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trans-Clovamide

Alias: N-trans-Caffeoy-L-dopa; trans-Clovamide
Cat No.:V16698 Purity: ≥98%
Clovamide (trans-Clovamide) is a natural phenolic compound that is a potent antioxidant.
trans-Clovamide
trans-Clovamide Chemical Structure CAS No.: 53755-02-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Clovamide (trans-Clovamide) is a natural phenolic compound that is a potent antioxidant. Clovamide is an excellent ROS and oxygen radical scavenger. Clovamide also has anti~inflammatory and neuro-protective (neuro-protection) properties. Clovamide is an antimicrobial agent active against the human pathogens influenza A subtype H5N1, Trypanosoma evansi, and Heliobacter pylori.
trans-Clovamide (Clovamide) is a naturally occurring caffeoyl conjugate belonging to the N-phenylpropenoyl-L-amino acid amide class, identified in cocoa (Theobroma cacao L.) and red clover (Trifolium pratense). It is a natural phenolic compound that is a potent antioxidant and an excellent ROS and oxygen radical scavenger. Clovamide also has anti-inflammatory and neuroprotective properties. It is an antimicrobial agent active against the human pathogens influenza A subtype H5N1, Trypanosoma evansi, and Helicobacter pylori.
Biological Activity I Assay Protocols (From Reference)
Targets
trans-Clovamide does not have a single specific molecular target but exerts its effects through multiple mechanisms. It is a potent antioxidant that scavenges reactive oxygen species (ROS) and oxygen radicals. It has shown neuroprotective effects (EC50s = 0.9-3.7 µM) in several in vitro models of neuronal death. It is a substrate for cocoa polyphenol oxidase and inhibits the growth of Phytophthora species. It also inhibits pectinases and proteases.
ln Vitro
In three in vitro models of neuronal death—oxidative stress, excitotoxicity, and OGD/reoxygenation—clovamide shielded neurons from harm. With an EC50 value of 3.6 µM, Clovamide (10-100 µM) effectively prevents cell death in human neuroblastoma cells (SH-SY5Y). Additionally, PPARγ expression is markedly increased by clonamide [2]. Clovamide is a substrate for cocoa polyphenol oxidase, contributes to enzymatic browning, and inhibits the growth of three diseases belonging to the genus Phytophthora cocoa. In vitro, clovamide inhibits pectinases and proteases [3].
In vitro, trans-Clovamide protects neurons from harm in three in vitro models of neuronal death: oxidative stress, excitotoxicity, and OGD/reoxygenation. With an EC50 value of 3.6 µM, Clovamide (10-100 µM) effectively prevents cell death in human neuroblastoma cells (SH-SY5Y). Additionally, PPARγ expression is markedly increased by Clovamide. Clovamide is a substrate for cocoa polyphenol oxidase, contributes to enzymatic browning, and inhibits the growth of three diseases belonging to the genus Phytophthora cocoa.
ln Vivo
In vivo, trans-Clovamide has been studied for its potential therapeutic applications. As a natural compound with antioxidant, anti-inflammatory, and neuroprotective properties, it may have beneficial effects in various disease models. Its antimicrobial activity against human pathogens suggests potential for treating infections. However, specific in vivo efficacy data from animal models are limited in the available literature.
Enzyme Assay
In vitro enzyme or receptor binding (non-cell) assays for trans-Clovamide are not typically performed, as it does not have a single specific target. Its antioxidant activity can be assessed using cell-free assays such as DPPH radical scavenging or ABTS radical scavenging assays. Its ability to inhibit ROS and oxygen radicals can be measured using fluorescence-based assays. Neuroprotective activity is assessed in cell-based models of neuronal death.
Cell Assay
In vitro cell-based assays for trans-Clovamide are performed using human neuroblastoma cells (SH-SY5Y). Cells are treated with Clovamide at concentrations ranging from 10-100 µM, and cell death is measured in models of oxidative stress, excitotoxicity, and OGD/reoxygenation. The EC50 for neuroprotection is determined. PPARγ expression is measured to assess the compound's effects on gene expression.
Animal Protocol
In vivo animal experiments for trans-Clovamide are limited in the available literature. As a natural product, it may be studied in animal models of neurodegenerative diseases, inflammation, or infection. The compound's antioxidant and anti-inflammatory properties suggest potential for study in models of oxidative stress-related conditions. However, specific animal experimental protocols are not well-documented.
ADME/Pharmacokinetics
Pharmacokinetic (PK) properties of trans-Clovamide have not been extensively characterized. The compound has a molecular weight of 359.33 and a molecular formula of C18H17NO7. It appears as an off-white to light yellow solid powder. It has a LogP of 0.84 and a density of 1.5±0.1 g/cm3. The boiling point is 777.0±60.0 °C at 760 mmHg. The compound is typically stored under appropriate conditions for research use.
Toxicity/Toxicokinetics
Toxicology (toxicology) data for trans-Clovamide are limited. As a natural phenolic compound found in cocoa and red clover, it is generally considered safe at moderate doses. Its antioxidant properties may provide protective effects. However, its safety profile in the context of therapeutic use requires further evaluation. The compound is for research use only.
References

[1]. Antioxidant studies by hydrodynamic voltammetry and DFT, quantitative analyses by HPLC-DAD of clovamide, a natural phenolic compound found in Theobroma Cacao L. beans. Food Chem. 2021 Mar 30;341(Pt 2):128260.

[2]. Clovamide and rosmarinic acid induce neuroprotective effects in in vitro models of neuronal death. Br J Pharmacol. 2009 Jul;157(6):1072-84.

Additional Infomation
Trans-chloramide is a tyrosine derivative. It has been reported to be found in red clover, cocoa, and ebony, and data are available. See also: Red clover flowers (partial); cis-chloramide (note moved to).
Other information: trans-Clovamide is a naturally occurring caffeoyl conjugate identified in the antioxidant polyphenolic fraction of cocoa. It is also known as N-trans-Caffeoyl-L-dopa. The compound has antioxidant, anti-inflammatory, neuroprotective, and antimicrobial properties. Its CAS number is 53755-02-5.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H17NO7
Molecular Weight
359.33
Exact Mass
359.1
CAS #
53755-02-5
PubChem CID
6506968
Appearance
Off-white to light yellow solid powder
Density
1.5±0.1 g/cm3
Boiling Point
777.0±60.0 °C at 760 mmHg
Flash Point
423.7±32.9 °C
Vapour Pressure
0.0±2.8 mmHg at 25°C
Index of Refraction
1.723
LogP
0.84
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
6
Heavy Atom Count
26
Complexity
524
Defined Atom Stereocenter Count
1
SMILES
C1=CC(=C(C=C1C[C@@H](C(=O)O)NC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
InChi Key
GPZFXSWMDFBRGS-UXONFWTHSA-N
InChi Code
InChI=1S/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3+/t12-/m0/s1
Chemical Name
(2S)-3-(3,4-dihydroxyphenyl)-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]propanoic acid
Synonyms
N-trans-Caffeoy-L-dopa; trans-Clovamide
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 : ~125 mg/mL (~347.87 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.79 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 20.8 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: ≥ 2.08 mg/mL (5.79 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 20.8 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: ≥ 2.08 mg/mL (5.79 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 20.8 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 2.7830 mL 13.9148 mL 27.8296 mL
5 mM 0.5566 mL 2.7830 mL 5.5659 mL
10 mM 0.2783 mL 1.3915 mL 2.7830 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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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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