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7-Methoxyflavone is a natural compound and non-steroidal because it binds reversibly with aromatase which is an enzyme that helps produce estrogen through the conversion of androgen (testosterone) to estrogen. It has strong aromatase inhibiting properties, superior bioavailability, and strong resistance to hepatic metabolism/breakdown.

ChEBI: 7-Methoxyflavone is a member of flavonoids and an ether.

7-methoxyflavone is popular nowadays as one of the most powerful aromatase inhibitor and testosterone booster. It is isolated from Zornia brasiliensis. It might change how the body breaks down chemicals called hormones. Some people think this might cause the body to have more of the hormone called testosterone. Testosterone can help build muscle, but can also cause serious side effects.

7-Methoxyflavone is a flavone that has been found in Z. brasiliensis and has diverse biological activities. It inhibits aromatase (IC50 = 1.9 μM in a cell-free assay) and LPS-induced nitric oxide (NO) production by 17.74% in RAW 264.7 macrophages when used at a concentration of 20 μM. 7-Methoxyflavone activates androgen and/or glucocorticoid receptor transcriptional activity in a reporter assay and has antinociceptive effects in the acetic acid-induced writhing test in mice (ED50 = 82.5 μmol/kg).

1-(2-Hydroxyphenyl)-3-aryl-1,3-propanedione 1a (0.5 g) was mixed with malic acid (1.0 eq.) and placed in an oil bath preheated to 140 °C and reacted for 10 min; or in a microwave reactor for 5 min. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was cooled to room temperature and diluted by adding water (10 mL) and ethyl acetate (10 mL). Subsequently, solid NaHCO3 was added to neutralize the reaction mixture. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (2 x 10 mL). All organic extracts were combined and dried with anhydrous sodium sulfate and subsequently concentrated under vacuum. The crude product was purified by silica gel column chromatography using a mixed solvent system of hexane-ethyl acetate to give the target product 7-methoxy-2-phenyl-4H-benzopyran-4-one in high yield.

[1] Letters in Organic Chemistry, 2014, vol. 11, # 8, p. 601 - 605
[2] Heterocyclic Communications, 2007, vol. 13, # 1, p. 77 - 81
[3] Letters in Organic Chemistry, 2015, vol. 12, # 8, p. 574 - 583
[4] Letters in Organic Chemistry, 2016, vol. 13, # 10, p. 734 - 741
[5] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 5, p. 1919 - 1920