Basic information
- CAS
485-72-3- Standard SMILES
COc1ccc(-c2coc3cc(O)ccc3c2=O)cc1- InChIKey
HKQYGTCOTHHOMP-UHFFFAOYSA-N- Molecular formula
- C16H12O4
- Average molar mass
- 268.26 g/mol
- Monoisotopic mass
- 268.07355886
Overview
Formononetin is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by a methoxy group at position 4'. It has a role as a plant metabolite and a phytoestrogen. It is a member of 4'-methoxyisoflavones and a member of 7-hydroxyisoflavones. It is functionally related to a daidzein. It is a conjugate acid of a formononetin(1-).
Names & identifiers
- Preferred name
- Formononetin
- IUPAC
- 7-hydroxy-3-(4-methoxyphenyl)chromen-4-one
- English name
- Formononetin
- Molecular formula
- C16H12O4
- Molecular weight
- 268.26
Names & synonyms
formononetin485-72-3Biochanin BFormononetol7-Hydroxy-4'-methoxyisoflavone7-hydroxy-3-(4-methoxyphenyl)chromen-4-oneFlavosilMyconateNeochaninMycotech4'-O-methyldaidzeinDTXSID4022311
Show more names
FormononetineForMonentinFormononetin (50 mg)biocanin
NSC-93360295DQC67BJCHEBI:180887-hydroxy-4'-methoxy-isoflavoneDTXCID502311RefChem:5842207-623-97-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Database identifiers
- CAS
485-72-3- PubChem CID
- 5280378
- DTXSID
DTXSID4022311- ChEMBL
CHEMBL242341- ChEBI
CHEBI:18088- UNII
- 295DQC67BJ
- EC Number
- 207-623-9
- Nikkaji
- J12.525C
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 395
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]
CosmeticsPersonal care product
LogP3.32
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point256 - 258 °C
Physical DescriptionSolid
Collision Cross Section
171.4 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID4022311]
156.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
169.04 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
155.34 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
168.5 Ų [M-H]-
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (97.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 14-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25409
Hazard Classes and CategoriesSkin Irrit. 2 (97.7%)
Safety data
- wgk
- 3
- rtecs
- DJ3100114
- hs_code
- 29329990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 37/39-26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- REACH Registrations
- Inactive
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Chemistry & industry
Pharmacology
Metabolism/MetabolitesFormononetin has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid and Daidzein.
MeSH Pharmacological ClassificationCompounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.
Cellular LocationsMembrane
Applications
DescriptionFormononetin (485-72-3) is a naturally occurring isoflavone isolated from Astragalus and other plants. Increases adipocyte thermogenesis by modulating PPARγ activity.1Activates AMP-activated protein kinase/β-catenin signaling to inhibit adipogenesis.2Accelerates wound repair by increasing expression of Egr-1 transcription factor.3Potential cancer chemopreventive and chemotherapeutic.4Provides neuroprotection against traumatic brain injury by inhibition of neuroinflammation in a rat model.5
UsesAn isoflavone found in a variety of plants. When metabolized in the rumen this compound transforms into a potent estrogen.
UsesFormononetin is an isoflavone found as one of the main plant estrogens in animal feed. When metabolized in the rumen this compound transforms into a potent estrogen.
UsesFormononetin is an isoflavonoid phytoestrogenic compound found in soy-based foods and is the precursor of daidzein . It acts as an agonist of the aryl hydrocarbon receptor with an EC50 value of 0.13 μM. Formononetin has been reported to possess antitumor and antiviral activity.
General DescriptionFormononetin belongs to the isoflavones class of polyphenols.
Upstream & downstream products
Upstream raw materials
Related reactions
8 records
Compound notes
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