5,7-Dihydroxy-3-p-methoxyphenyl-4H-chromen-4-on

5,7-Dihydrox -4'-methoxyisoflavone Chemische Eigenschaften,Einsatz,Produktion Methoden

• S-Sätze Betriebsanweisung:

  S22:Staub nicht einatmen.
  S24/25:Berührung mit den Augen und der Haut vermeiden.

• Beschreibung

  Biochanin A is a natural isoflavone with diverse biological actions, most notably as a phytoestrogen. It can affect hormone levels by inhibiting 5α-reductase and 17β-hydroxysteroid dehydrogenase or altering aromatase (CYP19A1) activity. Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein , another phytoestrogen with diverse effects. Biochanin A also intersects with signaling through peroxisome proliferator-activated receptors (PPARs), as it activates PPARγ (EC₅₀ = 19 μM) and has also been shown to activate a PPARα promoter. Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis. Biochanin A also inhibits fatty acid amide hydrolase (IC₅₀ = 2.4 μM) and acts as an agonist of the aryl hydrocarbon receptor (EC₅₀ = 0.25 μM).

• Chemische Eigenschaften

  Off-White Solid

• Verwenden

  An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene

• Verwenden

  It has putative benefits in dietary cancer prophylaxis. It has also been found to inhibit fatty acid amide hydrolase and to act as agonist of PPARgamma, nuclear receptor that is current pharmacological target for the treatment of diabetes type 2. It acts as an antineoplastic agent. It is a selective agonist at ER-β estrogen receptors, and may have chemopreventive efficacy against breast cancer. In line with its low activity at ER-α estrogen receptors, it is essentially devoid of uterotrophic activity. Biochanin A is also a ligand for the aryl hydrocarbon receptor (AhR). It reduces arterial resistance and enhances microcirculation perhaps via effects on potassium and/or calcium ion channels. Induction of sulfotransferases for xenobiotic detoxification has been proposed as a mechanism of its cancer preventive effects. It is a nitric oxide synthase inhibitor and apoptosis inducer

• Verwenden

  phytoestrogen

• Definition

  ChEBI: Biochanin A is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at position 5 and a methoxy group at position 4'. A phytoestrogen, it has putative benefits in dietary cancer prophylaxis. It has a role as a phytoestrogen, a plant metabolite, an EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor, a tyrosine kinase inhibitor and an antineoplastic agent. It is a member of 7-hydroxyisoflavones and a member of 4'-methoxyisoflavones. It is a conjugate acid of a biochanin A(1-).

• Allgemeine Beschreibung

  Biochanin A (BCA) is synthesized in vitro from phloroglucinol. A series of steps involving FriedelCrafts reaction results in an intermediate product 1-(2,4,6-trihydroxyphenyl)-2-(4 methoxyphenyl) ethanone, which post cyclization leads to BCA. It is catabolized to isoflavone genistein post ingestion.

• Biochem/physiol Actions

  Biochanin A is an isoflavone phytoestrogen found in red clover (Trifolium pratense) that is a selective agonist at ER-β estrogen receptors, and may have chemopreventive efficacy against breast cancer. In line with its low activity at ER-α estrogen receptors, it is essentially devoid of uterotrophic activity. Biochanin A is also a ligand for the aryl hydrocarbon receptor (AhR). It reduces arterial resistance and enhances microcirculation perhaps via effects on potassium and/or calcium ion channels. Induction of sulfotransferases for xenobiotic detoxification has been proposed as a mechanism of its cancer preventive effects.

• Synthese

  

  15485-66-2

  

  68-12-2

  

  491-80-5

  The general procedure for the synthesis of 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one from 2-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone and N,N-dimethylformamide was carried out as follows: ethyl ether boron trifluoride (3 mL, 24 mmol) was added dropwise to 3 mL anhydrous N,N-dimethylformamide containing 8 mmol of 2-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone (2,4,6-trihydroxyphenyl)acetonide, under the conditions of cooling in ice bath and vigorous stirring. 2-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone to 3 mL of anhydrous N,N-dimethylformamide. After stopping the cooling, trichlorophosphorus (0.9 mL, 9.6 mmol) was added slowly and dropwise. After all components were mixed well, the reaction mixture was stirred at 60-70°C for 2 hours. After completion of the reaction, the mixture was poured into acidified water and the precipitate was filtered out. The crude product was purified by column chromatography using hexane and ethyl acetate (8:2, v/v) as eluents to afford the target compound 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one (a) in 61% yield with a melting point of 212-214 °C. Elemental analysis (C16H12O5) Calculated values: C, 67.60; H, 4.25; O, 28.14; measured values: C, 67.57; H, 4.27; O, 28.15.1H NMR (DMSO-d6, 400 MHz): δ 12.94 (s, 1H, 5-OH), 10.92 (s, 1H, 7-OH), 8.38 ( s, 1H, 2-H), 7.50 (d, J = 8.0 Hz, 2H, Ar-H), 7.0 (d, J = 8.0 Hz, 2H, Ar-H), 6.40 (s, 1H, Ar-H), 5.77 (s, 1H, Ar-H), 3.79 (s, 3H, OCH3).13C NMR (DMSO-d6, 100 MHz): δ 180.0, 164.3, 161.9, 159.17, 157.5, 154.2, 130.1, 122.9, 121.9, 113.7, 104.4, 99.0, 93.6, 55.1. ESI-MS: m/z 285 [M + H]+. FT-IR (KBr, cm-1): 3312 (O-H), 3007 (C-H aromatic), 3007 (C-H aromatic), 3007 (C-H aromatic). 3007 (C-H aromatic), 2950 (C-H aliphatic), 1642 (C=O).

• Einzelnachweise

  [1] Synthetic Communications, 2000, vol. 30, # 3, p. 469 - 484
  [2] Chemistry and Biodiversity, 2015, vol. 12, # 6, p. 963 - 979
  [3] Chemistry of Natural Compounds, 2013, vol. 49, # 2, p. 235 - 241
  [4] Khim. Prir. Soedin., 2013, # 2, p. 203 - 208,6
  [5] Journal of Chemistry, 2018, vol. 2018,

5,7-Dihydrox -4'-methoxyisoflavone Upstream-Materialien And Downstream Produkte

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