Hydroxylupanine

Formula: C₁₅H₂₄N₂O₂
Molecular weight: 264.3633
IUPAC Standard InChI: InChI=1S/C15H24N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h10-14,18H,1-9H2
IUPAC Standard InChIKey: JVYKIBAJVKEZSQ-UHFFFAOYSA-N
CAS Registry Number: 15358-48-2
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Stereoisomers:
- 13β-hydroxylupanine
Other names: 7,14-Methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one, dodecahydro-9-hydroxy-, [7S-(7α,7aβ,9β,14α,14aα)]-; Lupanine, 13α-hydroxy-; Alkaloid C 2, from Cadia purpurea; Jamaidine; Luparine, hydroxy-; Oxylupanine; 13α-Hydroxylupanine; 13-Hydroxylupanin; 13-Hydroxylupanine; 13-Oxylupanine; d-Hydroxylupanine; Lupanine,13-hydroxy; (+)-13-Hydroxylupanine; 7,14-Methano-2H,11H-dipyrido(1,2-a:1',2'-e)(1,5)diazocin-11-one, dodecahydro-2-hydroxy-, (2S-(2α,7β,7aβ,14β,14aα))-; Hydroxylupanin; Lupanine, hydroxy-; NSC 70827
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Other data available:
- Mass spectrum (electron ionization)
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Gas Chromatography

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

Normal alkane RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	DB-5	2410.	Przybylak, Ciesiolka, et al., 2005	He, 180. C @ 2. min, 5. K/min, 300. C @ 10. min; Column length: 30. m; Column diameter: 0.25 mm
Capillary	DB-1	2400.	Greinwald, Reyes-Chilpa, et al., 1996	He, 6. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 150. C; T_end: 300. C
Capillary	DB-1	2400.	Greinwald, Henrichs, et al., 1995	He, 6. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 150. C; T_end: 300. C
Capillary	DB-1	2400.	van Wyk, Greinwald, et al., 1995	6. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 150. C; T_end: 300. C
Capillary	DB-1	2395.	Greinwald, Canto, et al., 1992	He, 6. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 150. C; T_end: 300. C
Capillary	DB-1	2410.	Wink and Witte, 1991	30. m/0.32 mm/1.0 μm, Helium, 150. C @ 1. min, 10. K/min; T_end: 300. C
Capillary	SE-30	2408.	Wink, Witte, et al., 1983	He, 6. K/min; Column length: 15. m; Column diameter: 0.26 mm; T_start: 150. C; T_end: 270. C
Capillary	SE-30	2410.	Wink, Witte, et al., 1981	He, 6. K/min; Column length: 15. m; Column diameter: 0.26 mm; T_start: 150. C; T_end: 270. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-1	2402.	El-Shazly, Ateya, et al., 2001	Helium; Column length: 15. m; Column diameter: 0.317 mm; Program: 150 0C (2 min) ¹5 0C/min -> 250 0C 25 0C/min -> 300 0C (5 min)
Capillary	DB-1	2402.	Greinwald, van Rensen, et al., 1995	He; Column length: 30. m; Column diameter: 0.32 mm; Program: 150C (2min) => 10C/min => 250C => 20C/min => 300C (5min)
Capillary	DB-1	2400.	Wink, Meissner, et al., 1995	Column length: 30. m; Column diameter: 0.3 mm; Program: not specified
Capillary	SE-54	2410.	Detzel and Wink, 1993	15. m/0.25 mm/0.16 μm, Helium; Program: 150 0C (2 min) 15 0C/min -> 250 0C 25 0C/min -> 200 0C (10 min)

References

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Przybylak, Ciesiolka, et al., 2005
Przybylak, J.K.; Ciesiolka, D.; Wysocka, W.; García-López, P.M.; Ruiz-López, M.A.; Wysocki, W.; Gulewicz, K., Alkaloid profiles of Mexican wild lupin and an effect of alkaloid preparation from Lupinus exaltatus seeds on growth and yield of paprika (Capsicum annuum L.), Ind. Crops Prod., 2005, 21, 1, 1-7, https://doi.org/10.1016/j.indcrop.2003.12.001 . [all data]

Greinwald, Reyes-Chilpa, et al., 1996
Greinwald, R.; Reyes-Chilpa, R.; Ross, J.H.; Witte, L.; Czygan, F.-C., A survey of alkaloids in the genera Harpalyce and Brongniartia (Fabaceae - Brongniartieae), Biochem. Syst. Ecol., 1996, 24, 7/8, 749-755. [all data]

Greinwald, Henrichs, et al., 1995
Greinwald, R.; Henrichs, C.; Veen, G.; Ross, J.H.; Witte, L.; Czygan, F.-C., A survey of alkaloids in templetonia biloba (Benth.) Polhill (Fabaceae: Brongniartieae), Biochem. Syst. Ecol., 1995, 23, 6, 649-654, https://doi.org/10.1016/0305-1978(95)00035-6 . [all data]

van Wyk, Greinwald, et al., 1995
van Wyk, B.-E.; Greinwald, R.; Witte, L., Alkaloid variation in the Lupinus pusillus group (Fabaceae: tribe Genisteae), Biochem. Syst. Ecol., 1995, 23, 5, 533-537, https://doi.org/10.1016/0305-1978(95)00036-T . [all data]

Greinwald, Canto, et al., 1992
Greinwald, R.; Canto, P.; Bachmann, P.; Witte, L.; Czygan, F.-C., Distribution and taxdonomic significance of alkaloids in the Genista cinerea agregat, Biochem. Syst. Ecol., 1992, 20, 1, 75-81, https://doi.org/10.1016/0305-1978(92)90074-N . [all data]

Wink and Witte, 1991
Wink, M.; Witte, L., Storage of quinolizidine alkaloids in Macrosiphum albifrons and Aphis genistae (Homoptera: Aphididae), Entomol. Gener., 1991, 15, 4, 237-254, https://doi.org/10.1127/entom.gen/15/1991/237 . [all data]

Wink, Witte, et al., 1983
Wink, M.; Witte, L.; Hartmann, T.; Theuring, C.; Volz. V., Accumulation of quinolizidine alkaloids in plants and cell suspension cultures: genera lupinus, cytisus, baptisia, genista, laburnum, and sophora, Planta Medica, 1983, 48, 4, 253-257, https://doi.org/10.1055/s-2007-969928 . [all data]

Wink, Witte, et al., 1981
Wink, M.; Witte, L.; Hartmann. T., Quinolizidine Alkaloid Composition of Plants and of Photomixotrophis Cell Suspension Cultures of Sarothamnus scoparius and Orobanche rapum-genistae, Planta Medica, 1981, 43, 12, 342-352, https://doi.org/10.1055/s-2007-971522 . [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]

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]

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]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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