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SENECIONINE

Product Name
SENECIONINE
CAS No.
130-01-8
Chemical Name
SENECIONINE
Synonyms
SENECIONIN;qlgn;Aureine;Sencionine;SENECIONINE;Senecionine-RM;Senecionine(AS);Senecionine/Aureine;Senecionine in methanol;16-dione,12-hydroxy-senecionan-1
CBNumber
CB6491042
Molecular Formula
C18H25NO5
Formula Weight
335.39
MOL File
130-01-8.mol
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SENECIONINE Property

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

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
45
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
VT5710000
F 
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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Precautionary statements

P262Do not get in eyes, on skin, or on clothing.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
17806
Product name
Senecionine
Purity
≥95.0% (GC)
Packaging
1mg
Price
$284
Updated
2023/06/20
Sigma-Aldrich
Product number
17806
Product name
Senecionine
Purity
≥95.0% (GC)
Packaging
5mg
Price
$959
Updated
2023/06/20
Cayman Chemical
Product number
25145
Product name
Senecionine
Purity
≥98%
Packaging
1mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
25145
Product name
Senecionine
Purity
≥98%
Packaging
5mg
Price
$168
Updated
2024/03/01
Sigma-Aldrich
Product number
PHL89789
Product name
Senecionine
Purity
phyproof? Reference Substance
Packaging
10mg
Price
$514
Updated
2024/03/01
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SENECIONINE Chemical Properties,Usage,Production

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)

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Preparation Products

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View Lastest Price from SENECIONINE manufacturers

Career Henan Chemical Co
Product
Senecionine 130-01-8
Price
US $9.80/KG
Min. Order
1g
Purity
＞98%
Supply Ability
20 tons
Release date
2020-02-10

130-01-8, SENECIONINERelated Search:

2-(Diethylamino)ethyl methacrylate (+)-3-METHYLHEXANEDIOIC ACID 3-METHOXYPYRROLIDINE senecionine N-oxide (R)-3-METHOXYPYRROLIDINE 2-(Diethylamino)-ethyl acrylate SENECIONINE 3-Methyladipic acid SENECIONINE(RG) (R)-ETHYL 3-METHYL-2-HYDROXYBUTANOATE 3-ETHOXYPYRROLIDINE retronecine 3-(DIMETHYLAMINO)PROPYL ACRYLATE anacrotine 3-BUTOXYPYRROLIDINE 3-PROPOXYPYRROLIDINE ETHYL 5-METHYL-5-HEXENOATE (S)-ALLYL LACTATE

  • (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
  • Senecionine/Aureine
  • qlgn
  • [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-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-
  • Senecionine in methanol
  • Senecionine(AS)
  • Senecionine-RM
  • Vincamine Impurity 5( Vincamine EP Impurity D)
  • 130-01-8
  • Alkaloids