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383449

Sigma-Aldrich

3-Formylchromone

97%

Synonym(s):

4-Oxo-4H-1-benzopyran-3-carboxaldehyde

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About This Item

Empirical Formula (Hill Notation):
C10H6O3
CAS Number:
17422-74-1
Molecular Weight:
174.15
EC Number:
241-451-5
MDL number:
MFCD00014667
UNSPSC Code:
12352100
PubChem Substance ID:
24863967
NACRES:
NA.22

Assay

97%

form

solid

mp

151-153 °C (lit.)

SMILES string

O=CC1=COc2ccccc2C1=O

InChI

1S/C10H6O3/c11-5-7-6-13-9-4-2-1-3-8(9)10(7)12/h1-6H

InChI key

FSMYWBQIMDSGQP-UHFFFAOYSA-N

Gene Information

human ... PTPN1(5770)

General description

Electrospray ionization mass spectrometry (ESI-MS) of protonated 3-formylchromone (3-FC) shows loss of H2 as a major fragmentation route to yield a ketene cation, which on reaction with water forms a protonated carboxylic acid. The invivo salubrious effects of 3-FC against nitrosodiethylamine (NDEA) mediated early hepatocellular carcinogenesis has been investigated. Synthesis and characterization of 3-FC and its derivatives has been reported.

Application

3-Formylchromone may be used in the following studies:
  • Preparation of library of novel (E)-3-(2-arylcarbonyl-3-(arylamino)allyl)-4H-chromen-4-ones, by three-component domino reactions with (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones and anilines under catalyst-free conditions.
  • Facile and ecofriendly synthesis of new chromonyl chalcones.
  • Synthesis of 3-(2-hydroxybenzoyl)quinolines and 7H-chromeno[3,2-c]quinolin-7-ones.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

199222

Chromone

Muhammed Bilaal Ismail et al.
Nucleosides, nucleotides & nucleic acids, 38(12), 950-971 (2019-07-11)
Herein, we report the DNA interaction studies of rhenium(I) and -(V) compounds with Schiff base chelates encompassing biologically relevant moieties. More specifically, the DNA interaction capabilities of these rhenium complexes were probed using Gel Electrophoresis and Calf Thymus-DNA titrations monitored
Pitchaimani Prasanna et al.
Beilstein journal of organic chemistry, 10, 459-465 (2014-03-13)
The three-component domino reactions of (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones, 3-formylchromone and anilines under catalyst-free conditions afforded a library of novel (E)-3-(2-arylcarbonyl-3-(arylamino)allyl)-4H-chromen-4-ones in good to excellent yields and in a diastereoselective transformation. This transformation generates one C-C and one C-N bond and presumably proceeds
Andrey S Plaskon et al.
The Journal of organic chemistry, 73(15), 6010-6013 (2008-07-03)
A facile and versatile procedure for the synthesis of 3-(2-hydroxybenzoyl)quinolines and 7H-chromeno[3,2-c]quinolin-7-ones was elaborated on the basis of TMSCl-mediated recyclization of 3-formylchromone with various anilines. Limitations and scope of this methodology were established, and a possible mechanism for the heterocyclizations
Koichi Takao et al.
Bioorganic chemistry, 83, 432-437 (2018-11-15)
A series of eighteen pyrano[4,3-b][1]benzopyranone derivatives (1a-9b) were synthesized, and structure-activity relationships of their monoamine oxidase (MAO) A and B, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) inhibitory activities were evaluated. Most of the synthesized compounds exhibited weak inhibitory activity toward MAO-A
Pedatsur Neta et al.
Rapid communications in mass spectrometry : RCM, 28(17), 1871-1882 (2014-08-05)
Electrospray ionization mass spectrometry (ESI-MS) of many protonated aldehydes shows loss of CO as a major fragmentation pathway. However, we find that certain aldehydes undergo loss of H2 followed by reaction with water in the collision cell. This complicates interpretation
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