Senecionine

Base Information

• Chemical Name: Senecionine
• CAS No.: 130-01-8
• Deprecated CAS: 11002-70-3,11024-76-3
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• UNII: BO6N1U5YG6
• ChEMBL ID: CHEMBL362153
• DSSTox Substance ID: DTXSID40871615
• Metabolomics Workbench ID: 53429
• NSC Number: 89935
• Wikidata: Q2083871
• Wikipedia: Senecionine
• Mol file: 130-01-8.mol

Synonyms:integerrimine;intergerrimine;senecionine;senecionine citrate (1:1);senecionine citratre;senecionine, (15E)-isomer;squalidine

Chemical Property of Senecionine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 236 ºC(lit.)
• Refractive Index: 1.5100 (estimate)
• Boiling Point: 563.7°Cat760mmHg
• PKA: 12.81±0.40(Predicted)
• Flash Point: 294.7°C
• PSA: 76.07000
• Density: 1.25g/cm³
• LogP: 1.13070
• Storage Temp.: −20°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 335.17327290
• Heavy Atom Count: 24
• Complexity: 611

Purity/Quality:

≥98% ^*data from raw suppliers

Senecionine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CC=C1CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O)C
• Isomeric SMILES: C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C
• Description: This hepatotoxic alkaloid is widely distributed among the Senecio species, being found in S. aureus, S. ilicifolius Thunb., S. integerrirnus, S. pseudaarnica, S. squaUdus, S. viscosus and S. vulgaris. The base is laevorotatory with [α]D - 54.6° (CHCI3 ) and the crystals sublime at 130-140°CfO.2 mm. The nitrate has m.p. 214°C;[α]D - 34.2° (H2 0); the aurichloride, m.p. 186°C; the picrate, m.p. 191°C and the methiodide, m.p. 249°C. Alkaline hydrolysis furnishes retronecine and senecic acid (6-hydroxy-5-methyl-2-heptene-3 :6-dicarboxylic acid). Senecionine is a pyrrolizidine alkaloid that has been found in S. vulgaris and has hepatotoxic properties. It is metabolized by the cytochrome P450 (CYP) isoform CYP3A in the liver to the detoxification product senecionine N-oxide and reactive metabolites including dehydropyrrolizidine alkaloids and dehydrotetronecine. Senecionine (20 μM) induces mitochondrial depolarization and fragmentation in primary cultured mouse hepatocytes and increases apoptosis in a concentration-dependent manner. In rats, senecionine (35 mg/kg, p.o.) induces liver injury, increases serum levels of bilirubin and various bile acids, including taurocholic acid, glycocholic acid, and deoxycholic acid, and increases the activity of alanine aminotransferase and aspartate aminotransferase in serum. Senecionine-induced hepatotoxicity is associated with lipid peroxidation and glutathione depletion.

Technology Process of Senecionine

There total 81 articles about Senecionine 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: 81.0%

senecionine (methylthio)methyl ether (157240-89-6) → senecionine (130-01-8,480-79-5,480-80-8,82535-12-4,86782-21-0)

Guidance literature:

With trityl tetrafluoroborate; In dichloromethane; for 6.5h; Ambient temperature;

DOI:10.1246/bcsj.67.1990

Reference yield: 81.0%

integerrimine (methylthio)methyl ether (107338-96-5) → (-)-integerrimine (130-01-8,480-79-5,480-80-8,82535-12-4,86782-21-0)

Guidance literature:

With trityl tetrafluoroborate; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)85017-0

Reference yield:

senecic acid (13588-16-4) → senecionine (130-01-8,480-79-5,480-80-8,82535-12-4,86782-21-0)

Guidance literature:

Multi-step reaction with 7 steps

2: Ac₂O / 24 h / 40 °C

3: 97 percent / 1 M aq. KOH / methanol / 2.5 h / Heating

4: DCC / CH₂Cl₂ / 2.5 h / Ambient temperature

5: 1.) Bu₂SnO / 1.) C₆H₆, reflux, 23 h, 2.) toluene, from 0 deg C to RT, 60 min

6: DMAP, (+/-)-10-camphorsulfonic acid, DCC / CHCl₃ / 144 h / Ambient temperature

7: 81 percent / triphenylcarbenium tetrafluoroborate / CH₂Cl₂ / 6.5 h / Ambient temperature

With dmap; potassium hydroxide; camphor-10-sulfonic acid; trityl tetrafluoroborate; acetic anhydride; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; In methanol; dichloromethane; chloroform;

DOI:10.1246/bcsj.67.1990

upstream raw materials:

O-(tert-Butyldimethylsilyl)integerrimine

9-O-(tert-Butyldimethylsilyl)retronecine

(2R,3R)-5-(1-Hydroxy-ethyl)-2,3-dimethyl-6-oxo-tetrahydro-pyran-2-carboxylic acid methyl ester

(4R,5R)-5-<<2-(Trimethylsilyl)ethoxy>carbonyl>-4,5-dimethyl-2(E)-ethylidene-5-pentanolide

Downstream raw materials:

Dihydrosyneilesinolid B

integerrimine N-oxide

senecionine pyrrole

senecic acid

Refernces

• 1、 Narasaka, Koichi,Sakakura, Toshiyasu,Uchimaru, Tadafumi,Morimoto, Kiyoshi,Mukaiyama, Teruaki. "A TOTAL SYNTHESIS OF (+/-)-INTEGERRIMINE". . p. 455 - 458. Retrieved 1982.
• 2、 Niwa,Sakata,Yamada. "A synthesis of senecionine, a representative of hepatoxic, macrocyclic pyrrolizidine alkaloids of retronecine type". . p. 1990 - 1993. Retrieved 1994.
• 3、 White, James D.,Amedio, John C.,Gut, Samuel,Ohira, Susumu,Jayasinghe, Lalith R.. "Stereoselective Synthesis of the Pyrrolizidine Alkaloids (-)-Integerrimine and (+)-Usaramine". . p. 2270 - 2284. Retrieved 2007/10/02.