jacobine
senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15-alpha,20S)- (9CI)
 
Notes:
None found
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CAS Number: 6870-67-3Picture of molecule3D/inchi
Other(deleted CASRN): 471-14-7
FDA UNII: GM32U80H1R
Beilstein Number: 0054580
XlogP3-AA: 0.30 (est)
Molecular Weight: 351.39945000
Formula: C18 H25 N O6
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 2.878e+005 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:
 None found
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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:
intravenous-mouse LD50  77 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 69, 1942.

unreported-rat LD50  60 mg/kg
Cancer Research. Vol. 28, Pg. 2237, 1968.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for jacobine usage levels up to:
 not for fragrance use.
 
Recommendation for jacobine 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
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EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 442741
National Institute of Allergy and Infectious Diseases: Data
 (15S,20S)-12-hydroxy-15,20-dihydro-15,20-epoxysenecionan-11,16-dione
Chemidplus: 0006870673
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References:
 (15S,20S)-12-hydroxy-15,20-dihydro-15,20-epoxysenecionan-11,16-dione
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 442741
Pubchem (sid): 134986638
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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
KEGG (GenomeNet): C10339
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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 jacobaea
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Synonyms:
(15alpha,20R)15,20-epoxy-15,20-dihydro-12-hydroxy-senecionan-11,16-dione
(15alpha,20R)15,20-epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione
(15S,20S)-12-hydroxy-15,20-dihydro-15,20-epoxysenecionan-11,16-dione
 senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15-alpha,20S)- (9CI)
 spiro[1,6-dioxacyclododecino[2,3,4-gh]pyrrolizine-3(2H),2'-oxirane]-2,7(4H)-dione, 5,6,9,11,13,14,14a,14b-octahydro-6-hydroxy-3',5,6-trimethyl-, (3S,3'S,5R,6R,1
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Articles:
PubMed: Quantification of the Pyrrolizidine Alkaloid Jacobine in Crassocephalum crepidioides by Cation Exchange High-Performance Liquid Chromatography.
PubMed: The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips.
PubMed: Are effects of common ragwort in the Ames test caused by pyrrolizidine alkaloids?
PubMed: Testing the generalist-specialist dilemma: the role of pyrrolizidine alkaloids in resistance to invertebrate herbivores in Jacobaea species.
PubMed: Toxicity of pyrrolizidine alkaloids to Spodoptera exigua using insect cell lines and injection bioassays.
PubMed: Development and validation of a rapid multiplex ELISA for pyrrolizidine alkaloids and their N-oxides in honey and feed.
PubMed: Pyrrolizidine alkaloid composition influences cinnabar moth oviposition preferences in Jacobaea hybrids.
PubMed: Effects of root herbivory on pyrrolizidine alkaloid content and aboveground plant-herbivore-parasitoid interactions in Jacobaea vulgaris.
PubMed: Tandem chain extension-Mannich reaction: an approach to β-proline derivatives.
PubMed: Malaria-infected mice live until at least day 30 after a new artemisinin-derived thioacetal thiocarbonate combined with mefloquine are administered together in a single, low, oral dose.
PubMed: Differential tissue distribution of metabolites in Jacobaea vulgaris, Jacobaea aquatica and their crosses.
PubMed: The relationship between structurally different pyrrolizidine alkaloids and western flower thrips resistance in F(2) hybrids of Jacobaea vulgaris and Jacobaea aquatica.
PubMed: Three-component, one-flask synthesis of rhodanines (thiazolidinones).
PubMed: [Pyrrolizidine alkaloids of Senecio cannabifolius var. integrilifolius].
PubMed: The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in Jacobaea vulgaris.
PubMed: Pyrrolizidine alkaloids in honey: comparison of analytical methods.
PubMed: NMR metabolomics of thrips (Frankliniella occidentalis) resistance in Senecio hybrids.
PubMed: Formation of gamma-lactones through CAN-mediated oxidative cleavage of hemiketals.
PubMed: Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang).
PubMed: Pyrrolizidine alkaloid profiles of the Senecio cineraria group (Asteraceae).
PubMed: Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update.
PubMed: Pyrrolizidine alkaloid level in Senecio bicolor (Wilid.) Tod, ssp. cineraria (DC.) from middle Europe.
PubMed: Variation in pyrrolizidine alkaloid patterns of Senecio jacobaea.
PubMed: Metabolism of pyrrolizidine alkaloids by Peptostreptococcus heliotrinreducens and a mixed culture derived from ovine ruminal fluid.
PubMed: Alkaloids from Senecio aquaticus.
PubMed: Determination of pyrrolizidine alkaloids in honey from selected sites by solid phase extraction and HPLC-MS.
PubMed: Major factors for the susceptibility of guinea pig to the pyrrolizidine alkaloid jacobine.
PubMed: Hydrolysis rates of pyrrolizidine alkaloids derived from Senecio jacobaea.
PubMed: Glutathione conjugation with the pyrrolizidine alkaloid, jacobine.
PubMed: Effects of antibacterial agents on in vitro ovine ruminal biotransformation of the hepatotoxic pyrrolizidine alkaloid jacobine.
PubMed: Microsomal metabolism of pyrrolizidine alkaloids from Senecio jacobaea. Isolation and quantification of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine and N-oxides by high performance liquid chromatography.
PubMed: Genotoxicity of the pyrrolizidine alkaloid jacobine in rats.
PubMed: Genotoxicity of a variety of pyrrolizidine alkaloids in the hepatocyte primary culture-DNA repair test using rat, mouse, and hamster hepatocytes.
PubMed: Mutagenic responses of tansy ragwort (Senecio jacobaea) plant, pyrrolizidine alkaloids and metabolites in goat milk with the Salmonella/mammalian-microsome mutagenicity test.
PubMed: Induction of endogenous avian tumor virus gene expression by pyrrolizidine alkaloids.
PubMed: Pyrrolizidine alkaloid-induced alterations in benzo[alpha]pyrene metabolism and binding of benzo[alpha]pyrene metabolites to deoxyribonucleic acid.
PubMed: Comparison of the toxicities of Senecio jacobaea, Senecio vulgaris and Senecio glabellus in rats.
PubMed: Effect of dietary Senecio jacobaea and injected Senecio alkaloids and monocrotaline on guinea pigs.
PubMed: Comparative effects of the pyrrolizidine alkaloids jacobine and monocrotaline on hepatic drug metabolising enzymes in the rat.
PubMed: Nicotinic acid metabolism enzymic preparation and absolute configuration of the substrate for 2,3-dimethylmalate lyase.
PubMed: Pyrrolizidine alkaloids: their occurrence in honey from tansy ragwort (Senecio jacobaea L.)
PubMed: Jacobine.
PubMed: Senecionine, Seneciphylline, Jacobine and Otosenine from Senecio cineraria.
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