Laudanosoline

Base Information

• Chemical Name: Laudanosoline
• CAS No.: 485-33-6
• Molecular Formula: C₁₇H₁₉NO₄
• Molecular Weight: 301.342
• European Community (EC) Number: 207-613-4
• DSSTox Substance ID: DTXSID60964073
• Nikkaji Number: J182.227F
• Wikidata: Q27114681
• Metabolomics Workbench ID: 68008
• ChEMBL ID: CHEMBL19844
• Mol file: 485-33-6.mol

Synonyms:laudanosoline;laudanosoline hydrobromide

Chemical Property of Laudanosoline

Chemical Property:

• Vapor Pressure: 1.28E-12mmHg at 25°C
• Melting Point: 232-234 °C(lit.)
• Boiling Point: 548°Cat760mmHg
• Flash Point: 323°C
• PSA: 111.85000
• Density: 1.373g/cm³
• LogP: 2.98380
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 301.13140809
• Heavy Atom Count: 22
• Complexity: 380

Purity/Quality:

99% ^*data from raw suppliers

DL-LAUDANOSOLINE HYDROBROMIDE TRIHYDRATE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)O)O)O)O

Technology Process of Laudanosoline

There total 7 articles about Laudanosoline 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:

6,7-bisbenzyloxy-1-(3,4-bisbenzyloxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline (79832-22-7) → Laudanosoline (485-33-6,47210-40-2,57231-32-0,57231-31-9)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; for 2h;

DOI:10.1039/P19810002016

Reference yield:

→ Laudanosoline (485-33-6,47210-40-2,57231-32-0,57231-31-9)

Guidance literature:

With aluminium trichloride; at 160 - 165 ℃;

Reference yield:

6,7-bis-benzyloxy-1-(3,4-bis-benzyloxy-benzyl)-3,4-dihydro-isoquinoline (56632-97-4) → Laudanosoline (485-33-6,47210-40-2,57231-32-0,57231-31-9)

Guidance literature:

Multi-step reaction with 3 steps

1: ethyl acetate / 144 h / in the dark

2: sodium borohydride / ethanol / 0 °C

3: 25 mg / hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h

With hydrogenchloride; sodium tetrahydroborate; hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate;

DOI:10.1039/P19810002016

upstream raw materials:

4,5,3',4'-tetramethoxy-2-vinyl-stilbene

6,7-bisbenzyloxy-1-(3,4-bisbenzyloxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

Norlaudanosolin

6,7-bis-benzyloxy-1-(3,4-bis-benzyloxy-benzyl)-3,4-dihydro-isoquinoline

Downstream raw materials:

[2-(3,4-dimethoxy-styryl)-4,5-dimethoxy-phenethyl]-dimethyl-amine

Refernces

• 1、 Battersby, Alan R.,Jones, Raymond C. F.,Kazlauskas, Rymantas,Thornber, Craig W.,Ruchirawat, Somsak,Staunton, James. "Biosynthesis. Part 24. Speculative Incorporation Experiments with 1-Benzylisoquinolines and a Logical Approach via C6-C2 and C6-C3 Precursors to the Biosynthesis of Hasubanonine and Protostephanine". . p. 2016 - 2029. Retrieved 2007/10/02.