senecionine-N-oxide
senecionan-11,16-dione, 12-hydroxy-, 4-oxide
 
Notes:
None found
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    • BOC Sciences
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      Product(s):
      13268-67-2 Senecionine-N-oxide 95%
       
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CAS Number: 13268-67-2Picture of molecule3D/inchi
Other(deleted CASRN): 11045-26-4
Nikkaji Web: J371.923E
MDL: MFCD01750097
XlogP3-AA: 0.50 (est)
Molecular Weight: 351.39945000
Formula: C18 H25 N O6
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
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Google Scholar: with word "odor"Search
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Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 5.882e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
Senecionine-N-oxide 95%
Sigma-Aldrich
For experimental / research use only.
Senecionine-n-oxide phyproof® Reference Substance
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for senecionine-N-oxide usage levels up to:
 not for fragrance use.
 
Recommendation for senecionine-N-oxide flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Dietary exposure assessment to pyrrolizidine alkaloids in the European population
View page or View pdf
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5380876
National Institute of Allergy and Infectious Diseases: Data
Chemidplus: 0013268672
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References:
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5380876
Pubchem (sid): 135065633
Pherobase: View
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C15612
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 senecio vulgaris
Search Trop  Picture
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Synonyms:
 senecionan-11,16-dione, 12-hydroxy-, 4-oxide
 senecionine N-oxide
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Articles:
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.
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