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2-Methoxycinnamic acid

2-Methoxycinnamic acid is a noncompetitive tyrosinase inhibitor.
2-Methoxycinnamic acid
2-Methoxycinnamic acid Chemical Structure CAS No.: 6099-03-2
Product category: Tyrosinase
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2-Methoxycinnamic acid is a noncompetitive tyrosinase inhibitor.
2-Methoxycinnamic acid is a naturally occurring cinnamic acid derivative found in plants such as Pulsatilla cernua. It is a noncompetitive inhibitor of tyrosinase, an enzyme critical in melanin biosynthesis. The compound effectively reduces melanin production, making it valuable in studies focused on pigmentation disorders and skin whitening applications. It has a role as a Brassica napus metabolite and an EC 1.14.18.1 (tyrosinase) inhibitor. 2-Methoxycinnamic acid has a molecular weight of 178.18.
Biological Activity I Assay Protocols (From Reference)
Targets
2-Methoxycinnamic acid targets tyrosinase, the key enzyme in melanin biosynthesis. It is a noncompetitive inhibitor of tyrosinase. By inhibiting tyrosinase, the compound reduces melanin production. It also functions as a Brassica napus metabolite.
ln Vitro
2-Methoxycinnamic acid demonstrates potent in vitro tyrosinase inhibitory activity. It is a noncompetitive inhibitor of tyrosinase. The compound effectively reduces melanin production in vitro. It has been identified as a tyrosinase inhibitor from Pulsatilla cernua root-derived materials.
ln Vivo
In vivo activity data for 2-Methoxycinnamic acid are not extensively documented. Its ability to inhibit tyrosinase and reduce melanin production suggests potential in vivo efficacy for skin lightening. Further in vivo studies are needed to fully characterize its therapeutic potential.
Enzyme Assay
The in vitro enzyme assay for 2-Methoxycinnamic acid involves measuring its inhibition of tyrosinase activity. Mushroom tyrosinase is commonly used as a model enzyme. The assay typically uses L-DOPA as a substrate, and the formation of dopachrome is monitored spectrophotometrically at 475 nm. 2-Methoxycinnamic acid is incubated with the enzyme and substrate at various concentrations. The IC50 value is determined by fitting the inhibition data to a dose-response curve.
Cell Assay
In vitro cellular assays for 2-Methoxycinnamic acid typically use B16 melanoma cells or human melanocytes to assess its effects on melanogenesis. Cells are treated with the compound at various concentrations. Melanin content is measured spectrophotometrically. Tyrosinase activity is assessed by measuring the oxidation of L-DOPA in cell lysates. The compound's ability to reduce melanin production is quantified.
Animal Protocol
In vivo animal experiments for 2-Methoxycinnamic acid are not extensively documented. As a tyrosinase inhibitor, standard in vivo studies would involve animal models of hyperpigmentation. The compound would be administered via topical or oral routes. Melanin content in skin and histopathological analysis would be assessed.
ADME/Pharmacokinetics
Pharmacokinetic properties of 2-Methoxycinnamic acid are not extensively documented. As a small molecule with a molecular weight of 178.18, the compound is expected to have reasonable bioavailability. Its cinnamic acid structure may influence its absorption, distribution, metabolism, and excretion. Further pharmacokinetic studies are necessary to fully characterize its PK profile.
Toxicity/Toxicokinetics
Toxicological data for 2-Methoxycinnamic acid are not extensively available. As a naturally occurring compound, it is generally considered to have a favorable safety profile. Standard cytotoxicity assays in cell lines may have been performed to assess safety margins. Further toxicological studies would be required for clinical development.
References

[1]. Tyrosinase inhibitors of Pulsatilla cernua root-derived materials. J Agric Food Chem. 2002 Mar 13;50(6):1400-3.

Additional Infomation
(E)-2-Methoxycinnamic acid is a cinnamic acid compound, specifically trans-cinnamic acid with a methoxy substituent at the 2-position of the benzene ring. It is a metabolite of Brassica napus and an inhibitor of tyrosinase (EC 1.14.18.1). It belongs to the cinnamic acid class and is a monomethoxybenzene compound. Functionally, it is related to trans-cinnamic acid.
See also: Cinnamomum cassia branches (partial).
2-Methoxycinnamic acid is a noncompetitive inhibitor of tyrosinase found in plants such as Pulsatilla cernua. It reduces melanin production and is used in research on pigmentation disorders and skin whitening. The compound has a molecular weight of 178.18. No clinical trials or regulatory approvals have been reported.
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 #
6099-03-2
PubChem CID
734154
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
325.1±17.0 °C at 760 mmHg
Melting Point
182-186 °C
Flash Point
130.3±14.4 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.591
LogP
2.42
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Heavy Atom Count
13
Complexity
198
Defined Atom Stereocenter Count
0
SMILES
COC1=CC=CC=C1/C=C/C(=O)O
InChi Key
FEGVSPGUHMGGBO-VOTSOKGWSA-N
InChi Code
InChI=1S/C10H10O3/c1-13-9-5-3-2-4-8(9)6-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-6+
Chemical Name
(E)-3-(2-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% 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.

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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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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:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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