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Cinnamic acid

Cat No.:V29876 Purity: ≥98%
Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM against glioblastoma, melanoma, prostate cancer, and lung cancer/tumor cells.
Cinnamic acid
Cinnamic acid Chemical Structure CAS No.: 621-82-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
Official Supplier of:
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Product Description
Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM against glioblastoma, melanoma, prostate cancer, and lung cancer/tumor cells.
Cinnamic acid (CAS#: 621-82-9) is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate, and lung carcinoma cells. The compound exerts anti-diabetic activity by improving glucose tolerance in vivo and stimulating insulin secretion in vitro. Its molecular formula is C9H8O2 with a molecular weight of 148.16 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Cinnamic acid targets cancer cells as an anti-proliferative agent with IC50s of 1-4.5 mM against glioblastoma, melanoma, prostate, and lung carcinoma cells. It also targets glucose metabolism, exerting anti-diabetic activity by improving glucose tolerance and stimulating insulin secretion. The compound has anti-inflammatory activity against formalin edema. It protects normal cells from the toxic effects of anti-cancer drugs.
ln Vitro
After three days of exposure, cinnamic acid (CINN) treatment of different tumor cells with epithelial and neuroectodermal origins led to dose-dependent growth suppression. The range of 1.2 to 4.5 mM is the inhibitory concentration (IC50) that causes a 50% decrease in the growth of tumor cells. Additionally, it was demonstrated that FS4 cells require 20 mM of cinnamic acid to produce an IC50 that is 5–20 times higher than that of tumor cells. Cinnamic acid not only prevents the growth of tumor cells but also causes morphological alterations that are compatible with the development of melanocytic cells. After being treated with 5 mM cinnamic acid for 5 days, melanoma 1011 cells showed signs of enlargement, a considerable rise in the cytoplasm to nucleus ratio, well-organized cytoskeleton, the formation of long dendritic processes, and high levels of melanization. Using a modified Boyden chamber with Matrigel-coated filters, an in vitro invasion experiment was used to evaluate changes in the capacity of melanoma 1011, A375 (M), and SKMEL28 cells to breakdown and penetrate tissue barriers after being treated with cinnamic acid. The three examined tumor cell lines showed a dose-dependent reduction of invasive capacity following three days of continuous cinnamic acid therapy. There is a 75–95% reduction in invasiveness after 5 mM cinnamic acid treatment [1].
In vitro, Cinnamic acid inhibits growth of various tumor cells of epithelial and neuroectodermal origin in a dose-dependent manner following a 3-day exposure. IC50 values range from 1 to 4.5 mM in glioblastoma, melanoma, prostate, and lung carcinoma cells. The compound stimulates insulin secretion in vitro. It has potential use in cancer intervention.
ln Vivo
In vivo, Cinnamic acid exerts anti-diabetic activity by improving glucose tolerance. Administered intraperitoneally to rats at 100 mg/kg, it produced no central-nervous-system, analgesic, or antipyretic effects, but was active as an anti-inflammatory agent against formalin edema. The compound protects normal cells from toxic effects of anti-cancer drugs.
Enzyme Assay
In vitro enzyme assays for Cinnamic acid involve measuring its anti-proliferative effects on cancer cells. Cells are cultured and treated with the compound at varying concentrations, and cell viability is assessed by MTT or CCK-8 assays. IC50 values are calculated from dose-response curves (1-4.5 mM). Insulin secretion is measured by ELISA in pancreatic beta cells. Anti-inflammatory activity is assessed by measuring inhibition of edema or cytokine production.
Cell Assay
In vitro cell-based assays for Cinnamic acid are conducted in cancer cell lines (glioblastoma, melanoma, prostate, lung carcinoma) and pancreatic beta cells. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with the compound at varying concentrations. Cell viability is assessed by MTT or CCK-8 assays. Insulin secretion is measured by ELISA. Experiments are performed in triplicate with appropriate positive and negative controls.
Animal Protocol
Cinnamic acid in vivo studies are conducted in animal models of cancer, diabetes, and inflammation. Animals are treated with Cinnamic acid via oral administration, intraperitoneal injection, or other routes. For cancer studies, tumor growth is monitored. For diabetes studies, glucose tolerance tests are performed. For anti-inflammatory studies, formalin edema models are used. Animals are monitored for clinical signs. Tissues and blood samples are collected for biochemical analysis at study endpoints.
ADME/Pharmacokinetics
Cinnamic acid (MW 148.16 g/mol, C9H8O2) is a monocarboxylic acid. It is also known as β-Phenylacrylic acid. The compound is soluble in organic solvents. It is stable under recommended storage conditions. Pharmacokinetic parameters such as half-life, bioavailability, and tissue distribution would be determined in species-specific studies. Cinnamic acid is used in cancer, diabetes, and anti-inflammatory research.
Toxicity/Toxicokinetics
Cinnamic acid is generally well-tolerated in preclinical studies. The compound is a natural product with established safety profiles. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation would be required for therapeutic development.
References

