Nor Reticuline

Base Information

• Chemical Name: Nor Reticuline
• CAS No.: 4781-58-2
• Molecular Formula: C18H21NO4
• Molecular Weight: 315.369
• Mol file: 4781-58-2.mol

Synonyms:(-)-Norreticuline;2-Demethylreticuline;(S)-Norreticuline;(-)-(S)-N-Norreticuline;

Chemical Property of Nor Reticuline

Chemical Property:

• PSA: 70.95000
• LogP: 2.87330

Purity/Quality:

95% ^*data from raw suppliers

NorReticuline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: Nor Reticuline, also known as (-)-Norreticuline, 2-Demethylreticuline, (S)-Norreticuline, or (-)-(S)-N-Norreticuline, is a biosynthetic intermediate in the alkaloid pathway of *Corydalis meifolia* Wall. It serves as a precursor in the stereospecific formation of alkaloids such as corlumine, cavidine, and yenshusomine, demonstrating efficient metabolic incorporation into these compounds. The study highlights its role in the regiospecific biogenetic pathway, confirming its importance as a key intermediate alongside reticuline in the biosynthesis of medically relevant alkaloids.

Technology Process of Nor Reticuline

There total 3 articles about Nor Reticuline 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:

(Z)-7-Acetoxy-1-<(3-acetoxy-4-methoxyphenyl)methylene>-2-acetyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline (104621-41-2) → (-)-Norreticuline (4781-58-2) + (+)-Norreticuline (57231-34-2)

Guidance literature:

With hydrogen; Δ-(R)-1; Multistep reaction. Title compound not separated from byproducts; 2.) deacetylation;

DOI:10.1021/ja00282a054

Reference yield:

C31H40N2O7SSi + methyl iodide (74-88-4) → (-)-Norreticuline (4781-58-2) + (+)-Norreticuline (57231-34-2)

Guidance literature:

C₃₁H₄₀N₂O₇SSi; methyl iodide; With potassium carbonate; In acetonitrile; at 80 ℃; for 18h;

With hydrogenchloride; In ethanol; dichloromethane; water; at 20 ℃; for 24h; Overall yield = 75 %; Overall yield = 32.5 mg;

DOI:10.1021/acs.joc.5b00509

Reference yield:

→ (-)-Norreticuline (4781-58-2)

Guidance literature:

'Isoquinolin' XXIXa, - kat. Hydr.;

upstream raw materials:

(Z)-7-Acetoxy-1-<(3-acetoxy-4-methoxyphenyl)methylene>-2-acetyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline

methyl iodide

Downstream raw materials:

C₁₈⁽¹⁴⁾CH₂₃NO₄

1,2-dehydronorreticuline

N-benzoyl-norreticuline

4',6-O,O-dimethylpapaveroline

Refernces

THE BIOSYNTHESIS OF THE ALKALOIDS OF CORYDALIS MEIFOLIA WALL.

10.1016/S0040-4020(01)87469-X

The study investigates the biosynthesis of alkaloids in Corydalis meifolia Wall., a plant used in traditional medicine. The researchers used tracer experiments to demonstrate that the alkaloids corlumine, cavidine, and yenshusomine are stereospecifically biosynthesized from (R)-(?)-reticuline. They fed various labeled precursors, including tyrosine, norreticuline, and reticuline, to young branches of the plant and observed the incorporation of these precursors into the target alkaloids. The results showed that certain precursors, like norreticuline and reticuline, were efficiently metabolized into the alkaloids, while others were not. The study also established the regiospecificity of the biosynthetic pathway by tracking the labeled atoms through various chemical transformations, confirming that reticuline is a true precursor of these alkaloids. The findings provide valuable insights into the biogenetic pathway of these medically relevant compounds.