CAS 15503-86-3

Retrorsine, N-oxide

Description:

Retrorsine N-oxide is a chemical compound classified as a pyrrolizidine alkaloid N-oxide. It is derived from retrorsine, which is known for its potential toxicity and hepatotoxic effects. The N-oxide form is characterized by the presence of an oxygen atom bonded to the nitrogen atom in the pyrrolizidine structure, which can influence its biological activity and toxicity. Retrorsine N-oxide is typically found in certain plant species, particularly those in the family Asteraceae. Its structural features include a bicyclic framework, which is common among pyrrolizidine alkaloids, and it may exhibit various pharmacological properties. However, like many alkaloids, it can pose health risks, including liver damage and carcinogenic effects, particularly with prolonged exposure or ingestion. Due to these potential hazards, the study of retrorsine N-oxide is significant in toxicology and pharmacology, especially concerning its implications in herbal medicine and food safety. Proper handling and awareness of its toxicological profile are essential in research and applications involving this compound.

Formula: C₁₈H₂₅NO₇

InChI: InChI=1S/C18H25NO7/c1-3-12-8-11(2)18(23,10-20)17(22)25-9-13-4-6-19(24)7-5-14(15(13)19)26-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-,19?/m1/s1

InChI key: InChIKey=IDIMIWQPUHURPV-WTWIWYCDSA-N

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

Synonyms:

• (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-6-(hydroxymethyl)-5-methyl-, 14-oxide, (3Z,5R,6S,14aR,14bR)-
• (5R,6S,14aR)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-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,6S,14aR,14bR)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione 12-oxide
• 12,18-Dihydroxysenecionan-11,16-dione 4-oxide
• Brn 0058804
• Ccris 4339
• Hsdb 3499
• Isatidine
• Retrorsine N-oxide
• Retrorsine oxide
• Senecionan-11,16-dione, 12,18-dihydroxy-, 4-oxide
• Senecionan-11,16-dione, 12,18-dihydroxy-, 4-oxide (9CI)
• [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-6-(hydroxymethyl)-5-methyl-, 12-oxide, (3Z,5R,6S,14aR,14bR)-
• cis-Retronecic acid ester of retronecine-N-oxide
• trans-15-Ethylidene-12beta-hydroxy-12alpha-hydroxymethyl-13beta-methylsenec-1-enine-4-oxide

Retrorsine N-oxide

CAS: 15503-86-3

Formula: C₁₈H₂₅NO₇

Color and Shape: Solid

Molecular weight: 367.3936

Ref: IN-DA001NKA

Retrorsine N-oxide

CAS: 15503-86-3

Isatidine is a pyrrolizidine alkaoid.

Formula: C₁₈H₂₅NO₇

Color and Shape: Solid

Molecular weight: 367.40

Ref: TM-T32198

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

Retrorsine-N-oxide 100 µg/mL in Water

Controlled Product

CAS: 15503-86-3

Formula: C₁₈H₂₅NO₇

Color and Shape: Single Solution

Molecular weight: 367.39

Ref: 04-A16812510WA-100

Isatidine

CAS: 15503-86-3

Formula: C₁₈H₂₅NO₇

Purity: 95%~99%

Color and Shape: Powder

Molecular weight: 367.398

Ref: BP-BPC0408

Retrorsine n-oxide

CAS: 15503-86-3

Natural alkaloid

Formula: C₁₈H₂₅NO₇

Purity: ≥ 95.0 % (HPLC)

Color and Shape: Powder

Molecular weight: 367.4

Ref: 5G-82630

Retrorsine N-Oxide

CAS: 15503-86-3

Stability Hygroscopic
Applications Retrorsine N-oxide is a pyrrolizidine alkaloid that is naturally found in Senecio isatideus, a flowering plant that is native to the Netherlands. Retrorsine N-oxide is also known to raise blood pressure and can induce abnormal changes in the liver if ingested by animals or humans.
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 Cooper, R.: Trop. Anim. Health Pro., 39, 439 (2007); Mattocks, A.: Xenobiotica, 1, 563 (1971); Neumann, C. & Boland, W.: Helv. Chim. Acta, 73, 754 (1990); Vera, R., et al.: J. Essent. Oil Res., 6, 21 (1994)

Formula: C₁₈H₂₅NO₇

Color and Shape: Neat

Molecular weight: 367.39

Ref: TR-R279005

Retrorsine N-oxide

CAS: 15503-86-3

Retrorsine N-oxide is a synthetic pyrrolizidine alkaloid derivative, which is meticulously synthesized in the laboratory. It originates from the structural modification of naturally occurring alkaloids found in certain plant species of the Senecio genus. The mode of action of Retrorsine N-oxide involves its biotransformation into reactive intermediates that form adducts with cellular macromolecules, particularly within the liver. These interactions result in the inhibition of cellular division and protein synthesis, significantly affecting hepatocyte function.

Formula: C₁₈H₂₅NO₇

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 367.39 g/mol

Ref: 3D-FR161591

Retrorsine N-oxide

CAS: 15503-86-3

Formula: C₁₈H₂₅NO₇

Molecular weight: 367.4

Ref: ST-EA-CP-R67001