Americanin A

Base Information

• Chemical Name: Americanin A
• CAS No.: 69506-79-2
• Molecular Formula: C₁₈H₁₆O₆
• Molecular Weight: 328.321
• NSC Number: 605545
• Nikkaji Number: J19.249J
• Mol file: 69506-79-2.mol

Synonyms:isoamericanin A

Chemical Property of Americanin A

Chemical Property:

• Vapor Pressure: 2.85E-15mmHg at 25°C
• Boiling Point: 600.5°C at 760 mmHg
• Flash Point: 222.8°C
• PSA: 96.22000
• Density: 1.389g/cm³
• LogP: 2.18330
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 328.09468823
• Heavy Atom Count: 24
• Complexity: 453

Purity/Quality:

≥98% （HPLC） ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1C=CC=O)OC(C(O2)C3=CC(=C(C=C3)O)O)CO
• Isomeric SMILES: C1=CC2=C(C=C1/C=C/C=O)OC(C(O2)C3=CC(=C(C=C3)O)O)CO

Technology Process of Americanin A

There total 11 articles about Americanin A 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%

(E)-3-[(2S,3S)-2-(3,4-Bis-methoxymethoxy-phenyl)-3-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-propenal (114590-84-0) → rac-Americanin-A (69506-79-2,76870-73-0,133906-60-2)

Guidance literature:

With hydrogenchloride; In methanol; for 2h; Ambient temperature;

DOI:10.1248/cpb.35.3603

Reference yield:

caffeic acid (331-39-5,501-16-6) → rac-Americanin-A (69506-79-2,76870-73-0,133906-60-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / cc. H₂SO₄ / 8 h / Heating

2: 1.) sodium hydride (NaH) / 1.) tetrahydrofuran (THF), 0 deg C to room temp., 1 h; 2.) THF, 0 deg C to room temp., 8 h

3: 78 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / -10 °C

4: 84 percent / tert-butyl hydroperoxide (70percent), vanadyl acetylacetonate / H₂O; CH₂Cl₂ / 6 h / Ambient temperature

5: 81 percent / aq. sodium hydroxide (1percent) / 2.5 h / 70 °C

6: 72 percent / CH₂Cl₂; pyridine / 6 h / -10 °C

7: 99 percent / potassium carbonate (K₂CO₃) / methanol / 0.5 h / Ambient temperature

8: 95 percent / H₂ / Pd-C (5percent) / ethyl acetate

9: 86 percent / potassium carbonate (K₂CO₃) / methanol / 0.5 h / Ambient temperature

10: 1.) sodium hydride (NaH) / 1.) THF, 0 deg C, 1 h; 2.) THF, room temp., 1 h

11: 76 percent / HCl (2N) / methanol / 2 h / Ambient temperature

With hydrogenchloride; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; vanadyl acetylacetonate; sulfuric acid; hydrogen; sodium hydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; ethyl acetate;

DOI:10.1248/cpb.35.3603

Reference yield:

Methyl caffeate (3843-74-1,67667-67-8) → rac-Americanin-A (69506-79-2,76870-73-0,133906-60-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) sodium hydride (NaH) / 1.) tetrahydrofuran (THF), 0 deg C to room temp., 1 h; 2.) THF, 0 deg C to room temp., 8 h

2: 78 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / -10 °C

3: 84 percent / tert-butyl hydroperoxide (70percent), vanadyl acetylacetonate / H₂O; CH₂Cl₂ / 6 h / Ambient temperature

4: 81 percent / aq. sodium hydroxide (1percent) / 2.5 h / 70 °C

5: 72 percent / CH₂Cl₂; pyridine / 6 h / -10 °C

6: 99 percent / potassium carbonate (K₂CO₃) / methanol / 0.5 h / Ambient temperature

7: 95 percent / H₂ / Pd-C (5percent) / ethyl acetate

8: 86 percent / potassium carbonate (K₂CO₃) / methanol / 0.5 h / Ambient temperature

9: 1.) sodium hydride (NaH) / 1.) THF, 0 deg C, 1 h; 2.) THF, room temp., 1 h

10: 76 percent / HCl (2N) / methanol / 2 h / Ambient temperature

With hydrogenchloride; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; vanadyl acetylacetonate; hydrogen; sodium hydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; ethyl acetate;

DOI:10.1248/cpb.35.3603

upstream raw materials:

(E)-3-[(2S,3S)-2-(3,4-Bis-methoxymethoxy-phenyl)-3-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-propenal

caffeic acid

Methyl caffeate

(E)-3-(3,4-bis(methoxymethoxy)phenyl)prop-2-en-1-ol

Downstream raw materials:

(2RS,3RS)-2-(3,4-Dimethoxyphenyl)-3-hydroxymethyl-1,4-benzodioxan-6-carbaldehyd

(2RS,3RS)-2-(3,4-Dimethoxyphenyl)-3-methoxymethyl-1,4-benzodioxan-6-carbaldehyd

(2RS,3RS)-3-Acetoxymethyl-2-(3,4-dimethoxyphenyl)-1,4-benzodioxan-6-carbaldehyd

(2RS,3RS)-2-(3,4-Dimethoxyphenyl)-3-methoxymethyl-1,4-benzodioxan-6-carbonsaeure

Refernces