Available from stock

Formononetin

SKU: F0339

Category: Phytochemicals

Synonyms: Biochanin B , NSC 93360 , 7-Hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one , 7-Hydroxy-3-(4-methoxyphenyl)chromone, 7-Hydroxy-4'-methoxyisoflavone; 485-72-3
CAS-Number: C₁₆H₁₂O₄
Molecular Formula: 268.26
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Appearance: White to off-white powder
Identity: 1H-NMR

Properties

Solvents: DMSO (30 mg/ml), DMF (30 mg/ml), ethanol (1 mg/ml)

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.

Transportation: Not dangerous goods

Description: Formononetin is an isoflavonoid phytoestrogenic compound found in soy-based foods and is the precursor of daidzein. It acts as an agonist of the aryl hydrocarbon receptor and a selective inhibitor of ADH γ (the γ-isoform of alcohol dehydrogenase). It displays potent antitumor, antiviral, anti-inflammatory (inhibits NLRP3 inflammasome), antioxidant, neuroprotective and neuroinflammatory properties. Also shown to have vasorelaxant, antihypertensive and antihyperglycemic (AMPK activator) properties. Induces cell cycle arrest and apoptosis in several cancer cells in vitro and in vivo and shows anti-angiogenic (FGFR2 inhibitor), anti-invasive and anti-migratory effects. Increases adipocyte thermogenesis by modulating PPARγ activity. Shown to promote early fracture healing through stimulating angiogenesis by up-regulating VEGFR-2/Flk-1 and endothelial repair and wound healing in a process involving the over-expression of Egr-1 transcription factor through the regulation of the ERK1/2 and p38 MAPK pathways.
Smiles: OC1=CC=C(C(C(C2=CC=C(OC)C=C2)=CO3)=O)C3=C1
InChi Key: HKQYGTCOTHHOMP-UHFFFAOYSA-N
References: (1) W.M. Keung, BBRC 215, 1137 (1995) , (2) S. Toda and Y. Shirataki, Phytother. Res. 13, 163 (1999) , (3) C.K. Wong & W.M. Keung, J. Steroid Biochem. Mol. Biol. 71, 191 (1999) , (4) B.L. Pool-Zobel, et al., Carcinogenesis 21, 1247 (2000) , (5) S. Medjakovic & A. Jungbauer , J. Steroid Biochem. Mol. Biol 108, 171 (2008) , (6) H. Mu, et al., Phytomedicine 16, 314 (2009) , (7) J.E . Huh, et al., Int. Immunopharmacol. 9, 1357 (2009) , (8) J.E . Huh, et al., Int. Immunopharmacol. 11, 46 (2011) , (9) T. Sun, et al., Acta Pharmacol. Sin. 32, 1009 (2011) , (10) J. Chen, et al., Horm. Metab. Res. 43, 681 (2011) , (11) M. Sun, et al., J. Alzheimers Dis. 28, 795 (2012) , (12) Y. Ye, et al., Horm. Metab. Res. 44, 263 (2012) , (13) K.K. Auyeung, et al., Oncol. Rep. 28, 2188 (2012) , (14) R. Zhou, et al., Horm. Metab. Res. 46, 753 (2014) , (15) Y. Yang, et al., Int. J. Clin. Exp. Pathol. 7, 8453 (2014) , (16) X.Y. Wu, et al., Oncotarget 6, 44563 (2015) , (17) H. Wang, et al., Virol. J. 12, 1 (2015) , (18) G. Qiu, et al., Exp. Biol. Med. 242, 223 (2017) , (19) J. Gautam, et al., Br. J. Nutr. 117, 645 (2017) , (20) T. Nie, et al., Br. J. Pharmacol. 175, 1439 (2018) , (21) D. Wu, et al., Mediators Inflamm. 2018, 3048532 (2018) , (22) A. El-Bakoush & O.A. Olajide, Int. Immunopharmacol. 61, 325 (2018)
InChi: InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3

