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23363-64-6

23363-64-6 Structure

23363-64-6 Structure
IdentificationBack Directory
[Name]

Chlorflavonin
[CAS]

23363-64-6
[Synonyms]

Chlorflavonin
Chlorflavonin >=98% (HPLC)
3'-Chloro-2',5-dihydroxy-3,7,8-trimethoxyflavone
2-(3-Chloro-2-hydroxyphenyl)-5-hydroxy-3,7,8-trimethoxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2-(3-chloro-2-hydroxyphenyl)-5-hydroxy-3,7,8-trimethoxy-
[Molecular Formula]

C18H15ClO7
[MDL Number]

MFCD32174337
[MOL File]

23363-64-6.mol
[Molecular Weight]

378.76
Chemical PropertiesBack Directory
[Boiling point ]

612.7±55.0 °C(Predicted)
[density ]

1.52±0.1 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

DMSO: 2mg/mL, clear
[form ]

powder
[pka]

6.61±0.40(Predicted)
[color ]

white to beige
[InChI]

1S/C18H15ClO7/c1-23-11-7-10(20)12-14(22)18(25-3)15(26-17(12)16(11)24-2)8-5-4-6-9(19)13(8)21/h4-7,20-21H,1-3H3
[InChIKey]

JLSQXYITDXJTKL-UHFFFAOYSA-N
[SMILES]

OC1=CC(OC)=C(C2=C1C(C(OC)=C(C3=C(O)C(Cl)=CC=C3)O2)=O)OC
Safety DataBack Directory
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Definition]

ChEBI: A dihydroxyflavone that is flavone substituted by a chloro group at position 3', hydroxy groups at positions 5 and 2' and methoxy groups at positions 3, 7 band 8 respectively.
[Biological Activity]

Originally isolated from Aspergillus candidus LinkChlorflavonin is a non-cytotoxic (up to 100 μM; MRC-5 and THP-1) antibiotic with antifungal activity against certain species of mold fungi (MIC = 0.08 μg/mL against A. amstelodamiA. fumigalusA. ochraceous; Paecilomyces variotii MIC = 2.5 μg/mLBotrytis cinerea MIC = 5 μg/mL). Chlorflavonin also exhibits antibiotic activity against M. tuberculosis (MIC90 = 1.56 μM) by targeting acetohydroxyacid synthase (AHAS) catalytic subunit ilvB1. Chlorflavonin is superior to streptomycin against M. tuberculosis inside infected macrophagessynergizes with isoniazid and delamanidleading to a complete sterilization in liquid cultures.
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