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α-Cyano-4-hydroxycinnamic acid

Alias: αCyano4hydroxycinnamic acid α Cyano 4 hydroxycinnamic acid
Cat No.:V38686 Purity: ≥98%
α-Cyano-4-hydroxycinnamic acid (α-Cyano-4-hydroxycinnamate) is a potent, noncompetitive inhibitor of monocarboxylate transporters (MCTs).
α-Cyano-4-hydroxycinnamic acid
α-Cyano-4-hydroxycinnamic acid Chemical Structure CAS No.: 28166-41-8
Product category: Monocarboxylate Transporter2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
α-Cyano-4-hydroxycinnamic acid (α-Cyano-4-hydroxycinnamate) is a potent, noncompetitive inhibitor of monocarboxylate transporters (MCTs). α-Cyano-4-hydroxycinnamic acid inhibits the mitochondrial pyruvate transporter with Ki of 6.3 μM. α-Cyano-4-hydroxycinnamic acid is used as a matrix in matrix-assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF) analysis to promote peptide ionization.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
α-Cyano-4-Hydroxycinnamic Acid (α-Cyano-4-Hydroxycinnamic Acid) prevents monocarboxylates like pyruvate and lactate from being transported [2]. Lung explants' epithelial circumference was lowered and branching morphogenesis was significantly inhibited by α-cyano-4-hydroxycinnamic acid (CHC; 0.5 and 1 mM) at 1 mM in a dose-dependent manner. region[2]. At a dosage of 100 μM, α-Cyano-4-hydroxycinnamic acid inhibits oxidized pyruvate's ability to absorb O2 in rat heart mitochondria quickly and nearly entirely. As low as 1 μM of inhibitor can cause inhibition, however it takes time for inhibition to manifest at this dosage [1].
References

[1]. The mitochondrial pyruvate carrier. Kinetics and specificity for substrates and inhibitors. Biochem J. 1975 Apr; 148(1): 85-96.

[2]. The Monocarboxylate Transporter Inhibitor α-cyano-4-hydroxycinnamic Acid Disrupts Rat Lung Branching. Cell Physiol Biochem. 2013;32(6):1845-56.

[3]. Improvement of Mass Spectrometry Analysis of Glycoproteins by MALDI-MS Using 3-aminoquinoline/α-cyano-4-hydroxycinnamic Acid. Anal Bioanal Chem. 2013 May;405(12):4289-93.

Additional Infomation
Alpha-cyano-4-hydroxycinnamic acid is a monohydroxycinnamic acid that is 4-hydroxycinnamic acid in which the hydrogen alpha- to the carboxy group is replaced by a cyano group. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of peptides and oligonucleotides. It has a role as a MALDI matrix material. It is a nitrile, a member of phenols and a monohydroxycinnamic acid.
See also: alpha-Cyano-4-hydroxycinnamate (annotation moved to).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₁₀H₇NO₃
Molecular Weight
189.17
Exact Mass
189.042
CAS #
28166-41-8
PubChem CID
5328791
Appearance
Light yellow to yellow solid powder
Density
1.4±0.1 g/cm3
Boiling Point
398.1±32.0 °C at 760 mmHg
Melting Point
245-250 °C(lit.)
Flash Point
194.5±25.1 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.674
LogP
1.53
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Heavy Atom Count
14
Complexity
292
Defined Atom Stereocenter Count
0
SMILES
C1=CC(=CC=C1/C=C(\C#N)/C(=O)O)O
InChi Key
AFVLVVWMAFSXCK-VMPITWQZSA-N
InChi Code
InChI=1S/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)/b8-5+
Chemical Name
(E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
Synonyms
αCyano4hydroxycinnamic acid α Cyano 4 hydroxycinnamic 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 : ~250 mg/mL (~1321.56 mM)
H2O : < 0.1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (11.00 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 (11.00 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 (11.00 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 5.2863 mL 26.4313 mL 52.8625 mL
5 mM 1.0573 mL 5.2863 mL 10.5725 mL
10 mM 0.5286 mL 2.6431 mL 5.2863 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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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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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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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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