Daphneticin

Base Information

• Chemical Name: Daphneticin
• CAS No.: 83327-22-4
• Molecular Formula: C₂₀H₁₈O₈
• Molecular Weight: 386.358
• DSSTox Substance ID: DTXSID80232266
• Nikkaji Number: J182.010I
• Wikidata: Q27106335
• Metabolomics Workbench ID: 68231
• ChEMBL ID: CHEMBL584162
• Mol file: 83327-22-4.mol

Synonyms:Daphneticin;83327-22-4;CHEBI:4320;C09924;(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one;9H-Pyrano(2,3-f)-1,4-benzodioxin-9-one, 2,3-dihydro-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-, (2R,3R)-;(2R,3R)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2H-[1,4]dioxino[2,3-h]chromen-9(3H)-one;AC1L4JR8;CHEMBL584162;DTXSID80232266;BDBM50198189;AKOS040763762;Q27106335;(2R,3R)-3-(4-hydroxy-3,5-dimethoxy-phenyl)-2-(hydroxymethyl)-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one

Chemical Property of Daphneticin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 619.5°Cat760mmHg
• Flash Point: 223.4°C
• PSA: 107.59000
• Density: 1.403g/cm³
• LogP: 2.38920
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 386.10016753
• Heavy Atom Count: 28
• Complexity: 581

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C2C(OC3=C(O2)C=CC4=C3OC(=O)C=C4)CO
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)[C@@H]2[C@H](OC3=C(O2)C=CC4=C3OC(=O)C=C4)CO

Technology Process of Daphneticin

There total 20 articles about Daphneticin 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: 12.3%

trans-sinapyl alcohol (20675-96-1) + daphnetin (486-35-1) → (+/-)-trans-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-hydroxymethyl-2,3-dihydro-1,4,5-trioxaphenanthren-6-one (83327-22-4)

Guidance literature:

With Na,K-phosphate buffer; tyrosinase; at 37 ℃; for 336h;

Reference yield: 5.8%

trans-sinapyl alcohol (20675-96-1) + daphnetin (486-35-1) → daphneticin (94062-47-2,104449-88-9) + (+/-)-trans-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-hydroxymethyl-2,3-dihydro-1,4,5-trioxaphenanthren-6-one (83327-22-4)

Guidance literature:

With silver(l) oxide; In methanol; benzene; for 18h; Ambient temperature;

Reference yield:

7-hydroxy-2H-chromen-2-one (93-35-6) → (2R,3R)-daphneticin (83327-22-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

2: 79 percent / AlCl₃ / 2 h / 160 °C

3: 94 percent / K₂CO₃ / acetone / 24 h / 20 °C

4: 94 percent / aq. H₂O₂; aq. NaOH / dioxane / 0.33 h / 10 °C

5: 90 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

6: 92 percent / H₂ / 5 percent Pd/C / ethyl acetate / 6 h / 20 °C

With pyridine; sodium hydroxide; aluminium trichloride; hydrogen; dihydrogen peroxide; potassium carbonate; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; ethyl acetate; acetone; 4: Baeyer-Villiger oxidation;

DOI:10.1016/S0957-4166(02)00482-2

upstream raw materials:

trans-sinapyl alcohol

daphnetin

trans-3,5-dimethoxy-4-hydroxycinnamic acid

(E)-4-acetoxy-3,5-dimethoxycinnamic acid