4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-, (2S)-

Base Information

• Chemical Name: 4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-, (2S)-
• CAS No.: 28590-40-1
• Molecular Formula: C17H16O6
• Molecular Weight: 316.3053
• ChEMBL ID: CHEMBL2234487
• Metabolomics Workbench ID: 27739,127437
• Nikkaji Number: J2.468.800C
• Wikidata: Q105158177
• Mol file: 28590-40-1.mol

Synonyms:Persicogenin;28590-40-1;4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-, (2S)-;Hesperetin-7-methyl ether;7-METHOXYHESPERETIN;CHEMBL2234487;SCHEMBL22485515;HY-N7636;AKOS040760625;MS-24656;CS-0134905;G18088;(S)-5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxychroman-4-one;(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one

Chemical Property of 4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-, (2S)-

Chemical Property:

• Vapor Pressure: 8.12E-14mmHg at 25°C
• Boiling Point: 574.9°Cat760mmHg
• Flash Point: 215°C
• PSA: 85.22000
• Density: 1.358g/cm³
• LogP: 2.82150
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 316.09468823
• Heavy Atom Count: 23
• Complexity: 427

Purity/Quality:

≥98% ^*data from raw suppliers

Persicogenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)OC)O)O
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)OC)O)O
• Uses: Persicogenin is a bioactive flavonoid synthesized from hesperidin with numerous biological and pharmacological properties. A natural product.

Technology Process of 4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-, (2S)-

There total 6 articles about 4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-, (2S)- 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: 55.0%

(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone (520-33-2,41001-90-5,69097-99-0) + methyl iodide (74-88-4) → 5,3′-dihydroxy-7,4′-dimethoxyflavanone (5928-45-0,28590-40-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1021/jf9011467

Reference yield: 28.9%

methyl bromide (74-83-9) + hesperetin (520-33-2,41001-90-5,69097-99-0) → 3',5-dihydroxy-4',7-dimethoxydihydroflavone (28590-40-1)

Guidance literature:

With potassium carbonate; In acetone; at 56 ℃; for 10.5h;

DOI:10.1007/s00044-010-9462-7

Reference yield:

persicogenin 3'-glucoside → 3',5-dihydroxy-4',7-dimethoxydihydroflavone (28590-40-1)

Guidance literature:

With hydrogenchloride; In ethanol; for 2h; Heating;

DOI:10.1016/0031-9422(94)00810-G

upstream raw materials:

(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone

dimethyl sulfate

methyl iodide

methyl bromide