Acacetin

Acacetin Basic information
Product Name:Acacetin
Synonyms:5,7-DIHYDROXY-4'-METHOXYFLAVONE;LINARIGENIN;METHYL-4'-APIGENIN;ACACETIN;5,7-dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone;Abietic;ACACETIN(METHYL-4'-APIGENIN)(RG);ACACETIN WITH HPLC
CAS:480-44-4
MF:C16H12O5
MW:284.26
EINECS:207-552-3
Product Categories:Miscellaneous Reagents;inhibitor;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;Tri-substituted Flavones;Aromatics;Heterocycles;standardized herbal extract
Mol File:480-44-4.mol
Acacetin Structure
Acacetin Chemical Properties
Melting point 260-265 °C(lit.)
Boiling point 346.76°C (rough estimate)
density 1.2160 (rough estimate)
refractive index 1.6200 (estimate)
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Very Slightly, Heated)
pka6.51±0.40(Predicted)
form Solid
color Light Yellow to Green-Yellow to Dark Yellow
λmax335nm(EtOH)(lit.)
Merck 14,13
BRN 277879
InChIKeyDANYIYRPLHHOCZ-UHFFFAOYSA-N
LogP2.443 (est)
CAS DataBase Reference480-44-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS DJ3002000
3-8-10
HS Code 29329990
MSDS Information
ProviderLanguage
SigmaAldrich English
Acacetin Usage And Synthesis
DescriptionAcacetin is an O-methylated flavone found in various plants. It is reported to demonstrate spasmolytic, antinociceptive, anti-inflammatory, and antioxidant activity in various research models.
Chemical PropertiesYellow Solid
UsesVEGF expression inhibitor and tumor angiogenesis. A flavonoid with antiaggregatory activity in human blood.
DefinitionChEBI: A monomethoxyflavone that is the 4'-methyl ether derivative of apigenin.
Synthesis Reference(s)Tetrahedron Letters, 31, p. 6497, 1990 DOI: 10.1016/S0040-4039(00)97100-4
General DescriptionAcacetin belongs to the category of naturally occurring plant pigments called flavonoids found in vascular plants. It was first reported to be extracted from the leaves of Robinia pseuducacia. It has been used as an active component of traditional Chinese medicine Xuelianhua.
Biochem/physiol ActionsAcacetin has been noted to exhibit anti-peroxidative, anti-inflammatory, and anti-plasmodial properties. It has been posited to prevent the proliferation of Hep G2 cells, thereby causing cell apoptosis and subsequent anti-cancer action. It has antiarrhythmic properties and can be used in the treatment of Atrial fibrillation.
Enzyme inhibitorThis naturally occurring flavone (FW = 286.27 g/mol; CAS 480-44-4), also known as 5,7-dihydroxy-4’-methoxyflavone and 7-O-methylapigenin, and systematically named as 5,7-dihydroxy-2-(4-methoxyphenyl)-chromen-4- one, from the black locust Robinia pseudoacacia is the aglycon of linarin and acaciin and is biosynthesized by apigenin 4'-O-methyltransferase from S-adenosyl-methionine and 5,7,4’-trihydroxyflavone (apigenin), yielding Sadenosylhomocysteine and acacetin. The chemical synthesis of acacetin was accomplished by Robert Robinson, who was awarded the 1947 Nobel Prize in Chemistry for his work on alkaloids and organic synthesis. Target(s): glutathione S-transferase; xanthine oxidase, Ki = 0.11 μM; CYP1A; CYP1B1; glutathione-disulfide reductase; DNA topoisomerase I; [myosin light-chain] kinase; and protein-tyrosine kinase, or non-specific protein-tyrosine kinase.
3,4'-DIMETHOXY-3',5,7-TRIHYDROXYFLAVONE Solvent Red 43 3'-BENZYLOXY-4',5,6,7-TETRAMETHOXYFLAVONE TAMARIXETIN-7-O-RUTINOSIDE 5,7-DIHYDROXY-3',4',5'-TRIMETHOXYFLAVONE (E,E)-Farnesol 1-Hydroxyethylidene-1,1-diphosphonic acid Anisole (Trifluoromethoxy)benzene KAEMPFEROL-3,7,4'-TRIMETHYL ETHER 3'-BENZYLOXY-5,7-DIHYDROXY-3,4'-DIMETHOXYFLAVONE Triclosan p-Anisidine Chrysin p-Anisaldehyde QUERCETIN-3,7,3',4'-TETRAMETHYL ETHER CETYL PALMITATE Acacetin

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