G6649

Genistein

≥98% (HPLC), powder, tyrosine protein kinase inhibitor

• Synonym(s): 4′,5,7-Trihydroxyisoflavone, 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• Empirical Formula (Hill Notation): C₁₅H₁₀O₅
• CAS Number: 446-72-0
• Molecular Weight: 270.24
• Beilstein: 263823
• EC Number: 207-174-9
• MDL number: MFCD00016952
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278036
• NACRES: NA.77

Properties

• Product Name: Genistein, synthetic, ≥98% (HPLC), powder
• biological source: synthetic
• Quality Level: 200
• Assay: ≥98% (HPLC)
• form: powder
• color: off-white to yellow
• mp: 297.0-298.0 °C
• solubility: DMSO: soluble; ethanol: soluble
• storage temp.: −20°C
• SMILES string: Oc1ccc(cc1)C2=COc3cc(O)cc(O)c3C2=O
• InChI: 1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
• InChI key: TZBJGXHYKVUXJN-UHFFFAOYSA-N
• Gene Information: human ... AKT1(207), CYP19A1(1588), EGFR(1956), ESR1(2099), ESR2(2100) ; mouse ... Esr1(13982), Hexa(15211) ; rat ... Adora1(29290), Adora2a(25369), Ar(24208)

Description

General description

Genistein is an isoflavonoid present among Leguminosae family of plants. It is structurally similar to estrogen (estradiol-17β).[1]

Application

Genistein has been used:

• as a test compound to access its estrogeniic acivity[2]
• as an oestrogenic ligand to carry out identical reporter gene activation assays and also used to examine the binding of genistein to hERβ[3]
• as an endocytosis inhibitor to test the possible effect of endocytosed advanced glycation end - bovine serum albumin (AGE-BSA) on lysosomes[4]

Biochem/physiol Actions

Genistein is essential for plant-microbe interaction. It acts as a natural chemoprotectant and helps in preventing tumor progression and heart disorders. Genistein functionally shares estrogen′s action. It is useful in evaluating nutraceuticals and functional foods. Genistein exhibits antimicrobial action and can serve as a phytoalexin and phytoanticipin.[1]

Inhibitor of tyrosine protein kinase; competitive inhibitor of ATP in other protein kinase reactions. Antiangiogenic agent, down-regulates the transcription of genes involved in controlling angiogenesis.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Chloride Channels and Met pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

Genistein is soluble in DMSO and ethanol. It is also soluble in chlorform:methanol (1:1 (v:v), 10 mg/ml).

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves