CAS 480-81-9|Seneciphylline
| Common Name | Seneciphylline | ||
|---|---|---|---|
| CAS Number | 480-81-9 | Molecular Weight | 333.379 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 577.7±50.0 °C at 760 mmHg |
| Molecular Formula | C18H23NO5 | Melting Point | 217ºC |
| MSDS | ChineseUSA | Flash Point | 303.2±30.1 °C |
| Symbol | GHS06 | Signal Word | Danger |
Names
| Name | Seneciphylline |
|---|---|
| Synonym | More Synonyms |
Seneciphylline BiologicalActivity
| Description | Seneciphylline is a toxic pyrrolizidine alkaloid in Senecio plants[1]. Seneciphylline significantly increases the activities of epoxide hydrase and glutathione-S-transferase but causes reduction of cytochrome P-450 and related monooxygenase activities[2]. |
|---|---|
| Related Catalog | Research Areas >>CancerSignaling Pathways >>Metabolic Enzyme/Protease >>Cytochrome P450Signaling Pathways >>Metabolic Enzyme/Protease >>Gutathione S-transferase |
| References | [1]. Bandyopadhyay S, et al. Cytotoxicity of Senecio in macrophages is mediated via its induction of oxidative stress. Res Vet Sci. 2009 Aug;87(1):85-90. [2]. Kakrani HK, et al. Effect of seneciphylline and senecionine on hepatic drug metabolizing enzymes in rats. J Ethnopharmacol. 1984 Dec;12(3):271-8. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 577.7±50.0 °C at 760 mmHg |
| Melting Point | 217ºC |
| Molecular Formula | C18H23NO5 |
| Molecular Weight | 333.379 |
| Flash Point | 303.2±30.1 °C |
| Exact Mass | 333.157623 |
| PSA | 76.07000 |
| LogP | 0.81 |
| Vapour Pressure | 0.0±3.6 mmHg at 25°C |
| Index of Refraction | 1.581 |
| InChIKey | FCEVNJIUIMLVML-QPSVUOIXSA-N |
| SMILES | C=C1CC(=CC)C(=O)OC2CCN3CC=C(COC(=O)C1(C)O)C23 |
| Storage condition | 2-8℃ |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 77 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 77 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 80 mg/kg
- TOXIC EFFECTS :
- Lungs, Thorax, or Respiration - acute pulmonary edema Liver - hepatitis (hepatocellular necrosis), diffuse Blood - lymphoma, including Hodgkin's disease
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 150 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 90 mg/kg
- TOXIC EFFECTS :
- Lungs, Thorax, or Respiration - acute pulmonary edema Liver - hepatitis (hepatocellular necrosis), diffuse Blood - lymphoma, including Hodgkin's disease
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 322 mg/kg/2W-I
- TOXIC EFFECTS :
- Brain and Coverings - other degenerative changes Vascular - other changes Liver - other changes
- TYPE OF TEST :
- Sex chromosome loss and nondisjunction
MUTATION DATA - TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 600 ug/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 142,209,1985 *** REVIEWS *** IARC Cancer Review:Animal No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,319,1976 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,319,1976 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987
- TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 600 ug/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 142,209,1985 *** REVIEWS *** IARC Cancer Review:Animal No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,319,1976 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,319,1976 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987
Safety Information
| Symbol | GHS06 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H301 |
| Precautionary Statements | Missing Phrase - N15.00950417 |
| Hazard Codes | T |
| Risk Phrases | R23/24/25 |
| Safety Phrases | 1-20-24/25-45 |
| RIDADR | UN 1544 |
| Packaging Group | III |
| Hazard Class | 6.1(b) |
Articles18
More Articles| Interplant alkaloid variation and Senecio vernalis toxicity in cattle. Vet. Hum. Toxicol. 43(3) , 147-51, (2001) Senecio vernalis and other plants containing pyrrolizidine alkaloids (PA) are implicated in the poisoning of cattle. The liver is a known target organ. In this study the content of the alkaloids senec... | |
| Pyrrolizidine alkaloids in pollen and pollen products. Mol. Nutr. Food. Res. 54(2) , 292-300, (2010) Recently, 1,2-dehydropyrrolizidine alkaloid (PA) ester alkaloids, found predominantly as their N-oxides (PANOs, pyrrolizidine N-oxides), have been reported in both honey and in pollen obtained directl... | |
| Mutagenic activity of the pyrrolizidine alkaloids seneciphylline and senkirkine in Drosophila and their transfer into rat milk. Food Chem. Toxicol. 22(3) , 223-5, (1984) Seneciphylline and senkirkine, two pyrrolizidine alkaloids that occur in animal feeds and medicinal herbs, respectively, have been tested for their ability to produce sex-linked recessive lethals in m... |
Synonyms
| (3Z,6R,14aR,14bR)-3-Ethylidene-6-hydroxy-6-methyl-5-methylene-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione |
| Jacodine |
| [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)- |
| a-Longilobine |
| α-Longilobine |
| (15Z)-12-Hydroxy-13,19-didehydrosenecionan-11,16-dione |
| seneciphylline |
| (3Z,6R,14aR,14bR)-3-Ethyliden-6-hydroxy-6-methyl-5-methylen-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizin-2,7-dion |
| (3Z,6R,14aR,14bR)-3-éthylidène-6-hydroxy-6-méthyl-5-méthylène-3,4,5,6,9,11,13,14,14a,14b-décahydro[1,6]dioxacyclododécino[2,3,4-gh]pyrrolizine-2,7-dione |
