Reticuline

Base Information

• Chemical Name: Reticuline
• CAS No.: 485-19-8
• Deprecated CAS: 7344-79-8,3466-53-3
• Molecular Formula: C19H23 N O4
• Molecular Weight: 329.396
• European Community (EC) Number: 207-611-3
• UNII: X35Z551WT4
• DSSTox Substance ID: DTXSID001317199
• Nikkaji Number: J12.961E
• Wikipedia: Reticuline
• Wikidata: Q6122828
• Metabolomics Workbench ID: 38373
• ChEMBL ID: CHEMBL235212
• Mol file: 485-19-8.mol

Synonyms:reticuline;reticuline hydrochloride, (+,-)-isomer;reticuline perchlorate;reticuline, (+,-)-isomer;reticuline, (R)-isomer;reticuline, 14C-labeled, (+,-)-isomer

Chemical Property of Reticuline

Chemical Property:

• Vapor Pressure: 8.11E-11mmHg at 25°C
• Melting Point: 125-126ºC
• Refractive Index: 1.6800 (estimate)
• Boiling Point: 504.9°Cat760mmHg
• PKA: 9.95±0.10(Predicted)
• Flash Point: 259.2°C
• PSA: 62.16000
• Density: 1.217g/cm³
• LogP: 2.82460
• Storage Temp.: -20?C Freezer
• 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% ^*data from raw suppliers

Reticuline >98%,StandardReferencesGrade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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: (S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol, also known as (+)-reticuline, is a key biosynthetic precursor in the formation of alkaloids such as corlumine, cavidine, and yenshusomine in *Corydalis meifolia* Wall. The study confirms that (R)-reticuline, the enantiomer of (S)-reticuline, is stereospecifically incorporated into these alkaloids, highlighting the importance of reticuline derivatives in the plant's biosynthetic pathway. While the research focuses on (R)-reticuline, the (S)-form is structurally analogous and serves as a critical intermediate in alkaloid biosynthesis, demonstrating regiospecific metabolic transformations. This underscores the role of reticuline isomers in the production of bioactive alkaloids in medicinal plants.

Technology Process of Reticuline

There total 51 articles about 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: 80.0%

reticuline (1699-46-3,7096-86-8) → (+)-(S)-reticuline (485-19-8)

Guidance literature:

With borane-ammonia complex; recombinant monoamine oxidase D₁₁ from Aspergillus niger; oxygen; In aq. phosphate buffer; dimethyl sulfoxide; at 37 ℃; for 48h; pH=7.7; Time; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1039/c4cy00642a

Reference yield:

1-(3'-benzyloxy-4'-methoxybenzyl)-7-benzyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (916-40-5) → (+)-(S)-reticuline (485-19-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; acetic acid; for 6h; under 2585.7 Torr;

Reference yield:

reticuline (1699-46-3,7096-86-8) → (R)-reticuline (485-19-8,1699-46-3,3968-19-2,7096-86-8,14752-49-9) + (+)-(S)-reticuline (485-19-8)

Guidance literature:

With Escherichia coli monoamine oxidase MAO-N D₁₁; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/anie.201400027

upstream raw materials:

1-(3'-benzyloxy-4'-methoxybenzyl)-7-benzyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

isovanillin

3-methoxy-4-(phenylmethoxy)benzaldehyde

2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine

Downstream raw materials:

L-Reticulin-diacetat

tetrahydroberberrubine

(6aS)-6,11,12,14-tetrahydro-9-methoxy-6aH-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-8-ol

(S)-scoulerine

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.