What is 5-methyl-7-methoxyisoflavone?

Fig 1. (a) general structure of flavones (b) structure of 5-methyl-7-methoxyisoflavone

5-Methyl-7-methoxyisoflavone (C17H14O3, CAS registry No. 82517-12-2) is a white to off-white crystalline powder. Its melting point is 116-120 oC and flash point is 217.5 oC. It is insoluble in water. 5-Methyl-7-methoxyisoflavone should store in cool place and keep container tightly closed in a dry and well-ventilated place.

5-Methyl-7-methoxyisoflavone is a sensational, non-steroidal anabolic isoflavones, which are widely available as dietary supplements, often in concentrations that are significantly higher than those naturally found in food. Isoflavones are phytoestrogens, which are structurally similarly to endogenous estrogen and have a high binding affinity to the primary estrogen receptor in the vascular wall.  5-Methyl-7-methoxyisoflavone presents a methoxy group at C7, found in some natural isoflavones, and an untypical methyl group at C5. It shows 3 times more potent than isoflavones for increasing muscle mass and endurance. It is regarded as the perfect anabolic agent that offers benefits such as increasing lean mass without the side-effects of steroids. It is believed to considerably increase the levels of potassium, nitrogen, calcium and phosphorous retention making it an unmatched and superior anabolic horsepower supplement. It can be used for fat loss, increase vitality and muscle gain besides the maintenance of low cholesterol level and strengthen bones.

Some studies have shown that 5-methyl-7-methoxyisoflavone have the anabolic (muscle-building and bone-building) properties, resulting increased protein synthesis and decreased cortisol blood level from animal studies[1]. A recent study showed that 5-methyl-7-methoxyisoflavone metabolites can induce cross reaction with 11-nor-9-carboxy-Δ9-tetrahydrocannabinol (THC-COOH) antibodies and cause false-positive results in urinary immunoassay screening tests for cannabinoids[2].

The in vivo metabolism of 5-methyl-7-methoxyisoflavone, presents in a dietary supplement, has been investigated by gas chromatography coupled to high accuracy mass spectrometry. Eight metabolites of methoxyisoflavone were isolated. The corresponding accurate mass spectra are specific for isoflavone structures and revealed a retro-Diels-Alder fragmentation. O-demethylation and hydroxylation represent the main phase I biotransformation reactions for the methoxylated flavonoids. 5-methyl-7-methoxyisoflavone can undergo either a direct mono-hydroxylation reaction or a di-hydroxylation of the B ring, depending on the sequence of the two phase I biotransformation pathways; the above hydroxylation reactions can also be preceded by an O-demethylation of the molecule, leading to the formation of additional metabolites[3].

References

[1]Kreider, R. B.; Wilborn, C. D.; Taylor, L.; Campbell, B.; Almada, A. L.; Collins, R.; Cooke, M.; Earnest, C. P.; Greenwood, M.; Kalman, D. S.; Kerksick, C. M.; Kleiner, S. M.; Leutholtz, B.; Lopez, H.; Lowery, L. M.; Mendel, R.; Smith, A.; Spano, M.; Wildman, R.; Willoughby, D. S.; Ziegenfuss, T. N.; Antonio, J., ISSN exercise & sport nutrition review: research & recommendations. Journal of the International Society of Sports Nutrition 2010, 7.
[2]Lecompte, Y.; Perrin, M.; Daude, B.; Arpino, P., Méthoxyisoflavone et dépistage du cannabis dans les urines : mise en évidence d’une réaction croisée peu connue. Annales de Toxicologie Analytique 2012, 24 (1), 49-58.
[3]https://pubchem.ncbi.nlm.nih.gov/compound/2734290
[4]https://www.chemspider.com/Chemical-Structure.2016043.html?rid=4145e184-7019-4e44-a049-2f81bd99e79