5-Methyl-7-methoxyisoflavone

5-Methyl-7-methoxyisoflavone
Names
	IUPAC name 7-Methoxy-5-methylisoflavone
	Systematic IUPAC name 7-Methoxy-5-methyl-3-phenyl-4H-1-benzopyran-4-one
	Other names Methoxyisoflavone
Identifiers
CAS Number	82517-12-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	2016043;
ECHA InfoCard	100.126.888
PubChem CID	2734290;
UNII	NHW23TRU3M ;
CompTox Dashboard (EPA)	DTXSID201002754 ;
	InChI InChI=1S/C17H14O3/c1-11-8-13(19-2)9-15-16(11)17(18)14(10-20-15)12-6-4-3-5-7-12/h3-10H,1-2H3 Key: WGOUYULOZZRTFS-UHFFFAOYSA-N; InChI=1/C17H14O3/c1-11-8-13(19-2)9-15-16(11)17(18)14(10-20-15)12-6-4-3-5-7-12/h3-10H,1-2H3 Key: WGOUYULOZZRTFS-UHFFFAOYAN;
	SMILES O=C\1c3c(O/C=C/1c2ccccc2)cc(OC)cc3C;
Properties
Chemical formula	C17H14O3
Molar mass	266.296 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5-Methyl-7-methoxyisoflavone, commonly referred to simply as methoxyisoflavone, is a chemical compound marketed as a bodybuilding supplement. However, there is no meaningful clinical evidence to support its usefulness.^[1]^[2] A study published in 2006 examined the effect of methoxyflavone on training adaptations and markers of muscle anabolism and catabolism. No measurable effects were observed in athletic performance or in levels of testosterone and cortisol.^[3]

Consumption of 5-methyl-7-methoxyisoflavone can produce false positive results in urinary tests for cannabinoid use.^[4]^[5]

References

^ "Methoxyisoflavone". NYU Langone Medical Center. July 2012. Archived from the original on August 19, 2014. There is no meaningful evidence to indicate that methoxyisoflavone is useful as a sports supplement.
^ "Methoxyisoflavone". EBSCO CAM Review Board. Retrieved April 15, 2015.
^ Wilborn, Colin D; Taylor, Lemuel W; Campbell, Bill I; Kerksick, Chad; Rasmussen, Chris J; Greenwood, Michael; Kreider, Richard B (2006). "Effects of Methoxyisoflavone, Ecdysterone, and Sulfo-Polysaccharide Supplementation on Training Adaptations in Resistance-Trained Males". Journal of the International Society of Sports Nutrition. 3 (2): 19–27. CiteSeerX 10.1.1.274.1063. doi:10.1186/1550-2783-3-2-19. PMC 2129166. PMID 18500969.
^ Lecompte, Yannick; Perrin, Martine; Daude, Bernard; Arpino, Patrick (2012). "Méthoxyisoflavone et dépistage du cannabis dans les urines : mise en évidence d'une réaction croisée peu connue" [Methoxyisoflavone and urine cannabinoid screening: evidence of a poorly known cross-reactivity]. Annales de Toxicologie Analytique (in French). 24 (1): 49–58. doi:10.1051/ata/2012002.
^ Lecompte, Yannick; Rosset, Martine; Richeval, Camille; Humbert, Luc; Arpino, Patrick (2014). "UPLC-ESI-Q-TOF-MSE identification of urinary metabolites of the emerging sport nutrition supplement methoxyisoflavone in human subjects". Journal of Pharmaceutical and Biomedical Analysis. 96: 127–134. doi:10.1016/j.jpba.2014.03.031. PMID 24742771.

External links

Hu, Wei-Xiao; Qian, Hong-Sheng; Rao, Guo-Wu (2004). "Structure of 5-methyl-7-methoxy-isoflavone". Journal of Chemical Crystallography. 34 (11): 793. doi:10.1007/s10870-004-7655-y. S2CID 96359776.

[1] "Methoxyisoflavone". NYU Langone Medical Center. July 2012. Archived from the original on August 19, 2014. There is no meaningful evidence to indicate that methoxyisoflavone is useful as a sports supplement.

[2] "Methoxyisoflavone". EBSCO CAM Review Board. Retrieved April 15, 2015.

[3] Wilborn, Colin D; Taylor, Lemuel W; Campbell, Bill I; Kerksick, Chad; Rasmussen, Chris J; Greenwood, Michael; Kreider, Richard B (2006). "Effects of Methoxyisoflavone, Ecdysterone, and Sulfo-Polysaccharide Supplementation on Training Adaptations in Resistance-Trained Males". Journal of the International Society of Sports Nutrition. 3 (2): 19–27. CiteSeerX 10.1.1.274.1063. doi:10.1186/1550-2783-3-2-19. PMC 2129166. PMID 18500969.

[4] Lecompte, Yannick; Perrin, Martine; Daude, Bernard; Arpino, Patrick (2012). "Méthoxyisoflavone et dépistage du cannabis dans les urines : mise en évidence d'une réaction croisée peu connue" [Methoxyisoflavone and urine cannabinoid screening: evidence of a poorly known cross-reactivity]. Annales de Toxicologie Analytique (in French). 24 (1): 49–58. doi:10.1051/ata/2012002.

[5] Lecompte, Yannick; Rosset, Martine; Richeval, Camille; Humbert, Luc; Arpino, Patrick (2014). "UPLC-ESI-Q-TOF-MSE identification of urinary metabolites of the emerging sport nutrition supplement methoxyisoflavone in human subjects". Journal of Pharmaceutical and Biomedical Analysis. 96: 127–134. doi:10.1016/j.jpba.2014.03.031. PMID 24742771.

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