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

• Product Name: Calycosin, ≥98% (HPLC)
• InChI key: QAGGICSUEVNSGH-UHFFFAOYSA-N
• 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
• 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
• Quality Level: 100

Description

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)[1]
• to analyze its effect on the growth of nasopharyngeal carcinoma cells by modulating the long non-coding RNA, Ewing sarcoma-associated transcript 1(EWSAT1)[2]
• to evaluate its effect on the left ventricular ejection fraction in rat model with myocardial ischemia[3]

Biochem/physiol Actions

Calycosin exhibits various therapeutic properties such as anti-inflammatory, antioxidant, antiviral, and neuroprotective effects.[1][4] It is shown to exercise its anticarcinogenic effects against the cluster of breast cancer, osteosarcoma, hepatocellular carcinoma, and colorectal cancer.[2] 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).[3][5] It has been found to show hyperpermeability induced by the conditions of low osmolarity.[4] Finally, calycosin is being suggested to be used as a prodrug for the treatment of hypoxia-related vascular diseases.[6]

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.

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.[1][2]

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