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:
Product Name
Formononetin, ≥99.0% (TLC)
InChI key
HKQYGTCOTHHOMP-UHFFFAOYSA-N
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 string
COc1ccc(cc1)C2=COc3cc(O)ccc3C2=O
assay
≥99.0% (TLC)
form
solid
mp
257-261 °C
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
Quality Level
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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.
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).
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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Tao Sun et al.
Acta pharmacologica Sinica, 32(8), 1009-1018 (2011-08-06)
To investigate the mechanisms underlying the vasorelaxant effect of formononetin, an O-methylated isoflavone, in isolated arteries, and its antihypertensive activity in vivo. Arterial rings of superior mesenteric arteries, renal arteries, cerebral basilar arteries, coronary arteries and abdominal aortas were prepared
Jangho Lee et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 81, 153418-153418 (2020-12-11)
Atopic dermatitis (AD) is an inflammatory chronic skin disease that is characterized by the dysfunction or lack of skin barrier proteins. Recent studies have proposed that the pharmacological upregulation of skin barrier proteins is an effective treatment for AD. Aryl
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
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
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
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