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(E)-3-(4-Methoxyphenyl)acrylic acid ((E)-3-(4-Methoxyphenyl)acrylic acid)

Cat No.:V72578 Purity: ≥98%
(E)-3-(4-Methoxyphenyl)acrylic acid (compound 3) can be extracted from Arachis hypogaea, Scrophularia buergeriana Miquel, Aquilegia vulgaris, Anigozanthos preissii, etc.
(E)-3-(4-Methoxyphenyl)acrylic acid ((E)-3-(4-Methoxyphenyl)acrylic acid)
(E)-3-(4-Methoxyphenyl)acrylic acid ((E)-3-(4-Methoxyphenyl)acrylic acid) Chemical Structure CAS No.: 943-89-5
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
(E)-3-(4-Methoxyphenyl)acrylic acid (compound 3) can be extracted from Arachis hypogaea, Scrophularia buergeriana Miquel, Aquilegia vulgaris, Anigozanthos preissii, etc. (E)-3-(4-Methoxyphenyl)acrylic acid has significant hepatoprotective activity, anti-amnesia, enhanced cognitive activity, hypoglycemic and neuro-protection activity.
(E)-3-(4-Methoxyphenyl)acrylic acid, also known as 4-methoxycinnamic acid, is a methoxycinnamic acid with a single methoxy substituent at the 4-position on the phenyl ring. With a molecular weight of 178.18 and formula C10H10O3, it can be extracted from various plants including Arachis hypogaea and Scrophularia buergeriana. It is functionally related to cinnamic acid.
Biological Activity I Assay Protocols (From Reference)
Targets
(E)-3-(4-Methoxyphenyl)acrylic acid has multiple biological targets and activities. It exhibits significant hepatoprotective activity, anti-amnesia effects, enhanced cognitive activity, hypoglycemic effects, and neuro-protection activity. Its mechanisms of action may involve modulation of oxidative stress, inflammation, and metabolic pathways, though specific molecular targets are not definitively identified.
ln Vitro
In vitro, (E)-3-(4-Methoxyphenyl)acrylic acid demonstrates significant hepatoprotective activity, protecting liver cells from damage. It also shows anti-amnesic, cognition-enhancing, antihyperglycemic, and neuroprotective activities in various in vitro assays. These activities suggest it may modulate oxidative stress, inflammatory responses, and neuronal signaling pathways.
ln Vivo
In vivo, (E)-3-(4-Methoxyphenyl)acrylic acid exhibits significant hepatoprotective activity, protecting the liver from injury in animal models. It also demonstrates anti-amnesic effects, enhanced cognitive activity, hypoglycemic effects, and neuro-protection activity. These in vivo activities support its potential therapeutic applications in liver disease, cognitive disorders, diabetes, and neurodegenerative conditions.
Enzyme Assay
In vitro enzyme assays with (E)-3-(4-Methoxyphenyl)acrylic acid typically involve studying its effects on enzymes involved in oxidative stress, inflammation, or metabolic pathways. Standard assays may measure antioxidant activity (e.g., DPPH radical scavenging), enzyme inhibition (e.g., alpha-glucosidase, acetylcholinesterase), or anti-inflammatory activity (e.g., COX inhibition). These assays help characterize its mechanism of action.
Cell Assay
In vitro cell culture experiments with (E)-3-(4-Methoxyphenyl)acrylic acid involve treating various cell lines such as hepatocytes, neuronal cells, or immune cells with the compound. Cells are treated at various concentrations for defined periods, and endpoints include cell viability, oxidative stress markers, inflammatory cytokine production, and gene expression analysis. These experiments characterize its cytoprotective and neuroprotective effects.
Animal Protocol
In vivo animal experiments with (E)-3-(4-Methoxyphenyl)acrylic acid typically involve using rodent models of liver injury, cognitive impairment, diabetes, or neurodegeneration. The compound is administered orally or intraperitoneally at various doses for defined periods. Key endpoints include assessment of liver function (ALT, AST), cognitive performance (behavioral tests), blood glucose levels, and histopathological examination of tissues.
ADME/Pharmacokinetics
The pharmacokinetic (PK) properties of (E)-3-(4-Methoxyphenyl)acrylic acid have not been extensively characterized. As a small, lipophilic molecule, it is expected to be absorbed from the gastrointestinal tract and distributed throughout the body. It is likely metabolized through phase I and phase II metabolic pathways and excreted in urine and bile. Specific PK parameters such as Cmax, Tmax, AUC, and half-life would need to be determined in future studies.
Toxicity/Toxicokinetics
(E)-3-(4-Methoxyphenyl)acrylic acid has a low toxicity profile based on its natural occurrence in plants and traditional use. It is not considered a hazardous substance. For research use, standard laboratory safety practices are sufficient. It has a melting point of 173.5°C and is a white to off-white solid. Comprehensive toxicology studies have not been published.
References

[1]. Uncommon secondary metabolites from Etlingera pavieana rhizomes. Nat Prod Res. 2016 Oct;30(19):2215-9.

Additional Infomation
4-Methoxycinnamic acid is a methoxycinnamic acid with a single methoxy substituent at the 4-position of the benzene ring. It is functionally related to cinnamic acid. It has been reported in Baccharis subdentata, Scrophularia buergeriana, and other organisms with relevant data. See also: 4-Methoxycinnamic acid (note moved to).
(E)-3-(4-Methoxyphenyl)acrylic acid (4-methoxycinnamic acid) is a natural compound with significant hepatoprotective, anti-amnesic, cognition-enhancing, hypoglycemic, and neuroprotective activities. It can be extracted from various plants including Arachis hypogaea and Scrophularia buergeriana. The compound is not a drug and has no approved therapeutic indications. It is available for laboratory research use only as a tool for studying hepatoprotection, neuroprotection, and metabolic regulation.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H10O3
Molecular Weight
178.18
Exact Mass
178.062
CAS #
943-89-5
Related CAS #
7340-42-3 (hydrochloride salt)
PubChem CID
699414
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
342.6±17.0 °C at 760 mmHg
Melting Point
173.5ºC
Flash Point
138.6±14.4 °C
Vapour Pressure
0.0±0.8 mmHg at 25°C
Index of Refraction
1.591
LogP
2.36
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Heavy Atom Count
13
Complexity
190
Defined Atom Stereocenter Count
0
SMILES
COC1=CC=C(C=C1)/C=C/C(=O)O
InChi Key
AFDXODALSZRGIH-QPJJXVBHSA-N
InChi Code
InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+
Chemical Name
(E)-3-(4-methoxyphenyl)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)
Solubility Data
Solubility (In Vitro)
DMSO: 100 mg/mL (561.23 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.03 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 (14.03 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (14.03 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 5.6123 mL 28.0615 mL 56.1230 mL
5 mM 1.1225 mL 5.6123 mL 11.2246 mL
10 mM 0.5612 mL 2.8062 mL 5.6123 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
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  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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