formononetin
isoflavone, 7-hydroxy-4'-methoxy-

Sponsors

Name: 7-hydroxy-3-(4-methoxyphenyl)chromen-4-one
CAS Number: 485-72-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 207-623-9
FDA UNII: 295DQC67BJ
Nikkaji Web: J12.525C
Beilstein Number: 237979
MDL: MFCD00016948
XlogP3-AA: 2.80 (est)
Molecular Weight: 268.26844000
Formula: C16 H12 O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidants, skin conditioning, skin protecting
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 256.50 °C. @ 760.00 mm Hg
Boiling Point: 479.40 °C. @ 760.00 mm Hg (est)
Flash Point: 362.00 °F. TCC ( 183.40 °C. ) (est)
logP (o/w): 2.960 (est)
Soluble in:
 water, 157.3 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
skin conditioning
skin protecting agents
 
Suppliers:
BOC Sciences
For experimental / research use only.
Formonentin >98%
Odor: characteristic
Use: Formononetin is a phytoestrogen from the root of Astragalus membranaceus and an O-methylated isoflavone.
Coompo
For experimental / research use only.
Formononetin from Plants ≥99%
Odor: characteristic
Use: Formononetin increases soluble-AβPPa (sAβPPa) secretion and thus protects human-AβPP Swedish mutation cell (N2a-AβPP cell) from hypoxia-induced apoptosis. Using hypoxic N2a-AβPP cell as an in vitro model of AD-like pathology, we confirmed that regular treatment with formononetin could have neuroprotective effects, followed respectively by reduced caspase 3 activity and increased cell viability. Strikingly, our data revealed that the caspase 3-blocking effect of formononetin was largely mediated by stimulation of a-secretase cleavage of AβPP, and increasing the secretion of its soluble form, sAβPPa. Moreover, the protective effect of formononetin was totally inhibited by TAPI-2, an a-secretase complex inhibitor, suggesting the role of the sAβPPa pathway in the neuroprotective response to formononetin. We also found that the stimulative effect of formononetin on a-secretase activity was mainly conducted by upregulating ADAM10 expression at the transcriptional level. Altogether, our study provides novel insights into how formononetin mediates stimulation of the ADAM10-sAβPPa pathway and exerts a neuronal protective effect. Formononetin significantly increased growth factors such as transforming growth factor-beta 1 (TGF-β1), vascular endothelial growth factor (VEGF), platelet-derived growth factor (PDGF) and basic fibroblast growth factor (bFGF) in human umbilical vein endothelial cells (HUVECs). Formononetin also increased the expression of Egr-1 transcription factor by 3.2- and 10.5-fold, compared with recombinant VEGF125 in HUVECs. The formononetin-mediated 12%43% increase induced endothelial cell proliferation and recovered the migration of wounded HUVECs. In an ex vivo angiogenesis assay, formononetin produced a larger capillary sprouting area than produced using recombinant VEGF125. Cell proliferation and migration of HUVECs were also greater in the presence of formonectin than VEGF125. Western blot analysis of scratch-wounded confluent HUVECs showed that formononetin induced the phosphorylation of extracellular signal-regulated kinase (ERK) and slightly inhibited the phosphorylation of p38 mitogen-activated protein kinase (MAPK). The formononetin-mediated sustained activation of Egr-1 was suppressed by the ERK inhibitor PD98059 and the p38 inhibitor SB203580. PD98059 inhibited the formononetin-induced endothelial proliferation and repair in scratch-wounded HUVECs, SB203580 increased the cell proliferation and wound healing. Formononetin accelerate wound closure rate as early as day 3 after surgery and consistently observed until day 10 after in wound animal model. These data suggest that formononetin promotes endothelial repair and wound healing in a process involving the over-expression of Egr-1 transcription factor through the regulation of the ERK1/2 and p38 MAPK pathways. Formononetin causes vasodilatation via two pathways: (1) endothelium-independent pathway, probably due to inhibition of voltage-dependent Ca2+ channels and intracellular Ca2+ release; and (2) endothelium-dependent pathway by releasing NO. Both the pathways may contribute to its antihypertensive effect.
EMD Millipore
For experimental / research use only.
Formononetin
ExtraSynthese
For experimental / research use only.
Formononetin (HPLC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Formononetin ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Formononetin ≥99.0% (TLC)
TCI AMERICA
For experimental / research use only.
Formononetin >98.0%(HPLC)(T)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: antioxidants, skin conditioning, skin protecting
Recommendation for formononetin usage levels up to:
 not for fragrance use.
 
