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(E)-3,4-Dimethoxycinnamic acid ((E)-3,4-Dimethoxycinnamic acid; (E)-O-Methylferulic acid) 14737-89-4

(E)-3,4-Dimethoxycinnamic acid ((E)-3,4-Dimethoxycinnamic acid; (E)-O-Methylferulic acid) 14737-89-4

CAS No.: 14737-89-4

(E)-3,4-Dimethoxycinnamic acid is a less active isomer of 3,4-Dimethoxycinnamic acid. 3,4-Dimethoxycinnamic acid exerts
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(E)-3,4-Dimethoxycinnamic acid is a less active isomer of 3,4-Dimethoxycinnamic acid. 3,4-Dimethoxycinnamic acid exerts anti-apoptotic effects on L-02 cells through the ROS-mediated signaling pathway.

Physicochemical Properties


Molecular Formula C11H12O4
Molecular Weight 208.21
Exact Mass 208.073
CAS # 14737-89-4
PubChem CID 717531
Appearance White to off-white solid powder
Density 1.2±0.1 g/cm3
Boiling Point 367.4±27.0 °C at 760 mmHg
Melting Point 181-183ºC(lit.)
Flash Point 144.0±17.2 °C
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.574
LogP 2.24
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 4
Heavy Atom Count 15
Complexity 237
Defined Atom Stereocenter Count 0
SMILES

COC1=C(C=C(C=C1)/C=C/C(=O)O)OC

InChi Key HJBWJAPEBGSQPR-GQCTYLIASA-N
InChi Code

InChI=1S/C11H12O4/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3-7H,1-2H3,(H,12,13)/b6-4+
Chemical Name

(E)-3-(3,4-dimethoxyphenyl)prop-2-enoic acid
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


ln Vitro In L-02 cells exposed to ethanol, 3,4-Dimethoxycinnamic acid (Methyl ferulic acid; 25, 50, and 100 µM) reduces the apoptosis caused by ethanol[1]. At 25, 50, and 100 µM, 3,4-dimethoxycinnamic acid inhibits the expression levels of p22phox and Nox4 in L-02 cells[1]. In L-02 cells, treatment with 3,4-dimethoxycinnamic acid at 25, 50, and 100 µM reduces the activation of MAPK caused by ethanol[1].
References

[1]. Methyl ferulic acid exerts anti-apoptotic effects on L-02 cells via the ROS-mediated signalingpathway. Int J Oncol. 2018 Jul;53(1):225-236.

Additional Infomation 3,4-dimethoxycinnamic acid is a methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively. It is functionally related to a trans-cinnamic acid. It is a conjugate acid of a 3,4-dimethoxy-(E)-cinnamate.
3,4-Dimethoxycinnamic acid has been reported in Bacopa monnieri, Populus nigra, and other organisms with data available.

Solubility Data


Solubility (In Vitro) DMSO : 50 mg/mL (240.14 mM)
Solubility (In Vivo) Solubility in Formulation 1: ≥ 2.5 mg/mL (12.01 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (12.01 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

Solubility in Formulation 3: ≥ 2.5 mg/mL (12.01 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.8028 mL 24.0142 mL 48.0284 mL
5 mM 0.9606 mL 4.8028 mL 9.6057 mL
10 mM 0.4803 mL 2.4014 mL 4.8028 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.