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
• Uses: Precursor of many aporphine and morphine-type alkaloids. Reticulin can be used to improve production of morphinan alkaloids, as well as its anti-inflammatory properties. It can also be used to lead scaffolds as PDE5A inhibitors and antihypertensives.

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:

salutaridine

(R)-(-)-<2',6',8-3H3>reticuline

isoboldine

corytuberine

Refernces

• 1、 Ruiz-Olalla, Andrea,Würdemann, Martien A.,Wanner, Martin J.,Ingemann, Steen,Van Maarseveen, Jan H.,Hiemstra, Henk. "Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids". . p. 5125 - 5132. Retrieved 2015/05/27.
• 2、 Schrittwieser, Joerg H.,Groenendaal, Bas,Willies, Simon C.,Ghislieri, Diego,Rowles, Ian,Resch, Verena,Sattler, Johann H.,Fischereder, Eva-Maria,Grischek, Barbara,Lienhart, Wolf-Dieter,Turner, Nicholas J.,Kroutil, Wolfgang. "Deracemisation of benzylisoquinoline alkaloids employing monoamine oxidase variants". . p. 3657 - 3664. Retrieved 2015/02/05.