Recommendation for formononetin flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):
Preparatory work to support the risk assessment for peri- and postmenopausal women taking food supplements containing isolated isoflavones
View page or View pdf
Risk assessment for peri- and post-menopausal women taking food supplements containing isolated isoflavones
View page or View pdf
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5280378
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 7-hydroxy-3-(4-methoxyphenyl)chromen-4-one
Chemidplus: 0000485723
RTECS: DJ3100114 for cas# 485-72-3
 
References:
 7-hydroxy-3-(4-methoxyphenyl)chromen-4-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5280378
Pubchem (sid): 135023641
 
Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C00858
HMDB (The Human Metabolome Database): HMDB05808
FooDB: FDB012219
Export Tariff Code: 2932.99.7000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other): note
 baboonwood
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 bean mung bean
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 bean mung bean plant
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 chickpea seed
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 clover red clover
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 fenugreek
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 fenugreek plant
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 pea
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 soybean seed
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 soybean shoot
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Synonyms:
4H-1-benzopyran-4-one, 7-hydroxy-3- (4-methoxyphenyl)-
4H-1-benzopyran-4-one, 7-hydroxy-3-(4-methoxyphenyl)-
4H-1-benzopyran-4-one, 7-hydroxy-3-(4-methoxyphenyl)- (9CI)
 biochanin B
isoflavone, 7-hydroxy-4'-methoxy-
isoflavone, 7-hydroxy-4'-methoxy- (8CI)
 formonetin
 formonoetin
 formononectin
 formononetine
 formononetol
7-hydroxy-3-(4-methoxy-phenyl)-chromen-4-one
7-hydroxy-3-(4-methoxyphenyl)-4-benzopyrone
7-hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
7-hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one
7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-on
7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
7-hydroxy-3-(4-methoxyphenyl)chromen-4-one
7-hydroxy-3-(4-methoxyphenyl)chromone
7-hydroxy-3-(4'-methoxyphenyl)-4H-benzopyran-4-one
7-hydroxy-4'-methoxy-Isoflavone (8CI)
7-hydroxy-4'-methoxyisoflavanone
7-hydroxy-4'-methoxyisoflavone
7-hydroxy-4'-methoxyisoflavone*4'-O-methyldaidzein
 neochanin
 

Articles:

