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Merck

47752

Sigma-Aldrich

Formononetin

≥99.0% (TLC)

Synonim(y):

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

Wzór empiryczny (zapis Hilla):
C16H12O4
Numer CAS:
Masa cząsteczkowa:
268.26
Beilstein:
237979
Numer WE:
Numer MDL:
Kod UNSPSC:
12352200
Identyfikator substancji w PubChem:
NACRES:
NA.47

Próba

≥99.0% (TLC)

Postać

solid

mp

257-261 °C

Zastosowanie

metabolomics
vitamins, nutraceuticals, and natural products

ciąg SMILES

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

Klucz InChI

HKQYGTCOTHHOMP-UHFFFAOYSA-N

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Opis ogólny

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).

Zastosowanie

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

Działania biochem./fizjol.

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.

Opakowanie

Bottomless glass bottle. Contents are inside inserted fused cone.
This page may contain text that has been machine translated.

Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

dust mask type N95 (US), Eyeshields, Gloves


Certyfikaty analizy (CoA)

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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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Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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