Formononetin
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MedKoo CAT#: 540142

CAS#: 485-72-3

Description: Formononetin is found in Fabaceae (soy). It displays a wide variety of biological activityes, including decreasing expression of pro-imflammatory cytokines, incudicng apoptosis in prostate cancer cells, lowering systolic blood pressure and inhibiting attachment and motility of Giardia.

Chemical Structure

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Formononetin
CAS# 485-72-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540142
Name: Formononetin
CAS#: 485-72-3
Chemical Formula: C16H12O4
Exact Mass: 268.07
Molecular Weight: 268.260
Elemental Analysis: C, 71.64; H, 4.51; O, 23.86

Price and Availability

Size Price Availability Quantity
1g USD 280
5g USD 700
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Synonym: Biochanin B; Formononetol Formononetin; Formononetin; NSC 93360; NSC93360; NSC-93360

IUPAC/Chemical Name: 7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

InChi Key: HKQYGTCOTHHOMP-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=C1C(C2=CC=C(OC)C=C2)=COC3=CC(O)=CC=C13

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Formononetin (Formononetol; Flavosil) is a bioactive component extracted from the red clover; inhibits the proliferation of DU-145/PC-3 cells in a dose-dependent manner.
In vitro activity: Functionally, FMNT (formononetin) could protect against ox-LDL-induced inflammatory reaction, oxidative stress, and apoptosis in HUVECs. Moreover, FMNT attenuated ox-LDL-mediated inactivation of PPAR-γ signaling. Reference: Bioengineered. 2021 Dec;12(1):4887-4898. https://pubmed.ncbi.nlm.nih.gov/34369277/
In vivo activity: The results show that FMN (formononetin) alleviated ConA-induced liver injury of mice in a dose-dependent manner. Moreover, pretreatment with FMN inhibited the apoptosis of hepatocytes in the ConA-treated mice through downregulating the expression of pro-apoptotic proteins (Bax, cleaved caspase 9, and cleaved caspase 3) and upregulating the expression of anti-apoptotic protein (Bcl-2). It was also found that the levels of proinflammatory cytokines were greatly reduced in the serum and liver tissues of mice pretreated with FMN. Reference: Biochem Cell Biol. 2021 Apr;99(2):231-240. https://pubmed.ncbi.nlm.nih.gov/33749318/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 38.0 141.65
DMF 30.0 111.83
DMF:PBS (pH 7.2) (1:1) 0.5 1.86

Preparing Stock Solutions

The following data is based on the product molecular weight 268.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Zhang B, Hao Z, Zhou W, Zhang S, Sun M, Li H, Hou N, Jing C, Zhao M. Formononetin protects against ox-LDL-induced endothelial dysfunction by activating PPAR-γ signaling based on network pharmacology and experimental validation. Bioengineered. 2021 Dec;12(1):4887-4898. doi: 10.1080/21655979.2021.1959493. PMID: 34369277. 2. Wu J, Xu W, Ma L, Sheng J, Ye M, Chen H, Zhang Y, Wang B, Liao M, Meng T, Zhou Y, Chen H. Formononetin relieves the facilitating effect of lncRNA AFAP1-AS1-miR-195/miR-545 axis on progression and chemo-resistance of triple-negative breast cancer. Aging (Albany NY). 2021 Jul 21;13(14):18191-18222. doi: 10.18632/aging.203156. Epub 2021 Jul 21. PMID: 34289449; PMCID: PMC8351708. 3. Liu G, Zhao W, Bai J, Cui J, Liang H, Lu B. Formononetin protects against concanavalin-A-induced autoimmune hepatitis in mice through its anti-apoptotic and anti-inflammatory properties. Biochem Cell Biol. 2021 Apr;99(2):231-240. doi: 10.1139/bcb-2020-0197. Epub 2021 Mar 22. PMID: 33749318. 4. Li T, Zhang S, Chen F, Hu J, Yuan S, Li C, Wang X, Zhang W, Tang R. Formononetin ameliorates the drug resistance of Taxol resistant triple negative breast cancer by inhibiting autophagy. Am J Transl Res. 2021 Feb 15;13(2):497-514. PMID: 33594306; PMCID: PMC7868832.
In vitro protocol: 1. Zhang B, Hao Z, Zhou W, Zhang S, Sun M, Li H, Hou N, Jing C, Zhao M. Formononetin protects against ox-LDL-induced endothelial dysfunction by activating PPAR-γ signaling based on network pharmacology and experimental validation. Bioengineered. 2021 Dec;12(1):4887-4898. doi: 10.1080/21655979.2021.1959493. PMID: 34369277. 2. Wu J, Xu W, Ma L, Sheng J, Ye M, Chen H, Zhang Y, Wang B, Liao M, Meng T, Zhou Y, Chen H. Formononetin relieves the facilitating effect of lncRNA AFAP1-AS1-miR-195/miR-545 axis on progression and chemo-resistance of triple-negative breast cancer. Aging (Albany NY). 2021 Jul 21;13(14):18191-18222. doi: 10.18632/aging.203156. Epub 2021 Jul 21. PMID: 34289449; PMCID: PMC8351708.
In vivo protocol: 1. Liu G, Zhao W, Bai J, Cui J, Liang H, Lu B. Formononetin protects against concanavalin-A-induced autoimmune hepatitis in mice through its anti-apoptotic and anti-inflammatory properties. Biochem Cell Biol. 2021 Apr;99(2):231-240. doi: 10.1139/bcb-2020-0197. Epub 2021 Mar 22. PMID: 33749318. 2. Li T, Zhang S, Chen F, Hu J, Yuan S, Li C, Wang X, Zhang W, Tang R. Formononetin ameliorates the drug resistance of Taxol resistant triple negative breast cancer by inhibiting autophagy. Am J Transl Res. 2021 Feb 15;13(2):497-514. PMID: 33594306; PMCID: PMC7868832.

