(R)-Reticuline

Base Information

• Chemical Name: (R)-Reticuline
• CAS No.: 3968-19-2
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.396
• DSSTox Substance ID: DTXSID80331501
• Nikkaji Number: J471.974C
• Wikidata: Q82096614
• Metabolomics Workbench ID: 50910
• ChEMBL ID: CHEMBL401501
• Mol file: 3968-19-2.mol

Synonyms:(R)-Reticuline;3968-19-2;R-RETICULINE;(-)-reticuline;(R)-(-)-reticuline;CHEBI:17428;(1R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol;(1R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol;(R)-N-methylnorreticuline;(1R)-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol;CHEMBL401501;SCHEMBL9587509;DTXSID80331501;(R)-Reticuline (>80per cent ee);AKOS030242061;NCGC00247617-01;A13830;C05178;F14593

Chemical Property of (R)-Reticuline

Chemical Property:

• Vapor Pressure: 8.11E-11mmHg at 25°C
• Melting Point: >200°C (dec.)
• Boiling Point: 504.9°C at 760 mmHg
• Flash Point: 259.2°C
• PSA: 62.16000
• Density: 1.217g/cm³
• LogP: 2.82460
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 329.16270821
• Heavy Atom Count: 24
• Complexity: 407

Purity/Quality:

98%Min ^*data from raw suppliers

(R)-Reticuline(>80%ee) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)O)O)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@H]1CC3=CC(=C(C=C3)OC)O)O)OC
• General Description: L-Reticuline, also known as (R)-Reticuline, is a key intermediate in the biosynthesis of various alkaloids in *Corydalis meifolia* Wall., serving as a stereospecific precursor for compounds such as corlumine, cavidine, and yenshusomine. Its efficient incorporation into these alkaloids highlights its central role in their biogenetic pathway.

Technology Process of (R)-Reticuline

There total 31 articles about (R)-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: 93.0%

(R)-7-Benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline (864-68-6) → (R)-reticuline (485-19-8,1699-46-3,3968-19-2,7096-86-8,14752-49-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr;

DOI:10.1016/S0040-4039(00)97306-4

Reference yield: 88.0%

Acetic acid (R)-((S)-4-acetoxy-7-benzyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-(3-benzyloxy-4-methoxy-phenyl)-methyl ester (133343-36-9,133343-39-2,140687-97-4) → (R)-reticuline (485-19-8,1699-46-3,3968-19-2,7096-86-8,14752-49-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; isopropyl alcohol; under 38000 Torr;

DOI:10.1016/S0040-4039(00)97306-4

Reference yield: 69.0%

Acetic acid (R)-((S)-7-benzyloxy-4-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-(3-benzyloxy-4-methoxy-phenyl)-methyl ester (133343-35-8,133357-53-6,140842-51-9,140851-50-9,140851-53-2) → (R)-reticuline (485-19-8,1699-46-3,3968-19-2,7096-86-8,14752-49-9)

Guidance literature:

With hydrogen; oxalic acid; palladium on activated charcoal; In isopropyl alcohol; under 38000 Torr;

DOI:10.1016/S0040-4039(00)97306-4

upstream raw materials:

1,2-dehydroreticulinium iodide

(R)-7-Benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline

Acetic acid (R)-((S)-7-benzyloxy-4-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-(3-benzyloxy-4-methoxy-phenyl)-methyl ester

Acetic acid (R)-((S)-4-acetoxy-7-benzyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-(3-benzyloxy-4-methoxy-phenyl)-methyl ester

Downstream raw materials:

yenhusomine

cavidine

(+)-adlumine

isoboldine

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.

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