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

Uses

Used in Pharmaceutical Applications:
Calycosin is used as a pharmaceutical agent for its antioxidant properties. Its ability to neutralize harmful free radicals and protect cells from oxidative damage makes it a valuable compound in the development of medications targeting various diseases and conditions.
Used in Nutraceutical Applications:
Calycosin is used as a nutraceutical ingredient for its potential health benefits. It can be incorporated into dietary supplements and functional foods to support overall health and well-being.
Used in Cosmetic Applications:
Calycosin is used as an active ingredient in the cosmetic industry for its antioxidant and anti-aging properties. It can be found in skincare products designed to protect the skin from environmental stressors and promote a youthful appearance.
Used in Agricultural Applications:
Calycosin can be used in the agricultural industry as a natural antioxidant to extend the shelf life of perishable products and improve their overall quality.

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

• 1131-94-8 homoisovanillic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 108-46-3 recorcinol 
• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 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.

A method of chemical synthesis mao Ruiyi flavonoid (by machine translation)

The invention relates to a method for preparing mao Ruiyi flavonoid, comprises the following steps: to resorcinol and 3 - hydroxy -4 - methoxy acetic acid (as the starting material, to make the 3 ', 7 - dihydroxy -4' - methoxyisoflavone, then through the acetylation reaction to obtain the double-b acylated product 3 ', 7 - acetoxy -4' - methoxyisoflavone; selective shall get rid of the 7 bit on the hydroxy protecting group and gets the 7 - hydroxy -3 '- acetoxy -4' - methoxyisoflavone; the 7 position hydroxy generating glycosidic bond to obtain 3 '- acetoxy -4' - methoxyisoflavone - 7 - O - beta - D - tetra-substituted-based glucoside, finally through complete hydrolysis, removing the protecting group to obtain mao Ruiyi flavonoid, namely calycosin - 7 - O - beta - D - glucoside. The invention develops mao Ruiyi flavonoid glycoside of chemical synthesis method, this synthetic route raw materials are easy, and the cost is low, mild reaction conditions. (by machine translation)

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.

Biosynthesis of the A/B/C/D-Ring System of the Rotenoid Amorphigenin by Amorpha fruticosa Seedlings

With phenylalanine as the starting point, the biosynthesis of the characteristic rotenoid A/B/C/D-ring system of amorphigenin is studied using Amorpha fruticosa seedlings.The course of the biosynthesis can be divided into four phases represented by the bordered and interconnecting Schemes 1, 3, 6 and 7 which summarise the Chalcone-Flavanone Phase, the Flavanone-Isoflavone Phase, the Hydroxylation/Methoxylation Phase and the Rotenoid Phase.By using an INADEQUATE NMR experiment involving the administration of acetate, the type of folding forming ring-D isdemonstrated by 13C-13C coupling and is interpreted as involving a polyketide containing a glutaconate segment which cyclises by a Claisen condensation.The resulting chalcone is cyclised, enzymically and stereospecifically, to 4',7-dihydroxyflavanone.The latter flavanone undergoes aryl migration, in a manner similar to that found in isoflavone biosynthesis, to give 7-hydroxy-4'-methoxyisoflavone.Possible mechanisms for the flavanone-isoflavone rearrangement are discussed, including a proposal that the initiating step involves attack on ring-A and is similar to the first stage of the aromatic hydroxylation of tyrosine to dopa.Although possessing no 4'-hydroxy group in ring-A, the mechanism is also applicable to the recently discovered rotenoids of the Boerhaavia and Iris type, and it provides an explanation for the biogenesis of natural spirobenzocyclobutanes from dihydroeucominoids.Six suitably substituted isoflavonoids labelled with 13C or 3H are synthesized and are used to show that the next hydroxylation (and probably methylation) involves C-3' rather than C-2' in 7-hydroxy-4'-methoxyisoflavone.Whilst the methylations involveS-adenosylmethionine, the hydroxylating enzymes are probably very similar to the flavanone-isoflavone-rearranging enzyme.The closure of ring-B to form finally the rotenoid system probably involves conjugate addition of a methoxyl radical.Prenylation and oxidative modifications are characteristically late-stage processes.