6972-61-8

Basic information

• Product Name: 2,4-DIMETHOXYCINNAMIC ACID
• Synonyms: 3-(2,4-Dimethoxyphenyl)propenoic acid;2-Propenoic acid, 3-(2,4-dimethoxyphenyl)-;Einecs 230-208-9;3-(2,4-DiMethoxyphenyl)acrylic acid;3-(2,4-dimethoxyphenyl)-2-propenoicaci;3-(2,4-dimethoxyphenyl)-2-propenoicacid;OTAVA-BB BB7015052308;RARECHEM BK HW 0035
• CAS NO: 6972-61-8
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21
• EINECS: 230-208-9
• Mol File: 6972-61-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 192-194 °C(lit.)
• Boiling Point: 384.4 °C at 760 mmHg
• Flash Point: 151.8 °C
• Appearance: /
• Density: 1.203 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,4-DIMETHOXYCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIMETHOXYCINNAMIC ACID(6972-61-8)
• EPA Substance Registry System: 2,4-DIMETHOXYCINNAMIC ACID(6972-61-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• RTECS: UD3334500
• Hazardous Substances Data: 6972-61-8(Hazardous Substances Data)

Usage

General Description

2,4-DIMETHOXYCINNAMIC ACID, also known as DIMETHOXYCINNAMIC ACID, is a chemical compound with the molecular formula C11H12O4. It is a white crystalline solid that is insoluble in water but soluble in organic solvents. 2,4-DIMETHOXYCINNAMIC ACID has been studied for its potential applications in the pharmaceutical and cosmetic industries, as well as for its antioxidant and anti-inflammatory properties. It is also used as an intermediate in the synthesis of various drugs and other organic compounds. The compound is generally considered to be safe for use in these applications, but further research is needed to fully understand its potential benefits and risks.

Upstream product

• 141-82-2 malonic acid 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 4887-24-5 triacetoxyborane 

Downstream Products

• 22174-29-4 3-(2,4-dimethoxyphenyl) propionic acid 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 72071-66-0 3-(2,4-Dimethoxy-phenyl)-3-hydroxyamino-propionic acid 
• 91-52-1 2,4 dimethoxybenzoic acid 
• 34841-02-6 3-amino-3-(2,4-dimethoxyphenyl)propanoic acid 
• 99699-42-0 3-(2,4-dihydroxyphenyl)prop-2-enoic acid 
• 1427204-70-3 C₁₄H₁₆N₂O₃S 

Relevant articles and documents

New coumarin/sulfocoumarin linked phenylacrylamides as selective transmembrane carbonic anhydrase inhibitors: Synthesis and in-vitro biological evaluation

Two novel series of phenylacrylamide linked coumarins and sulfocoumarins (6a-p, 8a-i, and 14a-g) were synthesized and evaluated against four physiologically relevant human carbonic anhydrases (hCAs, EC 4.2.1.1), isoforms hCA I, hCA II, hCA IX and hCA XII for their inhibitory action. All new compounds when screened for carbonic anhydrase inhibitory activity have shown selective inhibition towards the tumor associated isoforms hCA IX and XII over CA I and II, with inhibition constants in the submicromolar to low nanomolar range. Compound 6b and 14g exhibited significant inhibition with low nanomolar potency against hCA IX, whereas 6k was effective against hCA XII. Compounds 6b, 14g and 6k may be considered as lead molecules for future development of cancer therapeutics based on a novel mechanism of action.

Design, synthesis, and docking studies of afatinib analogs bearing cinnamamide moiety as potent EGFR inhibitors

Two series of afatinib derivatives bearing cinnamamide moiety (10a-n and 11a-h) were designed, synthesized and evaluated for the IC50 values against four cancer cell lines (A549, PC-3, MCF-7 and Hela). Two selected compounds (10e, 10k) were further evaluated for the inhibitory activity against EGFR and VEGFR2/KDR kinases. Seven of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 values in single-digit μM to nanomole range. Three of them are equal to more active than positive control afatinib against one or more cell lines. The most promising compound 10k showed the best activity against A549, PC-3, MCF-7 and Hela cancer cell lines and EGFR kinase, with the IC50 values of 0.07 ± 0.02 μM, 7.67 ± 0.97 μM, 4.65 ± 0.90 μM and 4.83 ± 1.28 μM, which were equal to more active than afatinib (0.05 ± 0.01 μM, 4.1 ± 2.47 μM, 5.83 ± 1.89 μM and 6.81 ± 1.77 μM), respectively. Activity of compounds 10e (IC50 9.1 nM) and 10k (IC50 3.6 nM) against EGFR kinase were equal to the reference compound afatinib (IC50 1.6 nM). Structure-activity relationships (SARs) and docking studies indicated that replacement of the aqueous solubility 4-(dimethylamino)but-2-enamide group by cinnamamide moiety didn't decrease the antitumor activity. The results suggested that methoxy substitution had a significant impact on the activity and methoxy substituted on C-4 or C-2,3,4 position was benefit for the activity.

Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents

A series of ninety-seven diarylpentanoid derivatives were synthesized and evaluated for their anti-inflammatory activity through NO suppression assay using interferone gamma (IFN-γ)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Twelve compounds (9, 25, 28, 43, 63, 64, 81, 83, 84, 86, 88 and 97) exhibited greater or similar NO inhibitory activity in comparison with curcumin (14.7 ± 0.2 μM), notably compounds 88 and 97, which demonstrated the most significant NO suppression activity with IC50 values of 4.9 ± 0.3 μM and 9.6 ± 0.5 μM, respectively. A structure-activity relationship (SAR) study revealed that the presence of a hydroxyl group in both aromatic rings is critical for bioactivity of these molecules. With the exception of the polyphenolic derivatives, low electron density in ring-A and high electron density in ring-B are important for enhancing NO inhibition. Meanwhile, pharmacophore mapping showed that hydroxyl substituents at both meta- and para-positions of ring-B could be the marker for highly active diarylpentanoid derivatives.