(1R,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

• ChemBase ID: 155939
• Molecular Formular: C18H25NO5
• Molecular Mass: 335.3948
• Monoisotopic Mass: 335.17327291
• SMILES: C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C
• Canonical SMILES: C/C=C/1\C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3
• InChI: InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/t11-,14-,15-,18-/m1/s1
• InChIKey: HKODIGSRFALUTA-XKLVTHTNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^1^4,^1^7]heptadec-11-ene-3,8-dione
• IUPAC Traditional name: senecionine
• Synonyms: Senecionine

Database IDs

• CAS Number: 130-01-8
• MDL Number: MFCD00221720
• Beilstein Number: 8162955
• PubChem SID: 162250077; 24850715
• PubChem CID: 5281733

CALCULATED PROPERTIES

• Acid pKa: 12.370863
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.003747926
• LogD (pH = 7.4): 1.4551188
• Log P: 1.6438626
• Molar Refractivity: 89.4066 cm^3
• Polarizability: 34.92372 Å^3
• Polar Surface Area: 76.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 236 °C(lit.)
• Optical Rotation: [α]25/D -55.1°, c = 0.034% in chloroform

Safety Information

• RTECS: VT5710000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.0% (GC)
• Grade: analytical standard
• Empirical Formula (Hill Notation): C18H25NO5

DETAILS

Sigma Aldrich - 17806

Application
Senecionine has been used in a study to observe the gender-dependent difference of glutathione antioxidant system and its influence on hepatotoxic pyrrolizidine alkaloid isoline-induced liver injury. Senecionine has also been used in a study to observe a new metabolic pathway for pyrrolizidine alkaloids.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 17806.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 37031

Reconstitution
Dried down, 50 μg/mL after reconstitution with 1 mL of water