Salutaridine, (-)-

Base Information

• Chemical Name: Salutaridine, (-)-
• CAS No.: 4090-18-0
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38
• European Community (EC) Number: 683-153-1
• UNII: 7UOY4F98SF
• DSSTox Substance ID: DTXSID201026889
• Nikkaji Number: J7.824G
• Wikidata: Q27268875
• Metabolomics Workbench ID: 133696
• ChEMBL ID: CHEMBL402782
• Mol file: 4090-18-0.mol

Synonyms:salutaridine;salutaridine, (+-)-isomer;salutaridine, (9alpha,13alpha)-isomer;sinoacutine

Chemical Property of Salutaridine, (-)-

Chemical Property:

• Vapor Pressure: 5.93E-12mmHg at 25°C
• Melting Point: 198℃
• Refractive Index: 1.645
• Boiling Point: 532.5 °C at 760 mmHg
• PKA: 9.28±0.40(Predicted)
• Flash Point: 275.8 °C
• PSA: 59.00000
• Density: 1.33g/cm³
• LogP: 1.87610
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 327.14705815
• Heavy Atom Count: 24
• Complexity: 613

Purity/Quality:

95%-98% ^*data from raw suppliers

Sinoacutin 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C=C(C(=O)C=C2C1CC4=C3C(=C(C=C4)OC)O)OC
• Isomeric SMILES: CN1CC[C@@]23C=C(C(=O)C=C2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC
• Uses: Sinoacutine is an isoquinoline alkaloid used as a prolyl oligopeptidase inhibitor.

Technology Process of Salutaridine, (-)-

There total 20 articles about Salutaridine, (-)- 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: 96.2%

O4-acetylsalutaridine (2611-69-0) → salutaridine (4090-18-0,23979-21-7,1936-18-1)

Guidance literature:

With sodium hydroxide; In ethanol; water; Ambient temperature;

Reference yield:

(R)-reticuline (485-19-8,1699-46-3,3968-19-2,7096-86-8,14752-49-9) → salutaridine (4090-18-0,23979-21-7,1936-18-1)

Guidance literature:

In water; at 37 ℃; for 0.666667h; microsomal-bound cytochrome P-450 NADPH from pig liver; pH 7.75; 0.3 M tricine buffer;

DOI:10.1016/S0040-4039(00)79765-6

Reference yield:

O6-demethylsalutaridine (27669-33-6) → salutaridine (4090-18-0,23979-21-7,1936-18-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 74.83 percent / pyridine / 20 h / Ambient temperature

2: 99.67 percent / diethylamine / ethanol / 6 h / Ambient temperature

3: 91.1 percent / CHCl₃; methanol; diethyl ether / 0.58 h / 0 - 5 °C

4: 96.2 percent / 10percent NaOH / ethanol; H₂O / Ambient temperature

With sodium hydroxide; diethylamine; In pyridine; methanol; diethyl ether; ethanol; chloroform; water;

upstream raw materials:

(S)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-4,4-dimethoxy-cyclohex-2-enylmethyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

4,4-Dimethoxy-3-oxo-cyclohexanecarboxylic acid ethyl ester

(3-Bromomethyl-6,6-dimethoxy-cyclohex-1-enyloxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

thebaine

Refernces

• 1、 Grobe, Nadja,Kutchan, Toni M.,Zenk, Meinhart H.. "Rat CYP2D2, not 2D1, is functionally conserved with human CYP2D6 in endogenous morphine formation". experimental part. p. 1749 - 1753. Retrieved 2012/08/29.
• 2、 Amann,Zenk. "Formation of the morphine precursor salutaridine is catalyzed by a cytochrome P-450 enzyme in mammalian liver". . p. 3675 - 3678. Retrieved 2007/10/02.