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47752

Sigma-Aldrich

Formononetin

≥99.0% (TLC)

Synonyme(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

Formule empirique (notation de Hill):
C16H12O4
Numéro CAS:
485-72-3
Poids moléculaire :
268.26
Numéro Beilstein :
237979
Numéro CE :
207-623-9
Numéro MDL:
MFCD00016948
Code UNSPSC :
12352200
ID de substance PubChem :
57651100
Nomenclature NACRES :
NA.47

Pureté

≥99.0% (TLC)

Forme

solid

Pf

257-261 °C

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Chaîne 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

Clé InChI

HKQYGTCOTHHOMP-UHFFFAOYSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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
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
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
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
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