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130-01-8

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  • [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)-

    Cas No: 130-01-8

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  • High Quality Oled CAS 130-01-8 [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)-

    Cas No: 130-01-8

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  • 130-01-8 [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-

    Cas No: 130-01-8

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  • [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)- 130-01-8

    Cas No: 130-01-8

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130-01-8 Usage

Description

Different sources of media describe the Description of 130-01-8 differently. You can refer to the following data:
1. 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).
2. 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.

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)

Check Digit Verification of cas no

The CAS Registry Mumber 130-01-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 0 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 130-01:
(5*1)+(4*3)+(3*0)+(2*0)+(1*1)=18
18 % 10 = 8
So 130-01-8 is a valid CAS Registry Number.
InChI:InChI=1/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

130-01-8 Well-known Company Product Price

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  • Sigma-Aldrich

  • (37031)  Senecionine  analytical standard

  • 130-01-8

  • 37031-0.05MG

  • 9,652.50CNY

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  • Sigma-Aldrich

  • (50351)  Senecionine  analytical standard

  • 130-01-8

  • 50351-5MG

  • 5,961.15CNY

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130-01-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name senecionine

1.2 Other means of identification

Product number -
Other names Senecionine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:130-01-8 SDS

130-01-8Related news

Solubilization and characterization of a SENECIONINE (cas 130-01-8) N-oxygenase from Crotalaria scassellatii seedlings09/30/2019

Seeds of Crotalaria scassellatii (Fabaceae) store pyrrolizidine alkaloids as tertiary amines. During the beginning of seed germination the tertiary alkaloids are rapidly converted into the respective alkaloid N-oxides which are the ultimate forms of alkaloid transport, metabolism and storage in ...detailed

Determination of senkirkine and SENECIONINE (cas 130-01-8) in Tussilago farfara using microwave-assisted extraction and pressurized hot water extraction with liquid chromatography tandem mass spectrometry09/29/2019

Tussilago farfara (Kuan Donghua) is an important Chinese herbal medicine which has been shown to contain many bioactive compounds and widely used to relieve cough and resolve phlegm. However, besides therapeutic bioactive compounds, this herb has been found to contain toxic pyrrolizidine alkaloi...detailed

The comparative pharmacokinetics of two pyrrolizidine alkaloids, SENECIONINE (cas 130-01-8) and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS10/01/2019

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 humans through the consumption of plants and PA-c...detailed

Chemical diversity and variation of pyrrolizidine alkaloids of the SENECIONINE (cas 130-01-8) type: biological need or coincidence?09/26/2019

. Laboratory and field tracer experiments with 14C-labelled senecionine Noxide (SO) and distant biosynthetic precursors such as [14C]putrescine revealed that pyrrolizidine alkaloid N-oxides (PAs) in Senecio vernalis Waldstr. Kit. (Asteraceae) show no significant turnover over periods of up to 29...detailed

The Roles of CYP3A and CYP2B Isoforms in Hepatic Bioactivation and Detoxification of the Pyrrolizidine Alkaloid SENECIONINE (cas 130-01-8) in Sheep and Hamsters09/25/2019

The roles of cytochrome CYP3A and CYP2B isozymes in the bioactivation and detoxification of the pyrrolizidine alkaloid (PA) senecionine (SN) have been investigatedin vitrowith sheep and hamster hepatic microsomes. Our results show that the rate of SN activation measured by (±)-6,7-dihydro-7-hyd...detailed

130-01-8Relevant articles and documents

Total synthesis of optically active integerrimine, a twelve-membered dilactonic pyrrolizidine alkaloid of retronecine type. III. Regioselective elaboration of the unsymmetrical twelve-membered dilactone and total synthesis of (-)-integerrimine

Niwa,Miyachi,Uosaki,et al.

, p. 4609 - 4610 (1986)

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Identification of senecionine and senecionine N-oxide as antifertility constituents in Senecio vulgaris

Tu,Konno,Soejarto,Waller,Bingel,Molyneux,Edgar,Cordell,Fong

, p. 461 - 463 (1988)

The MeOH extract of Senecio vulgaris L., administered po to rats on Days 1-10 postcoitum, significantly decreased the number of normal fetuses per pregnant rat found at autopsy on Day 16. Additional experiments showed a similar activity for its hepatotoxic constituents senecionine and senecionine N-oxide, suggesting that the latter two compounds were probably responsible for the effect seen with the extract. No antifertility effects were seen in MeOH extract-treated hamsters.

Total Synthesis of Optically Active Integerrimine, a Twelve-membered Dilactonic Pyrrolizidine Alkaloid of Retronecine Type

Niwa, Haruki,Miyachi, Yasuyoshi,Okamoto, Osamu,Uosaki, Youichi,Kuroda, Akio,et al.

, p. 393 - 412 (2007/10/02)

A total synthesis of the natural enantiomer of integerrimine (1), a twelve-membered dilactonic pyrrolizidine alkaloid of retronecine type has been achieved through the enantioselective synthesis and regioselective coupling of (+)-retronecine (4) and (+)-integerrinecic acid (methylthio)methyl ether (6).

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