3), 56.5 (3-OCH3 and 5-OCH3). | | target | 5-HT Receptor | ERK | GABA Receptor | HIF-2 | | References | [1] MedChemComm, 2017, vol. 8, # 4, p. 755 - 766
[2] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 473 - 482
[3] Medicinal Chemistry Research, 2016, vol. 25, # 6, p. 1074 - 1086
[4] Chemistry Letters, 2003, vol. 32, # 12, p. 1186 - 1187
[5] Patent: US2004/118673, 2004, A1. Location in patent: Page 7 |
| | 3,4,5-Trimethoxycinnamic acid Preparation Products And Raw materials |
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