7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

Base Information

• Chemical Name: 7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• CAS No.: 19879-32-4
• Molecular Formula: C20H20O4
• Molecular Weight: 324.37000
• DSSTox Substance ID: DTXSID70415783
• Wikidata: Q72444915
• Metabolomics Workbench ID: 27204
• Mol file: 19879-32-4.mol

Synonyms:(2S)-7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one;bavachin;corylifolin (flavonoid)

Chemical Property of 7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

Chemical Property:

• Vapor Pressure: 4.52E-13mmHg at 25°C
• Boiling Point: 558.3oC at 760 mmHg
• PKA: 8.27±0.40(Predicted)
• Flash Point: 202.1oC
• PSA: 66.76000
• Density: 1.244
• LogP: 4.31300
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: ≤20mg/ml in ethanol;30mg/ml in DMSO;50mg/ml in dimethyl formamide
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 324.13615911
• Heavy Atom Count: 24
• Complexity: 474

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Bavachin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=CC2=C(C=C1O)OC(CC2=O)C3=CC=C(C=C3)O)C
• Description: Bavachin is a flavonoid first isolated from seeds of P. corylifolia. It is a phytoestrogen that activates the estrogen receptors ERα and ERβ (EC50s = 320 and 680 nM, respectively). Through this action, bavachin stimulates osteoblast proliferation and differentiation and prevents bone loss following ovariectomy in rats. Bavachin less potently inhibits acyl-coenzyme A:cholesterol acyltransferase (IC50 = 86 μM).
• Uses: Bavachin has therapeutic potential for type 2 diabetes by activating insulin signaling pathways. Also, it has anabolic and potent anticatabolic biological effects on chondrocytes. Strong inhibitor of human UDP-glucuronosyltransferase (UGT1A1)

Technology Process of 7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

There total 20 articles about 7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one 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: 76.0%

7,4'-dimethoxymethoxy-6-(3,3-dimethylallyl)-flavanone (934247-88-8) → (+/-)-bavachin (78316-27-5,19879-32-4)

Guidance literature:

With hydrogenchloride; In methanol; for 0.75h; Heating;

DOI:10.1002/ardp.200700057

Reference yield: 61.0%

(E)-1-(2-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one (128961-13-7) → (+/-)-bavachin (78316-27-5,19879-32-4) + buroussochalcone B (28448-85-3)

Guidance literature:

With carbon tetrabromide; In methanol; for 8h; Reflux;

DOI:10.1016/j.tet.2011.04.104

Reference yield:

4-methoxymethoxy-benzaldehyde (6515-21-5) → (+/-)-bavachin (78316-27-5,19879-32-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / aq. KOH / ethanol / 36 h / 20 °C

2: 72 percent / sodium acetate; water / ethanol / 24 h / Heating

3: 76 percent / aq. HCl / methanol / 0.75 h / Heating

With hydrogenchloride; potassium hydroxide; water; sodium acetate; In methanol; ethanol;

DOI:10.1002/ardp.200700057

upstream raw materials:

2-methyl-3-buten-2-ol

7,4'-dihydroxy-dihydroflavone

7,4'-dimethoxymethoxy-6-(3,3-dimethylallyl)-flavanone

(E)-1-(2-hydroxy-4-(methoxymethoxy)-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one

Refernces

• 1、 Sugamoto, Kazuhiro,Matsusita, Yoh-Ichi,Matsui, Kana,Kurogi, Chiaki,Matsui, Takanao. "Synthesis and antibacterial activity of chalcones bearing prenyl or geranyl groups from Angelica keiskei". . p. 5346 - 5359. Retrieved 2011/08/04.
• 2、 Krishnamurti, M.,Parthasarathi, J.. "New Syntheses of 4',7-Dihydroxy-6,8-di-C-prenylflavanone, Bavachin, Isobavachin and Related Compounds". . p. 247 - 248. Retrieved 2007/10/02.