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76466

Supelco

(−)-Sparteine

≥98.0% (GC)

Synonym(s):

(−)-Lupinidine

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About This Item

Empirical Formula (Hill Notation):
C15H26N2
CAS Number:
90-39-1
Molecular Weight:
234.38
EC Number:
201-988-8
MDL number:
MFCD00069653
UNSPSC Code:
23151817
PubChem Substance ID:
329767135
NACRES:
NA.22

Quality Level

100

assay

≥98.0% (GC)

form

liquid

optical activity

[α]/D -17.5±1.5°, c = 1 in ethanol

refractive index

n20/D 1.526-1.530
n20/D 1.528 (lit.)

bp

137-138 °C/1 mmHg (lit.)

density

1.02 g/mL at 25 °C (lit.)

SMILES string

C1CCN2C[C@@H]3C[C@@H](CN4CCCC[C@H]34)[C@@H]2C1

InChI

1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m0/s1

InChI key

SLRCCWJSBJZJBV-ZQDZILKHSA-N

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General description

Sparteine belongs to lupin alkaloid class of compounds.[1] It is a well-known neurological toxin.[2]

Application

(−)-Sparteine may be used as a chiral diamino ligand in the asymmetric catalysis reactions involving alkyllithium bases.[3][4] It may be used as a reference standard for the determination of (−)-sparteine in animal-derived food products by modified quick, easy, cheap, effective, rugged, and safe (CEN QuEChERS) extraction method followed by analysis using liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI/MS-MS).[5]

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pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF8296
BCCB5896
BCBV8015

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Diurnal cycle of sparteine production in Lupinus arcticus.
Sharam GJ and Turkington R
Canadian Journal of Botany. Journal Canadien De Botanique, 83(10), 1345-1348 (2005)
Microwave-assisted extraction of tanshinones from Salvia miltiorrhiza bunge with analysis by high-performance liquid chromatography.
Pan X, et al.
Journal of Chromatography A, 922(1-2), 371-375 (2001)
A modified QuEChERS method coupled with liquid chromatography-tandem mass spectrometry for the simultaneous detection and quantification of scopolamine, L-hyoscyamine, and sparteine residues in animal-derived food products.
Zheng W, et al.
Journal of Advanced Research (2018)
New chiral diamino ligands as sparteine analogues. Application to the palladium-catalyzed kinetic oxidative resolution of 1-phenyl ethanol.
Lesma G, et al.
Tetrahedron Asymmetry, 19(11), 1363-1366 (2008)
Synthesis of enantiomerically pure 2,2'-dihydroxy-1,1'-binaphthyl, 2,2'-diamino-1,1'-binaphthyl, and 2-amino-2'-hydroxy-1,1'-binaphthyl. Comparison of processes operating as diastereoselective crystallization and as second order asymmetric transformation.
Smrcina, M,. et al.
The Journal of Organic Chemistry, 57, 1917-1920 (1992)
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