Изолупанин

Description

Isolupanine (isolupanine, α-isolupanine, 11-isolupanine) is a quinolizidine alkaloid of lupine. Tetracyclic sparteine-type molecule with a lactam carbonyl group; in relation to lupanine it is an epimer at position 11, hence the synonym 11-epi-lupanine. Another structure designation is 4-oxo-2-isosparteine. The alkaloid accumulates in the seeds of species of the genus Lupinus, primarily in the narrow-leaved lupine (Lupinus angustifolius), where, together with angustifolin, it reaches high concentrations.

Basic Attributes

• CAS No.: 486-87-3
• Chemical formula: C15H24N2O
• Molecular weight: 248.36386
• Exact weight: 248.36
• EU number: 207-644-3
• Synonyms: 11-isolupanine, α-isolupanine, (+)-isolupanine, 11-epi-lupanine, 4-oxo-2-isosparteine
• Catalog section: alkaloids

Physico-chemical characteristics

• Density: 1.2 ± 0.1 g/cm³
• Melting point: 113 °C
• Boiling point: 396.7 ± 31.0 °C at 760 mm Hg. Art.
• Flash point: 172.7 ± 17.2 °C
• Refractive index: 1.581
• Specific rotation: D26 +39° (c = 0.77); D26 +65.9° (c = 3.4 in absolute ethanol)
• PSA: 23.55000
• XLogP3: 1.44

Implications for food safety

Isolupanine is one of the main quinolizidine alkaloids identified in the four main cultivated lupine species, along with lupanine, 13-hydroxylupanine, angustifoline and sparteine. Practical meaning of the group:

• the high content of alkaloids gives the seeds a bitter taste - hence the division of varieties into bitter (wild forms) and sweet (selection of the 1920s–1930s with a reduced level of alkaloids)
• quinolizidine alkaloids act as competitive inhibitors of acetylcholine and disrupt nerve signal transmission at the motor end plate
• with significant doses, acute anticholinergic intoxication is possible: blurred vision, headache, weakness, nausea
• the content of alkaloids in lupine and products based on it is standardized, which requires reliable quantitative determination

Scope of application

• analytical standard for the determination of quinolizidine alkaloids in lupine seeds and products containing lupine flour by HPLC and GC-MS methods
• reference substance in works on the selection of sweet lupine varieties and control of the alkaloid profile
• object of research on the biosynthesis of quinolizidine alkaloids in legumes
• comparative compound in the pharmacology of nicotinic cholinergic receptors

Storage and handling

GHS classification, hazard instructions, precautionary measures, transport codes and WGK class are not given in the product card. Considering that they are pharmacologically active alkaloids, handle with caution: gloves, safety glasses, hanging under a hood, avoiding inhalation of dust and contact with skin and mucous membranes. Store in a tightly closed container, in a dry place, away from light, away from food products. Residues and washes should be transferred to a licensed operator.