CAS 13268-67-2

senecionine N-oxide

Description:

Senecionine N-oxide is a pyrrolizidine alkaloid, a class of compounds known for their complex structures and potential biological activities. This substance is derived from senecionine, which is found in various plants, particularly those in the Asteraceae family. Senecionine N-oxide is characterized by its nitrogen-containing heterocyclic structure, which contributes to its pharmacological properties. It typically appears as a crystalline solid and is soluble in organic solvents. The compound has garnered attention due to its potential toxicity, particularly in relation to liver damage and carcinogenic effects associated with prolonged exposure or ingestion. Its mechanism of action often involves metabolic activation leading to the formation of reactive intermediates. As with many alkaloids, senecionine N-oxide may exhibit a range of biological activities, including antimicrobial and cytotoxic effects, although its safety profile necessitates caution in its use. Overall, while it holds interest for research, its toxicological implications are significant and warrant careful handling and study.

Formula: C₁₈H₂₅NO₆

InChI: InChI=1/C18H25NO6/c1-4-12-9-11(2)18(3,22)17(21)24-10-13-5-7-19(23)8-6-14(15(13)19)25-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4+/t11-,14-,15-,18-,19?/m1/s1

InChI key: InChIKey=PLGBHVNNYDZWGZ-GPUZEBNTSA-N

SMILES: O=N12[C@]3([C@@](CC1)(OC(=O)/C(=C\C)/C[C@@H](C)[C@@](C)(O)C(=O)OCC3=CC2)[H])[H]

Synonyms:

• (1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-3,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, 12-oxide, (3Z,5R,6R,14aR,14bR)-
• (3E,5R,6R,14aR,14bR)-3-ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione 12-oxide
• (5R,6R,14aR,14bR)-3-ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione 12-oxide
• 12-Hydroxysenecionan-11,16-dione 4-oxide
• Nsc 106677
• Senecionan-11,16-dione, 12-hydroxy-, 4-oxide
• Senecionine oxide
• [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-, 12-oxide, (3Z,5R,6R,14aR,14bR)-
• [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-, 12-oxide, (3Z,5R,6R,14aR,14bR)-[partial]-
• Senecionine N-oxide
• Senecionin-N-oxid

Senecionine N-oxide

CAS: 13268-67-2

Senecionine N-oxide: biosynthesized in Trichoderma lucidum roots, has antitumor properties, but can cause liver syndrome.

Formula: C₁₈H₂₅NO₆

Purity: 98%

Color and Shape: Solid

Molecular weight: 351.39

Ref: TM-TN2203

Senecionine N-oxide

CAS: 13268-67-2

Formula: C₁₈H₂₅NO₆

Molecular weight: 351.40

Ref: 7W-GY9519

Pyrrolizidine alkaloids Mixture 661 100 µg/mL in Methanol

Controlled Product

CAS: 101687-28-9, 10285-06-0, 10285-07-1, 127-30-0, 130-01-8, 13268-67-2, 15503-86-3, 2318-18-5, 303-33-3, 303-34-4, 38710-26-8, 41093-89-4, 480-54-6, 480-81-9, 520-68-3, 570-19-4, 6209-65-0, 65582-53-8, 72755-25-0, 95462-14-9, 95462-15-0

Color and Shape: Mixture

Ref: 04-A50000661ME

Senecionine-N-oxide 100 µg/mL in Water

Controlled Product

CAS: 13268-67-2

Formula: C₁₈H₂₅NO₆

Color and Shape: Single Solution

Molecular weight: 351.39

Ref: 04-A16934010WA-100

Senecionine N-oxide

CAS: 13268-67-2

Formula: C₁₈H₂₅NO₆

Purity: 95%~99%

Molecular weight: 351.399

Ref: BP-BP4019

Senecionine N-Oxide-d3

CAS: 13268-67-2

Formula: C₁₈H₂₂D₃NO₆

Molecular weight: 354.42

Ref: 4Z-S-110004

Senecionine N-Oxide

CAS: 13268-67-2

Formula: C₁₈H₂₅NO₆

Molecular weight: 351.40

Ref: 4Z-S-110002

Senecionine n-oxide

CAS: 13268-67-2

Natural alkaloid

Formula: C₁₈H₂₅NO₆

Purity: ≥ 95.0 % (HPLC)

Color and Shape: Powder

Molecular weight: 351.4

Ref: 5G-82631

Senecionine N-Oxide-D3

Controlled Product

CAS: 13268-67-2

Stability Hygroscopic
Applications Senecionine N-oxide-D3 is a labelled analogue of Senecionine N-oxide (S258655Senecionine N-oxide is the major pyrrolizidine alkaloid in Senecio vulgaris, a native herb of the British Isles. Senecionine N-oxide is hepatotoxic, and is suspected to be an antifertility agent in rats. Despite its toxicity, it is also being regarded as an antiproliferative agent for tumour growth.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Hartmann, T. & Toppel, G.: Phytochemistry, 26, 1639 (1987); Su, J., et al.: Org. Mag. Res., 11, 565 (1978); Tu, Z., et al.: J. Pharm. Sci., 77, 461 (1988)

Formula: C₁₈H₂₂D₃NO₆

Color and Shape: White To Brown

Molecular weight: 354.41

Ref: TR-S258657

Senecionine N-Oxide

CAS: 13268-67-2

Formula: C₁₈H₂₅NO₆

Color and Shape: Neat

Molecular weight: 351.39

Ref: TR-S258655

Senecionine N-oxide

CAS: 13268-67-2

Senecionine N-oxide is a pyrrolizidine alkaloid N-oxide, which is a naturally occurring chemical compound known for its toxicological properties. It is primarily sourced from plants belonging to the Senecio genus, which are widely distributed across various geographical regions. The mode of action of Senecionine N-oxide involves its bioactivation in the liver, where it is converted to reactive pyrrolic metabolites. These metabolites can form adducts with cellular macromolecules such as DNA and proteins, leading to hepatic necrosis and potentially mutagenic effects.

Formula: C₁₈H₂₅NO₆

Purity: Min. 95%

Molecular weight: 351.39 g/mol

Ref: 3D-FS161594

Senecionine N-Oxide

CAS: 13268-67-2

Formula: C₁₈H₂₅NO₆

Molecular weight: 351.4

Ref: ST-EA-CP-S80001