5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

Base Information

• Chemical Name: 5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• CAS No.: 68236-13-5
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.376
• Nikkaji Number: J1.132.707I
• Wikidata: Q105348646
• Pharos Ligand ID: J7NJVH6B6QHA
• ChEMBL ID: CHEMBL1537093
• Mol file: 68236-13-5.mol

Synonyms:68682-01-9;(2R/S)-6-PNG;6-Prenyl-rac-naringenin;6PNG;6-PNG;MLS000863575;5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one;SMR000440733;K 07047;2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one;(S)-4',5,7-Trihydroxy-6-prenylflavanone;5,7,4'-Trihydroxy-6-prenylflavanone;SCHEMBL145713;6 PNG;MEGxp0_001752;CHEMBL1537093;ACon1_000068;BDBM58016;cid_3519901;CHEBI:174571;HMS2271K08;BCP31580;4',5,7-Trihydroxy-6-prenylflavanone;NCGC00168825-01;MS-25192;HY-115681;CS-0120480;F82679;BRD-A11775589-001-01-8;5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chroman-4-one;2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-5,7-bis(oxidanyl)-2,3-dihydrochromen-4-one;5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-1-benzopyran-4-one

Chemical Property of 5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

Chemical Property:

• Vapor Pressure: 3.41E-15mmHg at 25°C
• Boiling Point: 604.2°C at 760 mmHg
• Flash Point: 219°C
• PSA: 86.99000
• Density: 1.314g/cm³
• LogP: 4.01860
• Storage Temp.: 2-8°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 340.13107373
• Heavy Atom Count: 25
• Complexity: 504

Purity/Quality:

98%Min ^*data from raw suppliers

6-Prenylnaringenin analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C2=C(C=C1O)OC(CC2=O)C3=CC=C(C=C3)O)O)C

Technology Process of 5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

There total 4 articles about 5,7-Dihydroxy-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: 37.6%

xanthohumol (569-83-5,6754-58-1) → sophoraflavanone B (53846-50-7,68682-02-0,72357-32-5) + 6-prenylnaringenin (68236-13-5,68682-01-9)

Guidance literature:

With lithium chloride; In N,N-dimethyl-formamide; at 198 ℃; for 0.15h; Overall yield = 76 percent; Microwave irradiation;

DOI:10.3390/molecules25174007

Reference yield: 29.6%

3,3-dimethylallyl diphosphate triammonium salt (1186-30-7,45126-99-6,69382-61-2) + naringenin (480-41-1) → 6-prenylnaringenin (68236-13-5,68682-01-9)

Guidance literature:

With indole prenyltransferase 7-DMATS; calcium chloride; In dimethyl sulfoxide; glycerol; at 37 ℃; for 16h; pH=7.5; Time; Kinetics; Enzymatic reaction;

DOI:10.1021/acs.jnatprod.5b00422

Reference yield: 6.0%

3-methyl-2-buten-1-ol (556-82-1) + naringenin (480-41-1) → 6-prenylnaringenin (68236-13-5,68682-01-9)

Guidance literature:

With aluminum oxide; In 1,2-dichloro-ethane; at 120 ℃; for 2h;

upstream raw materials:

2-methyl-3-buten-2-ol

naringenin

3,3-dimethylallyl diphosphate triammonium salt

xanthohumol

Refernces

• 1、 Riepl, Herbert,Urmann, Corinna. "Semi-Synthetic Approach Leading to 8-Prenylnaringenin and 6-Prenylnaringenin: Optimization of the Microwave-Assisted Demethylation of Xanthohumol Using Design of Experiments". . . Retrieved 2020/09/17.
• 2、 Tahara, Satoshi,Katagiri, Yasufumi,Ingham, John L.,Mizutani, Junya. "PRENYLATED FLAVONOIDS IN THE ROOTS OF YELLOW LUPIN". . p. 1261 - 1272. Retrieved 2007/10/02.