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ChemicalBook--->CAS DataBase List--->102067-84-5

102067-84-5

102067-84-5 Structure

102067-84-5 Structure
IdentificationBack Directory
[Name]

Sappanone A
[CAS]

102067-84-5
[Synonyms]

Sappanone A
(E)-7-hydroxy-3-[(3,4-dihydroxyphenyl)methylene]-chroman-4-one
3-[(3,4-Dihydroxyphenyl)methylene]-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one
[Molecular Formula]

C16H12O5
[MDL Number]

MFCD21333231
[MOL File]

102067-84-5.mol
[Molecular Weight]

284.26
Chemical PropertiesBack Directory
[Boiling point ]

605.5±55.0 °C(Predicted)
[density ]

1.521±0.06 g/cm3(Predicted)
[solubility ]

DMF: 20 mg/ml; DMSO: 15 mg/ml; Ethanol: 5 mg/ml; PBS (pH 7.2): 0.25 mg/ml
[form ]

A solid
[pka]

7.20±0.20(Predicted)
[color ]

Light yellow to yellow
Hazard InformationBack Directory
[Description]

Sappanone A is a homoisoflavonoid with diverse biological activities that has been isolated from the aerial parts of C. pulcherrima, the heartwood of C. sappan, and the stems of H. campechianum. In vitro, sappanone A inhibits 76.2, 59.2, 37.4, and 35.4% of FGFR1, KDR, c-Met, and c-Kit kinase activity, respectively, when used at a concentration of 10 μM. It also inhibits influenza viral neuraminidase (NA) with IC50 values of 0.7, 1.1, and 1 μM for H1N1, H3N2, and H9N2 influenza viral NAs, respectively. Sappanone A has antibacterial activity against Gram-positive B. subtilis, B. sphaericus, and S. aureus as well as Gram-negative K. aerogenes and C. violaceum. It also inhibits the growth of A. niger and C. albicans fungi. Sapannone A inhibits LPS-induced inflammatory responses in vitro and in vivo, reducing nitric oxide (NO), interleukin-6 (IL-6), and prostaglandin E2 (PGE2; Item No. 14010) production in RAW264.7 cells as well as LPS-induced mortality in mice. It also attenuates airway inflammation and mucus hypersecretion via activation of the Nrf2 signaling pathway in a mouse model of ovalbumin-induced asthma.
[Uses]

Sappanone A is a natural product flavonoid with some antioxidant properties that can be isolated from C. sappan.
[Biological Activity]

Sappanone A is a homoisoflavanone which exhibits anti-inflammatory effects via modulation of Nrf2 and NF-κB. Sappanone can attenuate allergic airway inflammation in Ovalbumin-induced asthma.
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