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Safety Information

17806

Sigma-Aldrich

Senecionine

≥95.0% (GC)

Synonym(s):

Aureine

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About This Item

Empirical Formula (Hill Notation):
C18H25NO5
CAS Number:
130-01-8
Molecular Weight:
335.39
Beilstein:
8162955
MDL number:
MFCD00221720
UNSPSC Code:
85151701
PubChem Substance ID:
57647679

Assay

≥95.0% (GC)

optical activity

[α]25/D −55.1°, c = 0.034% in chloroform

mp

236 °C (lit.)

storage temp.

−20°C

SMILES string

[H][C@@]12[C@H]3CCN1CC=C2COC(=O)[C@](C)(O)[C@H](C)C\C(=C\C)C(=O)O3

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/b12-4-/t11-,14-,15-,18-/m1/s1

InChI key

HKODIGSRFALUTA-JTLQZVBZSA-N

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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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 1 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK1603
BCCK3043
BCCC3656
1391296V
BCBL5357V

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Oana Cristina Seremet et al.
Molecular medicine reports, 17(6), 7757-7763 (2018-04-06)
Pyrrolizidine alkaloids (PAs) are a widespread class of hepatotoxic heterocyclic organic compounds found in approximately 3% of world flora. Some PAs have been shown to have genotoxic and carcinogenic effects. The present study focuses on the toxicity effects of four
Yu-Qi He et al.
Chemical research in toxicology, 23(3), 591-599 (2010-01-23)
Pyrrolizidine alkaloids (PAs) possess significant hepatotoxicity to humans and animals after metabolic activation by liver P450 enzymes. Metabolism pathways of PAs have been studied for several decades, including metabolic activation, hydroxylation, N-oxidation, and hydrolysis. However, the glucuronidation of intact PAs
Annika Reinhard et al.
Journal of chemical ecology, 35(9), 1086-1095 (2009-09-25)
Recent studies have shown the occurrence of plant derived pyrrolizidine alkaloids (PAs) in retail honeys and pollen loads, but little is known about how these compounds influence the fitness of foraging honey bees. In feeding experiments, we tested a mix
I Narberhaus et al.
Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology, 173(6), 483-491 (2003-06-13)
Several Longitarsus flea beetle species sequester pyrrolizidine alkaloids acquired from their Asteraceae and Boraginaceae host plants. We carried out feeding and injection experiments using radioactively labeled pyrrolizidine alkaloids to investigate the physiological mechanisms of uptake, metabolism and storage of alkaloids
Mirka Macel et al.
Phytochemistry, 65(7), 865-873 (2004-04-15)
We studied the variation in pyrrolizidine alkaloid (PA) patterns of lab-grown vegetative plants of 11 European Senecio jacobaea populations. Plants were classified as jacobine, erucifoline, mixed or senecionine chemotypes based on presence and absence of the PAs jacobine or erucifoline.
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