3-Acetylcoumarin - ≥98% , CAS No.3949-36-8

CAS: 3949-36-8 Cat. No.: A151700 Molecular Weight: 188.18 Beilstein Registry Number: 17(5)11,367

GRADE & PURITY ≥98%

Synonyms

3-Acetylcoumarin | NSC 31678 | CAS-3949-36-8 | 2,2-Biquinoline-4,4-dicarboxylic acid | AMY202003292 | Prestwick3_000891 | 2H-1-Benzopyran-2-one,3-acetyl- | Coumarin, 3-acetyl- | NCGC00179470-01 | 8-ACETYL DIMETHOXYCOUMARIN | AKOS001083007 | BSPBio_000702

Storage

Room temperature

Shipped In

Normal

Overview

FTIR and FT-Raman spectra of 3-acetylcoumarin has been reported. 3-Acetylcoumarin undergoes condensation with aryl aldehydes in chloroform in the presence of piperidine to yield coumarin derivatives containing 4-arylbut-3-en-2-one moiety.

Specifications

Synonyms

3-Acetylcoumarin | NSC 31678 | CAS-3949-36-8 | 2, 2-Biquinoline-4, 4-dicarboxylic acid | AMY202003292 | Prestwick3_000891 | 2H-1-Benzopyran-2-one, 3-acetyl- | Coumarin, 3-acetyl- | NCGC00179470-01 | 8-ACETYL DIMETHOXYCOUMARIN | AKOS001083007 | BSPBio_000702

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488185424
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488185424
• Canonical Smiles: CC(=O)C1=CC2=CC=CC=C2OC1=O
• IUPAC Name: 3-acetylchromen-2-one
• InChIKey: CSPIFKKOBWYOEX-UHFFFAOYSA-N
• INCHI: 1S/C11H8O3/c1-7(12)9-6-8-4-2-3-5-10(8)14-11(9)13/h2-6H,1H3
• Isomeric SMILES: CC(=O)C1=CC2=CC=CC=C2OC1=O
• WGK Germany: 3
• Molecular Weight: 188.18
• Beilstein: 17(5)11,367
• Reaxy-Rn: 143498
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=143498&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumarins and derivatives
• Alternative Parents: 1-benzopyrans Aryl alkyl ketones Pyranones and derivatives Benzenoids Heteroaromatic compounds Lactones Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumarin - Benzopyran - 1-benzopyran - Aryl alkyl ketone - Aryl ketone - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Ketone - Lactone - Oxacycle - Organoheterocyclic compound - Hydrocarbon derivative - Organooxygen compound - Organic oxygen compound - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP1A2 Tchem Cytochrome P450 1A2 (1 Activities)

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CA12 Tclin Carbonic anhydrase 12 (1 Activities)

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CA9 Tclin Carbonic anhydrase 9 (1 Activities)

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CA2 Tclin Carbonic anhydrase II (17698 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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MAOB Tclin Monoamine oxidase B (8835 Activities)

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PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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CA1 Tclin Carbonic anhydrase I (13240 Activities)

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APP Tclin Amyloid-beta A4 protein (8510 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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CA12 Tclin Carbonic anhydrase XII (6231 Activities)

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CA9 Tclin Carbonic anhydrase IX (8255 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KM12 (47707 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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SF-295 (48000 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UO-31 (46270 Activities)

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786-0 (47912 Activities)

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A549 (127892 Activities)

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NCI/ADR-RES (33767 Activities)

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EKVX (44102 Activities)

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NCI-H322M (45589 Activities)

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HCC 2998 (41480 Activities)

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HCT-116 (91556 Activities)

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Associated Targets(non-human)

Cryz Quinone oxidoreductase (288 Activities)

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Mus musculus (284745 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 123 °C
• Molecular Weight: 188.180 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 188.047 Da
• Monoisotopic Mass: 188.047 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 304.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Brian Musikavanhu, Tingting Pan, Quanhong Ma, Yongdi Liang, Zhaoli Xue, Lei Feng, Long Zhao.  (2024)  Dual detection of Hg2+ and Pb2+ by a coumarin-functionalized Schiff base in environmental and biosystems.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:38447440] [10.1016/j.saa.2024.124101]