Lupinine
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Lupinine
structure -
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CAS No:
486-70-4
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Formula:
C10H19NO
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Chemical Name:
Lupinine
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Synonyms:
2H-Quinolizine-1-methanol,octahydro-,(1R,9aR)-;Lupinine;2H-Quinolizine-1-methanol,octahydro-,(1R-trans)-;(1R,9aR)-Octahydro-2H-quinolizine-1-methanol;(-)-Lupinine;(-)-Octahydro-1H-quinolizine-1-methanol;NSC 21723;(1R,9aR)-(Octahydroquinolizin-1-yl)methanol;1-((1R,9aR)-Octahydroquinolizidin-1-yl)methanol;(R,R)-1-(Hydroxymethyl)octahydroindolizine;3000-87-1;31456-49-2
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CAS No:
Description
Crystalline solid, obtained as orthorhombic prisms from acetone; melts at 69°C(156.2°F); bp 270°C (518°F); strongly basic;soluble in water and organic solvents.
Lupinine is a bitter tasting quinolizidine alkaloid present in Lupinus species (lupins), plants of the family Fabaceae. The scientific literature contains many reports on the isolation and synthesis of this compound. The characteristically bitter taste of lupin beans, attributable to the alkaloids which they contain, renders them unsuitable for human and animal consumption. However, because lupin beans have potential nutritional value due to their high protein content, efforts have been made to reduce their alkaloid content, as well as to develop "sweet" varieties of Lupinus.
Lupinine is a quinolizidine alkaloid.
Characteristics
23.5
1.18110
1.04 g/cm3
70 °C
270 °C
160-164°C/4mm
1.525
0.000928mmHg at 25°C
D26 -25.9° (c = 3 in water); D28 -21° (c = 9.5 in alcohol)
135.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
III
6.1
1544
20/21/22-41
22-36/37-39-26
OK5802000
Xi
Irritant
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501
H302
UN 1544
Computed Properties
Molecular Weight:169.26
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:169.146664230
Monoisotopic Mass:169.146664230
Topological Polar Surface Area:23.5
Heavy Atom Count:12
Complexity:149
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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