(S)-Scoulerine

Base Information

• Chemical Name: (S)-Scoulerine
• CAS No.: 6451-73-6
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38
• Nikkaji Number: J92.838K
• Wikipedia: Scoulerine
• Wikidata: Q7438285
• Pharos Ligand ID: NCU8RTWKKGWA
• Metabolomics Workbench ID: 50787
• ChEMBL ID: CHEMBL1235966
• Mol file: 6451-73-6.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 (S)-Scoulerine

Chemical Property:

• Vapor Pressure: 9.39E-11mmHg at 25°C
• Melting Point: 192°C
• Boiling Point: 503.3oC at 760 mmHg
• PKA: 9.88±0.20(Predicted)
• Flash Point: 258.2oC
• PSA: 62.16000
• Density: 1.37g/cm3
• 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:

98%min ^*data from raw suppliers

S-(+)-Scoulerine ^*data from reagent 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
• Isomeric SMILES: COC1=C(C2=C(C[C@H]3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O
• Description: This form of the alkaloid is more widespread than the d-form, occurring in Corydalis caseana, C. micrantha, C. montana, C. scouleri, C. sibirica and Papaver somniferum. It has [α]26D - 318° (c 0.41, MeOH) or - 289° (c 0.62, MeOH). It forms pale grey needles when crystallized from MeOH. The hydrochloride has m.p. 268-9°C; the picrate, m.p. 206°C (dec.) and the diethyl ether, m.p. 155°C. The oxidation products are the same as for the preceding base.
• Uses: The S-(+)-enantiomer of Scoulerine, an alkaloid found in the opium poppy. (S)-Scoulerine is an alkaloid found in the opium poppy. (S)-Scoulerine acts as an antagonist at the α2-adrenoceptor, α1D-adrenoceptor and 5-HT receptor.

Technology Process of (S)-Scoulerine

There total 19 articles about (S)-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

Reactions of silyl enol ethers and lactone enolates with dimethyl(methylene)ammonium iodide. The bis α methylenation of pre vernolepin and pre vernomenin

10.1021/ja00437a058

The research focuses on the synthesis and reactions of various organic compounds, particularly those derived from Papaver somniferum and berberinoids. The purpose of the research was to explore the oxidation of the N-7 and C-8 bond in tetrahydroprotoberberine base (-)-scoulerine and its impact on the formation of phthalideisoquinoline derivatives, as well as to develop new pathways for the cleavage of the N-7 to C-8 bond in berberinoids. The study also investigated the use of di-methyl(methy1ene)ammonium iodide (7) in Mannich reactions and its potential in steroid synthesis, demonstrating the conversion of vicinal hydroxybutylrolactones into their α-methylene derivatives without the need for hydroxyl protection. The conclusions drawn from the research were that two pathways are available in the laboratory for the cleavage of the N-7 to C-8 bond of berberinoids, one involving the quinone methide route and the other through direct oxidation.