47752
Formononetin
≥99.0% (TLC)
Synonym(s):
7-Hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 7-Hydroxy-3-(4-methoxyphenyl)chromone, 7-Hydroxy-4′-methoxyisoflavone, Biochanin B, Daidzein 4′-methyl ether, Formonetin, Formononetol
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About This Item
Empirical Formula (Hill Notation):
C16H12O4
CAS Number:
Molecular Weight:
268.26
UNSPSC Code:
12352200
NACRES:
NA.47
PubChem Substance ID:
EC Number:
207-623-9
Beilstein/REAXYS Number:
237979
MDL number:
Quality Level
assay
≥99.0% (TLC)
form
solid
mp
257-261 °C
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
SMILES string
COc1ccc(cc1)C2=COc3cc(O)ccc3C2=O
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
InChI key
HKQYGTCOTHHOMP-UHFFFAOYSA-N
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General description
Formononetin is an O-methylated isoflavone, a phytoestrogen. It can be found in many legumes, different species of clovers primarily in Trifolium pratense L. (red clovers), and one of the main flavonoids found in Astragalus membranaceus (Huangqi).
Application
Formononetin has been used:
- as a reference standard to study export of multiple metabolites from Crocus sativus stigma extracts using liquid chromatography-photodiode array-high resolution mass spectrometry (LC-PDA-HRMS)
- as phytoestrogen-mimetic isoflavones to test its antioxidant effects in a biomimetic environment using chemiluminescence method
- as an authentic standard to test the isoflavones content level in both wild type and transgenic Medicago truncatula plant using high-performance liquid chromatography (HPLC)
- to test its effects as a potential Aryl hydrocarbon receptor (AhR)-agonist on the restoration of skin barrier proteins for Atopic dermatitis (AD) treatment using different keratinocyte cell lines and human skin equivalent (HSE) model
Biochem/physiol Actions
Formononetin elicits antioxidant, anti-inflammatory, anti-hyperlipidemic, and cardioprotective effects. It displays antidiabetic properties known to be effective against diabetic nephropathy in type 2 diabetes mellitus. Formononetin is a well-known anti-cancer and chemotherapeutic agent that is used in cancer therapy. It also displays antimicrobial, neuroprotective, and anti-hypertensive properties.
Isoflavone found in red clover. Effective against Giardia lamblia infection, at least partially by inducing detachment of trophozoites from intestinal mucosa.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Abdul Malik Tyagi et al.
Menopause (New York, N.Y.), 19(8), 856-863 (2012-07-12)
Formononetin (Formo) prevents ovariectomy (Ovx)-induced bone loss in rats. However, there are no reports on the curative effects of Formo. The objective of this study was to investigate the ability of Formo in restoring trabecular microarchitecture and promoting new bone
Feng Xu et al.
Drug metabolism and disposition: the biological fate of chemicals, 34(6), 913-924 (2006-03-02)
To profile absorption of Astragali Radix decoction and identify its orally absorbable constituents and their metabolites, four complementary in silico, in vitro, and in vivo methods, i.e., a computational chemistry prediction method, a Caco-2 cell monolayer model experiment, an improved
Kai-Ching Tay et al.
Frontiers in pharmacology, 10, 820-820 (2019-08-14)
Cancer, a complex yet common disease, is caused by uncontrolled cell division and abnormal cell growth due to a variety of gene mutations. Seeking effective treatments for cancer is a major research focus, as the incidence of cancer is on
Olivia Costantina Demurtas et al.
The Plant cell, 31(11), 2789-2804 (2019-09-25)
Compartmentation is a key strategy enacted by plants for the storage of specialized metabolites. The saffron spice owes its red color to crocins, a complex mixture of apocarotenoid glycosides that accumulate in intracellular vacuoles and reach up to 10% of
Juliana Machado Dutra et al.
Food chemistry, 359, 129975-129975 (2021-05-08)
Formononetin (FORM) is an isoflavone from the group of phytoestrogens that exhibits a broad spectrum of physiological effects beneficial to health through dependent and independent mechanisms of estrogen. This article aimed to present FORM main functions and future prospects for
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