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p-Hydroxycinnamic acid

Alias: p-Hydroxy-cinnamic acid p-Coumaric acid p-Cumaric acid NSC 59260
Cat No.:V29466 Purity: ≥98%
p-Hydroxycinnamic acid is a common edible phenol that can inhibit platelet activity.
p-Hydroxycinnamic acid
p-Hydroxycinnamic acid Chemical Structure CAS No.: 7400-08-0
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50g
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Product Description
p-Hydroxycinnamic acid is a common edible phenol that can inhibit platelet activity. Its IC50s for thromboxane B2 and prostaglandin E2 are 371 μM and 126 μM respectively.
p-Hydroxycinnamic acid (CAS# 7400-08-0), also known as p-coumaric acid, is a naturally occurring hydroxycinnamic acid characterized by a C6-C3 phenylpropanoid backbone with a para-hydroxyl group. It is a common dietary phenol found in various plant foods. This compound exhibits significant biological activities, including inhibition of platelet activity, antioxidant properties, and potential antimalarial and anti-osteoporotic effects.
Biological Activity I Assay Protocols (From Reference)
Targets
p-Hydroxycinnamic acid targets platelet activity by inhibiting thromboxane B₂ production and prostaglandin E₂ generation. It inhibits thromboxane B₂ production with an IC50 of 371 μM and inhibits lipopolysaccharide-induced prostaglandin E₂ generation with an IC50 of 126 μM. It also antagonizes NF-κB activation in MC3T3 preosteoblastic cells.
ln Vitro
Parahydroxycinnamic acid (p-coumaric acid) is a common plant metabolite having antioxidant and anti-inflammatory activities. p-Hydroxycinnamic acid (500 μM and 1 mM) reduced ADP-induced platelet aggregation (55·2 (SE 4·01)% and 35·6 (SE 2·35)%, respectively, relative to basal levels). Para-hydroxycinnamic acid changes platelet activity, a shear-inducing device that mimics primary hemostasis. p-Hydroxycinnamic acid also interferes with the arachidonic acid cascade, lowering thromboxane B2 generation and lipopolysaccharide-induced prostaglandin E2 production (IC50: 371 and 126 μM, respectively) [1].
In vitro, p-Hydroxycinnamic acid inhibits platelet activity. It inhibits thromboxane B₂ production with an IC50 of 371 μM and prostaglandin E₂ generation with an IC50 of 126 μM. At 500 μM and 1 mM, it reduces ADP-induced platelet aggregation by 55.2% and 35.6%, respectively, relative to basal levels. It may also have in vitro antimalarial activity.
ln Vivo
In vivo, p-Hydroxycinnamic acid has anti-osteoporotic properties. It antagonizes NF-κB activation in MC3T3 preosteoblastic cells, suggesting a role in bone metabolism and protection against osteoporosis. Its platelet inhibitory effects suggest potential cardiovascular protective properties. Further in vivo studies are needed to fully characterize its systemic effects.
Enzyme Assay
In vitro platelet aggregation assays for p-Hydroxycinnamic acid are conducted using human platelet-rich plasma. Platelets are pre-incubated with varying concentrations of the compound (typically 0.1-5 mM) and then stimulated with ADP or other agonists. Aggregation is measured using a platelet aggregometer, and the percentage of aggregation inhibition is calculated. Thromboxane B₂ and prostaglandin E₂ levels are measured by ELISA.
Cell Assay
Cellular assays for p-Hydroxycinnamic acid are performed using MC3T3 preosteoblastic cells to study NF-κB activation. Cells are treated with the compound at concentrations ranging from 0.1 to 2 mM. NF-κB activation is assessed by measuring p65 nuclear translocation or by luciferase reporter assays. Cytotoxicity is evaluated using MTT assays.
Animal Protocol
In vivo animal studies for p-Hydroxycinnamic acid have been conducted in models of osteoporosis. Rodents are administered the compound orally or intraperitoneally. Bone mineral density, bone histomorphometry, and serum markers of bone turnover are assessed. NF-κB activation in bone tissues can also be evaluated.
ADME/Pharmacokinetics
Pharmacokinetic properties of p-Hydroxycinnamic acid have been partially characterized. As a dietary phenol, it is absorbed following oral consumption and undergoes metabolism via conjugation reactions (sulfation, glucuronidation). It is a human endogenous metabolite. Plasma concentrations after dietary intake are typically in the low micromolar range. Its half-life and bioavailability are dependent on the form of administration.
Toxicity/Toxicokinetics
Toxicological data for p-Hydroxycinnamic acid are limited. As a common dietary phenol found in many plant foods, it is generally recognized as safe at dietary levels. No significant acute toxicity has been reported. High-dose studies would be required to establish a formal toxicological profile.
References

[1]. p-Coumaric acid, a common dietary phenol, inhibits platelet activity in vitro and in vivo. Br J Nutr. 2007 Mar;97(3):458-63.

Additional Infomation
4-Coumaric acid is a coumaric acid with a hydroxyl substituent at the C-4 position of the benzene ring. It is a plant metabolite and the conjugate acid of 4-coumaric acid ester. It has been reported to be present in tea (Camellia sinensis), camellia (Camellia reticulata), and several other organisms with relevant data. Trans-4-coumaric acid is a metabolite found or produced in Saccharomyces cerevisiae. See also: black cohosh (partial); wolfberry fruit (partial); blueberry leaf (partial)... See more...
p-Hydroxycinnamic acid (p-coumaric acid) is a naturally occurring dietary phenol that inhibits platelet activity (IC50: 371 μM for thromboxane B₂, 126 μM for PGE₂). It reduces ADP-induced platelet aggregation. It has anti-osteoporotic properties and antagonizes NF-κB activation in preosteoblastic cells. It is not a drug and has no clinical approval.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₉H₈O₃
Molecular Weight
164.16
Exact Mass
164.047
CAS #
7400-08-0
PubChem CID
637542
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
346.1±17.0 °C at 760 mmHg
Melting Point
212-214ºC
Flash Point
177.3±17.4 °C
Vapour Pressure
0.0±0.8 mmHg at 25°C
Index of Refraction
1.660
LogP
1.88
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Heavy Atom Count
12
Complexity
178
Defined Atom Stereocenter Count
0
SMILES
C1=CC(=CC=C1/C=C/C(=O)O)O
InChi Key
NGSWKAQJJWESNS-ZZXKWVIFSA-N
InChi Code
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
Chemical Name
(E)-3-(4-hydroxyphenyl)prop-2-enoic acid
Synonyms
p-Hydroxy-cinnamic acid p-Coumaric acid p-Cumaric acid NSC 59260
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 (~609.16 mM)
Ethanol : ~33.33 mg/mL (~203.03 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.23 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 (15.23 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 (15.23 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.


Solubility in Formulation 4: ≥ 2.08 mg/mL (12.67 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 of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of 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 5: ≥ 2.08 mg/mL (12.67 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.

Solubility in Formulation 6: ≥ 2.08 mg/mL (12.67 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 6.0916 mL 30.4581 mL 60.9162 mL
5 mM 1.2183 mL 6.0916 mL 12.1832 mL
10 mM 0.6092 mL 3.0458 mL 6.0916 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 volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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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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