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1: Li S, Dang Y, Zhou X, Huang B, Huang X, Zhang Z, Kwan YW, Chan SW, Leung GP, Lee SM, Hoi MP. Formononetin promotes angiogenesis through the estrogen receptor alpha-enhanced ROCK pathway. Sci Rep. 2015 Nov 16;5:16815. doi: 10.1038/srep16815. PubMed PMID: 26568398; PubMed Central PMCID: PMC4645220.

2: Wu XY, Xu H, Wu ZF, Chen C, Liu JY, Wu GN, Yao XQ, Liu FK, Li G, Shen L. Formononetin, a novel FGFR2 inhibitor, potently inhibits angiogenesis and tumor growth in preclinical models. Oncotarget. 2015 Dec 29;6(42):44563-78. doi: 10.18632/oncotarget.6310. PubMed PMID: 26575424; PubMed Central PMCID: PMC4792576.

3: Wang H, Zhang D, Ge M, Li Z, Jiang J, Li Y. Formononetin inhibits enterovirus 71 replication by regulating COX- 2/PGE₂ expression. Virol J. 2015 Mar 1;12:35. doi: 10.1186/s12985-015-0264-x. PubMed PMID: 25890183; PubMed Central PMCID: PMC4351682.

4: Lima Cavendish R, de Souza Santos J, Belo Neto R, Oliveira Paixão A, Valéria Oliveira J, Divino de Araujo E, Berretta E Silva AA, Maria Thomazzi S, Cordeiro Cardoso J, Zanardo Gomes M. Antinociceptive and anti-inflammatory effects of Brazilian red propolis extract and formononetin in rodents. J Ethnopharmacol. 2015 Sep 15;173:127-33. doi: 10.1016/j.jep.2015.07.022. Epub 2015 Jul 17. PubMed PMID: 26192808.

5: Zhou R, Xu L, Ye M, Liao M, Du H, Chen H. Formononetin inhibits migration and invasion of MDA-MB-231 and 4T1 breast cancer cells by suppressing MMP-2 and MMP-9 through PI3K/AKT signaling pathways. Horm Metab Res. 2014 Oct;46(11):753-60. doi: 10.1055/s-0034-1376977. Epub 2014 Jun 30. PubMed PMID: 24977660.

6: Hu W, Xiao Z. Formononetin induces apoptosis of human osteosarcoma cell line U2OS by regulating the expression of Bcl-2, Bax and MiR-375 in vitro and in vivo. Cell Physiol Biochem. 2015;37(3):933-9. doi: 10.1159/000430220. Epub 2015 Sep 18. PubMed PMID: 26381132.

7: Li T, Zhao X, Mo Z, Huang W, Yan H, Ling Z, Ye Y. Formononetin promotes cell cycle arrest via downregulation of Akt/Cyclin D1/CDK4 in human prostate cancer cells. Cell Physiol Biochem. 2014;34(4):1351-8. doi: 10.1159/000366342. Epub 2014 Oct 2. PubMed PMID: 25301361.

8: Liu Q, Sun Y, Zheng JM, Yan XL, Chen HM, Chen JK, Huang HQ. Formononetin sensitizes glioma cells to doxorubicin through preventing EMT via inhibition of histone deacetylase 5. Int J Clin Exp Pathol. 2015 Jun 1;8(6):6434-41. eCollection 2015. PubMed PMID: 26261519; PubMed Central PMCID: PMC4525853.

