13268-67-2

Basic information

• Product Name: senecionine N-oxide
• Synonyms: senecionine N-oxide;12-Hydroxysenecionan-11,16-dione 4-oxide;Senecionine oxide;Senecionin-N-oxid
• CAS NO: 13268-67-2
• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.397
• Mol File: 13268-67-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• PKA: 12.77±0.40(Predicted)
• CAS DataBase Reference: senecionine N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: senecionine N-oxide(13268-67-2)
• EPA Substance Registry System: senecionine N-oxide(13268-67-2)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 13268-67-2(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C18H25NO6/c1-4-12-9-11(2)18(3,22)17(21)24-10-13-5-7-19(23)8-6-14(15(13)19)25-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4+/t11-,14-,15-,18-,19?/m1/s1

Upstream product

• 130-01-8 senecionine 

Downstream Products

• 130-01-8 senecionine 

Relevant articles and documents

Characteristic ion clusters as determinants for the identification of pyrrolizidine alkaloid N-oxides in pyrrolizidine alkaloid-containing natural products using HPLC-MS analysis

Pyrrolizidine alkaloid (PA)-containing plants are widely distributed in the world. PAs are hepatotoxic, affecting livestock and humans. PA N-oxides are often present together with PAs in plants and also exhibit hepatotoxicity but with less potency. HPLC-MS is generally used to analyze PA-containing herbs, although PA references are unavailable in most cases. However, to date, without reference standards, HPLC-MS methodology cannot distinguish PA N-oxides from PAs because they both produce the same characteristic ions in mass spectra. In the present study, the mass spectra of 10 PA N-oxides and the corresponding PAs were systemically investigated using HPLC-MS to define the characteristic mass fragment ions specific to PAs and PA N-oxides. Mass spectra of toxic retronecine-type PA N-oxides exhibited two characteristic ion clusters at m/z 118-120 and 136-138. These ion clusters were produced by three unique fragmentation pathways of PA N-oxides and were not found in their corresponding PAs. Similarly, the nontoxic platynecine-type PA N-oxides also fragmented via three similar pathways to form two characteristic ion clusters at m/z 120-122 and 138-140. Further application of using these characteristic ion clusters allowed successful and rapid identification of PAs and PA N-oxides in two PA-containing herbal plants. Our results demonstrated, for the first time, that these characteristic ion clusters are unique determinants to discriminate PA N-oxides from PAs even without the availability of reference samples. Our findings provide a novel and specific method to differentiate PA N-oxides from PAs in PA-containing natural products, which is crucial for the assessment of their intoxication.

Identification of senecionine and senecionine N-oxide as antifertility constituents in Senecio vulgaris

The MeOH extract of Senecio vulgaris L., administered po to rats on Days 1-10 postcoitum, significantly decreased the number of normal fetuses per pregnant rat found at autopsy on Day 16. Additional experiments showed a similar activity for its hepatotoxic constituents senecionine and senecionine N-oxide, suggesting that the latter two compounds were probably responsible for the effect seen with the extract. No antifertility effects were seen in MeOH extract-treated hamsters.