SENECIONINE

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Product Name: SENECIONINE
CAS No.: 130-01-8
Chemical Name: SENECIONINE
Synonyms: SENECIONIN;qlgn;Aureine;Sencionine;SENECIONINE;Senecionine/Aureine;16-dione,12-hydroxy-senecionan-1;12-Hydroxysenecionan-11,16-dione;Senecionan-11,16-dione, 12-hydroxy-;(15cis)-12-Hydroxysenecionan-11,16-dione
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)
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)

SENECIONINE Preparation Products And Raw materials

Raw materials

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)-

Vincamine Impurity 5( Vincamine EP Impurity D)

130-01-8

Alkaloids