(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone

Base Information

• Chemical Name: (2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone
• CAS No.: 1268140-15-3
• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.402
• Hs Code.: 2932999099
• ChEMBL ID: CHEMBL1689340
• DSSTox Substance ID: DTXSID401109348
• Metabolomics Workbench ID: 65203
• Nikkaji Number: J2.921.533B
• Wikidata: Q27138359
• Mol file: 1268140-15-3.mol

Synonyms:5,7,3'-Trihydroxy-4'-methoxy-8-prenylflavanone;1268140-15-3;(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone;CHEMBL1689340;CHEBI:70018;8-(3,3-dimethylallyl)hesperetin;(2S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one;(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one;(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one;DTXSID401109348;HY-N2651;BDBM50339151;AKOS040761168;FS-9377;CS-0023072;Q27138359;(2S)-5,7,3''-trihydroxy-4''-methoxy-8-(3''''-methylbut-2''''-enyl)-flavonone

Chemical Property of (2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone

Chemical Property:

• Boiling Point: 616.0±55.0 °C(Predicted)
• PKA: 7.67±0.40(Predicted)
• PSA: 96.22000
• Density: 1.308±0.06 g/cm3(Predicted)
• LogP: 4.02720
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 370.14163842
• Heavy Atom Count: 27
• Complexity: 557

Purity/Quality:

99%+, ^*data from raw suppliers

5,7,3'-Trihydroxy-4'-methoxy-8-prenylflavanone ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)CC(O2)C3=CC(=C(C=C3)OC)O)C
• Isomeric SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC(=C(C=C3)OC)O)C

Technology Process of (2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone

There total 6 articles about (2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone 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: 99.0%

2-(3-acetoxy-4-methoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochroman-5,7-diyl diacetate → 4'-O-methyl-8-isoprenyl eriodictyol (1268140-15-3)

Guidance literature:

With methanol; ammonium acetate; at 50 - 55 ℃; for 24h; Inert atmosphere;

DOI:10.1055/s-0031-1290756

Reference yield: 45.1%

dimethylallyl diphosphate (358-72-5) + hesperetin (520-33-2,41001-90-5,69097-99-0) → 4'-O-methyl-8-isoprenyl eriodictyol (1268140-15-3)

Guidance literature:

With recombinant Sophora flavescens flavonoid prenyltransferase; magnesium chloride; In aq. buffer; at 40 ℃; for 2h; pH=9; stereospecific reaction; Kinetics; Enzymatic reaction;

DOI:10.1002/adsc.201300196

Reference yield:

(S)-5,7-diacetoxy-2-(3-acetoxy-4-methoxy-phenyl)-chroman-4-one (6274-73-3,73489-97-1) → 4'-O-methyl-8-isoprenyl eriodictyol (1268140-15-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1H-imidazole; thiophenol / 1-methyl-pyrrolidin-2-one / 0 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / -20 - 0 °C / Inert atmosphere

3: 5 h / 120 - 130 °C / Inert atmosphere

4: methanol; ammonium acetate / 24 h / 50 - 55 °C / Inert atmosphere

With 1H-imidazole; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium acetate; thiophenol; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; 3: Claisen rearrangement;

DOI:10.1055/s-0031-1290756

upstream raw materials:

(S)-5,7-diacetoxy-2-(3-acetoxy-4-methoxy-phenyl)-chroman-4-one

2-(3-acetoxy-4-methoxyphenyl)-7-hydroxy-4-oxochroman-5-yl acetate

hesperetin

dimethylallyl diphosphate

Refernces

• 1、 Kawamura, Tomoyuki,Hayashi, Moemi,Mukai, Rie,Terao, Junji,Nemoto, Hisao. "An efficient method for C8-prenylation of flavonols and flavanones". . p. 1308 - 1314. Retrieved 2012/06/30.