Structure via PubChem · Public domain (PubChem)
genistein
Sign in to saveAlso known as 5,7,4'-trihydroxyisoflavone, 4',5,7-trihydroxyisoflavone, Differenol A, 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, Sophoricol, 4',5, 7-Trihydroxyisoflavone, Prunetol, Genisterin
Genistein (C15H10O5) is a plant-derived, aglycone isoflavone. Genistein has the highest content of all isoflavones in soybeans and soy products, such as tempeh. As a type of phytoestrogen, genistein is classed as an endocrine disrupting chemical due to its estrogenic activity in vitro and in vivo. Consequently, excessive consumption of soy products has been linked to disruption of the reproductive organs, such as the uterus, breast, and testis.
Chemical data
- Formula
- C15H10O5
- Molecular weight
- 270.24 g/mol
- IUPAC name
- 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
- SMILES
- C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
- InChIKey
- TZBJGXHYKVUXJN-UHFFFAOYSA-N
- XLogP
- 2.7
- Polar surface area
- 87 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
13,909 papers- Genistein.Phytochemistry · 2002
- Genistein: Dual Role in Women's Health.Nutrients · 2021
- Genistein Effects on Various Human Disorders Mediated via Nrf2 Signaling.Current molecular medicine · 2024
- Genistein: A promising phytoconstituent with reference to its bioactivities.Phytotherapy research : PTR · 2024
- Effects of Genistein on Common Kidney Diseases.Nutrients · 2022
via PubMed
Wikidata facts
- Subclass of
- isoflavone
- Has part
- carbon
- Mass
- 270.053
Show 8 more facts
- melting point
- 300
- subject has role
- metabolite
- chemical formula
- C₁₅H₁₀O₅
- canonical SMILES
- C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
- Commons category
- Genistein
- found in taxon
- broad bean
- different from
- genistin
- has characteristic
- bitterness
via Wikidata · CC0
~6 min read
Encyclopedic overview
11 sectionsContents
- Natural occurrence
- In soybean products
- Biosynthesis
- Metabolism, bioavailability, and safety
- Potential for estrogenic activity
- Human research
- Laboratory research
- Anthelmintic
- Related compounds
- See also
- References
Genistein (C15H10O5) is a plant-derived, aglycone isoflavone. Genistein has the highest content of all isoflavones in soybeans and soy products, such as tempeh. As a type of phytoestrogen, genistein is classed as an endocrine disrupting chemical due to its estrogenic activity in vitro and in vivo. Consequently, excessive consumption of soy products has been linked to disruption of the reproductive organs, such as the uterus, breast, and testis.
It was first isolated in 1899 from the dyer's broom, Genista tinctoria; hence, the chemical name. The compound structure was established in 1926, when it was found to be identical with that of prunetol. It was chemically synthesized in 1928. Genistein is a primary secondary metabolite of the Trifolium species and Glycine max (soy).
Excerpted from Wikipedia’s “genistein” article, available under the CC BY-SA 4.0 licence.