[1]. Cinnamic acid: a natural product with potential use in cancer intervention. Int J Cancer. 1995 Jul 28;62(3):345-50.

Additional Infomation
Cinnamic acid is a monocarboxylic acid composed of acrylic acid with a phenyl substituent at the 3-position. It is found in cinnamon (Cinnamomum cassia) and is a plant metabolite. It belongs to the styrene class and the cinnamic acid class of compounds, and is also the conjugate acid of cinnamic esters. Trans-cinnamic acid is a metabolite found or produced by Escherichia coli (K12 strain, MG1655 strain). Cinnamic acid has been reported to exist in morning glory (Ipomoea leptophylla), tea tree (Camellia sinensis), and other organisms with relevant data. The molecular formula of cinnamic acid is C6H5CHCHCOOH. It is an odorless, white crystalline acid, slightly soluble in water. Its melting point is 133°C and its boiling point is 300°C. Cinnamic acid is a metabolite of Saccharomyces cerevisiae, produced or discovered by the yeast. See also: Cinnamon (one of the ingredients); Sodium cinnamate (active ingredient); Chinese cinnamon (one of the ingredients)... See more...
Cinnamic acid (β-Phenylacrylic acid) has potential use in cancer intervention with IC50s of 1-4.5 mM against glioblastoma, melanoma, prostate, and lung carcinoma cells. It exerts anti-diabetic activity by improving glucose tolerance and stimulating insulin secretion. The compound is anti-inflammatory against formalin edema. Its molecular formula is C9H8O2 with a molecular weight of 148.16 g/mol. All applications are limited to non-human research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H8O2
Molecular Weight
148.1586
Exact Mass
148.052
CAS #
621-82-9
PubChem CID
444539
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
265.0±0.0 °C at 760 mmHg
Melting Point
133 °C
Flash Point
189.5±9.6 °C
Vapour Pressure
0.0±0.5 mmHg at 25°C
Index of Refraction
1.616
LogP
2.41
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Heavy Atom Count
11
Complexity
155
Defined Atom Stereocenter Count
0
SMILES
C1=CC=C(C=C1)/C=C/C(=O)O
InChi Key
WBYWAXJHAXSJNI-VOTSOKGWSA-N
InChi Code
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
Chemical Name
(E)-3-phenylprop-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)
Ethanol :≥ 50 mg/mL (~337.47 mM)
DMSO : ~50 mg/mL (~337.47 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.87 mM) (saturation unknown) in 10% EtOH + 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 EtOH 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 (16.87 mM) (saturation unknown) in 10% EtOH + 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 EtOH 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 (16.87 mM) (saturation unknown) in 10% EtOH + 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 EtOH 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 6.7495 mL 33.7473 mL 67.4946 mL
5 mM 1.3499 mL 6.7495 mL 13.4989 mL
10 mM 0.6749 mL 3.3747 mL 6.7495 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • 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)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • 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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