α-Cyano-4-hydroxycinnamic Acid - Moligand™, 10mM in DMSO , Inhibitor of mitochondrial pyruvate carrier 1;Inhibitor of mitochondrial pyruvate carrier 2, CAS No.28166-41-8, Inhibitor of mitochondrial pyruvate carrier 1;Inhibitor of mitochondrial pyruvate carrier 2

CAS: 28166-41-8 Cat. No.: C422987 Formula: C10H7NO3 Molecular Weight: 189.17 Beilstein Registry Number: 3271430 EC Number: 248-879-1
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GRADE & PURITY Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools. 10mM in DMSO
Synonyms
NCGC00094622-01 | AMY11197 | BRD-K60302405-001-02-9 | Dimethiotazine | DTXSID501018295 | MLS002207285 | (2E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid | 2-Cyano-3-(4-hydroxyphenyl)propenoic acid | 2-Cyano-3-(4-hydroxyphenyl)-2-propenoic acid | a-Cyano-
Storage
Store at -80°C
Shipped In
Dry ice packs + Cold packs
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Size
USA
Germany (EU)*
Price
Qty
1ml
C422987-1ml
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$58.90

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Why this grade

Moligand™, 10mM in DMSO Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 45 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Overview

Product Introduction

α-Cyano-4-hydroxycinnamic acid is the commonly used matrix for analyzing peptides by matrix-assisted laser desorption/ionization mass spectrometry. It inhibits the monophenolase activity and diphenolase activity of mushroom tyrosinase.

Application

α-Cyano-4-hydroxycinnamic acid (CHC) was used in encapsulation of CHC into NaY zeolite. It was used as matrix to investigate the activity of the paclitaxel derivatives using several well-established in vitro angiogenesis assays.

Specifications

Synonyms
NCGC00094622-01 | AMY11197 | BRD-K60302405-001-02-9 | Dimethiotazine | DTXSID501018295 | MLS002207285 | (2E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid | 2-Cyano-3-(4-hydroxyphenyl)propenoic acid | 2-Cyano-3-(4-hydroxyphenyl)-2-propenoic acid | a-Cyano-
Specifications & Purity
Moligand™, 10mM in DMSO
Biochemical and Physiological Mechanisms
Monocarboxylic acid transport (MCT) inhibitor. Exhibits antitumoral and antiangiogenic activity in gliomas in vivo . Decreases glycolytic metabolism, migration, and invasion in U251 cells. Enhances the effect of the DNA-methylating antitumor agent temozol
Storage
Store at -80°C
Shipped In
Dry ice packs + Cold packs
This product requires cold chain shipping. Ground and other economy services are not available.
Grade
Moligand™
Action Type
INHIBITOR
Mechanism of action
Inhibitor of mitochondrial pyruvate carrier 1;Inhibitor of mitochondrial pyruvate carrier 2
Names and Identifiers
Pubchem Sid
Canonical Smiles
C1=CC(=CC=C1C=C(C#N)C(=O)O)O
IUPAC Name
(E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
InChIKey
AFVLVVWMAFSXCK-VMPITWQZSA-N
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+
Isomeric SMILES
C1=CC(=CC=C1/C=C(\C#N)/C(=O)O)O
WGK Germany
3
Molecular Weight
189.17
Beilstein
3271430
Reaxy-Rn
8201999
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8201999&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
SubclassHydroxycinnamic acids and derivatives
Intermediate Tree Nodes Not available
Direct ParentHydroxycinnamic acids
Alternative Parents Coumaric acids  Cinnamic acids  1-hydroxy-2-unsubstituted benzenoids  Benzene and substituted derivatives  Nitriles  Monocarboxylic acids and derivatives  Carboxylic acids  Organopnictogen compounds  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular FrameworkAromatic homomonocyclic compounds
Substituents Cinnamic acid - Coumaric acid - Coumaric acid or derivatives - Hydroxycinnamic acid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Benzenoid - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Carbonitrile - Nitrile - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
External Descriptors phenols - nitrile - monohydroxycinnamic acid
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
MPC2 Tbio Mitochondrial pyruvate carrier 2 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
MPC1 Tbio Mitochondrial pyruvate carrier 1 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SiHa (2051 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC16A1 Tchem Monocarboxylate transporter 1 (146 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GPR35 Tchem G-protein coupled receptor 35 (2643 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC16A3 Tchem Monocarboxylate transporter 4 (196 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC16A7 Tchem Monocarboxylate transporter 2 (11 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
Hdac6 Histone deacetylase 6 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNK2 Potassium channel subfamily K member 2 (9 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
Melt Point(°C)245-250℃
Molecular Weight189.170 g/mol
XLogP31.400
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass189.043 Da
Monoisotopic Mass189.043 Da
Topological Polar Surface Area81.300 Ų
Heavy Atom Count14
Formal Charge0
Complexity292.000
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds1
Covalently-Bonded Unit Count1
Documents & Articles
Citations of This Product
Solution Calculators
Reviews

Customer Reviews

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