Hydroxylupanine | CAS#15358-48-2 | bis-quinolizidine alkaloid

MedKoo Cat#: 596103 | Name: Hydroxylupanine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Hydroxylupanine is a dimer of bis-quinolizidine alkaloid.

Chemical Structure

Hydroxylupanine

CAS#15358-48-2

Theoretical Analysis

MedKoo Cat#: 596103

Name: Hydroxylupanine

CAS#: 15358-48-2

Chemical Formula: C15H24N2O2

Exact Mass: 264.1838

Molecular Weight: 264.36

Elemental Analysis: C, 68.15; H, 9.15; N, 10.60; O, 12.10

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

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Synonym

Hydroxylupanine; Alkaloid C 2, from Cadia purpurea; 4-25-00-00082 (Beilstein Handbook Reference); (+)-13-Hydroxylupanine; BRN 0087896; BRN0087896; BRN-0087896; Jamaidine; Lupanine, hydroxy- (6CI); Oxylupanine;

IUPAC/Chemical Name

(2S,7S,7aR,14S,14aS)-2-hydroxydodecahydro-2H,11H-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one

InChi Key

JVYKIBAJVKEZSQ-YHQUGGNUSA-N

InChi Code

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/t10-,11-,12-,13+,14-/m0/s1

SMILES Code

O=C1CCC[C@@]2([H])N1C[C@@]3([H])[C@@](C[C@@H](O)CC4)([H])N4C[C@]2([H])C3

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 264.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Jasiewicz B, Pospieszny T. Mass spectrometry of bis-quinolizidine alkaloids: unexpected dimerization in electron ionization mass spectrometry. Acta Chim Slov. 2013;60(4):833-41. PubMed PMID: 24362987. 2: Korir E, Kiplimo JJ, Crouch NR, Moodley N, Koorbanally NA. Quinolizidine alkaloids from Sophora velutina subsp. zimbabweensis (Fabaceae: Sophoreae). Nat Prod Commun. 2012 Aug;7(8):999-1003. PubMed PMID: 22978215. 3: Ganzera M, Krüger A, Wink M. Determination of quinolizidine alkaloids in different Lupinus species by NACE using UV and MS detection. J Pharm Biomed Anal. 2010 Dec 15;53(5):1231-5. doi: 10.1016/j.jpba.2010.05.030. Epub 2010 Jun 8. PubMed PMID: 20580181. 4: Boschin G, Annicchiarico P, Resta D, D'Agostina A, Arnoldi A. Quinolizidine alkaloids in seeds of lupin genotypes of different origins. J Agric Food Chem. 2008 May 28;56(10):3657-63. doi: 10.1021/jf7037218. PubMed PMID: 18433102. 5: Lee MJ, Pate JS, Harris DJ, Atkins CA. Synthesis, transport and accumulation of quinolizidine alkaloids in Lupinus albus L. and L. angustifolius L. J Exp Bot. 2007;58(5):935-46. Epub 2006 Dec 22. PubMed PMID: 17189595. 6: Reinhard H, Rupp H, Sager F, Streule M, Zoller O. Quinolizidine alkaloids and phomopsins in lupin seeds and lupin containing food. J Chromatogr A. 2006 Apr 21;1112(1-2):353-60. Epub 2005 Dec 15. PubMed PMID: 16359686. 7: Okada T, Hirai MY, Suzuki H, Yamazaki M, Saito K. Molecular characterization of a novel quinolizidine alkaloid O-tigloyltransferase: cDNA cloning, catalytic activity of recombinant protein and expression analysis in Lupinus plants. Plant Cell Physiol. 2005 Jan;46(1):233-44. Epub 2005 Jan 19. PubMed PMID: 15659437. 8: Sagen AL, Gertsch J, Becker R, Heilmann J, Sticher O. Quinolizidine alkaloids from the curare adjuvant Clathrotropis glaucophylla. Phytochemistry. 2002 Dec;61(8):975-8. PubMed PMID: 12453529. 9: Torres KB, Quintos NR, Necha LL, Wink M. Alkaloid profile of leaves and seeds of Lupinus hintonii C. P. Smith. Z Naturforsch C. 2002 Mar-Apr;57(3-4):243-7. PubMed PMID: 12064721. 10: Pistelli L, Bertoli A, Giachi I I, Morelli I I, Rubiolo P, Bicchi C. Quinolizidine alkaloids from Genista ephedroides. Biochem Syst Ecol. 2001 Feb 1;29(2):137-141. PubMed PMID: 11106841. 11: Hirai MY, Suzuki H, Yamazaki M, Saito K. Biochemical and partial molecular characterization of bitter and sweet forms of Lupinus angustifolius, an experimental model for study of molecular regulation of quinolizidine alkaloid biosynthesis. Chem Pharm Bull (Tokyo). 2000 Oct;48(10):1458-61. PubMed PMID: 11045450. 12: Robbins MC, Petterson DS, Brantom PG. A 90-day feeding study of the alkaloids of Lupinus angustifolius in the rat. Food Chem Toxicol. 1996 Aug;34(8):679-86. PubMed PMID: 8883468. 13: Petterson DS, Greirson BN, Allen DG, Harris DJ, Power BM, Dusci LJ, Ilett KF. Disposition of lupanine and 13-hydroxylupanine in man. Xenobiotica. 1994 Sep;24(9):933-41. PubMed PMID: 7810174. 14: Suzuki H, Murakoshi I, Saito K. A novel O-tigloyltransferase for alkaloid biosynthesis in plants. Purification, characterization, and distribution in Lupinus plants. J Biol Chem. 1994 Jun 3;269(22):15853-60. PubMed PMID: 8195240. 15: Mühlbauer P, Witte L, Wink M. New ester alkaloids from lupins (genus lupinus). Planta Med. 1988 Jun;54(3):237-9. PubMed PMID: 17265260. 16: Petterson DS, Ellis ZL, Harris DJ, Spadek ZE. Acute toxicity of the major alkaloids of cultivated Lupinus angustifolius seed to rats. J Appl Toxicol. 1987 Feb;7(1):51-3. PubMed PMID: 3611597. 17: 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 Med. 1983 Aug;48(8):253-7. PubMed PMID: 17404991. 18: Priddis CR. Capillary gas chromatography of lupin alkaloids. J Chromatogr. 1983 May 20;261(1):95-101. PubMed PMID: 6874800. 19: Wink M, Hartmann T. Enzymatic synthesis of quinolizidine alkaloid esters: a tigloyl-CoA: 13-hydroxylupanine O-tigloyltransferase from Lupinus albus L. Planta. 1982 Jan;156(6):560-5. doi: 10.1007/BF00392781. PubMed PMID: 24272737. 20: Wink M, Schiebel HM, Witte L, Hartmann T. Quinolizidine alkaloids from plants and their cell suspension cultures. Planta Med. 1982 Jan;44(1):15-20. PubMed PMID: 17402075.