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SENECIONINE

Basic information Safety Supplier Related

SENECIONINE Basic information

Product Name:
SENECIONINE
Synonyms:
  • (15cis)-12-Hydroxysenecionan-11,16-dione
  • 12-Hydroxysenecionan-11,16-dione
  • 16-dione,12-hydroxy-senecionan-1
  • Aureine
  • Sencionine
  • Senecionan-11,16-dione, 12-hydroxy-
  • SENECIONIN
  • SENECIONINE
CAS:
130-01-8
MF:
C18H25NO5
MW:
335.39
Product Categories:
  • Alkaloids
Mol File:
130-01-8.mol
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SENECIONINE Chemical Properties

Melting point:
236 °C(lit.)
alpha 
D25 -55.1° (c = 0.034 in chloroform)
Boiling point:
472.03°C (rough estimate)
Density 
1.266 g/cm3
refractive index 
1.5100 (estimate)
storage temp. 
−20°C
solubility 
DMF: 5 mg/ml; DMSO: 2 mg/ml; Ethanol: 1 mg/ml; PBS (pH 7.2): 0.1 mg/ml
pka
12.81±0.40(Predicted)
form 
Solid
color 
White to off-white
optical activity
[α]25/D 55.1°, c = 0.034% in chloroform
BRN 
8162955
InChIKey
HKODIGSRFALUTA-JTLQZVBZSA-N
LogP
0.880 (est)
EPA Substance Registry System
Senecionine (130-01-8)
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Safety Information

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
45
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
VT5710000
10-23
HazardClass 
6.1(a)
PackingGroup 
II
Hazardous Substances Data
130-01-8(Hazardous Substances Data)
Toxicity
LD50 i.v. in mice: 64.12 ±2.24 mg/kg (Harris)

MSDS

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SENECIONINE Usage And Synthesis

Description

This hepatotoxic alkaloid is widely distributed among the Senecio species, being found in S. aureus, S. ilicifolius Thunb., S. integerrirnus, S. pseudaarnica, S. squaUdus, S. viscosus and S. vulgaris. The base is laevorotatory with [α]D - 54.6° (CHCI3 ) and the crystals sublime at 130-140°CfO.2 mm. The nitrate has m.p. 214°C;[α]D - 34.2° (H2 0); the aurichloride, m.p. 186°C; the picrate, m.p. 191°C and the methiodide, m.p. 249°C. Alkaline hydrolysis furnishes retronecine and senecic acid (6-hydroxy-5-methyl-2-heptene-3 :6-dicarboxylic acid).

Description

Senecionine is a pyrrolizidine alkaloid that has been found in S. vulgaris and has hepatotoxic properties. It is metabolized by the cytochrome P450 (CYP) isoform CYP3A in the liver to the detoxification product senecionine N-oxide and reactive metabolites including dehydropyrrolizidine alkaloids and dehydrotetronecine. Senecionine (20 μM) induces mitochondrial depolarization and fragmentation in primary cultured mouse hepatocytes and increases apoptosis in a concentration-dependent manner. In rats, senecionine (35 mg/kg, p.o.) induces liver injury, increases serum levels of bilirubin and various bile acids, including taurocholic acid, glycocholic acid, and deoxycholic acid, and increases the activity of alanine aminotransferase and aspartate aminotransferase in serum. Senecionine-induced hepatotoxicity is associated with lipid peroxidation and glutathione depletion.

Uses

Senecionine is a pyrrolizidine alkaloid with the potential to affect hepatic drug metabolizing enzymes in rat cells.

Definition

ChEBI: A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio.

Safety Profile

Poison by intravenous,intraperitoneal, and possibly other routes. Anexperimental teratogen. Other experimental reproductiveeffects. Mutation data reported. When heated todecomposition it emits toxic fumes of NOx.

References

Grandval, Lajoux., Cornpt. rend., 120,1120 (1895)
Grandval, Lajoux., Bull. Soc. Chirn. Fr., 13,942 (1895)
Manske., Can. J. Res., S, 651 (1931)
Manske., ibid, 14B, 6 (1936)
Barger, Blackie., J. Chern. Soc., 584 (1937)
Blackie., Pharrn. J., 138,102 (1937)
Manske., Can. J. Res., 17B, I (1939)

SENECIONINESupplier

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0871-65217109 13211707573;
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