(-)-Lupinine

Catalog Number	ACM486704
CAS Number	486-70-4
Description	(-)-Lupinine is a natural compound that is found in the genus Lupinus. It has been used as an analytical method to determine the detection sensitivity of analytical methods. (-)-Lupinine also inhibits the synthesis of molecules that are involved in plant physiology. (-)-Lupinine can be extracted from plants using trifluoroacetic acid, which can be chemically transformed into other compounds. (-)-Lupinine has shown biological properties and has been shown to have effects on growth factor and natural compounds.
Synonyms	(1R,9aR)-Octahydro-2H-quinolizin-1-ylmethanol
Molecular Weight	169.26 g/mol
Molecular Formula	C10H19NO
Canonical SMILES	C1CCN2CCC[C@H]([C@H]2C1)CO
Storage	store at 2℃-8℃
Harmonized Tariff Code	Switzerland: 29339910 - USA: 2933999701 - Slovakia: 2933991000 - UK: 2939990090 - China: 2933990000
MDL Number	MFCD00213431

Case Study

Synthesis of Flavonoid-Containing Lupinine Derivatives

Bondarenko S P, et al. Chemistry of Natural Compounds, 2012, 48, 234-237.

A series of new 4-aminoquinoline derivatives containing a lupine amine moiety (2) prepared from (-)-lupinine and exhibiting antimalarial activity. Subsequently, the introduction of the lupinine moiety into natural flavonoids and their analogs was achieved through the reaction of flavonoids with lupinylamine and formalin.
Synthesis examples of lupine derivatives
· Upon heating formononetin (3a), 7-hydroxy-2-methoxyisoflavone (3b), and its 2-methyl derivative 3d, as well as 7-hydroxy-2-methylisoflavone (3c) from Glycyrrhiza glabra, in propan-2-ol with an equivalent amount of 2 and a two-fold excess of formalin, along with a catalytic amount of 4-(dimethylamino)pyridine (DMAP), derivatives of 9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one (4a-d) were produced in satisfactory yields.
· Just like the Mannich reaction observed for 7-hydroxyisoflavones, satisfactory yields were obtained without the need for prior preparation of N,N-bis-(hydroxymethyl)amine. Through aminomethylation, derivatives of the isomeric system 9,10-dihydro-2H,8H-chromeno[8,7-e][1,3]oxazin-2-one were successfully synthesized from 7-hydroxy-3-(3-methoxyphenyl)-coumarin, 7-hydroxy-3-(2,4-dimethoxyphenyl)-coumarin, and 7-hydroxy-3-(2,5-dimethoxyphenyl)-coumarin using lupinylamine and formalin in propan-2-ol.

Custom Q&A

What is the chemical formula of (-)-Lupinine?

The chemical formula of (-)-Lupinine is C10H19NO.

What is the melting point of (-)-Lupinine?

The melting point of (-)-Lupinine is 62-65°C.

How is (-)-Lupinine stored?

(-)-Lupinine is stored sealed in dry, at room temperature.

In which solvents is (-)-Lupinine soluble?

(-)-Lupinine is slightly soluble in chloroform, ethanol (sonicated), and methanol.

What is the hazard class of (-)-Lupinine?

The hazard class of (-)-Lupinine is 6.1.

What is the primary source of (-)-Lupinine?

(-)-Lupinine is present in numerous plants of the Lupinus family, with the most important sources being L. luteus, L. niger, and L. palmeri Wats.

What are the clinical applications of (-)-Lupinine?

The clinical applications of (-)-Lupinine are very limited.

How is (-)-Lupinine described in terms of its chemical properties?

(-)-Lupinine is described as a crystalline solid, obtained as orthorhombic prisms from acetone, with a melting point of 69°C and boiling point of 270°C. It is strongly basic and soluble in water and organic solvents.

What is the toxic action of (-)-Lupinine?

(-)-Lupinine is moderately toxic. Ingestion of high doses may produce nausea, convulsions, and respiratory failure.

Who successfully synthesized (-)-Lupinine after several unsuccessful attempts?

(-)-Lupinine was finally synthesized by Clemo and his co-workers after several unsuccessful attempts.

※ Please kindly note that our products are for research use only.