Aegeline

Base Information

• Chemical Name: Aegeline
• CAS No.: 456-12-2
• Deprecated CAS: 37791-13-2
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.354
• Hs Code.: 2924299090
• UNII: 60T59LN3SG
• DSSTox Substance ID: DTXSID101318019
• Metabolomics Workbench ID: 46043
• Mol file: 456-12-2.mol

Synonyms:aegeline;N-(2-hydroxy-2(4-methoxyphenyl)ethyl)-3-phenyl-2-propenamide

Chemical Property of Aegeline

Chemical Property:

• Melting Point: 178-179℃
• Boiling Point: 567.652 °C at 760 mmHg
• Flash Point: 297.105 °C
• PSA: 62.05000
• Density: 1.178 g/cm³
• LogP: 3.39850
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 297.13649347
• Heavy Atom Count: 22
• Complexity: 355

Purity/Quality:

≥98% ^*data from raw suppliers

Aegeline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(CNC(=O)C=CC2=CC=CC=C2)O
• Isomeric SMILES: COC1=CC=C(C=C1)C(CNC(=O)/C=C/C2=CC=CC=C2)O
• Uses: Aegeline, is a compound that can be extracted from Aegle marmelos leaves, a tree that grows in India. Research has found the essential oil of the tree to be effective against 21 types of bacteria. Aegeline, has also shown to have anti-obesity effects.

Technology Process of Aegeline

There total 8 articles about Aegeline 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: 90.0%

2-hydroxy-2-(4-methoxyphenyl)ethylammonium chloride (56766-24-6) + Cinnamoyl chloride (102-92-1,17082-09-6) → 2-propenamide, N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenyl-, (2E) (15298-36-9,15298-37-0,456-12-2)

Guidance literature:

With sodium hydroxide; In water; for 3h; Ambient temperature;

Reference yield:

N-(2-(4-methoxyphenyl)-2-oxoethyl)cinnamamide (95218-94-3) → 2-propenamide, N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenyl-, (2E) (15298-36-9,15298-37-0,456-12-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 10 ℃; Large scale;

Reference yield:

2-(4-methoxyphenyl)-2-(trimethylsilyloxy)acetonitrile (66985-48-6) → 2-propenamide, N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenyl-, (2E) (15298-36-9,15298-37-0,456-12-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BH₃-THF, 2.) HCl gas / 1.) THF, room temperature, 2.) ether

2: 90 percent / sodium hydroxide / H₂O / 3 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; borane-THF; In water;

upstream raw materials:

2-hydroxy-2-(4-methoxyphenyl)ethylammonium chloride

Cinnamoyl chloride

2-(4-methoxyphenyl)-2-(trimethylsilyloxy)acetonitrile

4-methoxy-benzaldehyde

Downstream raw materials:

3-phenyl-propionic acid-(β-hydroxy-4-methoxy-phenethylamide)

N-[2-(4-methoxyphenyl)-2-keto-ethyl]-cinnamamide

3-phenyl-propionic acid-(4-methoxy-phenacylamide)