Glycitein

Base Information

• Chemical Name: Glycitein
• CAS No.: 40957-83-3
• Molecular Formula: C16H12O5
• Molecular Weight: 284.268
• Hs Code.: 2914509090
• UNII: 92M5F28TVF
• DSSTox Substance ID: DTXSID40193960
• Nikkaji Number: J17.583H
• Wikipedia: Glycitein
• Wikidata: Q3109347
• NCI Thesaurus Code: C63949
• Metabolomics Workbench ID: 22242
• ChEMBL ID: CHEMBL513024
• Mol file: 40957-83-3.mol

Synonyms:7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one;glycitein

Chemical Property of Glycitein

Chemical Property:

• Appearance/Colour: Pale orange solid
• Vapor Pressure: 1.36E-12mmHg at 25°C
• Melting Point: >300°C
• Refractive Index: 1.668
• Boiling Point: 547.4 °C at 760 mmHg
• PKA: 7.03±0.20(Predicted)
• Flash Point: 210 °C
• PSA: 79.90000
• Density: 1.42 g/cm³
• LogP: 2.87980
• Storage Temp.: −20°C
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 284.06847348
• Heavy Atom Count: 21
• Complexity: 424

Purity/Quality:

NLT 98% ^*data from raw suppliers

Glycitein ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C(=O)C(=CO2)C3=CC=C(C=C3)O)O
• Description: Glycitein is an O-methylated isoflavone that comprises 5-10% of the total isoflavones in soy food products. This phytoestrogen is reported to have weak estrogenic activity, displacing estradiol binding at the estrogen receptor in vitro with an IC50 value of 3.94 μM. It suppresses the proliferation of osteoblasts and promotes differentiation from its progenitor. It has also been used to attenuate proliferation (10 μM) of aortic smooth muscle cells related to atherosclerotic vascular change in stroke-prone hypertensive rats and to protect against beta amyloid (Aβ)-induced toxicity and oxidative stress (100 μg/ml) in C. elegans expressing human Aβ.
• Uses: Glycitein may be used as a reference standard in the determination of glycitein in hydrolyzed dry soya extracts using reversed-phase high-performance liquid chromatography (RP-HPLC). Glycitein has been used as standard for the analysis of soy isoflavones and metabolites in urine. It has also been used to bind to recombinant estrogen and progesterone receptors to know the relative binding affinity (RBA) for detection of potential endocrine disruptors. The compund shows an anti-cancer activity, plasma cholesterol reduction, reduction in postmenopausal bone loss

Technology Process of Glycitein

There total 18 articles about Glycitein which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.4%

3-chloro-6-methoxy-7-hydroxy-4H-chromen-4-one + 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-70-3) → glycitein (40957-83-3)

Guidance literature:

With potassium carbonate; triphenylphosphine; palladium dichloride; In 1,4-dioxane; water; for 10h; Inert atmosphere; Reflux;

Reference yield: 85.0%

methanesulfonyl chloride (124-63-0) + 1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4'-hydroxyphenyl)ethanone (79744-58-4) → glycitein (40957-83-3)

Guidance literature:

With boron trifluoride diethyl etherate; In N,N-dimethyl-formamide; at 70 ℃; for 5.25h;

Reference yield: 80.0%

1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone (58115-20-1) → glycitein (40957-83-3)

Guidance literature:

With hydrogenchloride; In methanol; water; Heating / reflux;

upstream raw materials:

6,7,4'-trihydroxyisoflavone

methanol

daidzein

1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone

Downstream raw materials:

6,7,4'-trihydroxyisoflavone

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-(4-hydroxy-phenyl)-6-methoxy-4-oxo-4H-chromen-7-yloxy]-tetrahydro-pyran-3-yl ester

4'-O-hexanoylglycitein

C₁₆H₁₀⁽²⁾H₂O₅

Refernces

• 1、 Park, Hyun Young,Kim, Soo Hee,Kim, Gi Beom,Sim, Jae Young,Lim, Soon Sung,Kim, Myong Jo,Chun, Wanjoo,Kwon, Yong Soo. "A new isoflavone glycoside from the stem bark of Sophora japonica". . p. 1165 - 1168. Retrieved 2010.
• 2、 -. "Invention relates to a soybean in the process of synthesis method". . . Retrieved 2019/03/26.