jacobine
senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15-alpha,20S)- (9CI)
Identification
| Name | jacobine |
| CAS Number | 6870-67-3 |
| FDA UNII | GM32U80H1R |
| Molecular Formula | C18 H25 N O6 |
| Molecular Weight | 351.39945000 |
| Beilstein | 0054580 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 2.878e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intravenous-mouse LD50 77 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
No supplier data available
Potential Uses
Natural Occurrence
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
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.