9: Yang Y, Zhao Y, Ai X, Cheng B, Lu S. Formononetin suppresses the proliferation of human non-small cell lung cancer through induction of cell cycle arrest and apoptosis. Int J Clin Exp Pathol. 2014 Dec 1;7(12):8453-61. eCollection 2014. PubMed PMID: 25674209; PubMed Central PMCID: PMC4313991.

10: Andersen C, Kotowska D, Tortzen CG, Kristiansen K, Nielsen J, Petersen RK. 2-(2-Bromophenyl)-formononetin and 2-heptyl-formononetin are PPARγ partial agonists and reduce lipid accumulation in 3T3-L1 adipocytes. Bioorg Med Chem. 2014 Nov 1;22(21):6105-11. doi: 10.1016/j.bmc.2014.08.037. Epub 2014 Sep 8. PubMed PMID: 25262940.

11: Liu Y, He J, Chen X, Li J, Shen M, Yu W, Yang Y, Xiao Z. The proapoptotic effect of formononetin in human osteosarcoma cells: involvement of inactivation of ERK and Akt pathways. Cell Physiol Biochem. 2014;34(3):637-45. doi: 10.1159/000363029. Epub 2014 Aug 12. PubMed PMID: 25170541.

12: Sun T, Cao L, Ping NN, Wu Y, Liu DZ, Cao YX. Formononetin upregulates nitric oxide synthase in arterial endothelium through estrogen receptors and MAPK pathways. J Pharm Pharmacol. 2016 Mar;68(3):342-51. doi: 10.1111/jphp.12519. Epub 2016 Jan 20. PubMed PMID: 26786718.

13: Chen J, Zhang X, Wang Y, Ye Y, Huang Z. Formononetin promotes proliferation that involves a feedback loop of microRNA-375 and estrogen receptor alpha in estrogen receptor-positive cells. Mol Carcinog. 2016 Mar;55(3):312-9. doi: 10.1002/mc.22282. Epub 2015 Feb 7. PubMed PMID: 25663261.

14: Kim MH, Choi YY, Lee JE, Kim K, Yang WM. Topical Treatment of Hair Loss with Formononetin by Modulating Apoptosis. Planta Med. 2016 Jan;82(1-2):65-9. doi: 10.1055/s-0035-1557897. Epub 2016 Jan 12. PubMed PMID: 26756818.

15: Chen Z, Liu S, Cai Y, Xie K, Zhang W, Dong L, Liu Y, Zheng F, Dun Y, Li N. Suppressive effect of formononetin on platelet-derived growth factor-BB-stimulated proliferation and migration of vascular smooth muscle cells. Exp Ther Med. 2016 Sep;12(3):1901-1907. Epub 2016 Jul 13. PubMed PMID: 27588108; PubMed Central PMCID: PMC4997992.

16: Liang K, Ye Y, Wang Y, Zhang J, Li C. Formononetin mediates neuroprotection against cerebral ischemia/reperfusion in rats via downregulation of the Bax/Bcl-2 ratio and upregulation PI3K/Akt signaling pathway. J Neurol Sci. 2014 Sep 15;344(1-2):100-4. doi: 10.1016/j.jns.2014.06.033. Epub 2014 Jun 22. PubMed PMID: 24996490.

17: Zhu H, Zou L, Tian J, Lin F, He J, Hou J. Protective effects of sulphonated formononetin in a rat model of cerebral ischemia and reperfusion injury. Planta Med. 2014 Mar;80(4):262-8. doi: 10.1055/s-0033-1360340. Epub 2014 Feb 18. PubMed PMID: 24549929.

18: Jia WC, Liu G, Zhang CD, Zhang SP. Formononetin attenuates hydrogen peroxide (H2O2)-induced apoptosis and NF-κB activation in RGC-5 cells. Eur Rev Med Pharmacol Sci. 2014;18(15):2191-7. PubMed PMID: 25070826.

19: Liu XJ, Li YQ, Chen QY, Xiao SJ, Zeng SE. Up-regulating of RASD1 and apoptosis of DU-145 human prostate cancer cells induced by formononetin in vitro. Asian Pac J Cancer Prev. 2014;15(6):2835-9. PubMed PMID: 24761910.

20: Lo YL, Wang W. Formononetin potentiates epirubicin-induced apoptosis via ROS production in HeLa cells in vitro. Chem Biol Interact. 2013 Oct 5;205(3):188-97. doi: 10.1016/j.cbi.2013.07.003. Epub 2013 Jul 16. PubMed PMID: 23867903.