R0382

Retrorsine

≥90% (HPLC), powder, retronecine-type pyrrolizidine alkaloid

• Synonym(s): Retrorsin, Senecionan-11,16-Dione, 12,18-Dihydroxy- (9CI), β-Longilobine, 12,18-Dihydroxysenecionan-11,16-dione
• Empirical Formula (Hill Notation): C₁₈H₂₅NO₆
• CAS Number: 480-54-6
• Molecular Weight: 351.39
• UNSPSC Code: 12352200
• PubChem Substance ID: 24899338
• NACRES: NA.77

Properties

• product name: Retrorsine, ≥90% (HPLC)
• Assay: ≥90% (HPLC)
• mp: 208-211 °C (lit.)
• SMILES string: C\C=C1\C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23
• InChI: 1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-/m1/s1
• InChI key: BCJMNZRQJAVDLD-CQRYIUNCSA-N

Description

Application

Retrorsine has been used:

• as a mito-inhibitory pyrrolizidine alkaloid compound to induce necrotic liver injury in rats
• to induce hepatocellular injury in rats
• to arrest endogenous hepatocyte growth in mice

Biochem/physiol Actions

Retrorsine (RTS) is a retronecine-type pyrrolizidine alkaloid associated with Senecio and Crotalaria species. It belongs to the pyrrolizidine alkaloid family with mito-inhibitory property and elicits hepatotoxicity. It mediates the inactivation of cytochrome P450 3A4. Retrorsine also inhibits replication of fully differentiated hepatocytes.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300 + H310 + H330
• Precautionary Statements: P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• Hazard Classifications: Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves