(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
• Uses: (R)-Reticuline is the (R)-enantiomer of Reticuline, a tetrahydrobenzylisoquinoline alkaloid found in opium. (R)-Reticuline is converted into Salutaridine by a membrane-bound cytochrome P-450 enzyme fr om Papaver somniferum (R)-Reticuline is the (R)-enantiomer of Reticuline, a tetrahydrobenzylisoquinoline alkaloid found in opium. (R)-Reticuline is converted into Salutaridine by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum

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

• 1、 Schrittwieser, Joerg H.,Groenendaal, Bas,Resch, Verena,Ghislieri, Diego,Wallner, Silvia,Fischereder, Eva-Maria,Fuchs, Elisabeth,Grischek, Barbara,Sattler, Johann H.,MacHeroux, Peter,Turner, Nicholas J.,Kroutil, Wolfgang. "Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion". supporting information. p. 3731 - 3734. Retrieved 2014/04/17.
• 2、 Resch, Verena,Lechner, Horst,Schrittwieser, Joerg H.,Wallner, Silvia,Gruber, Karl,MacHeroux, Peter,Kroutil, Wolfgang. "Inverting the regioselectivity of the berberine bridge enzyme by employing customized fluorine-containing substrates". . p. 13173 - 13179. Retrieved 2013/01/15.