Sparteine

Formula: C₁₅H₂₆N₂
Molecular weight: 234.3803
IUPAC Standard InChI: 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-
IUPAC Standard InChIKey: SLRCCWJSBJZJBV-PYHGIMPFSA-N
CAS Registry Number: 90-39-1
Chemical structure:
This structure is also available as a 2d Mol file
Stereoisomers:
- 7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine, dodecahydro-, [7S-(7α,7aβ,14α,14aβ)]-
- Genisteine
Other names: 7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine, dodecahydro-, [7S-(7α,7aα,14α,14aβ)]-; (-)-Sparteine; L-sparteine; Lupinidin; Lupinidine; Spartein; 6β,7α,9α,11α-Pachycarpine; 7,14-Methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, dodecahydro-; Dodecahydro [7S-(7α,7aα,14α,14aβ)]-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine; Sparteinum
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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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Normal alkane RI, non-polar column, custom temperature program

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5 MS	DB-1	OV-1	DB-1	DB-1
Column length (m)	30.	15.	15.	15.	30.
Carrier gas		Helium	He	He	He
Substrate
Column diameter (mm)	0.25	0.317	0.25	0.25	0.32
Phase thickness (μm)
Program	100 0C (1 min) 40 0C/min -> 200 0C 5 0C/min -> 275 0C (15 min)	150 0C (2 min) ¹5 0C/min -> 250 0C 25 0C/min -> 300 0C (5 min)	120C (2min) => 10C/min => 250C => 15C/min => 300C	150C(2min) => 10C/min => 250C => 20C/min => 300C (10min)	150C (2min) => 10C/min => 250C => 20C/min => 300C (5min)
I	1785.	1785.	1780.	1780.	1785.
Reference	Cook, Lee, et al., 2009	El-Shazly, Ateya, et al., 2001	Asres, Tei, et al., 1997	Greinwald, Ross, et al., 1996	Greinwald, van Rensen, et al., 1995
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Other
Active phase	DB-1	DB-1	SE-54	DB-1	Methyl Silicone
Column length (m)	30.	30.	15.	30.
Carrier gas	He		Helium	He
Substrate
Column diameter (mm)	0.32	0.3	0.25	0.32
Phase thickness (μm)			0.16
Program	150C (2min) => 10C/min => 250C => 20C/min => 300C (5min)	not specified	150 0C (2 min) 15 0C/min -> 250 0C 25 0C/min -> 200 0C (10 min)	150C (2min) => 10C/min => 250C => 20C/min => 300C (5min)	not specified
I	1785.	1785.	1785.	1790.	1801.
Reference	Greinwald, Ross, et al., 1995	Wink, Meissner, et al., 1995	Detzel and Wink, 1993	Greinwald, Witte, et al., 1991	Ardrey and Moffat, 1981
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

Go To: Top, Normal alkane RI, non-polar column, custom temperature program, Notes

Cook, Lee, et al., 2009
Cook, D.; Lee, S.T.; GArdner, D.R.; Pfister, J.A.; Welch, K.D.; Green, B.T.; Davis, T.Z.; Panter, K.E., The alkaloids profiles of lupinus sulphureus, J. Agric. Food Chem., 2009, 57, 4, 1646-1653, https://doi.org/10.1021/jf803468q . [all data]

El-Shazly, Ateya, et al., 2001
El-Shazly, A.; Ateya, A.-M.M.; Wink, M., Quinolizidine alkaloid profiles of lupunus varius orientalis. L. albus albus, L. hartwegii, and L. densiflorus, Z. Naturforsch., 2001, 56c, 21-30. [all data]

Asres, Tei, et al., 1997
Asres, K.; Tei, A.; Wink, M., Quinolizidine alkaloids from the East-African legume Dicraeopetalum stipulare harms, Biochem. Syst. Ecol., 1997, 25, 4, 305-308, https://doi.org/10.1016/S0305-1978(97)00004-5 . [all data]

Greinwald, Ross, et al., 1996
Greinwald, R.; Ross, J.H.; Witte, L.; Czygan, F.-C., Alkaloids of Templetonia incana, Biochem. Syst. Ecol., 1996, 24, 5, 423-426, https://doi.org/10.1016/0305-1978(96)00024-5 . [all data]

Greinwald, van Rensen, et al., 1995
Greinwald, R.; van Rensen, I.; Veit, M.; Canto, P.; Witte, L., A chemical dichotomy in quinolizidine alkaloid accumulation within the section Spartioides of the genus Genista (Fabaceae: Genisteae), Biochem. Syst. Ecol., 1995, 23, 1, 89-97, https://doi.org/10.1016/0305-1978(95)93662-M . [all data]

Greinwald, Ross, et al., 1995
Greinwald, R.; Ross, J.H.; Witte, L.; Czygan, F.-C., The alkaloid pattern of Plagiocarpus axillaris (Fabaceae: Brongniartieae), Biochem. Syst. Ecol., 1995, 23, 6, 645-648, https://doi.org/10.1016/0305-1978(95)00059-3 . [all data]

Wink, Meissner, et al., 1995
Wink, M.; Meissner, C.; Witte, L., Patterns of quinolizidine alkaloids in 56 species of the genus Lupinus, Phytochemistry, 1995, 38, 1, 139-153, https://doi.org/10.1016/0031-9422(95)91890-D . [all data]

Detzel and Wink, 1993
Detzel, A.; Wink, M., Attraction. deterrence or intoxication of bees (Apis mellifera) by plant allelochemicals, Chemoecology, 1993, 4, 1, 8-18, https://doi.org/10.1007/BF01245891 . [all data]

Greinwald, Witte, et al., 1991
Greinwald, R.; Witte, L.; Wray, V.; Czygan, F.-C., The alkaloid pattern of Cytisophyllum sessilitolium (Fabaceae-Genisteae), Biochem. Syst. Ecol., 1991, 19, 3, 253-258, https://doi.org/10.1016/0305-1978(91)90010-W . [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Notes

Go To: Top, Normal alkane RI, non-polar column, custom temperature program, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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