Senecionine N-oxide

Base Information

• Chemical Name: Senecionine N-oxide
• CAS No.: 13268-67-2
• Deprecated CAS: 11045-26-4
• Molecular Formula: C18H25 N O6
• Molecular Weight: 351.4
• European Community (EC) Number: 805-146-6
• NSC Number: 106677
• DSSTox Substance ID: DTXSID901016615
• Nikkaji Number: J371.923E
• Wikidata: Q27104786
• Metabolomics Workbench ID: 52569
• ChEMBL ID: CHEMBL471683
• Mol file: 13268-67-2.mol

Synonyms:senecionine N-oxide

Chemical Property of Senecionine N-oxide

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 12.77±0.40(Predicted)
• Flash Point: °C
• PSA: 102.26000
• Density: g/cm³
• LogP: 1.16420
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 351.16818752
• Heavy Atom Count: 25
• Complexity: 656

Purity/Quality:

99% ^*data from raw suppliers

SenecionineN-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CC(C(C(=O)OCC2=CC[N+]3(C2C(CC3)OC1=O)[O-])(C)O)C
• Isomeric SMILES: C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(C)O)C
• Description: Senecionine N-oxide is a tertiary amine oxide. It derives from a senecionine.
• Uses: Senecionine N-oxide is the major pyrrolizidine alkaloid in Senecio vulgaris, a native herb of the British Isles. Senecionine N-oxide is hepatotoxic, and is suspected to be an antifertility agent in rats. Despite its toxicity, it is also being regarded as an antiproliferative agent for tumour growth.

Technology Process of Senecionine N-oxide

There total 4 articles about Senecionine N-oxide 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:

senecoinine → (+/-)-6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (73466-19-0) + integerrimine N-oxide (13268-67-2)

Guidance literature:

With ethylenediaminetetraacetic acid; NADPH-generating system; liver microsomes; In phosphate buffer; at 37 ℃; for 1h; pH=7.6; Further Variations:; Catalysts; Kinetics; Enzymatic reaction;

DOI:10.1016/S0378-4274(98)00152-0

Reference yield:

senecionine (130-01-8,480-79-5,480-80-8,82535-12-4,86782-21-0) → integerrimine N-oxide (13268-67-2)

Guidance literature:

With dihydrogen peroxide;

DOI:10.1002/jps.2600770522

Reference yield:

senecoinine → integerrimine N-oxide (13268-67-2)

Guidance literature:

With dihydrogen peroxide;

DOI:10.1002/jms.2969

upstream raw materials:

senecionine

Downstream raw materials:

senecionine

Refernces

• 1、 Huan, Jian-Ya,Miranda, Cristobal L.,Buhler, Donald R.,Cheeke, Peter R.. "Species differences in the hepatic microsomal enzyme metabolism of the pyrrolizidine alkaloids". . p. 127 - 137. Retrieved 2007/10/03.