20575-57-9

Basic information

• Product Name: CALYCOSIN
• Synonyms: CALYCOSIN;7,3'-DIHYDROXY-4'-METHOXYISOFLAVONE;3'-HYDROXYFORMONONETIN;3',7-DIHYDROXY-4'-METHOXYISOFLAVONE;3-(3-Hydroxy-4-methoxyphenyl)-7-hydroxy-4H-1-benzopyran-4-one;7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one;Astraisoflavone;Clycosin
• CAS NO: 20575-57-9
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• Product Categories: Iso-Flavones;The group of Astralosides;reference substance;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 20575-57-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 245～247℃
• Boiling Point: 536.8 °C at 760 mmHg
• Flash Point: 205.7 °C
• Appearance: white to light yellow/
• Density: 1.42g/cm³
• Vapor Pressure: 3.9E-12mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: 2-8°C
• Solubility: methanol: soluble1mg/mL, clear, colorless
• PKA: 6.94±0.20(Predicted)
• CAS DataBase Reference: CALYCOSIN(CAS DataBase Reference)
• NIST Chemistry Reference: CALYCOSIN(20575-57-9)
• EPA Substance Registry System: CALYCOSIN(20575-57-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 3462 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 20575-57-9(Hazardous Substances Data)

Usage

Definition

Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus and Trifolium pratense L. Calycosin is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position. It has a role as a metabolite and an antioxidant. It is a member of 7-hydroxyisoflavones and a member of 4'-methoxyisoflavones. It derives from an isoflavone. It is a conjugate acid of a calycosin(1-).

Pharmaceutical Properties

The potential pharmaceutical properties of calycosin in the treatment of tumors, inflammation, stroke, and cardiovascular diseases have gained increasing attention in the recent years. The literature survey showed that calycosin exhibits promising effects for the treatment of several diseases and that these effects may be due to its isoflavonoid and phytoestrogenic properties. The effects of calycosin most likely result from its interaction with the ER receptors on the cell membrane and the modulation of the MAPK signaling pathway. Through its effect on this pathway, calycosin can regulate several cell activities, such as apoptosis and angiogenesis, which enables its therapeutic functions.

InChI:InChI=1/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3

Upstream product

• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 1131-94-8 homoisovanillic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 108-46-3 recorcinol 
• 36754-72-0 2,4-dihydroxyphenyl 3'-hydroxy-4-methoxybenzyl ketone 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 22877-03-8 3',7-diacetoxy-4'-methoxyisoflavone 
• 20633-67-4 calycosin-7-O-β-D-glucopyranoside 

Relevant articles and documents

Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover)

Biochanin A and formononetin are the predominant isoflavones in red clover. In a previous study (J. Agric. Food Chem. 2002, 50, 4783-4790), it was demonstrated that human liver microsomes converted biochanin A and formononetin to genistein and daidzein. This paper now shows CYP1B1-catalyzed O-demethylation of biochanin A and formononetin to produce genistein and daidzein, respectively, which inhibit CYP1B1. Recombinant human CYP1A1 or CYP1B1 was incubated with biochanin A or formononetin. CYP1A1 catalyzed isoflavone 4′-O-demethylation and hydroxylations with similar efficiency, whereas CYP1B1 favored 4′-O-demethylation over hydroxylations. Three of the biochanin A metabolites (5,7,3′-trihydroxy-4′-methoxyisoflavone, 5,7,8-trihydroxy-4′-methoxyisoflavone, and 5,6,7-trihydroxy-4′- methoxyisoflavone) were characterized by 1H NMR spectroscopy and mass spectrometry. Daidzein (Ki = 3.7 μM) exhibited competitive inhibition of CYP1B1 7-ethoxyresorufin O-deethylase activity, and genistein (Ki = 1.9 μM) exhibited mixed inhibition. Biochanin A and/or formononetin may exert anticarcinogenic effects directly by acting as competitive substrates for CYP1B1 or indirectly through their metabolites daidzein and genistein, which inhibit CYP1B1.

CALYCOSIN AND ANALOGS THEREOF FOR THE TREATMENT OF ESTROGEN RECEPTOR BETA-MEDIATED DISEASES

Estrogenic compositions comprising calycosin and analogs thereof are provided. Also provided are methods of using said extracts to achieve an estrogenic effect, especially in a human, e.g. a female human. In some embodiments, the methods include treatment of climacteric symptoms. In some embodiments, the methods include treatment of estrogen receptor positive cancer, such as estrogen responsive breast cancer. In some embodiments, the methods include treatment or prevention of osteoporosis.