Scoulerine

Base Information

• Chemical Name: Scoulerine
• CAS No.: 6451-72-5
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80895057
• Nikkaji Number: J829.112H
• Wikipedia: Scoulerine
• Wikidata: Q27114086
• ChEMBL ID: CHEMBL191133
• Mol file: 6451-72-5.mol

Synonyms:aequaline;aequaline, (S)-isomer;discretamine;discretamine, (+-)-isomer;discretamine, (R)-isomer;discretamine, (S)-isomer;discretamine, hydrochloride, (S)-isomer;scoulerine;scoulerine, (S)-isomer

Chemical Property of Scoulerine

Chemical Property:

• Melting Point: 128 °C
• Boiling Point: 503.3±50.0 °C(Predicted)
• PKA: 9.88±0.20(Predicted)
• PSA: 62.16000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: 2.70840
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 327.14705815
• Heavy Atom Count: 24
• Complexity: 447

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O
• Uses: An alkaloid found in the opium poppy, and an antagonist at the α2-adrenoceptor, α1D-adrenoceptor and 5-HT receptor.

Technology Process of Scoulerine

There total 19 articles about Scoulerine 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: 47.0%

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)-scoulerine (605-34-5,6451-72-5,6451-73-6,6507-34-2)

Guidance literature:

With berberine bridge enzyme; tris hydrochloride; magnesium chloride; In toluene; at 40 ℃; for 24h; pH=9; optical yield given as %ee; enantioselective reaction; Darkness; Enzymatic reaction;

DOI:10.1021/jo201056f

Reference yield: 7.9%

(+)-(S)-reticuline (485-19-8) → isoboldine (3019-51-0,5164-93-2,13529-67-4,104597-61-7) + pallidine (25650-75-3) + S-(-)-coreximine (483-45-4) + (S)-scoulerine (605-34-5,6451-72-5,6451-73-6,6507-34-2)

Guidance literature:

With phosphate buffer; (S)-2-[3]pyridyl-pyrrolidine-1-carboxylic acid amide; NADPH; magnesium chloride; at 37 ℃; for 2h; rat liver microsomes;

Reference yield:

tetrahydropalmatine (483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8) → (-)-isocorypalmine (6487-33-8,6989-84-0,53447-14-6,483-34-1) + (S)-scoulerine (605-34-5,6451-72-5,6451-73-6,6507-34-2)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃; for 1h;

DOI:10.3390/molecules13092303

upstream raw materials:

(+)-(S)-reticuline

tetrahydropalmatine

isovanillin

homoisovanillic acid

Downstream raw materials:

tetrahydroberberrubine

(S)-stylopine

columbamine

(-)-isocorypalmine

Refernces

• 1、 Schrittwieser, Joerg H.,Resch, Verena,Wallner, Silvia,Lienhart, Wolf-Dieter,Sattler, Johann H.,Resch, Jasmin,MacHeroux, Peter,Kroutil, Wolfgang. "Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids". . p. 6703 - 6714. Retrieved 2011/10/18.
• 2、 Ma, Zhong-Ze,Xu, Wei,Jensen, Niels H.,Roth, Bryan L.,Liu-Chen, Lee-Yuan,Lee, David Y. W.. "Isoquinoline alkaloids isolated from Corydalis yanhusuo and their binding affinities at the dopamine D1 receptor". . p. 2303 - 2312. Retrieved 2008/12/22.