PubMed: Investigation of antioxidant interactions between Radix Astragali and Cimicifuga foetida and identification of synergistic antioxidant compounds.
PubMed: Comparative studies on the constituents, antioxidant and anticancer activities of extracts from different varieties of corn silk.
PubMed: The isoflavone irilone contributes to the estrogenic potential of dietary supplements containing red clover.
PubMed: Development of a food compositional database for the estimation of dietary intake of phyto-oestrogens in a group of postmenopausal women previously treated for breast cancer and validation with urinary excretion.
PubMed: A modified QuEChERS method as sample treatment before the determination of isoflavones in foods by ultra-performance liquid chromatography-triple quadrupole mass spectrometry.
PubMed: Distribution of isoflavones and coumestrol in neglected tropical and subtropical legumes.
PubMed: Germination dramatically increases isoflavonoid content and diversity in chickpea (Cicer arietinum L.) seeds.
PubMed: The membrane permeability of Astragali Radix-derived formononetin and calycosin is increased by Angelicae Sinensis Radix in Caco-2 cells: a synergistic action of an ancient herbal decoction Danggui Buxue Tang.
PubMed: Effects of sodium metavanadate and germination on the sprouting of chickpeas and its content of vanadium, formononetin and biochanin A in the sprouts.
PubMed: Effects of sodium selenite and germination on the sprouting of chickpeas (Cicer arietinum L.) and its content of selenium, formononetin and biochanin A in the sprouts.
PubMed: Condensed tannins and flavonoids from the forage legume sulla (Hedysarum coronarium).
PubMed: Association between dietary phyto-oestrogens and bone density in men and postmenopausal women.
PubMed: Occurrence and mass balance of isoflavones on an experimental grassland field.
PubMed: Phytoestrogen intake and cardiovascular risk markers in Bangladeshi postmenopausal women.
PubMed: ZnO-ZnS QDs interfacial heterostructure for drug and food delivery application: enhancement of the binding affinities of flavonoid aglycones to bovine serum albumin.
PubMed: Flavonoids from Radix Astragali induce the expression of erythropoietin in cultured cells: a signaling mediated via the accumulation of hypoxia-inducible factor-1α.
PubMed: PAMPA permeability, plasma protein binding, blood partition, pharmacokinetics and metabolism of formononetin, a methoxylated isoflavone.
PubMed: HPLC/DAD/MS and antioxidant activity of isoflavone-based food supplements.
PubMed: Quantification of five isoflavones and coumestrol in various solid agroenvironmental matrices using ¹³c₃-labeled internal standards.
PubMed: Yeast α-glucosidase inhibition by isoflavones from plants of Leguminosae as an in vitro alternative to acarbose.
PubMed: Differential effects of formononetin and cladrin on osteoblast function, peak bone mass achievement and bioavailability in rats.
PubMed: Study on the relevance between beany flavor and main bioactive components in Radix Astragali.
PubMed: Red clover (Trifolium pratense L.) isoflavones: root phenolic compounds affected by biotic and abiotic stress factors.
PubMed: Isoflavones in coffee: influence of species, roast degree, and brewing method.
PubMed: Breast, colorectal, and prostate cancer risk in the European Prospective Investigation into Cancer and Nutrition-Norfolk in relation to phytoestrogen intake derived from an improved database.
PubMed: Anticancer effects of flavonoid derivatives isolated from Millettia reticulata Benth in SK-Hep-1 human hepatocellular carcinoma cells.
PubMed: Enhancement of the encapsulation and transmembrane permeation of isoflavone-containing red clover extracts in phospholipid-based microemulsions using different extraction processes.
PubMed: Inhibition of angiogenesis and inflammation by an extract of red clover (Trifolium pratense L.).
PubMed: Equol in milk of dairy cows is derived from forage legumes such as red clover.
PubMed: Stimulating effects of Bacillus subtilis natto-fermented Radix astragali on hyaluronic acid production in human skin cells.
PubMed: [Synthesis, solubility, lipids-lowering and liver-protection activities of sulfonated formononetin].
PubMed: Effect of an isoflavones-containing red clover preparation and alkaline supplementation on bone metabolism in ovariectomized rats.
PubMed: Phytoestrogen content of cereals and cereal-based foods consumed in the UK.
PubMed: Effect of forage on the content of phyto-oestrogens in bovine milk.
PubMed: Astragalus membranaceus flavonoids (AMF) ameliorate chronic fatigue syndrome induced by food intake restriction plus forced swimming.
PubMed: Phytoestrogen content of foods of animal origin: dairy products, eggs, meat, fish, and seafood.
PubMed: Protective effect of isoflavones from Trifolium pratense on dopaminergic neurons.
PubMed: Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr. et Maxim.
PubMed: Dietary flavonoids and colorectal adenoma recurrence in the Polyp Prevention Trial.
PubMed: Determination of phytoestrogens in dietary supplements by LC-MS/MS.
PubMed: Phenolic compounds contribute to dark bran pigmentation in hard white wheat.
PubMed: Dietary phytoestrogens, including isoflavones, lignans, and coumestrol, in nonvitamin, nonmineral supplements commonly consumed by women in Canada.
PubMed: Quantification of six phytoestrogens at the nanogram per liter level in aqueous environmental samples using 13C3-labeled internal standards.
PubMed: Analysis of flavonoid phytoestrogens in botanical and ephedra-containing dietary supplements.
PubMed: High levels of equol in organic skimmed Finnish cow milk.
PubMed: [Study on the chemical constituents of flavones from corn silk].
PubMed: Anti-oxidant constituents of the roots and stolons of licorice (Glycyrrhiza glabra).
PubMed: Blockade of cytokine-induced endothelial cell adhesion molecule expression by licorice isoliquiritigenin through NF-kappaB signal disruption.
