B9938

Calycosin

≥98% (HPLC)

• Synonym(s): 3′,7-Dihydroxy-4′-methoxy-isoflavone, 3′-Hydroxyformononetin, Cyclosin
• Empirical Formula (Hill Notation): C₁₆H₁₂O₅
• CAS Number: 20575-57-9
• Molecular Weight: 284.26
• NACRES: NA.25
• PubChem Substance ID: 329773327
• UNSPSC Code: 12352200
• MDL number: MFCD00210598

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to light yellow
• solubility: methanol: 1 mg/mL, clear, colorless
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: 2-8°C
• SMILES string: O=C1C(C(C=C2)=CC(O)=C2OC)=COC3=CC(O)=CC=C13
• InChI: 1S/C16H12O5/c1-20-14-5-2-9(6-13(14)19)15-8-12(18)11-4-3-10(17)7-16(11)21-15/h2-8,17,19H,1H3
• InChI key: QAGGICSUEVNSGH-UHFFFAOYSA-N

Description

General description

Calycosin is a plant estrogen exhibiting both agonistic and antagonistic attitude towards estrogen. It is an isoflavone, occurring as the primary component of the Radix astragali extract.

Application

Calycosin has been used:

• to study its effect on the repression of glioblastomas by having an inhibitory effect on the expression of tyrosine-protein kinase Met (c-Met)
• to analyze its effect on the growth of nasopharyngeal carcinoma cells by modulating the long non-coding RNA, Ewing sarcoma-associated transcript 1(EWSAT1)
• to evaluate its effect on the left ventricular ejection fraction in rat model with myocardial ischemia

Biochem/physiol Actions

Calycosin exhibits various therapeutic properties such as anti-inflammatory, antioxidant, antiviral, and neuroprotective effects. It is shown to exercise its anticarcinogenic effects against the cluster of breast cancer, osteosarcoma, hepatocellular carcinoma, and colorectal cancer. It is also being promoted as a probable treatment for myocardial infarction due to its ability to hasten the process of angiogenesis and increase the expression of vascular endothelial growth factor (VEGF). It has been found to show hyperpermeability induced by the conditions of low osmolarity. Finally, calycosin is being suggested to be used as a prodrug for the treatment of hypoxia-related vascular diseases.

Isoflavone and phytoestrogen isolated froma traditional Chinese medicinal herb. Calycosin induces angiogenesis in HUVEC and promotes proliferation of estrogen-receptor positive cells in vivo and in vitro. Also functions as a vasorelaxant on rat thoracic aorta.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H317
• pcodes: P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364
• Hazard Classifications: Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable