senecionine-N-oxide

senecionan-11,16-dione, 12-hydroxy-, 4-oxide

CAS: 13268-67-2 C18 H25 N O6 MW: 351.39945000

Identification

Namesenecionine-N-oxide
CAS Number13268-67-2
FDA UNIISearch
Molecular FormulaC18 H25 N O6
Molecular Weight351.39945000
MDL NumberMFCD01750097
Nikkaji NumberJ371.923E

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Soluble in water, 5.882e+004 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for senecionine-N-oxide usage levels up tonot for fragrance use.
Recommendation for senecionine-N-oxide flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

senecio vulgaris

Synonyms

senecionan-11,16-dione, 12-hydroxy-, 4-oxide senecionine N-oxide PubMed: Pyrrolizidine alkaloid variation in Senecio vulgaris populations from native and invasive ranges. PubMed: First evidence of pyrrolizidine alkaloid N-oxide-induced hepatic sinusoidal obstruction syndrome in humans. PubMed: The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips. PubMed: Quantification of pyrrolizidine alkaloids in North American plants and honey by LC-MS: single laboratory validation. PubMed: UPLC TOF MS for sensitive quantification of naturally occurring pyrrolizidine alkaloids in Petasites hybridus extract (Ze 339). PubMed: Modulatory effect of Senecio brasiliensis (Spreng) Less. in a murine model of inflammation induced by carrageenan into the pleural cavity. PubMed: An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides. PubMed: The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS. PubMed: Safety assessment of food and herbal products containing hepatotoxic pyrrolizidine alkaloids: interlaboratory consistency and the importance of N-oxide determination. PubMed: Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang). PubMed: Direct evidence for membrane transport of host-plant-derived pyrrolizidine alkaloid N-oxides in two leaf beetle genera. PubMed: Comparison of hepatic in vitro metabolism of the pyrrolizidine alkaloid senecionine in sheep and cattle. PubMed: Evaporative light scattering detection of pyrrolizidine alkaloids. PubMed: Taste receptors for pyrrolizidine alkaloids in a monophagous caterpillar. PubMed: Uptake and metabolism of pyrrolizidine alkaloids in Longitarsus flea beetles (Coleoptera: Chrysomelidae) adapted and non-adapted to alkaloid-containing host plants. PubMed: Biochemical strategy of sequestration of pyrrolizidine alkaloids by adults and larvae of chrysomelid leaf beetles. PubMed: Structure-activity relationships of pyrrolizidine alkaloids in insect chemical defense against the orb-weaving spider Nephila clavipes. PubMed: Simultaneous determination of N-oxides and free bases of pyrrolizidine alkaloids by cation-exchange solid-phase extraction and ion-pair high-performance liquid chromatography. PubMed: The two facies of pyrrolizidine alkaloids: the role of the tertiary amine and its N-oxide in chemical defense of insects with acquired plant alkaloids. PubMed: The effect of spironolactone treatment on the cytochrome P450-mediated metabolism of the pyrrolizidine alkaloid senecionine by hepatic microsomes from rats and guinea pigs. PubMed: Differing embryotoxic effects of senecionine and senecionine-N-oxide on the chick embryo. PubMed: Flavin-containing monooxygenase: a major detoxifying enzyme for the pyrrolizidine alkaloid senecionine in guinea pig tissues. PubMed: Role of cytochrome P450IIIA4 in the metabolism of the pyrrolizidine alkaloid senecionine in human liver. PubMed: Mechanisms for pyrrolizidine alkaloid activation and detoxification. PubMed: Excretion and blood radioactivity levels following [14C]senecionine administration in the rat. PubMed: Sites of synthesis, translocation and accumulation of pyrrolizidine alkaloid N-oxides in Senecio vulgaris L. PubMed: Metabolic links between the biosynthesis of pyrrolizidine alkaloids and polyamines in root cultures of Senecio vulgaris. PubMed: Identification of senecionine and senecionine N-oxide as antifertility constituents in Senecio vulgaris. PubMed: Determination of pyrrolizidine alkaloid metabolites from mouse liver microsomes using tandem mass spectrometry and gas chromatography/mass spectrometry. PubMed: Alkaloid patterns and biosynthetic capacity of root cultures from some pyrrolizidine alkaloid producing Senecio species. PubMed: Two dihydropyrrolizine alkaloid metabolites isolated from mouse hepatic microsomes in vitro. PubMed: A new pyrrolizidine alkaloid metabolite, 19-hydroxysenecionine isolated from mouse hepatic microsomes in vitro. PubMed: Tumor inhibitors. XXII. Senecionine and senecionine N-oxide, the active principles of Senecio triangularis.