7-Hydroxycoumarin-3-carboxylic acid

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7-Hydroxycoumarin-3-carboxylic acid

7-Hydroxycoumarin-3-carboxylic acid | 779-27-1

Catalog Number F05-0014
Category Coumarin
Molecular Formula C10H6O5
Molecular Weight 206.15
Catalog Number Size Price Quantity
F05-0014 1 g $439

Product Introduction

7-Hydroxycoumarin-3-carboxylic acid is a none-activated, amine-reactive pH indicator.

Chemical Information

Synonyms Umbelliferone-3-carboxylic acid
Purity >98.0%(HPLC)
IUPAC Name 7-hydroxy-2-oxochromene-3-carboxylic acid
Canonical SMILES C1=CC2=C(C=C1O)OC(=O)C(=C2)C(=O)O
InChI InChI=1S/C10H6O5/c11-6-2-1-5-3-7(9(12)13)10(14)15-8(5)4-6/h1-4,11H,(H,12,13)
InChI Key LKLWLDOUZJEHDY-UHFFFAOYSA-N
Appearance Beige Crystalline
Melting Point 263 °C
MDL Number MFCD00017491
  • Product Specification
  • Application
Condition To Avoid Light Sensitive,Heat Sensitive
Storage <0 °C
Signal Warning
GHS Hazard Statements H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statement Codes P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.)

7-Hydroxycoumarin-3-carboxylic acid, a versatile coumarin derivative, boasts a plethora of applications due to its fluorescent properties and biological activities. Here are four key applications of this compound:

Fluorescent Probes: Standing as a stalwart fluorescent probe in biochemical and cell biology research, 7-Hydroxycoumarin-3-carboxylic acid shines brightly with its robust fluorescence emission, serving as an impeccable instrument for tracking molecular interactions and cellular processes. Researchers harness its capabilities in various assays to monitor enzyme activities, binding events, or visualize intricate cellular structures under high-powered microscopes.

Drug Discovery: Embodying an indispensable role in drug discovery and development, this compound acts as a pharmacophore for designing novel drugs. Its distinctive chemical structure engages with a myriad of biological targets, laying the groundwork for creating inhibitors, agonists, or antagonists. Particularly prized in high-throughput screening, it aids in pinpointing potential therapeutic candidates with precision and efficiency.

Environmental Monitoring: Playing a pivotal role in environmental monitoring, 7-Hydroxycoumarin-3-carboxylic acid, with its sensitivity and fluorescence properties, acts as a potent chemical indicator. It enables the detection of pollutants such as heavy metals in water. By analyzing fluctuations in its fluorescence, scientists can accurately assess levels of environmental contamination, facilitating proactive measures to safeguard ecosystems.

Photodynamic Therapy: Spearheading innovation in cancer treatment, 7-Hydroxycoumarin-3-carboxylic acid holds promise in photodynamic therapy (PDT). When activated by light, it triggers the generation of reactive oxygen species that induce targeted cell death in cancerous tissues. This targeted approach minimizes collateral damage to healthy cells, enhancing the efficacy of cancer treatments.

Computed Properties

XLogP3 1.8
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 5
Rotatable Bond Count 1
Exact Mass 206.02152329 g/mol
Monoisotopic Mass 206.02152329 g/mol
Topological Polar Surface Area 83.8Ų
Heavy Atom Count 15
Formal Charge 0
Complexity 333
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

Literatures

PMIDPublication DateTitleJournal
22392808 2012-07-01 Fluorescent assay for directed evolution of perhydrolases Journal of biomolecular screening
22500730 2012-07-01 Mechanism of radiation-induced reactions in aqueous solution of coumarin-3-carboxylic acid: effects of concentration, gas and additive on fluorescent product yield Free radical research
22276179 2012-01-01 TiO2 nanoparticles are phototoxic to marine phytoplankton PloS one
19877615 2009-11-25 Photoactive yellow protein-based protein labeling system with turn-on fluorescence intensity Journal of the American Chemical Society
17828251 2007-10-01 Expanding the promiscuity of a natural-product glycosyltransferase by directed evolution Nature chemical biology

Patents

Publication NumberTitlePriority Date
CN-114621752-A A room temperature phosphorescent water-based polymer anti-counterfeiting material and its preparation method and application 2021-12-03
CN-114621752-B A room temperature phosphorescent water-based polymer anti-counterfeiting material and its preparation method and application 2021-12-03
CN-113774021-A A kind of preparation method of biomaterial scaffold containing mesenchymal stem cell spheres 2021-08-25
WO-2022241110-A1 Coronavirus t cell epitopes, megapools and uses thereof 2021-05-13
CN-113200988-B Synthesis and application of bifunctional fluorescent probe for simultaneously detecting hydroxyl free radicals and viscosity 2021-05-11
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