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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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

17806-BULK:
17806-1MG:
17806-5MG:
17806-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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T Langer et al.
Planta medica, 62(3), 267-271 (1996-06-01)
We developed an immunoassay with antibodies against retrorsine to detect the closely related senecionine, the main alkaloid in various Asteraceae. Sensitivity is about 23 pg (68 fmol) for senecionine. Cross reactivity of monocrotalin, retrorsine N-oxide, senkirkine (< 0.1%), and seneciphylline
W G Chung et al.
Xenobiotica; the fate of foreign compounds in biological systems, 25(9), 929-939 (1995-09-01)
1. We have purified three P450s from the liver of the phenobarbital (PB)-treated guinea pig in order to evaluate the role of these enzymes in pyrrolizidine alkaloid (PA) metabolism. 2. PB treatment of guinea pig increased the hepatic microsomal conversion
Jennifer M Duringer et al.
American journal of veterinary research, 65(11), 1563-1572 (2004-11-30)
To compare hepatic metabolism of pyrrolizidine alkaloids (PAs) between sheep and cattle and elucidate the protective mechanism of sheep. Liver microsomes and cytosol from 8 sheep and 8 cattle. The PA senecionine, senecionine N-oxide (nontoxic metabolite) and 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP; toxic
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
Changhong Wang et al.
Analytical and bioanalytical chemistry, 401(1), 275-287 (2011-05-17)
Pyrrolizidine alkaloids (PAs) are considered to be one of the most hepatotoxic groups of compounds of plant origin and are present in about 3% of the world's flowering plants. Most PAs represent a considerable health hazard to both livestock and
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