PubMed: Estimated intakes of isoflavones and coumestrol in Korean population.
PubMed: Quantification and stability studies on the flavonoids of Radix hedysari.
PubMed: Analysis of isoflavones in foods and dietary supplements.
PubMed: Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan.
PubMed: Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages.
PubMed: The isoflavone content of commercially-available feline diets in New Zealand.
PubMed: Inverse association of antioxidant and phytoestrogen nutrient intake with adult glioma in the San Francisco Bay Area: a case-control study.
PubMed: Isoflavonoids are present in Arabidopsis thaliana despite the absence of any homologue to known isoflavonoid synthases.
PubMed: Evaluation of the botanical authenticity and phytochemical profile of black cohosh products by high-performance liquid chromatography with selected ion monitoring liquid chromatography-mass spectrometry.
PubMed: Antioxidant activity of isoflavones and their major metabolites using different in vitro assays.
PubMed: Thermal degradation kinetics of isoflavone aglycones from soy and red clover.
PubMed: Chemical and biological assessment of a chinese herbal decoction containing Radix Astragali and Radix Angelicae Sinensis: Determination of drug ratio in having optimized properties.
PubMed: High performance liquid chromatographic analysis of isoflavones in medicinal herbs.
PubMed: Seasonal variation of red clover (Trifolium pratense L., Fabaceae) isoflavones and estrogenic activity.
PubMed: Determination of isoflavones in dietary supplements containing soy, Red Clover and kudzu: extraction followed by basic or acid hydrolysis.
PubMed: Suppression of arachidonic acid metabolism and nitric oxide formation by kudzu isoflavones in murine macrophages.
PubMed: Red clover Trifolium pratense L. phytoestrogens: UV-B radiation increases isoflavone yield, and postharvest drying methods change the glucoside conjugate profiles.
PubMed: Supercritical fluid extraction of isoflavones from biological samples with ultra-fast high-performance liquid chromatography/mass spectrometry.
PubMed: Effects of the environment, cultivar, maturity, and preservation method on red clover isoflavone concentration.
PubMed: Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense).
PubMed: Isoflavones modulate the glucuronidation of estradiol in human liver microsomes.
PubMed: Evaluation of isoflavone aglycon and glycoside distribution in soy plants and soybeans by fast column high-performance liquid chromatography coupled with a diode-array detector.
PubMed: In vitro free radical and ONOO- scavengers from Sophora flavescens.
PubMed: Phytoestrogens derived from red clover: an alternative to estrogen replacement therapy?
PubMed: Identification of urinary metabolites of the red clover isoflavones formononetin and biochanin A in human subjects.
PubMed: Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover).
PubMed: Assessment of the reactivity of selected isoflavones against proteins in comparison to quercetin.
PubMed: LC/UV/ESI-MS analysis of isoflavones in Edamame and Tofu soybeans.
PubMed: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry.
PubMed: Phyto-oestrogen levels in foods: the design and construction of the VENUS database.
PubMed: Oxidative metabolism and genotoxic potential of major isoflavone phytoestrogens.
PubMed: Metabolism of biochanin A and formononetin by human liver microsomes in vitro.
PubMed: Intake of dietary phytoestrogens by Dutch women.
PubMed: Quantification of the group B soyasaponins by high-performance liquid chromatography.
PubMed: Intake of dietary phytoestrogens is low in postmenopausal women in the United States: the Framingham study(1-4).
PubMed: Quantitative determination of isoflavones and coumestrol in soybean by column liquid chromatography.
PubMed: Assessing phytoestrogen exposure in epidemiologic studies: development of a database (United States).
PubMed: LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense).
PubMed: Synthesis of haptens and conjugates for ELISAs of phytoestrogens. Development of the immunological tests.
PubMed: Development of a simple method for the determination of genistein, daidzein, biochanin A, and formononetin (biochanin B) in human urine.
PubMed: Phytoestrogen content of purified, open- and closed-formula laboratory animal diets.
PubMed: Phytoestrogen content in foods.
PubMed: Isoflavones in human breast milk and other biological fluids.
PubMed: Phytoestrogens have agonistic and combinatorial effects on estrogen-responsive gene expression in MCF-7 human breast cancer cells.
PubMed: Isoflavone content of infant foods and formulas.
PubMed: Isotope dilution gas chromatographic-mass spectrometric method for the determination of isoflavonoids, coumestrol, and lignans in food samples.
PubMed: Phytoestrogen content of foods--a compendium of literature values.
PubMed: Rapid HPLC analysis of dietary phytoestrogens from legumes and from human urine.
PubMed: High-performance liquid chromatographic analysis of phytoestrogens in soy protein preparations with ultraviolet, electrochemical and thermospray mass spectrometric detection.
PubMed: Oestrogenic activity of soya-bean products.
PubMed: Phytoestrogens: adverse effects on reproduction in California quail.
 
Notes:
intermediate to formation of rotenone; has a deleterious effect on sheep grazing in "estrogenic clover" pastures. Widespread isoflavone found in soy beans (Glycine max), red clover (Trifolium pratense and chick peas (Cicer arietinum). Potential nutriceutical Formononetin are abundant in vegetables. It is a phyto-oestrogen that is a polyphenolic non-steroidal plant compound with oestrogen-like biological activity (PMID: 16108819). It can be the source of considerable estrogenic activity (http://www.herbalchem.net/Intermediate.htm).
 
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