Welcome to LookChem.com Sign In|Join Free

Cas Database

20575-57-9

20575-57-9

Identification

  • Product Name:Calycosin

  • CAS Number: 20575-57-9

  • EINECS:

  • Molecular Weight:284.268

  • Molecular Formula: C16H12O5

  • HS Code:2932996560

  • Mol File:20575-57-9.mol

Synonyms:7-hydroxy-3-(3-hydroxy-4-methoxy-phenyl)chromen-4-one;4H-1-Benzopyran-4-one,7-hydroxy-3-(3- hydroxy-4-methoxyphenyl)-;7,3'-Dihydroxy-4'-methoxyisoflavone;

Post Buying Request Now
Entrust LookChem procurement to find high-quality suppliers faster

Safety information and MSDS view more

  • Pictogram(s):T

  • Hazard Codes:T

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:Usbiological
  • Product Description:Calycosin
  • Packaging:20mg
  • Price:$ 433
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:Calycosin
  • Packaging:10mg
  • Price:$ 700
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Calycosin ≥98% (HPLC)
  • Packaging:10mg
  • Price:$ 246
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Calycosin phyproof? Reference Substance
  • Packaging:10mg
  • Price:$ 254
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Calycosin United States Pharmacopeia (USP) Reference Standard
  • Packaging:50mg
  • Price:$ 536
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Calycosin 98%
  • Packaging:20 mg
  • Price:$ 533
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:JR MediChem
  • Product Description:Calycosin 98%
  • Packaging:20mg
  • Price:$ 1200
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:DC Chemicals
  • Product Description:Calycosin >98%,StandardReferencesGrade
  • Packaging:100 mg
  • Price:$ 600
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:DC Chemicals
  • Product Description:Calycosin >98%,StandardReferencesGrade
  • Packaging:250 mg
  • Price:$ 950
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:DC Chemicals
  • Product Description:Calycosin >98%,StandardReferencesGrade
  • Packaging:50 mg
  • Price:$ 400
  • Delivery:In stock
  • Buy Now

Relevant articles and documentsAll total 4 Articles be found

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

Roberts, Dean W.,Doerge, Daniel R.,Churchwell, Mona I.,Da Costa, Goncalo Gamboa,Marques, M. Matilde,Tolleson, William H.

, p. 6623 - 6632 (2004)

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)

-

Paragraph 0091-0096, (2017/07/21)

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

-

Page/Page column 15, (2009/10/21)

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

Bhandari, Prabha,Crombie, Leslie,Daniels, Peter,Holden, Ian,Bruggen, Nicholas Van,Whiting, Donald A.

, p. 839 - 850 (2007/10/02)

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.

Process route upstream and downstream products

Process route

homoisovanillic acid
1131-94-8

homoisovanillic acid

N,N-dimethyl-formamide
68-12-2,33513-42-7

N,N-dimethyl-formamide

recorcinol
108-46-3

recorcinol

calycosin
20575-57-9

calycosin

Conditions
Conditions Yield
homoisovanillic acid; recorcinol; With boron trifluoride diethyl etherate; at 85 - 90 ℃;
N,N-dimethyl-formamide; With phosphorus pentachloride; at 10 - 55 ℃; for 1h; Further stages;
1.6 mmol
2,4-dihydroxyphenyl 3'-hydroxy-4-methoxybenzyl ketone
36754-72-0

2,4-dihydroxyphenyl 3'-hydroxy-4-methoxybenzyl ketone

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

calycosin
20575-57-9

calycosin

Conditions
Conditions Yield
With piperidine; In N,N-dimethyl-formamide; for 1h; Heating;
62%
7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on
485-72-3

7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on

6,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
897-46-1

6,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

retusin
37816-19-6

retusin

calycosin
20575-57-9

calycosin

daidzein
486-66-8

daidzein

Conditions
Conditions Yield
With recombinant human cytochrome P450 1A1; In phosphate buffer; at 37 ℃; pH=7.4; Further Variations:; Reagents; Enzyme kinetics; Product distribution;
calycosin
20575-57-9

calycosin

Conditions
Conditions Yield
With boron trifluoride diethyl etherate; Vilsmeier reagent; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;
With hydrogenchloride; In methanol; water; for 1h; Reflux;
72%
UDP-glucose
133-89-1

UDP-glucose

calycosin
20575-57-9

calycosin

calycosin-7-O-β-D-glucopyranoside
20633-67-4

calycosin-7-O-β-D-glucopyranoside

Conditions
Conditions Yield
With flavonoid 7-O-glucosyltransferase from Andrographis paniculata; In methanol; at 30 ℃; for 12h; Enzymatic reaction;
β-D-glucose
492-61-5

β-D-glucose

calycosin
20575-57-9

calycosin

calycosin-7-O-β-D-glucopyranoside
20633-67-4

calycosin-7-O-β-D-glucopyranoside

Conditions
Conditions Yield
In water; at 110 ℃; for 2h;
calycosin
20575-57-9

calycosin

calycosin-7-O-β-D-glucopyranoside
20633-67-4

calycosin-7-O-β-D-glucopyranoside

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 12 h / 0 - 20 °C
2: potassium carbonate / dichloromethane; methanol / 8 h / 20 °C
3: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl-formamide; acetone / 24 h / 20 °C / Inert atmosphere
4: sodium methylate / methanol / 2 h / 0 °C
With tetrabutylammomium bromide; sodium methylate; potassium carbonate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
calycosin
20575-57-9

calycosin

ethylene dibromide
106-93-4

ethylene dibromide

7-(2-bromoethoxy)-3-(3-(2-bromoethoxy)-4-methoxyphenyl)-4H-chromen-4-one

7-(2-bromoethoxy)-3-(3-(2-bromoethoxy)-4-methoxyphenyl)-4H-chromen-4-one

Conditions
Conditions Yield
With triethylamine; In acetone; at 20 ℃; for 8h; pH=10;
60%
With triethylamine; In acetone; at 20 ℃; for 8h; pH=10; Solvent; Temperature;
60%
With triethylamine; In acetone; at 20 ℃; for 8h; pH=10;
60%
calycosin
20575-57-9

calycosin

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

C<sub>24</sub>H<sub>24</sub>O<sub>9</sub>

C24H24O9

Conditions
Conditions Yield
calycosin; With potassium carbonate; sodium iodide; In acetone; at 20 ℃; for 1h;
chloroacetic acid ethyl ester; at 45 ℃; for 4h; Reagent/catalyst; Temperature; Solvent;
70.5%
calycosin
20575-57-9

calycosin

C<sub>9</sub>H<sub>16</sub>ClNO<sub>3</sub>
1422515-45-4

C9H16ClNO3

C<sub>20</sub>H<sub>19</sub>NO<sub>6</sub>

C20H19NO6

Conditions
Conditions Yield
calycosin; In dimethyl sulfoxide; at 0 - 20 ℃; for 6h;
C9H16ClNO3; With trifluoroacetic acid; In dimethyl sulfoxide; at 0 ℃; for 3h;
0.7 g

Global suppliers and manufacturers

Global( 99) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Shanghai Upbio Tech Co.,Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-21-52196435
  • Emails:upbiocn@hotmail.com
  • Main Products:88
  • Country:China (Mainland)
  • Leader Biochemical Group
  • Business Type:Lab/Research institutions
  • Contact Tel:86-029-68895030
  • Emails:info@leader-biogroup.com
  • Main Products:62
  • Country:China (Mainland)
close
Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 20575-57-9
Post Buying Request Now
close
Remarks: The blank with*must be completed