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.

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)

Biological Activity

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).

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. 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.