Formononetin is an isoflavonoid phytoestrogenic compound found in soy-based foods and is the precursor of daidzein. It acts as an agonist of the aryl hydrocarbon receptor and a selective inhibitor of ADH γ (the γ-isoform of alcohol dehydrogenase). It displays potent antitumor, antiviral, anti-inflammatory (inhibits NLRP3 inflammasome), antioxidant, neuroprotective and neuroinflammatory properties. Also shown to have vasorelaxant, antihypertensive and antihyperglycemic (AMPK activator) properties. Induces cell cycle arrest and apoptosis in several cancer cells in vitro and in vivo and shows anti-angiogenic (FGFR2 inhibitor), anti-invasive and anti-migratory effects. Increases adipocyte thermogenesis by modulating PPARγ activity. Shown to promote early fracture healing through stimulating angiogenesis by up-regulating VEGFR-2/Flk-1 and endothelial repair and wound healing in a process involving the over-expression of Egr-1 transcription factor through the regulation of the ERK1/2 and p38 MAPK pathways.

SKU: F0339 Category: Phytochemicals

Additional information

Additional information

Synonyms	Biochanin B, NSC 93360, 7-Hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 7-Hydroxy-3-(4-methoxyphenyl)chromone, 7-Hydroxy-4'-methoxyisoflavone
Purity	≥98% (HPLC)
Appearance	White to off-white powder
CAS-Number	485-72-3
Molecular Formula	C16H12O4
Molecular Weight	268.26
Identity	1H-NMR
Solvents	DMSO (30 mg/ml), DMF (30 mg/ml), ethanol (1 mg/ml)
Smiles	OC1=CC=C(C(C(C2=CC=C(OC)C=C2)=CO3)=O)C3=C1
InChi Key	HKQYGTCOTHHOMP-UHFFFAOYSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Transportation	Not dangerous goods
References	(1) W.M. Keung, BBRC 215, 1137 (1995), (2) S. Toda and Y. Shirataki, Phytother. Res. 13, 163 (1999), (3) C.K. Wong & W.M. Keung, J. Steroid Biochem. Mol. Biol. 71, 191 (1999), (4) B.L. Pool-Zobel, et al., Carcinogenesis 21, 1247 (2000), (5) S. Medjakovic & A. Jungbauer , J. Steroid Biochem. Mol. Biol 108, 171 (2008), (6) H. Mu, et al., Phytomedicine 16, 314 (2009), (7) J.E . Huh, et al., Int. Immunopharmacol. 9, 1357 (2009), (8) J.E . Huh, et al., Int. Immunopharmacol. 11, 46 (2011), (9) T. Sun, et al., Acta Pharmacol. Sin. 32, 1009 (2011), (10) J. Chen, et al., Horm. Metab. Res. 43, 681 (2011), (11) M. Sun, et al., J. Alzheimers Dis. 28, 795 (2012), (12) Y. Ye, et al., Horm. Metab. Res. 44, 263 (2012), (13) K.K. Auyeung, et al., Oncol. Rep. 28, 2188 (2012), (14) R. Zhou, et al., Horm. Metab. Res. 46, 753 (2014), (15) Y. Yang, et al., Int. J. Clin. Exp. Pathol. 7, 8453 (2014), (16) X.Y. Wu, et al., Oncotarget 6, 44563 (2015), (17) H. Wang, et al., Virol. J. 12, 1 (2015), (18) G. Qiu, et al., Exp. Biol. Med. 242, 223 (2017), (19) J. Gautam, et al., Br. J. Nutr. 117, 645 (2017), (20) T. Nie, et al., Br. J. Pharmacol. 175, 1439 (2018), (21) D. Wu, et al., Mediators Inflamm. 2018, 3048532 (2018), (22) A. El-Bakoush & O.A. Olajide, Int. Immunopharmacol. 61, 325 (2018)
InChi	InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
Quantity	50 mg, Bulk